US3314888A - Extreme pressure lubricant compositions - Google Patents
Extreme pressure lubricant compositions Download PDFInfo
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- US3314888A US3314888A US371753A US37175364A US3314888A US 3314888 A US3314888 A US 3314888A US 371753 A US371753 A US 371753A US 37175364 A US37175364 A US 37175364A US 3314888 A US3314888 A US 3314888A
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- United States
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- grams
- extreme pressure
- oil
- carbon atoms
- sulfur
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- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims description 17
- 239000000314 lubricant Substances 0.000 title description 10
- 239000000654 additive Substances 0.000 claims description 14
- 230000000996 additive effect Effects 0.000 claims description 7
- 239000002199 base oil Substances 0.000 claims description 7
- 239000010687 lubricating oil Substances 0.000 claims description 6
- 230000001050 lubricating effect Effects 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- -1 thrust washers Chemical compound 0.000 description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 13
- 229910052717 sulfur Inorganic materials 0.000 description 13
- 239000011593 sulfur Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000005260 corrosion Methods 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004711 α-olefin Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000005461 lubrication Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000005069 Extreme pressure additive Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 2
- 229940073769 methyl oleate Drugs 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000009972 noncorrosive effect Effects 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 1
- URRHKOYTHDCSDA-UHFFFAOYSA-N 2,5,8,11-tetramethyldodec-2-ene Chemical group CC(C)CCC(C)CCC(C)CC=C(C)C URRHKOYTHDCSDA-UHFFFAOYSA-N 0.000 description 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical compound [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000003490 Thiodipropionic acid Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 description 1
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229940067597 azelate Drugs 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
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical group [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 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
- 230000002950 deficient Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 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
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000010699 lard oil Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 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 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
- 125000001117 oleyl 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])=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 1
- 238000011017 operating method Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000003466 welding Methods 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
- C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
-
- 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
- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
-
- 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
- C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
-
- 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
- C10N2040/02—Bearings
Definitions
- sulfur compounds in making extreme pressure lubricants is well-known.
- sulfurreacted fats and fatty oils such as sulfurized sperm oil and sulfurized lard oil have been used for many years in lubricants intended for use under extreme pressure conditions such as exist in heavily loaded gears.
- Other examples of materials which have been sulfurized to yield useful additives include unsaturated esters such as methyl oleate, olefins and olefin polymers such as dodecene and tetraisobutylene, and alicyclics such as alpha-pinene and its homologs.
- the sulfur and carboxyl group-containing additives of this invention are present in the oil in a minor amount sufficient to increase the load carrying capacity of the oil, e.g. about 0.1 to 5, preferably about 0.5 to 3,
- the compounds of this invention are o1l-soluble to the extent necessary to impart extreme pressure properties to the base oil and may be represented by the following structural formulas:
- R is an aliphatic hydrocarbon radical. of about 8 to 24 carbon atoms
- R is an aliphatic hydrocarbon radical of about 1 to 8 carbon atoms
- R" is a divalent aliphatic hydrocarbon radical of about 1 to 9 crbon atoms
- R' is an aliphatic hydrocarbon radical of about 1 to 20 carbon atoms
- the groups R, R, R" and R' are aliphatic including cycloaliphatic hydrocarbon groups and may contain acetylenic or olefinic bonds. Preferably, however, R, R, R and R' are essentially free of ethylenic and acetylenic unsaturation, that is, all of the carbon-to-carbon linkages in the chain are not less than 1.40 A., the interatomic distance of carbon atoms in a benzene ring.
- the R, R, 'F" and R' can be straight or branched and may be unsubstituted or substituted with non-interfering groups such as halides, hydroxyl, etc.
- Suitable groups are methyl, ethyl, butyl, hexyl, 2-ethyl-hexyl, octyl, dodecyl, tetradecyl, octadecyl, oleyl, cyclohexyl, other alkyl groups or the corresponding divalent alkylene groups.
- Example I 46 grams of thioglycolic acid (0.5 mol) and 127 grams of technical mixed alpha-olefins (Archer-Daniels- Midland Co., Adacene A5'1, mixed 12 to 20 carbon atom alpha-olefins, avg. MW of 230) (0.55 mol) were mixed with 300 grams of methyl ethyl ketone solvent and 0.2 gram of benzoyl peroxide. This mixture was refluxed at 87 C. for two hours, then filtered after cooling to remove separated crystals. The product was recrystallized from acetone to yield grams of material analyzing 8.7% sulfur and having an acid number (ASTM'D 664) of 169.
- technical mixed alpha-olefins (Archer-Daniels- Midland Co., Adacene A5'1, mixed 12 to 20 carbon atom alpha-olefins, avg. MW of 230) (0.55 mol) were mixed with 300 grams of methyl
- This product which is presumed to be a mixed alkyl B-mercapto acetic acid, was esterified by reacting 64 grams (est. 0.2 mol) with 65 grams (0.5 mol) of 2- ethyl hexanol in 200 grams of toluene solvent and in the presence of 0.2 gram p-toluene sulfonic acid, by refluxing at 118 C. pot temperature for 5 hours. A total of 3.75 ml. of water vs. 3.6 theory (for 0.2 mol) was recovered. The final product was recovered after vacuum stripping in a yield of 86 grams of an amber liquid, analyzing 7.0% sulfur and with an acid number of 0.7.
- Example I has the structural formula i RSOH2O OR where R is a mixed alkyl radical of 12 to 20 carbon atoms and R is a 2-ethy1 hexyl radical.
- Example II 89 grams of thiodipropionic acid (0.5 mol) and 260 grams of 2-ethyl hexanol (2 mols) were mixed with 300 grams of toluene solvent and refluxed at C. pot temmature for 23 hours with a recovery of 18.5 ml. of water s. 18.0 ml. theory. After vacuun stripping to remove olvent and excess alcohol, a yield of 188 grams of final
- Example 11 has the structural formula s (CI-IzCHaPl-ORM vhere R is a Z-ethyl hexyl radical.
- Example IV 34.2 grams of trimethylolethane tris (thioglycolate), equal to 0.1 mol, and 83 grams of Adacene A51 (0.36 mol) were mixed in 250 grams of toluene and 0.2 grams of benzoyl peroxide were added. The reaction mixture was refluxed at 110 C. for six hours, followed by vacuum stripping to remove the solvent and any unreacted olefin, to yield 99 grams of product analyzing 10.0% sulfur.
- Example IV has the structural formula 01130 (CH2O(L/CI'I2SR)3 where R is a mixed alkyl radical of 12 to carbon atoms.
- Example V 43.2 grams of pentaerythritol tetrakis (thioglycolate), equal to 0.1 mol, and grams of mixed alpha olefins (Archer-Daniels-Midland Co. Adacene A-12, mixed 10 to 14 carbon atom alpha-olefins, avg. MW of 170) (0.47 mol) were mixed together with 200 grams of toluene and 0.2 gram of benzoyl peroxide was added.
- Synthetic hydrocarbon oils of the alkylene polymer type or those derived from coal and shale may also be employed.
- Alkylene oxide polymers and their derivatives such as the propylene oxide polymers and their ethers and esters in which the terminal hydroxyl groups have been modified are also suitable.
- Synthetic oils of the carboxylic acid ester type including di'butyl adipate, di-2-ethylhexyl sebacate, di-n-hexyl fumaric polymer, di-lauryl azelate, and the like may be used along or in blends containing complex or polyesters or other thickening agents. These esters are frequently made from dibasic acids, alcohols and glycols of 6 to 12 carbon atoms.
- additives may be included in the lubricating oil composition of the present invention so long as they do not adversely affect the load carrying properties of the oil and its tendency not to corrode copper.
- the additives can be for example, extreme pressure agents, pour depressors, corrosion inhibitors, anti-foam agents, etc.
- the additives of this invention were evaluated in lubricant compositions by the Falex and SAE machine maximum load tests. These tests are well-known in the art, and a description of the detailed operating procedures are not repeated here. However, such details are given in Volume 32 of the Journal of the Institute of Petroleum, April 1946, for the Falex test; and in the CRC reference handbook under the designation L-17-545 for the SAE test.
- the lubricant compositions were also tested for copper corrosion by the well-known ASTM Standards test D130 at 212 F.
- Example V has the structural formula otol-rzoiiol-rsnni where R is a mixed alkyl radical having from 10 to 14 carbon atoms.
- the lubricating oil base stock used in the present invention is of lubricating viscosity and can be, for instance,
- R is an aliphatic hydrocarbon radical of about 8 to 24 carbon atoms
- R is an aliphatic hydrocarbon radical of about 1 to 8 carbon atoms
- R" is a divalent aliphatic hydrocarbon radical of about 1 to 9 carbon atoms
- n is an integer from 0 to 1
- tequals 4n is an integer from 0 to 1
- a lubricating oil composition consisting essentially of a major amount of a base oil of lubricating viscosity and about 0.1 to 5 weight percent of an oil-soluble additive having the structure 0 R,,C(R-O-iiRS-R-)t Where R is an aliphatic hydrocarbon radical of about 8 to 24 carbon atoms, R is an aliphatic hydrocarbon radical of about 1 to 8 carbon atoms, R is a divalent aliphatic hydrocarbon radical of about 1 to 9 carbon atoms, n is an integer from 0 to 1, and t equals 4-n.
- composition of claim 1 wherein the additive is i CH C(CH OGCHzSR)s wherein R is an alkyl radical of 12 to 20 carbon atoms. 4. The composition of claim 1 wherein the additive is 0 II o (CHZOCCHQSRWIH wherein R is an alkyl radical of 10 to 14 carbon atoms.
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Description
United States Patent CfiFice 3,314,888 Patented Apr. 18, 1967 This invention relates to new and useful sulfur additives for compounding extreme pressure lubricants. In particular, the invention concerns extreme pressure sulfur compounds that are relatively non-corrosive to copper and copper alloys.
The use of sulfur compounds in making extreme pressure lubricants is well-known. For example, sulfurreacted fats and fatty oils such as sulfurized sperm oil and sulfurized lard oil have been used for many years in lubricants intended for use under extreme pressure conditions such as exist in heavily loaded gears. Other examples of materials which have been sulfurized to yield useful additives include unsaturated esters such as methyl oleate, olefins and olefin polymers such as dodecene and tetraisobutylene, and alicyclics such as alpha-pinene and its homologs.
Although these compounds are generally satisfactory insofar as their primary function is concerned, which is to provide for lubrication under extreme pressure conditions, all of them are more or less deficient with respect to corrosive action on copper. In other words, whereas sulfur compounds of the types indicated above may function to improve lubrication of gears, for example, under conditions that would other-wise result in excessive wear or failure through seizure and welding, they may at the same time tend to corrode copper or bronze parts such as thrust washers, bearings, bushings, etc.
One reason for the corrosion may be found in a theory of extreme pressure additive action, which holds that it is necessary for an -EP material such as sulfur to react chemically with steel gear surfaces in order to form a chemical film, in this case iron sulfide, which actually serves as the lubricant when conditions of temperature, presure, etc. combine to destroy the mineral oil film normally present. This mode of action can be looked on as a corrosive process, in which a small amount of chemical wear is sacrificed to avoid a gross destructive failure. Unfortunately, the same chemical activity that is desirable for extreme pressure lubrication may be undesirable from the standpoint of corrosive attack on other parts which do not require an extreme pressure lubricant. It has been a problem therefore in compounding extreme presure gear lubricants to provide additives which have the necessary chemical activity insofar as the gear surfaces are concerned, but that are not so active as to cause undue corrosion of any part of the gear assembly.
It is an object of this invention to provide high pressure lubricant additives which do not cause significant copper corrosion. It has now been found that when a small effective amount of an extreme pressure additive which contains sulfur and carboxyl composition is relatively non-corrosive to copper and its alloys. The sulfur and carboxyl group-containing additives of this invention are present in the oil in a minor amount sufficient to increase the load carrying capacity of the oil, e.g. about 0.1 to 5, preferably about 0.5 to 3,
percent by weight.
The compounds of this invention are o1l-soluble to the extent necessary to impart extreme pressure properties to the base oil and may be represented by the following structural formulas:
R is an aliphatic hydrocarbon radical. of about 8 to 24 carbon atoms,
R is an aliphatic hydrocarbon radical of about 1 to 8 carbon atoms,
R" is a divalent aliphatic hydrocarbon radical of about 1 to 9 crbon atoms,
R' is an aliphatic hydrocarbon radical of about 1 to 20 carbon atoms,
11 is an integer from 0 to 1,
m equals 2n 2 equals 4n The groups R, R, R" and R' are aliphatic including cycloaliphatic hydrocarbon groups and may contain acetylenic or olefinic bonds. Preferably, however, R, R, R and R' are essentially free of ethylenic and acetylenic unsaturation, that is, all of the carbon-to-carbon linkages in the chain are not less than 1.40 A., the interatomic distance of carbon atoms in a benzene ring. The R, R, 'F" and R' can be straight or branched and may be unsubstituted or substituted with non-interfering groups such as halides, hydroxyl, etc. Examples of suitable groups are methyl, ethyl, butyl, hexyl, 2-ethyl-hexyl, octyl, dodecyl, tetradecyl, octadecyl, oleyl, cyclohexyl, other alkyl groups or the corresponding divalent alkylene groups.
The compounds of this invention may be more readily understood by reference to the following examples of their preparation.
Example I 46 grams of thioglycolic acid (0.5 mol) and 127 grams of technical mixed alpha-olefins (Archer-Daniels- Midland Co., Adacene A5'1, mixed 12 to 20 carbon atom alpha-olefins, avg. MW of 230) (0.55 mol) were mixed with 300 grams of methyl ethyl ketone solvent and 0.2 gram of benzoyl peroxide. This mixture was refluxed at 87 C. for two hours, then filtered after cooling to remove separated crystals. The product was recrystallized from acetone to yield grams of material analyzing 8.7% sulfur and having an acid number (ASTM'D 664) of 169. This product, which is presumed to be a mixed alkyl B-mercapto acetic acid, was esterified by reacting 64 grams (est. 0.2 mol) with 65 grams (0.5 mol) of 2- ethyl hexanol in 200 grams of toluene solvent and in the presence of 0.2 gram p-toluene sulfonic acid, by refluxing at 118 C. pot temperature for 5 hours. A total of 3.75 ml. of water vs. 3.6 theory (for 0.2 mol) was recovered. The final product was recovered after vacuum stripping in a yield of 86 grams of an amber liquid, analyzing 7.0% sulfur and with an acid number of 0.7.
The product of Example I has the structural formula i RSOH2O OR where R is a mixed alkyl radical of 12 to 20 carbon atoms and R is a 2-ethy1 hexyl radical.
Example II 89 grams of thiodipropionic acid (0.5 mol) and 260 grams of 2-ethyl hexanol (2 mols) were mixed with 300 grams of toluene solvent and refluxed at C. pot temmature for 23 hours with a recovery of 18.5 ml. of water s. 18.0 ml. theory. After vacuun stripping to remove olvent and excess alcohol, a yield of 188 grams of final |roduct analyzing 7.09% sulfur was obtained. The prodlct had an acid number (ASTMD 664) of 16, indicating he presence of about 2.5% unreacted acid.
The product of Example 11 has the structural formula s (CI-IzCHaPl-ORM vhere R is a Z-ethyl hexyl radical.
Example III (RSCHz 1-OCH2)2 Where R is mixed alkyl radical of 12 to 20 carbon atoms.
Example IV 34.2 grams of trimethylolethane tris (thioglycolate), equal to 0.1 mol, and 83 grams of Adacene A51 (0.36 mol) were mixed in 250 grams of toluene and 0.2 grams of benzoyl peroxide were added. The reaction mixture Was refluxed at 110 C. for six hours, followed by vacuum stripping to remove the solvent and any unreacted olefin, to yield 99 grams of product analyzing 10.0% sulfur.
The product of Example IV has the structural formula 01130 (CH2O(L/CI'I2SR)3 where R is a mixed alkyl radical of 12 to carbon atoms. Example V 43.2 grams of pentaerythritol tetrakis (thioglycolate), equal to 0.1 mol, and grams of mixed alpha olefins (Archer-Daniels-Midland Co. Adacene A-12, mixed 10 to 14 carbon atom alpha-olefins, avg. MW of 170) (0.47 mol) were mixed together with 200 grams of toluene and 0.2 gram of benzoyl peroxide was added. The reaction a solvent extracted or solvent refined mineral oil obtained in accordance with conventional methods of solvent refining lubricating oils. Generally, lubricating oils having viscosities from about 20 to 250 SUS at 210 F. are preferred. The base oil is present in major amounts and may be derived from parafiinic, naphthenic, asphaltic or mixed base petroleum crudes and if desired, a 'blend of solvent-treated Mid-Continent neutrals and Mid-Continent bright stocks may be employed. A particularly suitable base oil used in the preparation of the composition may be described as a lubricating mineral oil fraction having a viscosity index of about 100.
Synthetic hydrocarbon oils of the alkylene polymer type or those derived from coal and shale may also be employed. Alkylene oxide polymers and their derivatives such as the propylene oxide polymers and their ethers and esters in which the terminal hydroxyl groups have been modified are also suitable. Synthetic oils of the carboxylic acid ester type including di'butyl adipate, di-2-ethylhexyl sebacate, di-n-hexyl fumaric polymer, di-lauryl azelate, and the like may be used along or in blends containing complex or polyesters or other thickening agents. These esters are frequently made from dibasic acids, alcohols and glycols of 6 to 12 carbon atoms.
If desired other additives may be included in the lubricating oil composition of the present invention so long as they do not adversely affect the load carrying properties of the oil and its tendency not to corrode copper. The additives can be for example, extreme pressure agents, pour depressors, corrosion inhibitors, anti-foam agents, etc.
The additives of this invention were evaluated in lubricant compositions by the Falex and SAE machine maximum load tests. These tests are well-known in the art, and a description of the detailed operating procedures are not repeated here. However, such details are given in Volume 32 of the Journal of the Institute of Petroleum, April 1946, for the Falex test; and in the CRC reference handbook under the designation L-17-545 for the SAE test. The lubricant compositions were also tested for copper corrosion by the well-known ASTM Standards test D130 at 212 F.
Examples VI to XIV The tests referred to were made on blends of the sulfur additives in a 200 SUS at 100 neutral oil at equal sulfur content in order to clearly demonstrate the efficacy of the sulfur as contained in the compounds of this invention. Results are shown in the following table.
TABLE Wt. Percent Falex Load, SAE Load, ASTM D130 Sample Additive (Percent in Blend) Added Sulfur lbs. lbs. Copper in Blend Corrosion Dodecylmereapto methane CII2 SC12II25 2 (1.0%). 0.15 1 Suliurized dodeeene (0.6% 0.15 4 Sulfurized methyl oleate (1.0%) 0. 15 3 Compound of Example I (1.0%). 0. 15 1 Compound of Example II (2.2%)... 0.15 1 Compound of Example 111 (1.6%) 0.15 1 Compound of Example IV (1.6%) 0.15 1 Compound of Example V (1.4%)... 0.15 1, 500 410 1 None None 1, 000 90 1 mixture was refluxed at 115 C. for six hours, after which the solvent and any unreacted olefin were removed by vacuum stripping, yielding 103 grams of product analyzing 11.1% sulfur.
The product of Example V has the structural formula otol-rzoiiol-rsnni where R is a mixed alkyl radical having from 10 to 14 carbon atoms.
The lubricating oil base stock used in the present invention is of lubricating viscosity and can be, for instance,
These data demonstrate that the compounds of this invention prov1de extreme pressure lubricants which are and a small amount effective to increase the load carrying capacity of the base oil of an oil-soluble additive having the structure R'.,-o-(R"-o- 'i-R"-sR),
Where R is an aliphatic hydrocarbon radical of about 8 to 24 carbon atoms, R is an aliphatic hydrocarbon radical of about 1 to 8 carbon atoms, R" is a divalent aliphatic hydrocarbon radical of about 1 to 9 carbon atoms, n is an integer from 0 to 1, and tequals 4n.
2. A lubricating oil composition consisting essentially of a major amount of a base oil of lubricating viscosity and about 0.1 to 5 weight percent of an oil-soluble additive having the structure 0 R,,C(R-O-iiRS-R-)t Where R is an aliphatic hydrocarbon radical of about 8 to 24 carbon atoms, R is an aliphatic hydrocarbon radical of about 1 to 8 carbon atoms, R is a divalent aliphatic hydrocarbon radical of about 1 to 9 carbon atoms, n is an integer from 0 to 1, and t equals 4-n.
3. The composition of claim 1 wherein the additive is i CH C(CH OGCHzSR)s wherein R is an alkyl radical of 12 to 20 carbon atoms. 4. The composition of claim 1 wherein the additive is 0 II o (CHZOCCHQSRWIH wherein R is an alkyl radical of 10 to 14 carbon atoms.
References Cited by the Examiner UNITED STATES PATENTS 2,216,751 10/1940 Rosen 252-486 2,683,119 7/1954 Smith et al 25248.6 2,947,599 8/1960 Ennis 25248.6 3,144,422 8/1964 Homberg 260-481 3,158,576 11/1964 Rudel et a1 252-48.6 3,189,547 6/1965 Calhoun 25248.6
DANIEL E. WYMAN, Primary Examiner. L. G. XIARHOS, Assistant Examiner.
Claims (1)
1. A LUBRICATING OIL COMPOSITION CONSISTING ESSENTIALLY OF A MAJOR AMOUNT OF A BASE OIL OF LUBRICATING VISCOSITY AND A SMALL AMOUNT EFFECTIVE TO INCREASE THE LOAD CARRYING CAPACITY OF THE BASE OIL OF AN OIL-SOLUBLE ADDITIVE HAVING THE STRUCTURE
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|---|---|---|---|
| US371753A US3314888A (en) | 1964-06-01 | 1964-06-01 | Extreme pressure lubricant compositions |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US371753A US3314888A (en) | 1964-06-01 | 1964-06-01 | Extreme pressure lubricant compositions |
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|---|---|
| US3314888A true US3314888A (en) | 1967-04-18 |
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| US371753A Expired - Lifetime US3314888A (en) | 1964-06-01 | 1964-06-01 | Extreme pressure lubricant compositions |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4076639A (en) * | 1976-08-30 | 1978-02-28 | Mobil Oil Corporation | Lubricant compositions |
| US4174284A (en) * | 1978-08-14 | 1979-11-13 | Phillips Petroleum Company | Hydrocarbylpolythiobenzoic acids as anti-oxidation additives |
| US4239636A (en) * | 1978-10-23 | 1980-12-16 | Exxon Research & Engineering Co. | Thio-bis-(alkyl lactone acid esters) and thio-bis-(hydrocarbyl diacid esters) are useful additives for lubricating compositions |
| US4248723A (en) * | 1977-06-23 | 1981-02-03 | Ciba-Geigy Corporation | Acetal derivatives as extreme pressure additives for lubricants |
| US4260503A (en) * | 1977-08-31 | 1981-04-07 | Ciba-Geigy Corporation | Mercaptan as an additive for lubricants |
| JPS578294A (en) * | 1980-06-20 | 1982-01-16 | Nippon Mining Co Ltd | Lubricating oil composition used in flon atmosphere |
| JPS5785893A (en) * | 1980-11-18 | 1982-05-28 | Idemitsu Kosan Co Ltd | Cold rolling mill oil |
| US4335004A (en) * | 1980-01-11 | 1982-06-15 | Phillips Petroleum Company | Lubricating compositions containing diesters of dimercapto ethers |
| US4729839A (en) * | 1986-05-29 | 1988-03-08 | Phillips Petroleum Company | Water soluble lubricating additives |
| US5162405A (en) * | 1987-12-24 | 1992-11-10 | Elf Atochem North America, Inc. | Single-functional and mixtures of multi-functional oligomeric performance additive compositions and their uses |
| US5225091A (en) * | 1988-08-01 | 1993-07-06 | Exxon Chemical Patents Inc. | Ethylene alpha-olefin polymer substituted thiocarboxylic acid lubricant dispersant additives |
| US5576470A (en) * | 1994-08-29 | 1996-11-19 | Henkel Corporation | Polyol esters of ether carboxylic acids and fiber finishing methods |
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| US3189547A (en) * | 1959-07-03 | 1965-06-15 | Shell Oil Co | Lubricating compositions |
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| US2216751A (en) * | 1935-05-14 | 1940-10-08 | Standard Oil Dev Co | Heavy metal salts of thioether carboxylic acids |
| US2683119A (en) * | 1949-11-16 | 1954-07-06 | Standard Oil Dev Co | Compounded lubricant |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4076639A (en) * | 1976-08-30 | 1978-02-28 | Mobil Oil Corporation | Lubricant compositions |
| US4248723A (en) * | 1977-06-23 | 1981-02-03 | Ciba-Geigy Corporation | Acetal derivatives as extreme pressure additives for lubricants |
| US4260503A (en) * | 1977-08-31 | 1981-04-07 | Ciba-Geigy Corporation | Mercaptan as an additive for lubricants |
| US4174284A (en) * | 1978-08-14 | 1979-11-13 | Phillips Petroleum Company | Hydrocarbylpolythiobenzoic acids as anti-oxidation additives |
| US4239636A (en) * | 1978-10-23 | 1980-12-16 | Exxon Research & Engineering Co. | Thio-bis-(alkyl lactone acid esters) and thio-bis-(hydrocarbyl diacid esters) are useful additives for lubricating compositions |
| US4335004A (en) * | 1980-01-11 | 1982-06-15 | Phillips Petroleum Company | Lubricating compositions containing diesters of dimercapto ethers |
| JPS578294A (en) * | 1980-06-20 | 1982-01-16 | Nippon Mining Co Ltd | Lubricating oil composition used in flon atmosphere |
| JPS5785893A (en) * | 1980-11-18 | 1982-05-28 | Idemitsu Kosan Co Ltd | Cold rolling mill oil |
| US4729839A (en) * | 1986-05-29 | 1988-03-08 | Phillips Petroleum Company | Water soluble lubricating additives |
| US5162405A (en) * | 1987-12-24 | 1992-11-10 | Elf Atochem North America, Inc. | Single-functional and mixtures of multi-functional oligomeric performance additive compositions and their uses |
| US5225091A (en) * | 1988-08-01 | 1993-07-06 | Exxon Chemical Patents Inc. | Ethylene alpha-olefin polymer substituted thiocarboxylic acid lubricant dispersant additives |
| US5576470A (en) * | 1994-08-29 | 1996-11-19 | Henkel Corporation | Polyol esters of ether carboxylic acids and fiber finishing methods |
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