US3248325A - Lubricating composition - Google Patents
Lubricating composition Download PDFInfo
- Publication number
- US3248325A US3248325A US391328A US39132864A US3248325A US 3248325 A US3248325 A US 3248325A US 391328 A US391328 A US 391328A US 39132864 A US39132864 A US 39132864A US 3248325 A US3248325 A US 3248325A
- Authority
- US
- United States
- Prior art keywords
- weight percent
- lubricating
- molybdenum
- sulfide
- arylene sulfide
- 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
Links
- 239000000203 mixture Substances 0.000 title claims description 24
- 230000001050 lubricating effect Effects 0.000 title description 19
- 229920000642 polymer Polymers 0.000 claims description 20
- 239000000314 lubricant Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- -1 arylene sulfide Chemical compound 0.000 description 24
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 9
- 239000002199 base oil Substances 0.000 description 8
- 239000012990 dithiocarbamate Substances 0.000 description 8
- 239000004519 grease Substances 0.000 description 7
- 239000004734 Polyphenylene sulfide Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229920000069 polyphenylene sulfide Polymers 0.000 description 6
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229920001903 high density polyethylene Polymers 0.000 description 3
- 239000004700 high-density polyethylene Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003495 polar organic solvent Substances 0.000 description 3
- 229910052979 sodium sulfide Inorganic materials 0.000 description 3
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical group [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101100436077 Caenorhabditis elegans asm-1 gene Proteins 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 101100204282 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) Asm-1 gene Proteins 0.000 description 2
- 241000605112 Scapanulus oweni Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- FPLIHVCWSXLMPX-UHFFFAOYSA-M lithium 12-hydroxystearate Chemical compound [Li+].CCCCCCC(O)CCCCCCCCCCC([O-])=O FPLIHVCWSXLMPX-UHFFFAOYSA-M 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- KHYKFSXXGRUKRE-UHFFFAOYSA-J molybdenum(4+) tetracarbamodithioate Chemical compound C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S KHYKFSXXGRUKRE-UHFFFAOYSA-J 0.000 description 2
- ZKZAYPCZGZAZAG-UHFFFAOYSA-J n,n-dibutylcarbamodithioate;molybdenum(4+) Chemical compound [Mo+4].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC ZKZAYPCZGZAZAG-UHFFFAOYSA-J 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- SSUBAQORPAUJGD-UHFFFAOYSA-N 1-methylpyrrolidin-2-one;pyrrolidin-2-one Chemical compound O=C1CCCN1.CN1CCCC1=O SSUBAQORPAUJGD-UHFFFAOYSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-hydroxyoctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- RJPKXYJWDKGKGW-UHFFFAOYSA-N dihexylcarbamodithioic acid Chemical compound CCCCCCN(C(S)=S)CCCCCC RJPKXYJWDKGKGW-UHFFFAOYSA-N 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000005078 molybdenum compound Substances 0.000 description 1
- 150000002752 molybdenum compounds Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M5/00—Solid or semi-solid compositions containing as the essential lubricating ingredient mineral lubricating oils or fatty oils and their use
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/04—Elements
- C10M2201/041—Carbon; Graphite; Carbon black
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/10—Compounds containing silicon
- C10M2201/105—Silica
-
- 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
-
- 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
- C10M2205/022—Ethene
-
- 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
- C10M2205/14—Synthetic waxes, e.g. polythene waxes
-
- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty 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
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/066—Thiocarbamic type compounds
- C10M2219/068—Thiocarbamate metal salts
-
- 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
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only 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
- 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
- C10M2229/02—Unspecified siloxanes; Silicones
-
- 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
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/06—Groups 3 or 13
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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—Semi-solids; greasy
Definitions
- This invention relates to lubricating compositions. In one of its aspects, it relates to a lubricating composition comprising a minor amount of a metal dithiocarbamate and a polymerof arylene sulfide. In another of its aspects, the invention relates to a method for improving the lubricating qualities of a natural or synthetic base oil by adding thereto a derivative of a dithiocarbamic acid and a polymer of arylene sulfide. In a further aspect of this invention, the arylene sulfide polymers used are prepared by reacting at least one polyhalo-substituted aromatic compound with an alkali metal sulfide in a polar organic solvent. In a still further aspect of the invention the metallic derivative of dithiocarbamic acid is a molybdenum dithiocarbamate.
- the properties of a lubricant can be improved by adding a minor amount of a metal dithiocarbamate and a polymer of arylene sulfide. It has been found that lubricants containing .01 to weight percent of a metal dithiocarbamate and .1 to 50 weight percent of arylene sulfide polymers synergis' tically exhibit improved lubricating properties particularly when formulated into greases used to reduce wear on metallic surfaces.
- dithiocarbamate compounds which are applicable 3,248,325 Patented Apr. 26, 1966 for use in this invention are those which correspond to the following general formula:
- R can be hydrogen or alkyl, cycloalkyl, aryl, aralkyl, or alkaryl radicals having up to 20 carbon atoms and Me can be molybdenum, Zinc, lead, cadmium, magnesium, tin, aluminum, and iron, and n is the valence of Me.
- Molybdenum dithiocarbamate Molybdenum dimethyldithiocarbamate Molybdenum di-n-butyldithiocarbamate Molybdenum di-n-dodecyldithiocarbamate Molybdenum dibenzyldithiocarbamate Molybdenum di(4-tert-butylphenyl)dithiocarbamate Zinc diphenyldithiocarbamate Zinc methylethyldithiocarbamate Zinc di-sec-amyldithiocarbamate Lead di-n-eicosyldit-hiocarbamate Lead dicyclohexyldithiocarbamate Cadmium diethyldithiocarbamate Magnesium methylphenyldithiocarbamate Tin di-sec-butyldithiocarbamate Aluminum -di(2-ethylhexyl)dithiocarbamate Iron
- the reaction is preferably carried out in a reaction medium comprising a polar organic compound which is a solvent for the reactants and which is stable at the reaction conditions.
- N-methylpyrrolidone is a preferred reaction medium.
- the arylene sulfide polymers used in this invention are not the subject of this application per se as they are claimed elsewhere.
- polyhalo-substitutedaromatic compounds which can be employed as primary reactants for the preparation of the arylene sulfide polymer are represented by the formulas:
- the compounds of the above general formulas which are preferred are those which contain not more than three halogen atoms and preferably are dihalo-substituted compounds.
- Some specific examples of the polyhalo-substituted compounds of the above general formulas which can be used in preparing the poly(arylene sulfide) component of the present invention are:
- the alkali metal sulfide reactants for the polymer formation are the monosulfides of sodium, potassium, lithium, rubidium, and cesium.
- the preferred sulfide reactant is sodium sulfide and its hydrates.
- Polar organic solvents applicable as the medium in which the metal sulfide reacts with the polyhalo-substuted compound to form the polymer component of the inventive composition include the classes of amides, lactams, sulfones, and the like. Some examples are:
- lubricating compositions may comprise a mineral oil base such as conventionally refined crude oil lubricating stocks having viscosities in the range of 50-1500 SUS (100 F.).
- synthetic base oils may also be used. These latter include polymerized olefins, copolymers of alkylene glycols and oxides, organic esters of polybasic organic and inorganic acids, silicone polymers and the like.
- the additives of the present invention have particular application in grease compositions which comprise suitably refined mineral oils thickened by at least one agent such as metallic soaps, high molecular weight olefin polymers, carbon black, finely divided silica and the like.
- a metal dithiocarbamate and an arylene sulfide polymer in the lubricating compositions can vary over a wide range; the amount of metal dithiocarbamate compound can be in the range of about 0.01 to about weight percent, preferably about 0.1 to 4 percent, and the arylene sulfide polymer can be in the range of from about 0.1 to about 50 weight percent, preferably about 0.5 to 10 percent, based on the total lubricant composition.
- a particularly effective ratio of dithiocarbamate to polymer is 1:1.
- the remainder of the lubricant composition can comprise the aforementioned base oils and various other conventional additives such as those normally used as thickeners, antioxidants, VI improvers, pour point depressants, corrosion inhibitors, demulsifie'rs, detergents, foam inhibitors, and the like.
- the lubricant compositions of the present invention are prepared by using conventional techniques.
- the base oils and other ingredients, including the additives of this invention are brought together in a mixing vessel.
- the solid ingredients should be in a fine state of subdivision.
- With constant agitation the mixture is heated and blended at temperatures ranging from to 500 F. for a period of time sufiicient to attain maximum homogeneity and effectiveness.
- the blend is then cooled to room temperature.
- the invention can be further illustrated by the following example.
- Example 1 The invention additives were tested in a commercial grease composition (Philube ASM) which consisted of one Weight percent high density polyethylene, 9 weight percent lithium 12-hydroxystearate, with the remainder being a 500 SUS (100 F.) conventionally refined neutral oil having a viscosity index of 89. To this base grease were added minor quantities of polyphenylene sulfide (FPS) and a molybdenum dibutyldithiocarbamate (Vanderbilt OD 623). The resulting composition was subjected to a wear test in a Shell 4 ball tester.
- PARASM commercial grease composition
- FPS polyphenylene sulfide
- Vanderbilt OD 623 molybdenum dibutyldithiocarbamate
- the polyphenylene sulfide was prepared by charging a solution of 1 g. mole of sodium sulfide in 1 liter N-methylpyrrolidone (previously dried'by heating at 190 C. in flowing nitrogen) into a 316 SS rocker-bomb together with 1 g. mole p-dichlorobenzene.
- the bomb and contents were brought to a temperature of 565 F. in about three hours and then maintained at 560570 F. and at a pressure of about 200 p.s.i.g. for three more hours.
- the bomb was then cooled, the contents filtered, and the finely divided solid washed repeatedly and alternately with water and methanol. The solid was finally dried at C. under vacuum.
- the powdery material had a melting point of 280 C. and an ash content of 0.32 weight percent. Elemental analysis showed 0.71 percent Cl, 28.6 percent S, 3.9 percent H, and 66.5 percent C.
- the Shell 4 ball tester is a conventional grease testing device (Precision Scientific Catalog No. 75015) wherein three /2" diameter (52100 steel) balls are fixedly mounted in a cup filled with the test grease (about 10 ml.). A fourth ball is mounted on a rotatable spindle in a position contacting the three fixed balls. The fourth ball is then rotated at 1800 r.p.m. for one minute under a load of 80 kg. After this period the wear on the three fixed balls is microscopically measured, averaged, and reported in terms of microns wear.
- p is a whole integer selected from the group consisting of 0 and 1; and a mineral oil having a viscosity in the range of -l500 SUS F.).
- a lubricating composition consisting essentially of a refined neutral oil containing about one weight percent high density polyethylene, 9 weight percent lithium l 2-hydroxystearate having a viscosity index of 89, 0.5 weight percent of a polymer prepared by reacting p-dichlorobenzene with sodium sulfide in N-methylpyrrolidone, and 0.5 Weight percent molybdenum dibutyldithiocarbamate.
- a lubricating composition consisting essentially of a refined neutral oil containing about one Weight percent high density polyethylene, 9 weight percent lithium 12- hydroxystearate having a viscosity index of 89, 0.5 weight percent of a polymer prepared by reacting an aromatic halide with an alkali metal sulfide in a polar organic solvent, and 0.5 weight percent of molybdenum dithiocarbamate.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
United States Patent 3,248,325 LUBRICATING COMPOSITION John P. Graham, South Plainfield, N..I., assignor to Phillips Petroleum Company, a corporation of Delaware No Drawing. Filed Aug. 21, 1964, Ser. No. 391,328 5 (Jlaims. (Cl. 25233.6)
This invention relates to lubricating compositions. In one of its aspects, it relates to a lubricating composition comprising a minor amount of a metal dithiocarbamate and a polymerof arylene sulfide. In another of its aspects, the invention relates to a method for improving the lubricating qualities of a natural or synthetic base oil by adding thereto a derivative of a dithiocarbamic acid and a polymer of arylene sulfide. In a further aspect of this invention, the arylene sulfide polymers used are prepared by reacting at least one polyhalo-substituted aromatic compound with an alkali metal sulfide in a polar organic solvent. In a still further aspect of the invention the metallic derivative of dithiocarbamic acid is a molybdenum dithiocarbamate.
Expansion of science and technology has brought new demands on industry for development of lubricants with improved properties. In this space age, for example, it is required that metallic parts coact with one another for extended periods of time under various and sundry conditions of temperature, pressure, and atmosphere. Further, new products require parts to function with minimum wear for extended periods of time without servicing. The automobile industry, for example, has extended the time between servicing of automobiles. Various new lubricants have been developed for these purposes. Some new lubricants generally are produced by adding organic or organometallic compounds to various base oils.-
I have now discovered that a composition with unexpected excellent lubricating properties results when minor amounts of a metal dithiocarbamate and a polymer of arylene sulfide are added to a lubricant base. The wear which results from using the combination of the dithiocarbamate and the arylene sulfide polymer is less than that which results from either of these compounds used singularly.
It is an object of this invention to provide a lubricating composition. It is a further object of this invention to improve the lubricating qualities of natural and synthetic base oils. It is a further object of this invention to provide a combination of additives for a lubricating base oil which operate in an unexpectedly beneficial manner. It is a further object of this invention to provide a composition which will decrease the wear on bearing surfaces.
Other aspects, objects, and the several advantages of this invention are apparent from the study of this disclosure and the appended claims.
According to the present invention, the properties of a lubricant can be improved by adding a minor amount of a metal dithiocarbamate and a polymer of arylene sulfide. It has been found that lubricants containing .01 to weight percent of a metal dithiocarbamate and .1 to 50 weight percent of arylene sulfide polymers synergis' tically exhibit improved lubricating properties particularly when formulated into greases used to reduce wear on metallic surfaces.
The dithiocarbamate compounds which are applicable 3,248,325 Patented Apr. 26, 1966 for use in this invention are those which correspond to the following general formula:
R wherein R can be hydrogen or alkyl, cycloalkyl, aryl, aralkyl, or alkaryl radicals having up to 20 carbon atoms and Me can be molybdenum, Zinc, lead, cadmium, magnesium, tin, aluminum, and iron, and n is the valence of Me. Some examples are:
Molybdenum dithiocarbamate Molybdenum dimethyldithiocarbamate Molybdenum di-n-butyldithiocarbamate Molybdenum di-n-dodecyldithiocarbamate Molybdenum dibenzyldithiocarbamate Molybdenum di(4-tert-butylphenyl)dithiocarbamate Zinc diphenyldithiocarbamate Zinc methylethyldithiocarbamate Zinc di-sec-amyldithiocarbamate Lead di-n-eicosyldit-hiocarbamate Lead dicyclohexyldithiocarbamate Cadmium diethyldithiocarbamate Magnesium methylphenyldithiocarbamate Tin di-sec-butyldithiocarbamate Aluminum -di(2-ethylhexyl)dithiocarbamate Iron di-n-hexyldithiocarbamate The arylene sulfide polymers which are applicable for use in this invention are those prepared by reacting at least one polyhalo-substituted aromatic compound with an alkali metal sulfide. The reaction is preferably carried out in a reaction medium comprising a polar organic compound which is a solvent for the reactants and which is stable at the reaction conditions. N-methylpyrrolidone is a preferred reaction medium. The arylene sulfide polymers used in this invention are not the subject of this application per se as they are claimed elsewhere.
The polyhalo-substitutedaromatic compounds which can be employed as primary reactants for the preparation of the arylene sulfide polymer are represented by the formulas:
(Y) Ill-cf (III) l ooh I (Ya-nip cot-t radicals and combinations of these containing from 1 to 12 carbon atoms, inclusive; n is an integer of 2 to 6, inclusive; b is an integer of 2 to 8, inclusive; 6 is an integer of 2 to 10, inclusive; e is an integer of 1 to 5, inclusive; g is an integer of O to 4, inclusive; and p is a whole integer selected from the group consisting of and 1.
The compounds of the above general formulas which are preferred are those which contain not more than three halogen atoms and preferably are dihalo-substituted compounds. Some specific examples of the polyhalo-substituted compounds of the above general formulas which can be used in preparing the poly(arylene sulfide) component of the present invention are:
1,2-dichlorobenzene 2,5 -dichlorotoluene 1,4-diiodobenzene 1,4-difluorobenzene 1,2,4,5-tetrabromobenzene 1-n-butyl-2,5-dichlorobenzene 1,4-dibromo-2,3,5,6-tetrafluorobenzene 4-chlorobromobenzene 1-cyclohexyl-2,5-diiodobenzene 1-n-dodecyl-2,5-dichlorobenzene 1,3 ,5-trichloro-2,4,6-triphenylbenzene 1,4-dichloro-7,S-diethylnaphthalene 1,4-dichloroanthracene 4,4'-dichlorobiphenyl 3,3,3"-trichloro-p-terphenyl and the like.
The alkali metal sulfide reactants for the polymer formation are the monosulfides of sodium, potassium, lithium, rubidium, and cesium. The preferred sulfide reactant is sodium sulfide and its hydrates.
Polar organic solvents applicable as the medium in which the metal sulfide reacts with the polyhalo-substuted compound to form the polymer component of the inventive composition include the classes of amides, lactams, sulfones, and the like. Some examples are:
N-methyl-2-pyrrolidone Pyrrolidone Caprolactam Tetramethylurea Sulfolane Dimethylacetamide Low molecular weight polyamides and the like.
The combination 'of the above described organometallic compounds and arylene sulfide polymers can be used with beneficial results in a variety of lubricating compositions. These lubricating compositions may comprise a mineral oil base such as conventionally refined crude oil lubricating stocks having viscosities in the range of 50-1500 SUS (100 F.). In addition to these natural base oils, synthetic base oils may also be used. These latter include polymerized olefins, copolymers of alkylene glycols and oxides, organic esters of polybasic organic and inorganic acids, silicone polymers and the like.
The additives of the present invention have particular application in grease compositions which comprise suitably refined mineral oils thickened by at least one agent such as metallic soaps, high molecular weight olefin polymers, carbon black, finely divided silica and the like.
The usage of a metal dithiocarbamate and an arylene sulfide polymer in the lubricating compositions can vary over a wide range; the amount of metal dithiocarbamate compound can be in the range of about 0.01 to about weight percent, preferably about 0.1 to 4 percent, and the arylene sulfide polymer can be in the range of from about 0.1 to about 50 weight percent, preferably about 0.5 to 10 percent, based on the total lubricant composition. A particularly effective ratio of dithiocarbamate to polymer is 1:1. The remainder of the lubricant composition can comprise the aforementioned base oils and various other conventional additives such as those normally used as thickeners, antioxidants, VI improvers, pour point depressants, corrosion inhibitors, demulsifie'rs, detergents, foam inhibitors, and the like.
The lubricant compositions of the present invention are prepared by using conventional techniques. For example, the base oils and other ingredients, including the additives of this invention, are brought together in a mixing vessel. For maximum convenience in mixing and subsequent lubricating effectiveness, the solid ingredients should be in a fine state of subdivision. With constant agitation the mixture is heated and blended at temperatures ranging from to 500 F. for a period of time sufiicient to attain maximum homogeneity and effectiveness. The blend is then cooled to room temperature.
The invention can be further illustrated by the following example.
Example The invention additives were tested in a commercial grease composition (Philube ASM) which consisted of one Weight percent high density polyethylene, 9 weight percent lithium 12-hydroxystearate, with the remainder being a 500 SUS (100 F.) conventionally refined neutral oil having a viscosity index of 89. To this base grease were added minor quantities of polyphenylene sulfide (FPS) and a molybdenum dibutyldithiocarbamate (Vanderbilt OD 623). The resulting composition was subjected to a wear test in a Shell 4 ball tester.
The polyphenylene sulfide (PPS) was prepared by charging a solution of 1 g. mole of sodium sulfide in 1 liter N-methylpyrrolidone (previously dried'by heating at 190 C. in flowing nitrogen) into a 316 SS rocker-bomb together with 1 g. mole p-dichlorobenzene. The bomb and contents were brought to a temperature of 565 F. in about three hours and then maintained at 560570 F. and at a pressure of about 200 p.s.i.g. for three more hours. The bomb was then cooled, the contents filtered, and the finely divided solid washed repeatedly and alternately with water and methanol. The solid was finally dried at C. under vacuum. Four additional runs were carried out in an essentially identical manner and the finished products were blended. The powdery material had a melting point of 280 C. and an ash content of 0.32 weight percent. Elemental analysis showed 0.71 percent Cl, 28.6 percent S, 3.9 percent H, and 66.5 percent C.
The Shell 4 ball tester is a conventional grease testing device (Precision Scientific Catalog No. 75015) wherein three /2" diameter (52100 steel) balls are fixedly mounted in a cup filled with the test grease (about 10 ml.). A fourth ball is mounted on a rotatable spindle in a position contacting the three fixed balls. The fourth ball is then rotated at 1800 r.p.m. for one minute under a load of 80 kg. After this period the wear on the three fixed balls is microscopically measured, averaged, and reported in terms of microns wear.
The results of the testing are seen in the table below. Prior to evaluation, the additives and the base grease were blended for 30 minutes in a Hobart mixer.
Grease: Shell 4-ball wear, microns Philube ASM 2200 Philube ASM 1 wt. percent OD 623 (molybdenum compound) 1860 Philube ASM 1 wt. percent PPS (polyphenylene sulfide) 1500 Philube ASM 0.5 wt. percent OD 623 and 0.5
wt. percent PPS 1040 It can be seen from the above data that less wear occurred when using a combination of the two ingredients than the addition effect of that which occurred when either ingredient was used singularly.
Reasonable variation and modification are possible within the scope of the foregoing disclosure and the appended swig (X) n 8+ b (Y) 10-0 K/ (X) (III) e (X) e -e 4-1 D )5-e wherein each X is a halogen selected from the group consisting of chlorine, bromine, iodine, and fluorine; each Y is selected from the group consisting of hydrogen, and alkyl, cycloalkyl, anyl radicals and combinations of these containing from 1 to 12 carbon atoms, inclusive; n is an integer of 2 to 6, inclusive; [2 is an integer of 2 to 8, inclusive; c is an integer of 2 to 10, inclusive; e is an integer of 1 to 5, inclusive; 3 is an integer of 0 to 4,
inclusive; and p is a whole integer selected from the group consisting of 0 and 1; and a mineral oil having a viscosity in the range of -l500 SUS F.).
2. A lubricating composition consisting essentially of a refined neutral oil containing about one weight percent high density polyethylene, 9 weight percent lithium l 2-hydroxystearate having a viscosity index of 89, 0.5 weight percent of a polymer prepared by reacting p-dichlorobenzene with sodium sulfide in N-methylpyrrolidone, and 0.5 Weight percent molybdenum dibutyldithiocarbamate.
3. A lubricating composition consisting essentially of a refined neutral oil containing about one Weight percent high density polyethylene, 9 weight percent lithium 12- hydroxystearate having a viscosity index of 89, 0.5 weight percent of a polymer prepared by reacting an aromatic halide with an alkali metal sulfide in a polar organic solvent, and 0.5 weight percent of molybdenum dithiocarbamate. I
4. A lubricating composition according to claim 1 wherein the ratio of said arylene sulfide polymer to said molybdenum d ithiocarbarnate is 1:1.
5. A lubricating composition according to claim 1 wherein the weight percentage of said arylene sulfide polymer is 0.5 and the Weight percentage of said molybdenum dithiocanbamate is 0.5 based on the weight of lubricant.
References Cited by the Examiner UNITED STATES PATENTS 2,921,902 1/1960 Watson 252--33.6 3,098,103 7/ 1-963 Reifsohneider 252-45 X 3,133,020 5/1964 Scott 252-335 3,139,405 6/ 1964 Farmer et al 25233.6
DANIEL E. WYMAN, Primary Examiner.
Claims (1)
1. A LUBRICANT COMPOSITION COMPRISING .01 TO 10 WEIGHT PERCENT MOLYBEDENUM DIFTHIOCARBAMATE, 0.1 TO 50 WEIGHT PERCENT ARYLENE SULFIDE POLYMER PREPARED BY REACTING AN ALKALI METAL SUFLIDE WITH A POLYHALO-SUBSTITUTED AROMATIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF COMPOUNDS OF FORMULAS:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US391328A US3248325A (en) | 1964-08-21 | 1964-08-21 | Lubricating composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US391328A US3248325A (en) | 1964-08-21 | 1964-08-21 | Lubricating composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3248325A true US3248325A (en) | 1966-04-26 |
Family
ID=23546166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US391328A Expired - Lifetime US3248325A (en) | 1964-08-21 | 1964-08-21 | Lubricating composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3248325A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3354129A (en) * | 1963-11-27 | 1967-11-21 | Phillips Petroleum Co | Production of polymers from aromatic compounds |
| US3380951A (en) * | 1965-06-29 | 1968-04-30 | Phillips Petroleum Co | Solutions of poly |
| US3396110A (en) * | 1964-11-30 | 1968-08-06 | Phillips Petroleum Co | Lubricant comprising sulfurcontaining polymer |
| US3432468A (en) * | 1966-03-28 | 1969-03-11 | Inventa Ag | Heat-resistant polythioethers and method for their production |
| US3458486A (en) * | 1964-09-04 | 1969-07-29 | Phillips Petroleum Co | Production of polymers from cyclic compounds |
| US3478000A (en) * | 1967-11-20 | 1969-11-11 | Phillips Petroleum Co | Recovery of poly(arylene sulfides) |
| US3658659A (en) * | 1969-09-24 | 1972-04-25 | Phillips Petroleum Co | Separating p-dichlorobenzene from n-methyl pyrrolidone by steam distillation |
| US4115344A (en) * | 1977-07-05 | 1978-09-19 | Phillips Petroleum Company | Mold corrosion inhibition in poly(arylene) sulfide processing |
| US4178258A (en) * | 1978-05-18 | 1979-12-11 | Edwin Cooper, Inc. | Lubricating oil composition |
| US4931516A (en) * | 1986-08-04 | 1990-06-05 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for producing polyarylene sulfide in titanium vessel with addition of water |
| WO1991013955A1 (en) * | 1990-03-07 | 1991-09-19 | Exxon Research And Engineering Company | Lubricating grease composition |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2921902A (en) * | 1957-06-03 | 1960-01-19 | Texaco Inc | Lubricating composition containing a synergistic extreme pressure additive |
| US3098103A (en) * | 1962-06-27 | 1963-07-16 | Dow Chemical Co | Purely para thioether polymers |
| US3133020A (en) * | 1960-11-21 | 1964-05-12 | Continental Oil Co | Extreme pressure lubricants |
| US3139405A (en) * | 1961-05-29 | 1964-06-30 | Vanderbilt Co R T | Extreme pressure lubricants |
-
1964
- 1964-08-21 US US391328A patent/US3248325A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2921902A (en) * | 1957-06-03 | 1960-01-19 | Texaco Inc | Lubricating composition containing a synergistic extreme pressure additive |
| US3133020A (en) * | 1960-11-21 | 1964-05-12 | Continental Oil Co | Extreme pressure lubricants |
| US3139405A (en) * | 1961-05-29 | 1964-06-30 | Vanderbilt Co R T | Extreme pressure lubricants |
| US3098103A (en) * | 1962-06-27 | 1963-07-16 | Dow Chemical Co | Purely para thioether polymers |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3354129A (en) * | 1963-11-27 | 1967-11-21 | Phillips Petroleum Co | Production of polymers from aromatic compounds |
| US3458486A (en) * | 1964-09-04 | 1969-07-29 | Phillips Petroleum Co | Production of polymers from cyclic compounds |
| US3396110A (en) * | 1964-11-30 | 1968-08-06 | Phillips Petroleum Co | Lubricant comprising sulfurcontaining polymer |
| US3380951A (en) * | 1965-06-29 | 1968-04-30 | Phillips Petroleum Co | Solutions of poly |
| US3432468A (en) * | 1966-03-28 | 1969-03-11 | Inventa Ag | Heat-resistant polythioethers and method for their production |
| US3478000A (en) * | 1967-11-20 | 1969-11-11 | Phillips Petroleum Co | Recovery of poly(arylene sulfides) |
| US3658659A (en) * | 1969-09-24 | 1972-04-25 | Phillips Petroleum Co | Separating p-dichlorobenzene from n-methyl pyrrolidone by steam distillation |
| US4115344A (en) * | 1977-07-05 | 1978-09-19 | Phillips Petroleum Company | Mold corrosion inhibition in poly(arylene) sulfide processing |
| US4178258A (en) * | 1978-05-18 | 1979-12-11 | Edwin Cooper, Inc. | Lubricating oil composition |
| US4931516A (en) * | 1986-08-04 | 1990-06-05 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for producing polyarylene sulfide in titanium vessel with addition of water |
| WO1991013955A1 (en) * | 1990-03-07 | 1991-09-19 | Exxon Research And Engineering Company | Lubricating grease composition |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3248325A (en) | Lubricating composition | |
| US3873454A (en) | Lubricant composition | |
| US3450770A (en) | Polyphenyl thioethers | |
| US3759827A (en) | Lubricant compositions | |
| US3396110A (en) | Lubricant comprising sulfurcontaining polymer | |
| US4517103A (en) | Lubricating compositions containing 5,5'-dithiobis(1,3,4-thiadiazole-2-thiol) | |
| US2653910A (en) | Extreme pressure lubricants | |
| US2962443A (en) | Steam turbine lubricant | |
| US4305831A (en) | Lubricant compositions | |
| US3285850A (en) | Solid film lubricants | |
| US3630897A (en) | Color stabilization of lubricating compositions | |
| US2467147A (en) | Low-temperature lubricant | |
| US3063943A (en) | Lubricant compositions | |
| JPH1121579A (en) | Lubricant for maintenance-free joint shaft | |
| JPH0328299A (en) | Urea grease composition | |
| US3793197A (en) | Lubricating grease composition | |
| US3278432A (en) | Extreme pressure lubricants containing sulfur | |
| US3384588A (en) | Lubricants containing p-polyphenyl | |
| US2852466A (en) | Grease compositions wherein the thickener comprises a metal salt of an nu-acylaminoorganocarboxylic acid | |
| US2734031A (en) | Lubricants containing polymers of | |
| US3926820A (en) | Grease compositions | |
| US3232872A (en) | Greases | |
| US3226323A (en) | Lubricant composition containing a haloalkanoic compound | |
| US3305484A (en) | Organic material stabilized with 3, 5-ditert-butyl-4-hydroxybenzoic acid | |
| US3793198A (en) | Lubricating and metal coating wax composition |