US2971915A - Lubricating oil compositions - Google Patents
Lubricating oil compositions Download PDFInfo
- Publication number
- US2971915A US2971915A US639237A US63923757A US2971915A US 2971915 A US2971915 A US 2971915A US 639237 A US639237 A US 639237A US 63923757 A US63923757 A US 63923757A US 2971915 A US2971915 A US 2971915A
- Authority
- US
- United States
- Prior art keywords
- acid
- oil
- composition
- lubricating oil
- methyl
- 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 42
- 239000010687 lubricating oil Substances 0.000 title claims description 12
- 150000002430 hydrocarbons Chemical group 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 description 23
- 239000003921 oil Substances 0.000 description 18
- 230000001050 lubricating effect Effects 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 150000007513 acids Chemical class 0.000 description 11
- 239000010688 mineral lubricating oil Substances 0.000 description 11
- 239000002480 mineral oil Substances 0.000 description 9
- 235000010446 mineral oil Nutrition 0.000 description 9
- -1 aliphatic dicarboxylic acids Chemical class 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000314 lubricant Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- XBWDUMFGSLBSGJ-UHFFFAOYSA-N 2,3-dimethylhexanedioic acid Chemical compound OC(=O)C(C)C(C)CCC(O)=O XBWDUMFGSLBSGJ-UHFFFAOYSA-N 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 3
- GAYWCADKXYCKCG-UHFFFAOYSA-N 5-pyridin-3-yl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1NC(=S)N=C1C1=CC=CN=C1 GAYWCADKXYCKCG-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000004435 Oxo alcohol Substances 0.000 description 3
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 3
- SYEOWUNSTUDKGM-UHFFFAOYSA-N beta-methyladipic acid Natural products OC(=O)CC(C)CCC(O)=O SYEOWUNSTUDKGM-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 3
- DWFUTNJGNBYHNN-UHFFFAOYSA-N 2,2,4-trimethylhexanedioic acid Chemical compound OC(=O)CC(C)CC(C)(C)C(O)=O DWFUTNJGNBYHNN-UHFFFAOYSA-N 0.000 description 2
- BTUDGPVTCYNYLK-UHFFFAOYSA-N 2,2-dimethylglutaric acid Chemical compound OC(=O)C(C)(C)CCC(O)=O BTUDGPVTCYNYLK-UHFFFAOYSA-N 0.000 description 2
- OEEUPULXQBRPEO-UHFFFAOYSA-N 2,4-Dimethyladipic acid Chemical compound OC(=O)CC(C)CC(C)C(O)=O OEEUPULXQBRPEO-UHFFFAOYSA-N 0.000 description 2
- ANUFAWHRSIJTHW-UHFFFAOYSA-N 2-methylheptanedioic acid Chemical compound OC(=O)C(C)CCCCC(O)=O ANUFAWHRSIJTHW-UHFFFAOYSA-N 0.000 description 2
- IVHJLPSVSILQFQ-UHFFFAOYSA-N 3-ethylhexanedioic acid Chemical compound OC(=O)CC(CC)CCC(O)=O IVHJLPSVSILQFQ-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N Heptanedioic acid Natural products OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N Suberic acid Natural products OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002895 organic esters Chemical class 0.000 description 2
- 150000003047 pimelic acids Chemical class 0.000 description 2
- 150000003442 suberic acids Chemical class 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 2
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
- WVUYYXUATWMVIT-UHFFFAOYSA-N 1-bromo-4-ethoxybenzene Chemical compound CCOC1=CC=C(Br)C=C1 WVUYYXUATWMVIT-UHFFFAOYSA-N 0.000 description 1
- NVRRUKJGVIPBEN-UHFFFAOYSA-N 10,10-dimethylundecan-1-ol Chemical compound CC(C)(C)CCCCCCCCCO NVRRUKJGVIPBEN-UHFFFAOYSA-N 0.000 description 1
- BTBHFYIGOCRXQF-UHFFFAOYSA-N 2,2,4-trimethyloctanedioic acid Chemical compound CC(C(=O)O)(CC(CCCC(=O)O)C)C BTBHFYIGOCRXQF-UHFFFAOYSA-N 0.000 description 1
- KEXGXAGJHHCTKD-UHFFFAOYSA-N 2,2-dimethyl-1-Octanol Chemical compound CCCCCCC(C)(C)CO KEXGXAGJHHCTKD-UHFFFAOYSA-N 0.000 description 1
- BTVZFIIHBJWMOG-UHFFFAOYSA-N 2,2-dimethylhexanedioic acid Chemical compound OC(=O)C(C)(C)CCCC(O)=O BTVZFIIHBJWMOG-UHFFFAOYSA-N 0.000 description 1
- UNPIHSQBNRKJBY-UHFFFAOYSA-N 2,3,4-trimethylhexanedioic acid Chemical compound OC(=O)CC(C)C(C)C(C)C(O)=O UNPIHSQBNRKJBY-UHFFFAOYSA-N 0.000 description 1
- LQNGULJVMSGMOE-UHFFFAOYSA-N 2,3-dimethylpentanedioic acid Chemical compound OC(=O)CC(C)C(C)C(O)=O LQNGULJVMSGMOE-UHFFFAOYSA-N 0.000 description 1
- LASHFHLFDRTERB-UHFFFAOYSA-N 2-propylpentan-1-ol Chemical compound CCCC(CO)CCC LASHFHLFDRTERB-UHFFFAOYSA-N 0.000 description 1
- DUHQIGLHYXLKAE-UHFFFAOYSA-N 3,3-dimethylglutaric acid Chemical compound OC(=O)CC(C)(C)CC(O)=O DUHQIGLHYXLKAE-UHFFFAOYSA-N 0.000 description 1
- HFJYFTGXXSIVNL-UHFFFAOYSA-N 3,3-dimethylhexanedioic acid Chemical compound OC(=O)CC(C)(C)CCC(O)=O HFJYFTGXXSIVNL-UHFFFAOYSA-N 0.000 description 1
- WDBZEBXYXWWDPJ-UHFFFAOYSA-N 3-(2-methylphenoxy)propanoic acid Chemical compound CC1=CC=CC=C1OCCC(O)=O WDBZEBXYXWWDPJ-UHFFFAOYSA-N 0.000 description 1
- NXDCNRPLRGMKHU-UHFFFAOYSA-N 3-Methylpimelic acid Chemical compound OC(=O)CC(C)CCCC(O)=O NXDCNRPLRGMKHU-UHFFFAOYSA-N 0.000 description 1
- QIOYMVALOOEDDF-UHFFFAOYSA-N 3-Methylsuberic acid Chemical compound OC(=O)CC(C)CCCCC(O)=O QIOYMVALOOEDDF-UHFFFAOYSA-N 0.000 description 1
- VDAVARPTDLMJIC-UHFFFAOYSA-N 3-ethylpentanedioic acid Chemical compound OC(=O)CC(CC)CC(O)=O VDAVARPTDLMJIC-UHFFFAOYSA-N 0.000 description 1
- MHJIVMDBOGBUHH-UHFFFAOYSA-N 3-propylhexan-1-ol Chemical compound CCCC(CCC)CCO MHJIVMDBOGBUHH-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 229940105305 carbon monoxide Drugs 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 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
- 150000002009 diols Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005530 etching Methods 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
- 238000011156 evaluation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000002311 glutaric acids Chemical class 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000010699 lard oil Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001993 wax 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
-
- 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/26—Carboxylic acids; Salts thereof
- C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M129/30—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms
- C10M129/34—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms polycarboxylic
-
- 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/26—Carboxylic acids; Salts thereof
- C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
- C10M129/42—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms polycarboxylic
-
- 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
- C10M2203/02—Well-defined aliphatic compounds
-
- 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
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/022—Well-defined aliphatic compounds saturated
-
- 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
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/024—Well-defined aliphatic compounds unsaturated
-
- 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
- C10M2203/04—Well-defined cycloaliphatic compounds
-
- 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
- C10M2203/06—Well-defined aromatic compounds
-
- 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
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
-
- 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
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl 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
- 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
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
-
- 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
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
-
- 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
- C10M2207/22—Acids obtained from polymerised unsaturated 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
- C10M2207/282—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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
-
- 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
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/402—Castor oils
-
- 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
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
-
- 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
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two 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
- C10M2209/105—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
- C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
-
- 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
- C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
-
- 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
Definitions
- the aliphatic dicarboxylic acids have the formula HOOCC H R COOH, wherein R is an alkyl radical of from 1 to 4 carbon atoms, n is an integer of from 3 to 6, m is an integer of from 1 to 6 inclusive, and the total number of carbonatoms in all Rs is from 1 to 6.
- the dibasic acids are C -alkyl substituted glutaric, adipic, pimelic or suberic acids, wherein the two acid groups are separated by a chain of from 3 to 6 carbon atoms.
- One or more of the connecting carbon atoms is substituted with alkyl, preferably methyl, radicals to a total of from 1 to 6 carbon atoms in all alkyl radicals in a given molecule, preferably no more than three.
- the acid groups must be separated by a chain of three to six carbon atoms to provide the superior extreme pressure properties and in addition the separating alkylene radical --C (H- R must contain at least one side-chain alkyl radical (R) in order to provide the minimum required oil solubility while not unduly adversely affecting the extreme pressure properties of the dibasic acid.
- Dibasic acids in which the acid groups are separated by less than three carbon atoms, such as succinic acid, or by more than six carbon atoms, such as sebasic acid have been found to be poor extreme pressure agents,
- the useful dibasic acids in general are marginally oilsoluble. However, they should be soluble in oil to the extent of at least about 0.5% by weight, better at least 1% by weight, but not over about 10% by weight and preferably not over about 5% by weight.
- the solubility of the acids in the oil can be increased by providing oilsoluble branched-chain aliphatic alcohols, in the oil as a solubilizing agent. These alcohols efiectively solubilize the dibasic acids of lower oil-solubility while the acids retain their extreme pressure properties in the oil.
- the dibasic acids are represented by such substances as the 2-; 2,2-, 2,3-, 3-, 3,3-, 4-, 4,4-, 2,4-, 2,5-, 2,3,4-, 2,3,5-, mono, di, and tri, methyl or ethyl or 2-, or 3-, monobutyl glutaric adipic, pimelic or suberic r 1C3 I acids.
- Preferred acids are 2-methyl glutaric acid, 2- 'methyl adipic acid, Z-methyl pimelic acid, Z-methyl suberic acid, 3-methyl glutaric acid, 3-methyl adipic acid, 3-methyl pimelic acid, 3-methyl suberic acid, 2,2-dimethyl glutaric acid, 2,2-dimethyl adipic acid, 2,3-dimethyl glutaric acid, 2,3-dimethyl adipic acid, 3,3-dimethyl adipic acid, 2,4-dimethyl adipic acid, 2,2,4-trimethyl adipic acid, 2,3,4-trimethyl adipic acid, 2,2,4-trimethyl suberic acid, 3-ethyl glutaric acid, 2-methyl, 3-ethyl adipic acid, 2- methyl-4-butyl suberic acid and mixturesthereof.
- alkanols efiectively solubilize the dibasic acids so that amounts of as high as 10% by weight, basedflon the total oil compositions, can be dispersed in the o' Particularly useful alkanols for the purpose of solubilizing the dibasic acids, without interfering with their extreme pressure activity, are the so-called 0x0 alcohols derived from branched-chain olefin's, such as polymers of lower-alkenes of 3 to 5 carbon atoms, and copolymers of mixtures of such alkenes by catalyzed reaction with car bon monoxide and hydrogen in accordance with the conditions of the0xo process, as is well known in the art.
- the composition of a typical C -oxo-alcohol mixture derived from' a mixture of C olefins, produced by polymerization of a typical refinery cracked gas fraction of C -C hydrocarbons,- is given in Table I.
- alkanols include 6-methyl-lheptanol, 2-n-propyl-l-pentanol, 3-n-propyl-l-hexanol, 2,2-dimethyl-l-octanol, 10,10-dimethyl-l-undecanol, 3- isopropyl-l-hepanol and mixtures thereof.
- the lubricating oils used in compositions of this invention can be a variety of synthetic or natural hydrocarbon oils having a viscosity range of from 5W SUS at 100" F. to 250 SUS at 210 F. (SAE viscosity number ranging from SAE 50 to SAE
- the natural hydrocarbon oils can be obtained from parafiinie, naphthenic, asphaltic or mixed base crudes, and/or mixtures thereof.
- Synthetic oils include polymerized olefins, alkylated aromatics, isomerized waxes, copolymers of alkylene glycols and alkyleneoxide (Ucon fluids) which are described in US. Patents 2,425755, 2,425,845 and 2,774,733 such as Ucon 50HB170, Ucon 50HB660 or Ucon LB550X and which are copolymers of ethylene and 1,2-propylene oxides the mono and diols as well as their ether derivatives; organic esters of an aliphtic dibasic acid such as di-Z-ethyl hexyl sebacate or di-Z-ethyl hexyl adipate and the like.
- hydrocarbon oils may be blended with fixed oils such as castor oil, lard oil and the like and/or synthetic oils as mentioned or silicone polymers and the like.
- Typical oils of this type are petroleum motor oils (A) which is I paraflinic in character and (B) which is naphthenic in character having the following properties:
- Composition C is representative of invention wherein the base oils are identified hereinabove Composition C:
- composition D 3-methyl adipic acid
- Composition I creased the load capacity from 600 to 10,000 pounds per 3-methyl glutarrc acid 3 square inch
- the higher alkyl-homolog, 3-hexadecyladipic C Oxo alcohol 3 acid gave an increase of only 800 from 600 to 1400 2,6-ditert butyl-4 methyl phenol 0.1 pounds per square inch.
- the dicarboxylic acids of this invention are useful also for providing superior load carrying properties in lubricating oils which contain minor amounts of other agents which are non-reactive with the dicarboxylic acids, such as silicone anti-foaming agents, alkylphenol antioxidants, polyacrylate ester viscosity-index improvers, and the like.
- a lubricating oil composition comprising a major amount of lubricating oil and from about 0.1% to about 2% of an aliphatic dicarboxylic acid having the formula HOOCC H R COOH wherein R in the side chain of the hydrocarbon group C I-l ll and is an alkyl radical of from 1 to 4 carbon atoms, )1 is an integer of from 3 to 6, m is an integer of from 1 to 6 inclusive and the total number of carbon atoms in all Rs is from 1 to 6.
- lubricating composition of claim 1 wherein the lubricating oil is selected from the group consisting of a polyoxy alkylene diol and the mono and diethcrs thereof.
- a lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1% to about 2% of C -C alkyl substituted glutaric acid.
- a lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1 to about 2% of a C -C alkyl substituted pimelic acid.
- a lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1% to about 2% of a C -C alkyl substituted adipic acid.
- a lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1% to about 2% of a C -C alkyl substituted suberic acid.
- a lubricating composition comprising a major 6 amount of a mineral lubricating oil and from about 0.1% to about 2% of B-methyl glutaric acid.
- a lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1% to about 2% of 3,3-dimethyl glutaric acid.
- a lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1% to about 2% of S-methyl adipic acid.
- a lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1% to about 2% of 2,3-dimethyl adipic acid.
- a lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1% to about 2% of 2-methyl pimelic acid.
- the lubricating composition of claim 9 containing a minor amount of a branched-chain alkanol.
- the lubricating composition of claim 10 containing a minor amount of a branched-chain alkanol.
- the lubricating composition of claim 12 containing a minor amount of a branched-chain alkanol.
Description
United States Patent 18 Claims. (CL 252-5) This invention relates to lubricants, particularly those suitable for lubrication under severe operating conditions,
such as under extreme high speed and at high temperatures.
It is well known that the high pressure occurring in certain types of gears and bearings may cause rupture of lubricant films with consequent damage to the machinery. It has been shown that various base lubricants can be improved in their protective properties for rubbing surfaces by the addition of certain substances, socalled extreme pressure agents, so that excessive wear, scutfing and seizure which normally follow a break in the film lubricant, can be minimized or prevented.
It is known that certain compounds of metal-reactive elements, such as certain compounds of chlorine, sulfur and phosphorus, as well as certain other compounds, such as some compounds of lead, impart extreme pressure properties to various lubricants. Notable among the substances heretofore used are the lead soaps, phosphoric acid esters, free or bound sulfur and certain chlorinated organic compounds. A principal objection to many of these extreme pressure agents is their generally high reactivity with the metallic surface, causing etching, corrosion and discoloration of the metal surface. Another objection to chemically reactive extreme pressure agents is that they alter the original chemical nature of the contacting surface, which under certain conditions is undesirable. Additionally, because of the activity of agents of this type, they usually are depleted rapidly resulting in only a temporary solution to the problem of extreme pressure lubrication.
It has now been discovered that improved extreme pressure lubricants are provided by a suitable lubricating oil containing certain marginally oil-soluble aliphatic dicarboxylic acids. The aliphatic dicarboxylic acids have the formula HOOCC H R COOH, wherein R is an alkyl radical of from 1 to 4 carbon atoms, n is an integer of from 3 to 6, m is an integer of from 1 to 6 inclusive, and the total number of carbonatoms in all Rs is from 1 to 6. The dibasic acids are C -alkyl substituted glutaric, adipic, pimelic or suberic acids, wherein the two acid groups are separated by a chain of from 3 to 6 carbon atoms. One or more of the connecting carbon atoms is substituted with alkyl, preferably methyl, radicals to a total of from 1 to 6 carbon atoms in all alkyl radicals in a given molecule, preferably no more than three.
The acid groups must be separated by a chain of three to six carbon atoms to provide the superior extreme pressure properties and in addition the separating alkylene radical --C (H- R must contain at least one side-chain alkyl radical (R) in order to provide the minimum required oil solubility while not unduly adversely affecting the extreme pressure properties of the dibasic acid. Dibasic acids in which the acid groups are separated by less than three carbon atoms, such as succinic acid, or by more than six carbon atoms, such as sebasic acid, have been found to be poor extreme pressure agents,
2,971,915 Patented Feb. 14, 1961 even when one or more of the connecting carbon atoms is substituted with an alkyl radical of from 1 to 6 or more carbon atoms. r
The useful dibasic acids in general are marginally oilsoluble. However, they should be soluble in oil to the extent of at least about 0.5% by weight, better at least 1% by weight, but not over about 10% by weight and preferably not over about 5% by weight. The solubility of the acids in the oil can be increased by providing oilsoluble branched-chain aliphatic alcohols, in the oil as a solubilizing agent. These alcohols efiectively solubilize the dibasic acids of lower oil-solubility while the acids retain their extreme pressure properties in the oil.
More specifically, the dibasic acids are represented by such substances as the 2-; 2,2-, 2,3-, 3-, 3,3-, 4-, 4,4-, 2,4-, 2,5-, 2,3,4-, 2,3,5-, mono, di, and tri, methyl or ethyl or 2-, or 3-, monobutyl glutaric adipic, pimelic or suberic r 1C3 I acids. Preferred acids are 2-methyl glutaric acid, 2- 'methyl adipic acid, Z-methyl pimelic acid, Z-methyl suberic acid, 3-methyl glutaric acid, 3-methyl adipic acid, 3-methyl pimelic acid, 3-methyl suberic acid, 2,2-dimethyl glutaric acid, 2,2-dimethyl adipic acid, 2,3-dimethyl glutaric acid, 2,3-dimethyl adipic acid, 3,3-dimethyl adipic acid, 2,4-dimethyl adipic acid, 2,2,4-trimethyl adipic acid, 2,3,4-trimethyl adipic acid, 2,2,4-trimethyl suberic acid, 3-ethyl glutaric acid, 2-methyl, 3-ethyl adipic acid, 2- methyl-4-butyl suberic acid and mixturesthereof.
These extreme pressure agents are miscible in mineral lubricating oils at room or storage temperatures up to about 2% by weight. When it is desired to incorporate an amount of dibasic acid in the oil in excess of its oilsolubility at room temperature, a branched-chain alkanol is useful. These alkanols efiectively solubilize the dibasic acids so that amounts of as high as 10% by weight, basedflon the total oil compositions, can be dispersed in the o' Particularly useful alkanols for the purpose of solubilizing the dibasic acids, without interfering with their extreme pressure activity, are the so-called 0x0 alcohols derived from branched-chain olefin's, such as polymers of lower-alkenes of 3 to 5 carbon atoms, and copolymers of mixtures of such alkenes by catalyzed reaction with car bon monoxide and hydrogen in accordance with the conditions of the0xo process, as is well known in the art. The composition of a typical C -oxo-alcohol mixture derived from' a mixture of C olefins, produced by polymerization of a typical refinery cracked gas fraction of C -C hydrocarbons,- is given in Table I.
TABLE I Alcohol Percent, wt.
3,5-dl'nethyl hexa 29 t s-dlmethvl hexanol 25 3,4-dlnethvl herannl 17 B-methvl heptanol 3. m hnptnnnl 16 b-ethyl horannl 2. 3 6,5-di'nethvl haxanol 1. 4 aalkyl alk h 4. 3 other! 5. 0
Other examples of suitable alkanols include 6-methyl-lheptanol, 2-n-propyl-l-pentanol, 3-n-propyl-l-hexanol, 2,2-dimethyl-l-octanol, 10,10-dimethyl-l-undecanol, 3- isopropyl-l-hepanol and mixtures thereof.
The lubricating oils used in compositions of this invention can be a variety of synthetic or natural hydrocarbon oils having a viscosity range of from 5W SUS at 100" F. to 250 SUS at 210 F. (SAE viscosity number ranging from SAE 50 to SAE The natural hydrocarbon oils can be obtained from parafiinie, naphthenic, asphaltic or mixed base crudes, and/or mixtures thereof.
3 Synthetic oils include polymerized olefins, alkylated aromatics, isomerized waxes, copolymers of alkylene glycols and alkyleneoxide (Ucon fluids) which are described in US. Patents 2,425755, 2,425,845 and 2,774,733 such as Ucon 50HB170, Ucon 50HB660 or Ucon LB550X and which are copolymers of ethylene and 1,2-propylene oxides the mono and diols as well as their ether derivatives; organic esters of an aliphtic dibasic acid such as di-Z-ethyl hexyl sebacate or di-Z-ethyl hexyl adipate and the like. The hydrocarbon oils may be blended with fixed oils such as castor oil, lard oil and the like and/or synthetic oils as mentioned or silicone polymers and the like. Typical oils of this type are petroleum motor oils (A) which is I paraflinic in character and (B) which is naphthenic in character having the following properties:
(SA 10W) (BAE 30) F -10 -5 1 i: 390 41s Viscosity, BUS at 210 F 44 58 Viscosity Index 90 G) Other suitable oils are the gas turbine lube oils having the following properties:
Grade 1010 1065 Flash, 000, F 300 Pour, F 10 Viscosity, SUS at 100 F- 59.4 Neutral Number 0. 02 0. 01 Ash None None Compositions A through 0 are representative of invention wherein the base oils are identified hereinabove Composition C:
garners Composition K. Percent wt. S-methyl adipic acid 2 Mineral oil (8) Balance Composition L:
3-ethyl adipic acid 2 C Oxo alcohol 3 Mineral oil (B) Balance Composition M:
2,3-dimethyl adipic acid 2 Ucon 501-18660 Balance Composition N:
2,3-dimethyl adipic acid 2 Ucon LB-SSOX Balance Composition 0:
2.3-dimethyl adipic acid 2 Di-2ethyl hexyl sebacate Balance Speed p m-- 3200 Oil temperature F... 100 Oil flow-rate cc./scc 10 Load in increments 5 min. at each setting.
Results of the evaluations are given in Table II; For purpose of comparison, the results obtained from the use of the base oil alone, and with other dicarboxylic acids, are also given in Table II.
TABLE II Spur gear machine test results Oompodtion 2,2-dimethyl glutaric acid 2 1010 mineral oil a ce Composition D:
3-methyl adipic acid 2 1010 mineral oil Balance Composition E: 1
2,4-dimethyl adipic acid 2 1.010 mineral .oil 3118 60 Composition/F:
2,2,4-trimethyl adipic acid 2 i358 1010 mineral oil Balance s m iner l 11am Composition ii'i 2-methyl pimelic acid 2 1010mm"! 600 C 0x0 alcohol 3 1010 mineral oil Balance thl'hus, the data show the outstanding enhancement of e load-carrying ability of the oil effected by the digf gggg acid 2 carboxylic acids of the invention, as represented by 1010 mineral oil Balance those of COmPOSIUOIIS A through 0. On the other hand,
r I malonic acid and succinic acid in which the two car- Composition 1: boxylic acid groups are separated by only one and two S-methyl glutaric acid 3 Carbon atoms, respectively, and C -alkenyl succinic acid C 0 l h l 3 in which oil-solubility is obtained by the C -hydrocar- 1010 mineral oil Balance bOn radical effected only a slight improvement. Also whereas 3-methyl adipic acid (Composition D) in- Composition I creased the load capacity from 600 to 10,000 pounds per 3-methyl glutarrc acid 3 square inch, the higher alkyl-homolog, 3-hexadecyladipic C Oxo alcohol 3 acid, gave an increase of only 800 from 600 to 1400 2,6-ditert butyl-4 methyl phenol 0.1 pounds per square inch. 1010 mineral oil Balance (a The dicarboxylic acids of this invention are useful also for providing superior load carrying properties in lubricating oils which contain minor amounts of other agents which are non-reactive with the dicarboxylic acids, such as silicone anti-foaming agents, alkylphenol antioxidants, polyacrylate ester viscosity-index improvers, and the like.
We claim as our invention:
1. A lubricating oil composition comprising a major amount of lubricating oil and from about 0.1% to about 2% of an aliphatic dicarboxylic acid having the formula HOOCC H R COOH wherein R in the side chain of the hydrocarbon group C I-l ll and is an alkyl radical of from 1 to 4 carbon atoms, )1 is an integer of from 3 to 6, m is an integer of from 1 to 6 inclusive and the total number of carbon atoms in all Rs is from 1 to 6.
2. The lubricating composition of claim 1 wherein the lubricating oil is a mineral lubricating oil.
3. The lubricating composition of claim 1 wherein the lubricating oil is selected from the group consisting of a polyoxy alkylene diol and the mono and diethcrs thereof.
4. The lubricating composition of claim 1 wherein the lubricating oil is an organic ester of an aliphatic dibasic acid.
5. A lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1% to about 2% of C -C alkyl substituted glutaric acid.
6. A lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1 to about 2% of a C -C alkyl substituted pimelic acid.
7. A lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1% to about 2% of a C -C alkyl substituted adipic acid.
8. A lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1% to about 2% of a C -C alkyl substituted suberic acid.
9. A lubricating composition comprising a major 6 amount of a mineral lubricating oil and from about 0.1% to about 2% of B-methyl glutaric acid.
10. A lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1% to about 2% of 3,3-dimethyl glutaric acid.
11. A lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1% to about 2% of S-methyl adipic acid.
12. A lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1% to about 2% of 2,3-dimethyl adipic acid.
13. A lubricating composition comprising a major amount of a mineral lubricating oil and from about 0.1% to about 2% of 2-methyl pimelic acid.
14. The lubricating composition of claim 9 containing a minor amount of a branched-chain alkanol.
15. The lubricating composition of claim 10 containing a minor amount of a branched-chain alkanol.
16. The lubricating composition of claim 11 containing a minor amount of a branched-chain alkanol.
17. The lubricating composition of claim 12 containing a minor amount of a branched-chain alkanol.
18. The lubricating composition of claim 13 containing therein a minor amount of a branched-chain alkanol.
References Cited in the file of this patent UNITED STATES PATENTS 2,133,734 Moser Oct. 18, 1938 2,158,096 Werntz May 16, 1939 2,334,158 Von Fuchs Nov. 9, 1943 2,402,825 Lovell et al June 25, 1946 2,452,319 Patterson et a1 Oct. 26, 1948 2,452,320 Kluge et a1. Oct. 26, 1948 2,459,717 Perry Jan. 18, 1949 2,548,493 Robey Apr. 10, 1951 2,788,326 Bondi et a1 Apr. 9, 1957
Claims (1)
1. A LUBRICATING OIL COMPOSITION COMPRISING A MAJOR AMOUNT OF LUBRICATING OIL AND FROM ABOUT 0.1% TO ABOUT 2% OF AN ALIPHATIC DICARBOXYLIC ACID HAVING THE FORMULA HOOCCNH2N-MRMCOOH WHEREIN R IN THE SIDE CHAIN OF THE HYDROCARBON GROUP CNH2N-MRM AND IS AN ALKYL RADICAL OF FROM 1 TO 4 CARBON ATOMS, N IS AN INTEGER OF FROM 3 TO 6, M IS AN INTEGER OF FROM 1 TO 6 INCLUSIVE AND THE TOTAL NUMBER OF CARBON ATOMS IN ALL R''S IS FROM 1 TO 6.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US639237A US2971915A (en) | 1957-02-11 | 1957-02-11 | Lubricating oil compositions |
GB4256/58A GB826102A (en) | 1957-02-11 | 1958-02-10 | Lubricating oil compositions |
FR1198787D FR1198787A (en) | 1957-02-11 | 1958-02-10 | Lubricating oil composition |
DEN14654A DE1063311B (en) | 1957-02-11 | 1958-02-10 | Lubricating oil |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US639237A US2971915A (en) | 1957-02-11 | 1957-02-11 | Lubricating oil compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
US2971915A true US2971915A (en) | 1961-02-14 |
Family
ID=24563282
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US639237A Expired - Lifetime US2971915A (en) | 1957-02-11 | 1957-02-11 | Lubricating oil compositions |
Country Status (4)
Country | Link |
---|---|
US (1) | US2971915A (en) |
DE (1) | DE1063311B (en) |
FR (1) | FR1198787A (en) |
GB (1) | GB826102A (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3223636A (en) * | 1961-05-23 | 1965-12-14 | Exxon Research Engineering Co | Lead corrosion inhibitor |
US3251774A (en) * | 1962-03-05 | 1966-05-17 | Standard Oil Co | Lubricant grease |
US3429817A (en) * | 1968-02-29 | 1969-02-25 | Exxon Research Engineering Co | Diester lubricity additives and oleophilic liquids containing the same |
DE2536119A1 (en) * | 1974-08-16 | 1976-03-04 | Beverolfabrieken | Anhydrous thermoforming agent and the process for its production |
US4414125A (en) * | 1979-12-01 | 1983-11-08 | Chemische Werke Huels Aktiengesellschaft | Alkali metal or amine salts of a mixture of 2- and 3-alkyladipic acids as corrosion inhibitors |
US4433163A (en) * | 1981-05-27 | 1984-02-21 | Lonza Ltd. | Process for the production of 3,3-dimethylglutaric acid or its esters |
US4511734A (en) * | 1981-05-12 | 1985-04-16 | Lonza Ltd. | Process for the production of 3,3-dimethylglutaric |
US4634795A (en) * | 1981-12-15 | 1987-01-06 | Epis S.A. | Long-chain α,ω-di-carboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
WO1989007638A1 (en) * | 1988-02-15 | 1989-08-24 | Nynäs Industri Ab | Method in the processing of aluminium and the use of certain acids in oils therefor |
US4908385A (en) * | 1986-10-08 | 1990-03-13 | Epis S.A. | α-halogenated dicarboxylic acids, pharmaceutical compositions and method of use |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE603401A (en) * | 1960-05-04 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2133734A (en) * | 1936-07-24 | 1938-10-18 | Shell Dev | Noncorrosive lubricating oil |
US2158096A (en) * | 1936-04-24 | 1939-05-16 | Du Pont | Lubricant |
US2334158A (en) * | 1941-09-29 | 1943-11-09 | Shell Dev | Rust-preventive composition |
US2402825A (en) * | 1943-06-23 | 1946-06-25 | Shell Dev | Method of preparing and purifying dicarboxylic acids |
US2452319A (en) * | 1943-12-08 | 1948-10-26 | Texas Co | Rust and oxidation inhibited lubricating compositions |
US2452320A (en) * | 1944-12-02 | 1948-10-26 | Texas Co | Oxidation-inhibited lubricating compositions |
US2459717A (en) * | 1946-01-23 | 1949-01-18 | Shell Dev | Organic lubricant composition |
US2548493A (en) * | 1948-08-03 | 1951-04-10 | Standard Oil Dev Co | Esters of trimethyladipic acid |
US2788326A (en) * | 1950-12-26 | 1957-04-09 | Shell Dev | Extreme pressure lubricant |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE465034A (en) * | 1941-02-18 |
-
1957
- 1957-02-11 US US639237A patent/US2971915A/en not_active Expired - Lifetime
-
1958
- 1958-02-10 DE DEN14654A patent/DE1063311B/en active Pending
- 1958-02-10 FR FR1198787D patent/FR1198787A/en not_active Expired
- 1958-02-10 GB GB4256/58A patent/GB826102A/en not_active Expired
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2158096A (en) * | 1936-04-24 | 1939-05-16 | Du Pont | Lubricant |
US2133734A (en) * | 1936-07-24 | 1938-10-18 | Shell Dev | Noncorrosive lubricating oil |
US2334158A (en) * | 1941-09-29 | 1943-11-09 | Shell Dev | Rust-preventive composition |
US2402825A (en) * | 1943-06-23 | 1946-06-25 | Shell Dev | Method of preparing and purifying dicarboxylic acids |
US2452319A (en) * | 1943-12-08 | 1948-10-26 | Texas Co | Rust and oxidation inhibited lubricating compositions |
US2452320A (en) * | 1944-12-02 | 1948-10-26 | Texas Co | Oxidation-inhibited lubricating compositions |
US2459717A (en) * | 1946-01-23 | 1949-01-18 | Shell Dev | Organic lubricant composition |
US2548493A (en) * | 1948-08-03 | 1951-04-10 | Standard Oil Dev Co | Esters of trimethyladipic acid |
US2788326A (en) * | 1950-12-26 | 1957-04-09 | Shell Dev | Extreme pressure lubricant |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3223636A (en) * | 1961-05-23 | 1965-12-14 | Exxon Research Engineering Co | Lead corrosion inhibitor |
US3251774A (en) * | 1962-03-05 | 1966-05-17 | Standard Oil Co | Lubricant grease |
US3429817A (en) * | 1968-02-29 | 1969-02-25 | Exxon Research Engineering Co | Diester lubricity additives and oleophilic liquids containing the same |
DE2536119A1 (en) * | 1974-08-16 | 1976-03-04 | Beverolfabrieken | Anhydrous thermoforming agent and the process for its production |
US4414125A (en) * | 1979-12-01 | 1983-11-08 | Chemische Werke Huels Aktiengesellschaft | Alkali metal or amine salts of a mixture of 2- and 3-alkyladipic acids as corrosion inhibitors |
US4511734A (en) * | 1981-05-12 | 1985-04-16 | Lonza Ltd. | Process for the production of 3,3-dimethylglutaric |
US4433163A (en) * | 1981-05-27 | 1984-02-21 | Lonza Ltd. | Process for the production of 3,3-dimethylglutaric acid or its esters |
US4634795A (en) * | 1981-12-15 | 1987-01-06 | Epis S.A. | Long-chain α,ω-di-carboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
US4689344A (en) * | 1981-12-15 | 1987-08-25 | Epis S.A. | Long-chain α,ω-dicarboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
US4908385A (en) * | 1986-10-08 | 1990-03-13 | Epis S.A. | α-halogenated dicarboxylic acids, pharmaceutical compositions and method of use |
WO1989007638A1 (en) * | 1988-02-15 | 1989-08-24 | Nynäs Industri Ab | Method in the processing of aluminium and the use of certain acids in oils therefor |
Also Published As
Publication number | Publication date |
---|---|
FR1198787A (en) | 1959-12-09 |
GB826102A (en) | 1959-12-23 |
DE1063311B (en) | 1959-08-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3224971A (en) | Borate esters and lubricant compositions containing said esters | |
US2636861A (en) | Hydraulic fluid | |
US3185644A (en) | Lubricating compositions containing amine salts of boron-containing compounds | |
US3637507A (en) | Aircraft hydraulic fluid and method of controlling acid buildup therein with acid acceptor | |
US3969237A (en) | Lubricant compositions containing benzotriazole derivatives as copper passivators | |
US2971915A (en) | Lubricating oil compositions | |
US3941708A (en) | Hydraulic fluid antioxidant system | |
US2994662A (en) | Lubricating compositions | |
US3041284A (en) | Lubricating compositions | |
US3115466A (en) | Synergistic antioxidants | |
US3668237A (en) | Amine salts of phosphinic acid esters | |
US3125528A (en) | Method of lubricating automotive | |
US3707501A (en) | Hydraulic fluids containing certain quaternary phosphonium salts of phosphorus acids | |
US3134737A (en) | Novel titanium compound and lubricating composition containing said compound | |
US3314888A (en) | Extreme pressure lubricant compositions | |
US2796404A (en) | Extreme pressure lubricant compositions | |
US2836565A (en) | Lubricating compositions | |
US2971912A (en) | Lubricating oil compositions | |
US3112271A (en) | Liquid hydrocarbon composition | |
US3728260A (en) | Additive for lubricating composition | |
US2999813A (en) | Lubricant comprising a sulfurized mineral oil and a polyvalent metal dithiocarbamate | |
US2956952A (en) | Lubricating oil compositions containing polymers of bis-(beta chloroethyl) vinyl phosphonate | |
US2902450A (en) | Lubricating oil composition | |
US3422017A (en) | Lubricant compositions containing amine salts | |
US3813339A (en) | Acid-terminated hydroxy ester compounds as lubricating oil additives |