US3182024A - Polyaminopyrrolidines in lubricating oils - Google Patents
Polyaminopyrrolidines in lubricating oils Download PDFInfo
- Publication number
- US3182024A US3182024A US266160A US26616063A US3182024A US 3182024 A US3182024 A US 3182024A US 266160 A US266160 A US 266160A US 26616063 A US26616063 A US 26616063A US 3182024 A US3182024 A US 3182024A
- Authority
- US
- United States
- Prior art keywords
- carbon atoms
- solution
- radical
- oil
- lubricating
- 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
- 239000010687 lubricating oil Substances 0.000 title claims description 21
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- 239000003921 oil Substances 0.000 claims description 18
- 230000001050 lubricating effect Effects 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- -1 alkenyl succinic anhydride Chemical compound 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- QFYXSLAAXZTRLG-UHFFFAOYSA-N pyrrolidine-2,3-dione Chemical compound O=C1CCNC1=O QFYXSLAAXZTRLG-UHFFFAOYSA-N 0.000 description 9
- 239000003599 detergent Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002199 base oil Substances 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 150000003235 pyrrolidines Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920001281 polyalkylene Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000004996 alkyl benzenes 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
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000007664 blowing Methods 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
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- AHMZKMOWTURMQK-UHFFFAOYSA-N hexyl-(4-methylpentan-2-yloxy)-silyloxysilane Chemical compound CCCCCC[SiH](O[SiH3])OC(C)CC(C)C AHMZKMOWTURMQK-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- UMFXQZRYLODQGW-UHFFFAOYSA-N nonanedioic acid;octanedioic acid Chemical compound OC(=O)CCCCCCC(O)=O.OC(=O)CCCCCCCC(O)=O UMFXQZRYLODQGW-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
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- 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
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- 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
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/04—Well-defined cycloaliphatic compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
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- 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
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- 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
- C10M2205/024—Propene
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- 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
- C10M2205/026—Butene
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/17—Fisher Tropsch reaction products
- C10M2205/173—Fisher Tropsch reaction products used as base material
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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- 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
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- 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
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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Definitions
- the various detergents which are added to crankcase oils to reduce this formation of sludges and varnishes are metal organic compounds, particularly those compounds wherein the metal is linked to an organic group through an oxygen atom.
- these metal-containing organic compounds have some efiectiveness as detergents for dispersing the precursors of deposits within the oil itself rather than permitting them to form added deposits on the engine parts, they have the dis advantage of forming ash deposits in the engine. These ash deposits lower engine performance by fouling spark plugs and valves, and contribute to preignition.
- lubricating oil compositions particularly useful for heavy duty service are obtained by incorporating certain N-polyaminopyrrolidines in oils of lubricating viscosity.
- polyarninopyrrolidines described herein are effective not only as detergents in lubricating oil compositions, but they also effectively neutralize acids which are formed.
- lubricating oil compositions containing the particular pyrrolidiues described herein diesel and gasoline engine parts remain remarkably free of deposits and varnish, even under severe operating conditions.
- polyaminopyrrolidines are 1-aminoalkyl-3-alkenylpyrrolidines wherein the alkenyl radical has at least carbon atoms, more preferably to 200 carbon atoms, and the alkyl radical has from 2 to 6 carbon atoms. These also include the 1-polyaminoalkyl-3-alkenyl pyrrolidines.
- the polyaminopyrrolidines can be represented by the formula:
- R is an alkenyl radical having from 30 to about 200 carbon atoms
- R is a divalent alkylene radical having from 2 to 6 carbon atoms
- x is a number from dissolved in 9 liters of ethyl ether.
- the R radicals may be derived from polyalkylene polyamine reactants.
- pyr-rolidines can be obtained by first preparing the pyrrolidinedione by the reaction of an olefinic hydrocarbon With maleic anhydride. The resulting alkenyl succinic anhydride is then reacted with the desired polyamine to form the pyrrolidinedione, which then can be reduced (hydrogenated) to form the corresponding pyrrolidine.
- polyalkylene polyamine reactants include diethylene triamine, dipropylene triamine, tetraethylene pentamine, pentaethylene hexamine, nonaethylenenedecamine, dihexamethylene triamine, etc.
- alkylaminoalkylene amines of the formula:
- R2 lEhN-Rl-N wherein R is an alkylene radical, and R and R are alkyl radicals having from 1 to 4 carbon times.
- the sum of carbon atoms in R R and R is preferably from 3 to 10.
- the polyaminopyrrolidines can be prepared by reducing the corresponding alkenyl pyrrolidinedione.
- Lubricating oils which can be used as base oils include a wide variety of lubricating oils, such as naphthenic base, paraffin base, and mixed base lubricating oils, other hydrocarbon lubricants, e.g., lubricating oils derived from coal products, and synthetic oils, e.g., alkylone polymers (such as polymers of propylene, butylene, etc., and the mixtures thereof), alkylene oxide-type polymers (e.g., propylene oxide polymers) and derivatives, including alkylene oxide polymers prepared by polymerizing the alkylene oxide in the presence of water or alcohols, e.g., ethyl alcohol, dicarboxylic acid esters (such as those which are prepared by esterifying such dicarboxylic acids as adipic acid, azelaic acid suberic acid, sebacic acid, alkanol succinic acid, fumaric acid, maleic acid, etc., with alcohols such as butyl alcohol, he
- bi phenyls and terphenyls alkyl biphenyl others, polymers of silicon (e.g., tetraethyl silicate, tetraisopropyl silicates, tetra(4-methyl-2-tetraethyl) silicate, hexyl (4-methyl-2 pentoxy) disiloxane, poly(methyl) siloxane, poly(rnethy1- phenyl) siloxane, etc.
- silicon e.g., tetraethyl silicate, tetraisopropyl silicates, tetra(4-methyl-2-tetraethyl) silicate, hexyl (4-methyl-2 pentoxy) disiloxane, poly(methyl) siloxane, poly(rnethy1- phenyl) siloxane, etc.
- the above base oils may be used individually or in combinations thereof, Wherever miscible or wherever made so by the use of mutual solvents.
- pyrrolidines can be used in oils of lubricating viscosity in amounts of 0.1% to 39% by Weight, preferably 0.25% to 5%, by weight.
- EXAMPLE II.PREPARATION OF l-(TRIETHYL- ENETETRAMINOETHYL) -3 POLYISOBUTENYL PYRROLIDINE A six hundred grams of approximately 45% petroleum oil solution of N-tetraethylene pentamine polyisobutenylpyrrolidinedione, wherein the polyisobutenyl radical had a molecular weight of about 850, was blended with 800 ml. of ethyl ether. This blend was slowly added to a solution of 30 g. of lithium aluminum hydride in 2500 ml. of ethyl ether. The mixture was stirred under reflux for 12 hours after which 300 ml. of water was slowly added.
- the ether solution was washed with aqueous sodium hydroxide and centrifuged.
- the ether was removed by heating at 150 C. at an absolute pressure of 2 mm. of mercury. Analysis showed a nitrogen content of 1.87% and an absence of carbonyl groups.
- the resulting pyrrolidinedione was reduced by slowly adding a solution consisting of 100 g. of the pyrrolidinedione dissolved in 100 ml. of dry ether to a stirred slurry of 3.5 g. of lithium aluminum hydride in 150 ml. of ether. This mixture was refluxed gently for 5 hours, treated with water, filtered, dried over potassium carbonate and heated to remove the solvent. On analysis, it was found that the total nitrogen content was 0.82%. Infrared analysis showed that no carbonyl groups were present.
- EXAMPLE V.-PREPARATION OF l-(6-AMINO- HEXYL) -3 -POLYISOBUTENYLPYRROLIDINE The pyrrolidinedione was first prepared by reacting 430 g. of an oil solution (35%) of polyisobutenyl succinic i anhydride (1030 mol wt.) with 350 g. of 1,6-hexanediamine. The solution was heated to 170 C. at an absolute pressure of 1 mm. of mercury to remove the excess diamine. The pyrrolidinedione was reduced by diluting with ether and dripping the ether solution into a dispersion of 15 g. of lithium aluminum hydride in 500 ml. of ether, followed by treatment in the manner set forth hereinabove.
- Table I hereinbelow presents engine data obtained with lubricating oil compositions containing 7.3% of the oil solution of the pyrrolidine of Example II hereinabove.
- the test was a Caterpillar l-H engine test run for the period of 120 hours.
- the PD Nos. refer to the piston discoloration rating. After the engine test, the three piston lands are examined visually. To a piston skirt which is completely black is assigned a PD number of 800; to one which is completely clean, a PD number of 0; to those intermediate between completely black and completely clean are assigned PD numbers intermediate in proportion to the extent and degree of darkening.
- the GD Nos. refer to the percentage deposits in the piston ring grooves; a 0 evaluation being a clean groove; and a number of being a groove full of deposits.
- the base oil was a California SAE 30 base oil.
- the lubricating oil compositions may contain other detergents, rust inhibitors, corrosion inhibitors, pour point depressants, oiliness agents, oxidation inhibitors, etc.
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and from 0.1% to 30% by weight, of l-aminoalkyl-B-alkenyl pyrrolidine wherein the alkenyl radical has from 30 to 200 carbon atoms and the alkyl radical has from 2 to 6 carbon atoms.
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and from 0.25% to 5% by weight, of 1-aminoalkyl-3-alkeny1 pyrrolidine wherein the alkenyl radical has from 30 to 200 carbon atoms and the alkyl radical has from 2 to 6 carbon atoms.
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and from 0.1% to 30% by weight of an N-aminoalkyl-pyrrolidine of the formula wherein R is an alkenyl radical having from 30 to 200 carbon atoms, R is a divalent alkylene radical having from 2 to 4 carbon atoms, and x is a number from 0 to 6.
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and from 0.1% to 30% by weight of an N-aminoalkyl-pyrrolidine of the formula R-CHCH3 N-RNR -NH Hg-CH g x wherein R is an alkenyl radical having from 30 to 200 carbon atoms, R is a divalent alkylene radical having 2 carbon atoms, and x is a number from to 6.
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and from 0.1% to 30% by weight of an N-aminoalkyl-pyrrolidine of the formula R-oH oH,
- R is an alkenyl radical having from 30 to 200 carbon atoms, and R is a divalent radical having 2 carbon atoms.
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and from 0.25% to 5% by weight of an N-arninoalkyl-pyrrolidine of the formula wherein R is an alkenyl radical having from 30 to 200 carbon atoms, and R is a divalent radical having 2 carbon atoms.
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and from 0.1% to 30% by weight of 1-(triethylenetetraminoethyl)- wherein R is an alkenyl radical having from to 200 carbon atoms, R is a divalent alkylene radical having from 2 to 4 carbon atoms and x is a number from O to 6.
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Description
United States Patent This invention pertains to lubricating oil compositions containing metal-free detergents having acid-neutralizing characteristics.
Present day internal combustion engines operate at high speeds and high compression ratios. When used in the so-called city stop-and-go driving, which includes the greater part of the driving conditions for a large percentage of todays automobiles, the internal combustion engines do not reach the most efiicient operating temperature. Under city driving conditions, large amounts of partial oxidation products are formed, and reach the crankcase of the engine by blowing past the piston rings. Most of these partial oxidation products are oil-insoluble, tending to form deposits on the various operating parts of the engine, such as the pistons, piston rings, etc. For the purpose of preventing the deposition of these products on the various engine parts, it is necessary to incorporate detergents in the lubricating oil compositions, thus keeping these polymeric products highly dispersed in a condition unfavorable for deposition on metals.
For the most part, the various detergents which are added to crankcase oils to reduce this formation of sludges and varnishes are metal organic compounds, particularly those compounds wherein the metal is linked to an organic group through an oxygen atom. Although these metal-containing organic compounds have some efiectiveness as detergents for dispersing the precursors of deposits within the oil itself rather than permitting them to form added deposits on the engine parts, they have the dis advantage of forming ash deposits in the engine. These ash deposits lower engine performance by fouling spark plugs and valves, and contribute to preignition.
It is a particular object of this invention to provide lubricating oil compositions which are compounded with metal-free detergents having acid-neutralizing characteristics.
Therefore, in accordance with this invention, it has been discovered that lubricating oil compositions particularly useful for heavy duty service are obtained by incorporating certain N-polyaminopyrrolidines in oils of lubricating viscosity.
The polyarninopyrrolidines described herein are effective not only as detergents in lubricating oil compositions, but they also effectively neutralize acids which are formed. Thus, by the use of lubricating oil compositions containing the particular pyrrolidiues described herein, diesel and gasoline engine parts remain remarkably free of deposits and varnish, even under severe operating conditions.
These polyaminopyrrolidines are 1-aminoalkyl-3-alkenylpyrrolidines wherein the alkenyl radical has at least carbon atoms, more preferably to 200 carbon atoms, and the alkyl radical has from 2 to 6 carbon atoms. These also include the 1-polyaminoalkyl-3-alkenyl pyrrolidines.
The polyaminopyrrolidines can be represented by the formula:
wherein R is an alkenyl radical having from 30 to about 200 carbon atoms, R is a divalent alkylene radical having from 2 to 6 carbon atoms, and x is a number from dissolved in 9 liters of ethyl ether.
0 to 8. The R radicals may be derived from polyalkylene polyamine reactants.
These pyr-rolidines can be obtained by first preparing the pyrrolidinedione by the reaction of an olefinic hydrocarbon With maleic anhydride. The resulting alkenyl succinic anhydride is then reacted with the desired polyamine to form the pyrrolidinedione, which then can be reduced (hydrogenated) to form the corresponding pyrrolidine.
Examples of polyalkylene polyamine reactants include diethylene triamine, dipropylene triamine, tetraethylene pentamine, pentaethylene hexamine, nonaethylenenedecamine, dihexamethylene triamine, etc.
In addition to polyalkylene polyamine reactants, other amines can be used, such as, alkylaminoalkylene amines of the formula:
R2 lEhN-Rl-N wherein R is an alkylene radical, and R and R are alkyl radicals having from 1 to 4 carbon times. The sum of carbon atoms in R R and R is preferably from 3 to 10.
The polyaminopyrrolidines can be prepared by reducing the corresponding alkenyl pyrrolidinedione.
Lubricating oils which can be used as base oils include a wide variety of lubricating oils, such as naphthenic base, paraffin base, and mixed base lubricating oils, other hydrocarbon lubricants, e.g., lubricating oils derived from coal products, and synthetic oils, e.g., alkylone polymers (such as polymers of propylene, butylene, etc., and the mixtures thereof), alkylene oxide-type polymers (e.g., propylene oxide polymers) and derivatives, including alkylene oxide polymers prepared by polymerizing the alkylene oxide in the presence of water or alcohols, e.g., ethyl alcohol, dicarboxylic acid esters (such as those which are prepared by esterifying such dicarboxylic acids as adipic acid, azelaic acid suberic acid, sebacic acid, alkanol succinic acid, fumaric acid, maleic acid, etc., with alcohols such as butyl alcohol, hexyl alcohol, Z-ethyl hexyl alcohol, dodecyl alcohol, etc.), liquid esters of acids of phosphorus, alkyl benzenes (e.g., monoalkyl benzene such as dodecyl benzene, tetradecyl benzene, etc., and dialkyl benzenes (e.g., nnonyl Z-ethyl hexyl benzene); polyphenyls (e.g. bi phenyls and terphenyls), alkyl biphenyl others, polymers of silicon (e.g., tetraethyl silicate, tetraisopropyl silicates, tetra(4-methyl-2-tetraethyl) silicate, hexyl (4-methyl-2 pentoxy) disiloxane, poly(methyl) siloxane, poly(rnethy1- phenyl) siloxane, etc.
The above base oils may be used individually or in combinations thereof, Wherever miscible or wherever made so by the use of mutual solvents.
These pyrrolidines can be used in oils of lubricating viscosity in amounts of 0.1% to 39% by Weight, preferably 0.25% to 5%, by weight.
The following examples illustrate the preparation of the pyrrolidines described herein.
EXAMPLE I. PREPARATION OF 1-(TRIETHYL- ENETETRAMINOETHYL) -3 OLYTSOBUTENYL PYRROLIDINE Forty-two grams of lithium aluminum hydride was Twelve hundred grams of approximately 45% petroleum oil solution of N-tetraethylene pentamine polyisobutenylpyrrolidine-dione, wherein the polyisobutenyl radical had a molecular weight of about 850 (the oil solution having a nitrogen content of 1.78%), was added to the ether solution over a period of 3 hours so as to maintain a gentle reflux. This solution was stirred while refluxing for an additional 6 hours. Thirty milliliters of water was slowly added over a period of 3 hours to decompose unreacted lithium aluminum hydride followed by the addition of 470 ml. of water. The mixture was allowed to settle and the ether layer was decanted and filtered. The ether solution was washed with aqueous sodium carbonate solution, centrifuged, dried over anhydrous sodium carbonate, filtered, and freed of solvent under vacuum.
The final product which had a nitrogen content of 1.50% of which 1.13% was basic nitrogen, was essentially free of lithium and aluminum. Infrared analysis showed that the carbonyl groups present in the original pyrrolidinedione were no longer present.
EXAMPLE II.PREPARATION OF l-(TRIETHYL- ENETETRAMINOETHYL) -3 POLYISOBUTENYL PYRROLIDINE A six hundred grams of approximately 45% petroleum oil solution of N-tetraethylene pentamine polyisobutenylpyrrolidinedione, wherein the polyisobutenyl radical had a molecular weight of about 850, was blended with 800 ml. of ethyl ether. This blend was slowly added to a solution of 30 g. of lithium aluminum hydride in 2500 ml. of ethyl ether. The mixture was stirred under reflux for 12 hours after which 300 ml. of water was slowly added. The ether solution was washed with aqueous sodium hydroxide and centrifuged. The ether was removed by heating at 150 C. at an absolute pressure of 2 mm. of mercury. Analysis showed a nitrogen content of 1.87% and an absence of carbonyl groups.
EXAMPLE III.PREPARATION OF I-(B-DIMETH- YLAMINOPROPYL)-3 POLYISOBUTENYLPYR- ROLIDINE Seven hundred grams of a 45% petroleum oil solution of N-dimethylaminopropyl polyisobutenyl pyrrolidinedione, the oil solution having a nitrogen content of 1.04%, was blended with 500 ml. of ethyl ether. This solution was slowly added to a solution consisting of 20 g. of lithium aluminum hydride in 750 m1. of ethyl ether. This solution was heated at reflux temperature overnight with agitation. Water was added, the solution filtered, dried over sodium sulfate, and the solvent removed by distillation to a temperature of 110 C. under vacuum. Analysis indicated a nitrogen content of 0.96%, and the absence of carbonyl groups.
EXAMPLE IV.PREPARATION OF 1-(2-AMINO- ETHY L) -3-POLYISOBUTENYLPYRROLIDINE Two hundred grams of a 34.9% petroleum oil solution of polyisobutenylsuccinic anhydride having a molecular weight of 1030 was blended with 300 ml. of xylene. This blend was dripped into 203 g. of warm, ethylenediamine with agitation. The mixture was distilled at 1 atm. to a pot temperature of 150 C. after which a vacuum was applied to the vessel and the temperature maintained at 170 C. for 2 hours.
On analysis, it was found that the nitrogen content was 0.90%, with the basic nitrogen content being 0.34%. This analysis showed that the product was an oil solution containing 34.5% active pyrrolidinedione material having a molecular weight of 1072.
The resulting pyrrolidinedione was reduced by slowly adding a solution consisting of 100 g. of the pyrrolidinedione dissolved in 100 ml. of dry ether to a stirred slurry of 3.5 g. of lithium aluminum hydride in 150 ml. of ether. This mixture was refluxed gently for 5 hours, treated with water, filtered, dried over potassium carbonate and heated to remove the solvent. On analysis, it was found that the total nitrogen content was 0.82%. Infrared analysis showed that no carbonyl groups were present.
EXAMPLE V.-PREPARATION OF l-(6-AMINO- HEXYL) -3 -POLYISOBUTENYLPYRROLIDINE The pyrrolidinedione was first prepared by reacting 430 g. of an oil solution (35%) of polyisobutenyl succinic i anhydride (1030 mol wt.) with 350 g. of 1,6-hexanediamine. The solution was heated to 170 C. at an absolute pressure of 1 mm. of mercury to remove the excess diamine. The pyrrolidinedione was reduced by diluting with ether and dripping the ether solution into a dispersion of 15 g. of lithium aluminum hydride in 500 ml. of ether, followed by treatment in the manner set forth hereinabove.
On analysis, the product was found to have a total nitrogen content of 0.88%.
Table I hereinbelow presents engine data obtained with lubricating oil compositions containing 7.3% of the oil solution of the pyrrolidine of Example II hereinabove.
The test was a Caterpillar l-H engine test run for the period of 120 hours.
The PD Nos. refer to the piston discoloration rating. After the engine test, the three piston lands are examined visually. To a piston skirt which is completely black is assigned a PD number of 800; to one which is completely clean, a PD number of 0; to those intermediate between completely black and completely clean are assigned PD numbers intermediate in proportion to the extent and degree of darkening.
The GD Nos. refer to the percentage deposits in the piston ring grooves; a 0 evaluation being a clean groove; and a number of being a groove full of deposits.
The base oil was a California SAE 30 base oil.
1 These test results were obtained in a Caterpillar L-l test under the MIL-k210i conditions. Thus, under the more severe supplement-1 conditions, the GD No. would be considerably higher.
In addition to the pyrrolidines described hereinabove, the lubricating oil compositions may contain other detergents, rust inhibitors, corrosion inhibitors, pour point depressants, oiliness agents, oxidation inhibitors, etc.
' We claim: 1. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and from 0.1% to 30% by weight, of l-aminoalkyl-B-alkenyl pyrrolidine wherein the alkenyl radical has from 30 to 200 carbon atoms and the alkyl radical has from 2 to 6 carbon atoms.
2. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and from 0.25% to 5% by weight, of 1-aminoalkyl-3-alkeny1 pyrrolidine wherein the alkenyl radical has from 30 to 200 carbon atoms and the alkyl radical has from 2 to 6 carbon atoms.
3. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and from 0.1% to 30% by weight of an N-aminoalkyl-pyrrolidine of the formula wherein R is an alkenyl radical having from 30 to 200 carbon atoms, R is a divalent alkylene radical having from 2 to 4 carbon atoms, and x is a number from 0 to 6.
4. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and from 0.1% to 30% by weight of an N-aminoalkyl-pyrrolidine of the formula R-CHCH3 N-RNR -NH Hg-CH g x wherein R is an alkenyl radical having from 30 to 200 carbon atoms, R is a divalent alkylene radical having 2 carbon atoms, and x is a number from to 6.
5. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and from 0.1% to 30% by weight of an N-aminoalkyl-pyrrolidine of the formula R-oH oH,
/N-R-LNR-\NHQ UH -CH, 4 wherein R is an alkenyl radical having from 30 to 200 carbon atoms, and R is a divalent radical having 2 carbon atoms.
6. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and from 0.25% to 5% by weight of an N-arninoalkyl-pyrrolidine of the formula wherein R is an alkenyl radical having from 30 to 200 carbon atoms, and R is a divalent radical having 2 carbon atoms.
7. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and from 0.1% to 30% by weight of 1-(triethylenetetraminoethyl)- wherein R is an alkenyl radical having from to 200 carbon atoms, R is a divalent alkylene radical having from 2 to 4 carbon atoms and x is a number from O to 6.
10. As a novel compound, 1-(3-dimethylaminopropyl)- 3-polyisobutenylpyrrolidine, wherein said polyisobutenyl radical contains from 30 to 200 carbon atoms.
References Cited by the Examiner UNITED STATES PATENTS 1/62 Anderson et al. 25251.5 3/63 Aspergren 260313 DANIEL E. WYMAN, Primary Examiner.
UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,182,024 May 4, 1965 Frank A. Stuart et a1.
It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.
Column 2, line 22, for "carbon times" read carbon atoms column 4, lines 70 to 75, for that portion of the formula reading column 5, lines 7 to 10, for that portion of the formula reading N-R read N-R Signed and sealed this 16th day of November 1965.
(SEAL) Attest:
ERNEST W. SWIDER EDWARD J. BRENNER Attesting Officer Commissioner of Patents
Claims (1)
1. A LUBRICATING OIL COMPOSITION COMPRISING A MAJOR PROPORTION OF AN OIL OF LUBRICATING VISCOSITY, AND FROM 0.1% TO 30% BY WEIGHT, OF 1-AMINOALKYL-3-ALKENYL PYRROLIDINE WHEREIN THE ALKENYL RADICAL HAS FROM 30 TO 200 CARBON ATOMS AND THE ALKYL RADICAL HAS FROM 2 TO 6 CARBON ATOMS.
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US266160A US3182024A (en) | 1963-03-19 | 1963-03-19 | Polyaminopyrrolidines in lubricating oils |
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US266160A US3182024A (en) | 1963-03-19 | 1963-03-19 | Polyaminopyrrolidines in lubricating oils |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3301784A (en) * | 1964-11-16 | 1967-01-31 | Chevron Res | Substituted pyrrolidinones as lubricating oil additives |
US3373112A (en) * | 1966-05-18 | 1968-03-12 | Chevron Res | Tris(hydrocarbyl alkylene polyamines) as lubricating oil detergents |
US3449249A (en) * | 1964-05-08 | 1969-06-10 | Shell Oil Co | Lubricant compositions |
US4092255A (en) * | 1974-12-12 | 1978-05-30 | Entreprise De Recherches Et D'activites Petrolieres (E.R.A.P.) | Novel lubricating compositions containing nitrogen containing hydrocarbon backbone polymeric additives |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3018250A (en) * | 1959-08-24 | 1962-01-23 | California Research Corp | Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides |
US3083139A (en) * | 1959-12-17 | 1963-03-26 | Upjohn Co | Therapeutic 1-(1, 2-diphenylethyl) pyrrolidine for the management of depression |
-
1963
- 1963-03-19 US US266160A patent/US3182024A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3018250A (en) * | 1959-08-24 | 1962-01-23 | California Research Corp | Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides |
US3083139A (en) * | 1959-12-17 | 1963-03-26 | Upjohn Co | Therapeutic 1-(1, 2-diphenylethyl) pyrrolidine for the management of depression |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3449249A (en) * | 1964-05-08 | 1969-06-10 | Shell Oil Co | Lubricant compositions |
US3301784A (en) * | 1964-11-16 | 1967-01-31 | Chevron Res | Substituted pyrrolidinones as lubricating oil additives |
US3373112A (en) * | 1966-05-18 | 1968-03-12 | Chevron Res | Tris(hydrocarbyl alkylene polyamines) as lubricating oil detergents |
US4092255A (en) * | 1974-12-12 | 1978-05-30 | Entreprise De Recherches Et D'activites Petrolieres (E.R.A.P.) | Novel lubricating compositions containing nitrogen containing hydrocarbon backbone polymeric additives |
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