US3884822A - Lubricant composition containing 3-amidopyridine corrosion inhibitor - Google Patents
Lubricant composition containing 3-amidopyridine corrosion inhibitor Download PDFInfo
- Publication number
- US3884822A US3884822A US377002A US37700273A US3884822A US 3884822 A US3884822 A US 3884822A US 377002 A US377002 A US 377002A US 37700273 A US37700273 A US 37700273A US 3884822 A US3884822 A US 3884822A
- Authority
- US
- United States
- Prior art keywords
- amidopyridine
- composition
- oil
- ssu
- lubricant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 239000000314 lubricant Substances 0.000 title claims abstract description 23
- 238000005260 corrosion Methods 0.000 title claims abstract description 15
- 230000007797 corrosion Effects 0.000 title claims abstract description 15
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 title claims description 6
- 239000003112 inhibitor Substances 0.000 title description 5
- 239000002184 metal Substances 0.000 claims abstract description 12
- 239000003921 oil Substances 0.000 claims description 16
- 230000001050 lubricating effect Effects 0.000 claims description 9
- 239000004519 grease Substances 0.000 claims description 8
- 239000002480 mineral oil Substances 0.000 claims description 6
- 239000010687 lubricating oil Substances 0.000 claims description 5
- 235000010446 mineral oil Nutrition 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract description 11
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract description 11
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract description 11
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract description 11
- 239000005642 Oleic acid Substances 0.000 abstract description 11
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract description 11
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract description 11
- 150000003927 aminopyridines Chemical class 0.000 abstract description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 238000009472 formulation Methods 0.000 description 4
- -1 2-ethyl hexyl Chemical group 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000013556 antirust agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- GQGTXJRZSBTHOB-UHFFFAOYSA-N 1-phenoxy-4-(4-phenoxyphenoxy)benzene Chemical class C=1C=C(OC=2C=CC(OC=3C=CC=CC=3)=CC=2)C=CC=1OC1=CC=CC=C1 GQGTXJRZSBTHOB-UHFFFAOYSA-N 0.000 description 1
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
- 101100261173 Arabidopsis thaliana TPS7 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- GLQOALGKMKUSBF-UHFFFAOYSA-N [amino(diphenyl)silyl]benzene Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(N)C1=CC=CC=C1 GLQOALGKMKUSBF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011436 cob Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960004979 fampridine Drugs 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical class [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- VWSUVZVPDQDVRT-UHFFFAOYSA-N phenylperoxybenzene Chemical class C=1C=CC=CC=1OOC1=CC=CC=C1 VWSUVZVPDQDVRT-UHFFFAOYSA-N 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/40—Six-membered ring containing nitrogen and carbon only
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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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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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10M2207/283—Esters of polyhydroxy compounds
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- C10M2207/286—Esters of polymerised unsaturated 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
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- 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
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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
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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
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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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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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
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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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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/10—Amides of carbonic or haloformic acids
- C10M2215/102—Ureas; Semicarbazides; Allophanates
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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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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen 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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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/30—Heterocyclic 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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- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/02—Esters of silicic acids
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- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
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- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/08—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds
- C10M2227/081—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds with a metal carbon bond belonging to a ring, e.g. ferocene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Definitions
- This invention relates to lubricant compositions and, in one of its aspects, relates more particularly to lubricant compositions having improved properties for prevention of metal corrosion in performing their functions. Still more particularly, in this aspect, the invention relates to lubricant compositions in the form of lubricating oils and greases containing additives effective for inhibiting metal corrosion.
- lubricants in the form of lubricating oils and greases, apart from performing their intended functions of lubricating metal parts, also exhibit the characteristic of permitting corrosion of metal surfaces with which they may come into contact.
- various additives have been suggested. Some of these additives have not proved to afford any appreciable improvement, while others, although more effective, have been found to be too costly.
- lubricant compositions containing, in an amount sufficient to inhibit metal corrosion, an amidopyridine obtained by reacting an aminopyridine and oleic acid.
- reaction product additives as more fully hereinafter described, are outstandingly effective in inhibiting the metal corrosion properties of lubricants and are also economical to use.
- the aforementioned amidopyridine may be incorporated in any lubricating media which may comprise liquid hydrocarbon oils, in the form of either a mineral oil or a synthetic oil, or in the form of a grease in which any of the aforementioned oils are employed as a vehicle.
- mineral oils, employed as the lubricant, or grease vehicle may be of any suitable lubricating viscosity range, as, for example, from about 45 SSU at 100 F. to about 6,000 SSU at 100 F., and, preferably, from about 50 to about 250 SSU at 210 F.
- These oils may have viscosity indexes varying from below zero to about 100 or higher. Viscosity indexes from about 70 to about 95 are preferred.
- the average molecular weights of these oils may range from about 250 to about 800.
- the lubricating oil is generally employed in an amount sufficient to balance the total grease composition, after accounting for the desired quantity of the thickening agent, and other additive components to be included in the grease formulation.
- Typical synthetic vehicles include polyisobutylene, polybutenes, hydrogenated polydecenes, polypropylene glycol, polyethylene glycol, trimethylol propane esters, neopentyl and pentaerythritol esters, di(2-ethyl hexyl) seba'cate. di(2-ethyl hexyl) adipate, dibutyl phthalate, fluorocarbons, silicate esters, silanes, esters of phosphorous-containing acids. liquid ureas, ferrocene derivatives, hydrogenated mineral oils, chain-type polyphenyls, siloxanes and silicones (polysiloxanes),
- alkyl-substituted diphenyl ethers typified by a butylsubstituted bis (p-phenoxy phenyl) ether, phenoxy phenylethers, etc.
- the aminopyridine and the oleic acid are reacted in a mol ratio of from 1:1 to about 1:2.
- the reaction may be carried out at a temperature from about C. to about 210 C., and preferably at a temperature from about 160 C. to about 200 C.
- the amidopyridine may be incorporated in the lubricant in any amount effective for inhibiting metal corrosion.
- the reaction product may be incorporated in the lubricant in an amount from about 0.1 to about 5%, and, preferably, in an amount from about 0.3 to about 3%, by weight, of the total lubricant composition.
- the xylene and excess oleic acid were removed by vacuum distillation.
- the resulting product was pure 4- amidopyridine as characterized by gas chromatography and infrared spectral analysis.
- the xylene and excess oleic acid were removed by vacuum distillation.
- the resulting product was pure 2- amidopyridine as characterized by gas chromatography and infrared spectral analysis.
- the xylene and excess oleic acid were removed by vacuum distillation.
- the resulting product was pure 3- amidopyridine as characterized by gas chromatography and infrared analysis.
- HUMIDITY CHAMBER RUST TESTS This is a general purpose and severe rust test. It utilizes a humidity chamber operated at 120 F. and 979 8% Relative Humidity with an air circulation rate of 150 cubic feet per minute.
- the test panels are 2 inches X 4 inches one-eighth inch polished steel plates of SAE 1010 steel of a 10 micron finish.
- the test is performed by first cleaning a new panel in naphtha, absolute methanol and xylene in that order. The air dried panel is then dipped in a test formulation for 1 minute and then drip-dried for 2 hours prior to insertion into the chamber. The panels are suspended in a vertical position within the chamber and can be continuously monitored through the glass dome of the chamber.
- the severity of the test can be judged by the rapid rusting rate (1 hour) of a panel coated only with a solvent-refined Mid-Continent SAE. 30 oil base stock, compared to complete rust inhibition for periods up to 5 days when utilizing a rust inhibitor in concentrations of 2 and 4.0% in the same oil.
- the following data indicate the formulations tested and the ratings show the number of days to achieve the first indication of rust and the degree of rust at that time.
- the degree of rust is given since some antirust agents will allow only a gradual rusting rate while some allow a sudden, catastrophic rusting rate after their inhibiting ability is depleted.
- composition as defined in claim 1 wherein said lubricant comprises a synthetic oil-based composition.
- composition as defined in claim 1 wherein said lubricant comprises an oil of lubricating viscosity in the range from about SSU at 100 F. to about 6,000 SSU at 100 F.
- composition as defined in claim 1 wherein said lubricant comprises an oil of lubricating viscosity in the range from about SSU at 210 F. to about 250 SSU at 210 F. r
- Additive Form ulation Days to first rust- Conc. Wt.% rating at that time S-Light, S-Moderate, 6-Trace 3-Trace, S-Heavy, 7-Moderate test.
- the comparative data of the foregoing humidity 'TPSA is tetrapropenylsuccinic anhydridc known to be an effective rust inhibitor and used as a reference in this 7.
- amidopyridines of the present invention in inhibiting metal corrosion.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Abstract
Lubricant compositions containing, in an amount sufficient to inhibit metal corrosion, an amidopyridine obtained by reacting an aminopyridine and oleic acid.
Description
United States Patent [1 1 Gemmill, Jr.
[451 May 20, 1975 1 LUBRICANT COMPOSITION CONTAINING 3-AMIDOPYRIDINE CORROSION INHIBITOR [75] Inventor: Robert M. Gemmill, Jr., Pitman,
[73] Assignee: Mobil Oil Corporation, New York,
[22] Filed: July 6, 1973 [21] App]. No.: 377,002
[52] US. Cl 252/51.5 A; 252/392; 252/403 [51] Int. Cl ClOm 1/32 [58] Field of Search 252/51.5 A, 392, 403
[56] References Cited UNITED STATES PATENTS 3,303,131 2/1967 Low et al 252/51.S A X Hotten 252/5l.5 A X Davies et a1, 252/52 R Primary ExaminerDelbert E. Gantz Assistant ExaminerAndrew H. Metz Attorney, Agent, or FirmChar1es A. Huggett; Raymond W. Barclay; Benjamin 1. Kaufman 7 Claims, No Drawings LUBRICANT COMPOSITION CONTAINING 3-AMIDOPYRIDINE CORROSION INHIBITOR BACKGROUND OF THE INVENTION 1. Field of the Invention.
This invention relates to lubricant compositions and, in one of its aspects, relates more particularly to lubricant compositions having improved properties for prevention of metal corrosion in performing their functions. Still more particularly, in this aspect, the invention relates to lubricant compositions in the form of lubricating oils and greases containing additives effective for inhibiting metal corrosion.
2. Description of the Prior Art.
The prior art has long recognized that lubricants, in the form of lubricating oils and greases, apart from performing their intended functions of lubricating metal parts, also exhibit the characteristic of permitting corrosion of metal surfaces with which they may come into contact. In order to control such corrosion, various additives have been suggested. Some of these additives have not proved to afford any appreciable improvement, while others, although more effective, have been found to be too costly.
SUMMARY OF THE INVENTION In accordance with the present invention, lubricant compositions are provided containing, in an amount sufficient to inhibit metal corrosion, an amidopyridine obtained by reacting an aminopyridine and oleic acid. These reaction product additives, as more fully hereinafter described, are outstandingly effective in inhibiting the metal corrosion properties of lubricants and are also economical to use.
The aforementioned amidopyridine may be incorporated in any lubricating media which may comprise liquid hydrocarbon oils, in the form of either a mineral oil or a synthetic oil, or in the form of a grease in which any of the aforementioned oils are employed as a vehicle. In general, mineral oils, employed as the lubricant, or grease vehicle, may be of any suitable lubricating viscosity range, as, for example, from about 45 SSU at 100 F. to about 6,000 SSU at 100 F., and, preferably, from about 50 to about 250 SSU at 210 F. These oils may have viscosity indexes varying from below zero to about 100 or higher. Viscosity indexes from about 70 to about 95 are preferred. The average molecular weights of these oils may range from about 250 to about 800. Where the lubricant is to be employed in the form ofa grease, the lubricating oil is generally employed in an amount sufficient to balance the total grease composition, after accounting for the desired quantity of the thickening agent, and other additive components to be included in the grease formulation.
In instances where synthetic oils, or synthetic oils employed as the vehicle for the grease, are desired in preference to mineral oils, or in combination therewith, various compounds of this type may be successfully utilized. Typical synthetic vehicles include polyisobutylene, polybutenes, hydrogenated polydecenes, polypropylene glycol, polyethylene glycol, trimethylol propane esters, neopentyl and pentaerythritol esters, di(2-ethyl hexyl) seba'cate. di(2-ethyl hexyl) adipate, dibutyl phthalate, fluorocarbons, silicate esters, silanes, esters of phosphorous-containing acids. liquid ureas, ferrocene derivatives, hydrogenated mineral oils, chain-type polyphenyls, siloxanes and silicones (polysiloxanes),
alkyl-substituted diphenyl ethers typified by a butylsubstituted bis (p-phenoxy phenyl) ether, phenoxy phenylethers, etc.
The aminopyridine and the oleic acid are reacted in a mol ratio of from 1:1 to about 1:2. In general, the reaction may be carried out at a temperature from about C. to about 210 C., and preferably at a temperature from about 160 C. to about 200 C. The amidopyridine may be incorporated in the lubricant in any amount effective for inhibiting metal corrosion. In many instances, the reaction product may be incorporated in the lubricant in an amount from about 0.1 to about 5%, and, preferably, in an amount from about 0.3 to about 3%, by weight, of the total lubricant composition.
The reaction between the aminopyridine and oleic acid may be illustrated as follows:
/ M1 +oleic acid @NH (H 2 6 DESCRIPTION OF SPECIFIC EMBODIMENTS The following examples and comparative data will serve to illustrate the novel metal corrosion inhibiting amidopyridines of the present invention, the method for their preparation and their'utility in lubricating media as antirust agents.
EXAMPLE 1PREPARATION OF 4-AMIDOPYRIDINE A mixture of 141.3 grams (0.50 mole) of oleic acid and 23.5 grams (0.25 mole) of 4-aminopyridine was reacted in the presence of 100 ml. xylene at l50-190 C. for about 38 hours to form a dark, red-amber colored, liquid product. The theoretical 4.5 grams (0.25 mole) of water was evolved by azeotropic distillation with the xylene.
The xylene and excess oleic acid were removed by vacuum distillation. The resulting product was pure 4- amidopyridine as characterized by gas chromatography and infrared spectral analysis.
EXAMPLE 2PREPARATION OF Z-AMIDOPYRIDINE A mixture of 141.3 grams (0.50 mole) of oleic acid and 23.5 grams (0.25 mole) of 2-aminopyridine was reacted in the presence of 100 ml xylene at 160170 C. for about 25 hours to form a dark, red-amber colored, liquid product. The theoretical 4.5 grams (0.25 mole) of water was evolved by azeotropic distillation with the xylene.
The xylene and excess oleic acid were removed by vacuum distillation. The resulting product was pure 2- amidopyridine as characterized by gas chromatography and infrared spectral analysis.
EXAMPLE 3PREPARATION OF 3-AM1DOPYRIDINE A mixture of 141.3 grams (0.50 mole) of oleic acid and 23.5 grams (0.25 mole) of 3-aminopyridine was reacted in the presence of 100 ml. xylene at -l85 C. for about 29 hours to form a dark, red-amber colored,
liquid product. The theoretical 4.5 grams (0.25 mole) of water was evolved by azeotropic distillation with the xylene.
The xylene and excess oleic acid were removed by vacuum distillation. The resulting product was pure 3- amidopyridine as characterized by gas chromatography and infrared analysis.
HUMIDITY CHAMBER RUST TESTS This is a general purpose and severe rust test. It utilizes a humidity chamber operated at 120 F. and 979 8% Relative Humidity with an air circulation rate of 150 cubic feet per minute. The test panels are 2 inches X 4 inches one-eighth inch polished steel plates of SAE 1010 steel of a 10 micron finish.
The test is performed by first cleaning a new panel in naphtha, absolute methanol and xylene in that order. The air dried panel is then dipped in a test formulation for 1 minute and then drip-dried for 2 hours prior to insertion into the chamber. The panels are suspended in a vertical position within the chamber and can be continuously monitored through the glass dome of the chamber.
The severity of the test can be judged by the rapid rusting rate (1 hour) of a panel coated only with a solvent-refined Mid-Continent SAE. 30 oil base stock, compared to complete rust inhibition for periods up to 5 days when utilizing a rust inhibitor in concentrations of 2 and 4.0% in the same oil.
The following data indicate the formulations tested and the ratings show the number of days to achieve the first indication of rust and the degree of rust at that time. The degree of rust is given since some antirust agents will allow only a gradual rusting rate while some allow a sudden, catastrophic rusting rate after their inhibiting ability is depleted.
amount of a lubricating oil or grease containing, in an amount sufficient to inhibit metal corrosion, a 3- amidopyridine having the structure:
0 ll (bu-c (on )7CH W H CH3 (CH2 70H 2. A composition as defined in claim 1 wherein said lubricant comprises a mineral oil-based composition.
3. A composition as defined in claim 1 wherein said lubricant comprises a synthetic oil-based composition.
4. A composition as defined in claim 1 wherein said lubricant comprises an oil of lubricating viscosity in the range from about SSU at 100 F. to about 6,000 SSU at 100 F.
5. A composition as defined in claim 1 wherein said lubricant comprises an oil of lubricating viscosity in the range from about SSU at 210 F. to about 250 SSU at 210 F. r
6. A composition as defined in claim 1 wherein said amidopyridine is present in an amount from about 0.l
to about 5%, by weight.
Additive Form ulation Days to first rust- Conc. Wt.% rating at that time S-Light, S-Moderate, 6-Trace 3-Trace, S-Heavy, 7-Moderate test.
The comparative data of the foregoing humidity 'TPSA is tetrapropenylsuccinic anhydridc known to be an effective rust inhibitor and used as a reference in this 7. A composition as defined in claim 1 wherein said chamber tests illustrate the efficacy of the novel amidopyridine is present in an amount from about 0.3
amidopyridines of the present invention in inhibiting metal corrosion.
to about 3%, by weight.
Claims (7)
1. A LUBRICATING COMPOSITION COMPRISING A MAJOR AMOUNT OF A LUBRICATING OIL OR GREASE CONTAINING, IN AN AMOUNT SUFFICIENT TO INHIBIT METAL CORROSION, A 3-AMIDOPYRIDINE HAVING THE STRUCTURE:
2. A composition as defined in claim 1 wherein said lubricant comprises a mineral oil-based composition.
3. A composition as defined in claim 1 wherein said lubricant comprises a synthetic oil-based composition.
4. A composition as defined in claim 1 wherein said lubricant comprises an oil of lubricating viscosity in the range from about 45 SSU at 100* F. to about 6,000 SSU at 100* F.
5. A composition as defined in claim 1 wherein said lubricant comprises an oil of lubricating viscosity in the range from about 50 SSU at 210* F. to about 250 SSU at 210* F.
6. A composition as defined in claim 1 wherein said amidopyridine is present in an amount from about 0.1 to about 5%, by weight.
7. A composition as defined in claim 1 wherein said amidopyridine is present in an amount from about 0.3 to about 3%, by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US377002A US3884822A (en) | 1973-07-06 | 1973-07-06 | Lubricant composition containing 3-amidopyridine corrosion inhibitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US377002A US3884822A (en) | 1973-07-06 | 1973-07-06 | Lubricant composition containing 3-amidopyridine corrosion inhibitor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3884822A true US3884822A (en) | 1975-05-20 |
Family
ID=23487369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US377002A Expired - Lifetime US3884822A (en) | 1973-07-06 | 1973-07-06 | Lubricant composition containing 3-amidopyridine corrosion inhibitor |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3884822A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4536312A (en) * | 1982-04-09 | 1985-08-20 | Mobil Oil Corporation | Sulfurized amine condensation products and lubricant compositions containing same |
| US4613343A (en) * | 1983-06-29 | 1986-09-23 | Mobil Oil Corporation | N-alkoxyalkylenediamine [organic acid reaction products] diamides and lubricants containing same |
| US4816171A (en) * | 1983-10-13 | 1989-03-28 | Mobil Oil Corporation | Lubricant compositions containing reaction products of formic acid and dialkylenetriamines |
| US4849119A (en) * | 1983-09-23 | 1989-07-18 | Mobil Oil Corporation | Diamine carboxylates and lubricant and fuel compositions containing same |
| US4861884A (en) * | 1985-10-15 | 1989-08-29 | The Dow Chemical Company | Compositions prepared from amino substituted pyrazines and carboxylic acids, carboxylic acid anhydrides, carboxylic acid esters or carboxylic acid halides |
| US4895702A (en) * | 1985-10-15 | 1990-01-23 | The Dow Chemical Company | Corrosion inhibitor compositions containing inhibitor prepared from amino substituted pyrazines and epoxy compounds |
| JPH0249096A (en) * | 1988-08-11 | 1990-02-19 | Maruwa Bussan Kk | Synthetic lubricant |
| US5013469A (en) * | 1989-08-24 | 1991-05-07 | Texaco Inc. | VI improver, dispersant, and anti-oxidant additive and lubricating oil composition containing same |
| US5238588A (en) * | 1989-08-24 | 1993-08-24 | Texaco Inc. | Dispersant, vi improver, additive and lubricating oil composition containing same |
| EP2610330A1 (en) | 2008-09-16 | 2013-07-03 | The Lubrizol Corporation | Method of lubricating an internal combustion engine |
| US9090847B2 (en) | 2011-05-20 | 2015-07-28 | Afton Chemical Corporation | Lubricant compositions containing a heteroaromatic compound |
| CN106831554A (en) * | 2017-01-05 | 2017-06-13 | 西安石油大学 | A kind of preparation method of high temperature non-phosphate inhibitor |
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| US3385790A (en) * | 1965-04-27 | 1968-05-28 | Monsanto Co | Antioxidant compositions |
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|---|---|---|---|---|
| US3367940A (en) * | 1963-01-02 | 1968-02-06 | Chevron Res | Beta-picolinamide derivatives |
| US3303131A (en) * | 1964-12-11 | 1967-02-07 | Shell Oil Co | Lubricant compositions |
| US3385790A (en) * | 1965-04-27 | 1968-05-28 | Monsanto Co | Antioxidant compositions |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4536312A (en) * | 1982-04-09 | 1985-08-20 | Mobil Oil Corporation | Sulfurized amine condensation products and lubricant compositions containing same |
| US4613343A (en) * | 1983-06-29 | 1986-09-23 | Mobil Oil Corporation | N-alkoxyalkylenediamine [organic acid reaction products] diamides and lubricants containing same |
| US4849119A (en) * | 1983-09-23 | 1989-07-18 | Mobil Oil Corporation | Diamine carboxylates and lubricant and fuel compositions containing same |
| US4816171A (en) * | 1983-10-13 | 1989-03-28 | Mobil Oil Corporation | Lubricant compositions containing reaction products of formic acid and dialkylenetriamines |
| US4861884A (en) * | 1985-10-15 | 1989-08-29 | The Dow Chemical Company | Compositions prepared from amino substituted pyrazines and carboxylic acids, carboxylic acid anhydrides, carboxylic acid esters or carboxylic acid halides |
| US4895702A (en) * | 1985-10-15 | 1990-01-23 | The Dow Chemical Company | Corrosion inhibitor compositions containing inhibitor prepared from amino substituted pyrazines and epoxy compounds |
| JPH0547599B2 (en) * | 1988-08-11 | 1993-07-19 | Maruwa Butsusan Kk | |
| JPH0249096A (en) * | 1988-08-11 | 1990-02-19 | Maruwa Bussan Kk | Synthetic lubricant |
| US5013469A (en) * | 1989-08-24 | 1991-05-07 | Texaco Inc. | VI improver, dispersant, and anti-oxidant additive and lubricating oil composition containing same |
| US5238588A (en) * | 1989-08-24 | 1993-08-24 | Texaco Inc. | Dispersant, vi improver, additive and lubricating oil composition containing same |
| EP2610330A1 (en) | 2008-09-16 | 2013-07-03 | The Lubrizol Corporation | Method of lubricating an internal combustion engine |
| US9982210B2 (en) | 2008-09-16 | 2018-05-29 | The Lubrizol Corporation | Composition containing heterocyclic compounds and a method of lubricating an internal combustion engine |
| US10550348B2 (en) | 2008-09-16 | 2020-02-04 | The Lubrizol Corporation | Composition containing heterocyclic compounds and a method of lubricating an internal combustion engine |
| US10913915B2 (en) | 2008-09-16 | 2021-02-09 | The Lubrizol Corporation | Composition containing heterocyclic compounds and a method of lubricating an internal combustion engine |
| US9090847B2 (en) | 2011-05-20 | 2015-07-28 | Afton Chemical Corporation | Lubricant compositions containing a heteroaromatic compound |
| CN106831554A (en) * | 2017-01-05 | 2017-06-13 | 西安石油大学 | A kind of preparation method of high temperature non-phosphate inhibitor |
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