US3287271A - Combined detergent-corrosion inhibitors - Google Patents
Combined detergent-corrosion inhibitors Download PDFInfo
- Publication number
- US3287271A US3287271A US427176A US42717665A US3287271A US 3287271 A US3287271 A US 3287271A US 427176 A US427176 A US 427176A US 42717665 A US42717665 A US 42717665A US 3287271 A US3287271 A US 3287271A
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- US
- United States
- Prior art keywords
- carbon atoms
- oil
- acid
- dicarboxylic acid
- product
- 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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- 238000005260 corrosion Methods 0.000 title description 14
- 239000003112 inhibitor Substances 0.000 title description 9
- 239000000203 mixture Substances 0.000 claims description 36
- 239000003921 oil Substances 0.000 claims description 32
- -1 AMINO GROUPS Chemical group 0.000 claims description 18
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 17
- 229920000768 polyamine Polymers 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 229940014800 succinic anhydride Drugs 0.000 claims description 10
- 239000010687 lubricating oil Substances 0.000 claims description 8
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000001721 carbon Chemical class 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 44
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 37
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 23
- 229960002317 succinimide Drugs 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 17
- 125000002947 alkylene group Chemical group 0.000 description 16
- 239000002199 base oil Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 12
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- 230000007797 corrosion Effects 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 229910052770 Uranium Inorganic materials 0.000 description 6
- 230000001050 lubricating effect Effects 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- LBKUUOYKGMXZQX-UHFFFAOYSA-N 2-octylbenzene-1,3-dicarboxylic acid Chemical compound C(CCCCCCC)C1=C(C(=O)O)C=CC=C1C(=O)O LBKUUOYKGMXZQX-UHFFFAOYSA-N 0.000 description 1
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 1
- HAYIPGIFANTODX-UHFFFAOYSA-N 4,6-dimethylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC(C)=C(C(O)=O)C=C1C(O)=O HAYIPGIFANTODX-UHFFFAOYSA-N 0.000 description 1
- PNWSHHILERSSLF-UHFFFAOYSA-N 4-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C(O)=O PNWSHHILERSSLF-UHFFFAOYSA-N 0.000 description 1
- GGPVXCLJAPHKQE-UHFFFAOYSA-N 4-propan-2-ylbenzene-1,3-dicarboxylic acid Chemical compound CC(C)C1=CC=C(C(O)=O)C=C1C(O)=O GGPVXCLJAPHKQE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005263 alkylenediamine group Chemical class 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229930192878 garvin Natural products 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- ZNAOFAIBVOMLPV-UHFFFAOYSA-N hexadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(C)=C ZNAOFAIBVOMLPV-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052742 iron Inorganic materials 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
- 238000005461 lubrication Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- JILXUIANNUALRZ-UHFFFAOYSA-N n',n'-diethylbutane-1,4-diamine Chemical compound CCN(CC)CCCCN JILXUIANNUALRZ-UHFFFAOYSA-N 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- GLDVKMPSACNWFV-UHFFFAOYSA-N n',n'-dipropylbutane-1,4-diamine Chemical compound CCCN(CCC)CCCCN GLDVKMPSACNWFV-UHFFFAOYSA-N 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
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-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
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 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
- 229920001281 polyalkylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/56—Amides; Imides
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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
- C10M2205/026—Butene
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—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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- 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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- 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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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/086—Imides
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
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- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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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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- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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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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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
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- C—CHEMISTRY; METALLURGY
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
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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
- 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
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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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
- 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
- C10M2229/042—Siloxanes with specific structure containing aromatic substituents
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/251—Alcohol-fuelled engines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/28—Rotary engines
Definitions
- This invention concerns novel lubricating oil compositions containing a combined detergent-corrosion inhibitor. More particularly, this invention concerns novel lubricat ing oil compositions containing amine carboxylic acid products as detergent-corrosion inhibitors.
- novel compositions which provide both corrosion inhibition and detergency are provided which are obtained by combining a polyamine with a high molecular weight succinic anhydride and then contacting the resulting product with a dicarboxylic acid, having the carboxyl groups separated by at least three annular carbon atoms (3 to 4 annular carbon atoms).
- the product is obtained by combining at an elevated temperature an alkenyl succinic anhydride, wherein the alkenyl group has from about 30 to 200 carbon atoms, with a polyamine free of unsaturation (both aliphatic and aromatic) and having from 2 to carbon atoms and from 2 to 10 nitrogen atoms; then combining at elevated temperatures the above product with an aromatic dicarboxylic acid, characterized by having carboxyl groups bonded to annular carbons separated by at least one annular carbon .atom (the carboxylic groups are, therefore, separated by at least three annular carbon atoms) and having a total of from 8 to 16 carbon atoms.
- alkenyl succinic anhydride reactant has the following formula:
- R is a hydrocarbon radical having from 3010 200 carbon atoms, preferably from about 50 to about 200 carbon atoms.
- the R radical of the above formula is readily obtained by polymerizing olefins of from 2 to 5 carbons, such as propylene, ethylene, isobutylene, pentene, etc., and mixtures thereof. Methods of polymerization are well known in the art, e.g., US. Patents Nos. 3,024,237, 3,024,195 and 3,018,291.
- the amine with which the alkenyl succinic anhydride is reacted is a polyamine having from 1 to 2 primary amino groups, is of from 2 to 20 carbon atoms, has from 1 to 11 nitrogen atoms, preferably 1 to 6 nitrogen atoms (as its only heteroatoms) and is free of unsaturation.
- the nitrogen atoms will be joined by :alkylene groups of from 2 to 6 carbon atoms, more usually of from 2 to 3 carbon atoms and, except the primary amino groups, will be substituted with hydrogen or lower alkyl, i.e., l to 6 carbon atoms, more usually of from 1 to 3 carbon atoms.
- T is alkylene of from 2 to 6 carbon atoms, more usually of from 2 to 3 carbon atoms
- x-l-y is an integer of from 1 to 10
- y is a cardinal number of from 0 to 2
- x is a cardinal number of from 0 to 10
- Y is either hydrogen, --TNU U or lower alkyl, U and U being either hydrogen or lower alkyl.
- the polyamines of the above formula will have from 2 to 20 carbon atoms, more usually from 4 to 16 carbon atoms.
- a preferred subgenus has the following formula:
- T is :alkylene of from 2 to 3 carbon atoms and x is an integer of from 1 to 10, more usually from 1 to 5.
- alkylene amines and polyalkylene amines of the following formula are diethylene triamine, triethylene tetramine, dipropylene triamine, tetraethylene pentamine, pentaethylene hexamine, no'naethylene deoamine, etc.
- alkyl-substituted alkylene diamines of the following formula wherein T is alkylene of from 2 to 6 carbon atoms, preferably 2 to 3 carbon atoms, and U and U are lower alkyl, i.e., alkyl of from 1 to 6 carbon atoms.
- Exemplifying compounds included in the above formula are dimethylaminopropylamine, diet-hylaminopropylamine, diethylaminobutylamine, dipropylaminobutylamine, diethyl aminoethylamine, etc.
- the total number of carbon atoms will generally be in the range of about 4 to 12, more usually 5 to 10.
- a further subgenus has the following formula:
- T is alkylene of from 2 to 6 carbon atoms and U is hydrogen or an alkyl radical of from 1 to 6 carbon atoms.
- U is hydrogen or an alkyl radical of from 1 to 6 carbon atoms.
- Illustrative of compounds exemplifying the above formula are N-(2-aminoethyl)piperazine, N-rnethyl-N'- (2 aminoet-hyDpiperaZine, N (3 aminopropylene) piperazine, etc.
- N-substituted alkenyl succinimides the products obtained by reacting alkenyl succinic anhydrides and the polyamines described above will be termed N-substituted alkenyl succinimides.
- the N-substituted alkenyl succinimides are prepared by reacting at elevated temperatures an alkenyl succinic anhydride with the desired polyamine, generally in the presence of an inert medium.
- the polyamine-anhydride mole ratio will generally be in the range of from 0.5:1 to 1:1, more usually in the range of 0.821.
- the temperature for the reaction will generally be from about 200 to 500 F., more usually from 225 to 400 F.
- the concentration of the reactants in the inert medium may range from 1 to 90 weight percent, but will more usually be from about 25 to 75 weight percent of the total reaction mixture.
- the time for the reaction will generally be from about one-half hour to 24 hours or more, more usually in the range of about 1 to 12 hours.
- the inert medium may be any dispersant or solvent that permits sufiicient contact between the reactants to provide a reasonable rate of reaction.
- the solvent should be a liquid under the reaction conditions.
- an oil of lubricating viscosity which is also a solvent, can be used, e.g., petroleum oils, such as paraffinic, aromatic and naphthenic oils.
- the carboxylic acids which find use in this invention are dicarboxylic acids of from 8 to 16 carbon atoms having from to 2 alkyl substituents of from 1 to 8 carbon atoms and the carboxyl groups are separated by at least three annular carbon atoms.
- the compounds may be described by the following formula:
- U is lower alkyl, i.e., alkyl of from 1 to 6 carbon atoms and x is a cardinal number of from 0 to 3, preferably from 0 to 1.
- Illustrative of compounds included in the above formula are isophthalic acid, terephthalic acid, 4-methyl isophthalic acid, 4-isopropyl isophthalic acid, 2-(tert.-butyl)terephthalic acid, 5-(tert.-butyl)-isophthalic acid, 2,5-(dimethyl)tereph thalic acid, 2,5-di(tert.-butyl)terephthalic acid, 4,6-di- (methyl)isophthalic acid, etc.
- the dicarboxylic acid will be combined with 1 mole of the N-substituted alkenyl succinimide.
- N-substituted alkenyl succinimides which have more than one basic titratable amino nitrogen atom, more than 1 mole of carboxylic acid per mole of succinimide may be used.
- the number of carboxylic acids which may be used will range from 1 to x, more usually from 1 to x1, but not less than about 1.
- the succinimide-dicarboxylic acid weight ratio in the finished lubricating oil composition will be less than 200:1, preferably less than 100:1, and more preferably in the range 50-1: 1.
- the combining of the succinimide with the carboxylic acid is achieved by heating the carboxylic acid and succinimide in the presence of an inert medium, generally an oil of lubricating viscosity, to a temperaturein the range of about 200 to about 300 F., more usually from about 270 to 290 F.
- an oil of lubricating viscosity is used as the medium, the composition may be prepared as a concentrate which may be diluted with other oils to form the final lubricating oil composition.
- the compounds of this invention may be used with various base oils which find use as lubricating oils, such as petroleum oils, i.e., naphthenic base, paraffin base and mixed base lubricating olls; synthetic oils, e.g., alkylene polymers (such as polymers of butylene, l-decene, etc.), alkylene oxide type polymers (e.g., propylene oxide polymers); dicarboxylic acid esters; liquid esters of acids of phosphorus; alkyl benzenes; alkyl biphenyl ethers; alkyl or aryl silicon compounds, etc.
- lubricating oils such as petroleum oils, i.e., naphthenic base, paraffin base and mixed base lubricating olls; synthetic oils, e.g., alkylene polymers (such as polymers of butylene, l-decene, etc.), alkylene oxide type polymers (e.g., propylene oxide polymers);
- the above base oils may be used individually or in combination whenever miscible or made so by the use of mutual solvents.
- the compounds of this invention can be used in oils of lubricating viscosity in amounts of from about 0.1 to weight percent. When the oil is used in an engine, usually the amount will be about 0.1 to 10 weight percent, more usually 0.25 to 5 weight percent. However, the oil compositions may be prepared as concentrates and diluted prior to use. As concentrates, the amount of the active compound may range from about 10 to 80 weight percent.
- the oil to be used in the enginethe dicarboxylic acid will be present in amounts of 0.001 to 0.75 weight percent, preferably 0.005 to 0.25 weight percent.
- the detergent-corrosion inhibitors of this invention are preferably used in conjunction with a metal salt of a phosphorodithioate, particularly zinc 0,0-di(hydrocarbyl)-phosphorodithioate, wherein the hydrocarbyl group is of from 4 to 36 carbon atoms.
- a metal salt of a phosphorodithioate particularly zinc 0,0-di(hydrocarbyl)-phosphorodithioate, wherein the hydrocarbyl group is of from 4 to 36 carbon atoms.
- Hydrocarbyl is intended a monovalent organic radical composed solely of carbon and hydrogen which may be aliphatic, aromatic, alicyclic, or combinations thereof, e.g., aralkyl.
- a preferred composition is to include with the detergentcorrosion inhibitors of this invention tricresyl phosphate.
- the addition of the tricresyl phosphate imparts the extreme pressure characteristics necessary for oils operating under heavy loads to avoid valve lifter scufiing and camshaft scuffing.
- the amount of the tricresyl phosphate will generally be in the range of about 0.1 to 3 weight percent.
- Example I A mixture of 36 -g. of terephathalic acid, 540 g. of a product prepared as in Example A (the polyisobutenyl radical contained 66 carbon atoms) and 756 g. of a California SAE 30 base oil was agitated at 295300 F. for 1.5 hours under a blanket of nitrogen.
- An oil concentrate of the above product was formed by blending with agitation 1250 g. of the above product and 1250 g. of a California paraffinic base oil having a viscosity of 150 SSU at 100 F. by heating the mixture at 280 F. for minutes.
- Example 11 A succinimide prepared as described in Example A (1970 g.) was charged to a reaction vessel and blanketed with nitrogen. The succinimide was then heated to 265 F. at which temperature 56.2 g. of terephthalic acid was then added. The temperature was then raised to 300 F. during a period of 1 hour and maintained for an additional 4 hours, then cooled to 250 F. and filtered.
- Example Ill The procedure of Example II was repeated using tert.- butyl isophthalic acid in place of terephthalic acid.
- Example IV The procedure of Example II was repeated using isophthalic acid in place of terephthalic acid.
- compositions of this invention were tested under numerous conditions to demonstrate their effectiveness as a combined detergent-corrosion inhibitor.
- the following data were obtained in a L-38 test, using a l-cylinder CLR engine. The test was for 40 hours, with an engine speed of 3150 rpm. The results are reported as the bearing weight loss in milligrams.
- the base oil was a Mid-Continent SAE 30 base oil.
- the succinimides prepared as previously described were combined with the indicated acid as described in exemplary Examples 1-14. The following table indicates the results.
- the succinimide is one prepared as described in Example A.
- TPA-terephthalic acid B-IPA-5-tert-.butyl isophthalio acid.
- TPA-terephthalic acid IPA-isophthalic acid.
- the base oil was a California parafiin base oil having a viscosity of about 500 SSU at 100 F.
- the succinimide and carboxylic acid were combined as described in exemplary Examples 14. The results were reported as bearing weight loss in milligrams.
- the oil contained 10 rnMJkg. of M 0,0-dialkyl phosphorodithioate (alkyl 0! from 4 to 6 carbon atoms), 2 rnM./kg. of M 0,0-dialkylphenyl phosphorodithioate (alkyl of from 12 to 15 carbon atoms). 2 wt. percent of a succinimide prepared as described in Example A and 0.15 wt. percent of tert.-butyl isophthalie acid.
- the compounds of this invention were also tested in the Steel Ball Rust Test.
- the test comprises immersing clean steel balls-whioh are pre-soaked in test oils for one minute at 115-l20 F. and then allowed to drain for one minutein an emulsified test oil (The emulsified test oil is prepared by rapidly stirring 300 ml. of the test oil with a 9 ml. solution of equal parts by volume of cone. HCl, conc. H 50 and glacial acetic acid.) for 20 hours with stirring at 140 F. The steel ball is then removed from the bath, rinsed with acetone and rated on a to scale, 10 being no rust, 0 being heavy rust.
- the oil used was a Mid-Continent SAE oil, containing 10 mM./leg. of Zn 0,0-dialkyl dithiophosphate (alkyl of of from 46 carbon atoms) and 2 mM./k-g. of Zn 0,0-dialkylphenyl phosphorodithioate (alkyl of from 12l5 carbon atoms).
- the preferred dicarboxylic acids are those having alkyl substituents of from 4 to 8 carbon atoms, e.g., tert.-butyl terephthalic acid, tert.-hexyl isophthalic acid, octyl isophthalic acid, etc.
- compositions which not only provide good detergency, but excellent corrosion inhibition, including rust inhibition. Under a variety of conditions, as demonstrated by generally accepted testing procedures, the compositions of this invention have provided excellent protect-ion for the engines. Furthermore, when combined with tricresyl phosphate, good extreme pressure characteristics are demonstrated.
- a lubricating oil composition comprising an oil of lubricating viscosity, and a product obtained by (1) reacting at a temperature in the range of from about 200 F. to 500 F:
- the weight ratio of the product of (1) to the dicarboxylic acid of (2) is less than 200:1, the product of reaction (1) and (2) being present in said oil composition in amount of 0.001 to 0.75 weight percent based on dicarboxylic acid content.
- composition according to claim 1 wherein said dicarboxylic acid is terephthalic acid.
- composition according to claim 1 wherein said dicarboxylic acid is isophthalic acid.
- composition according to claim 1 wherein said dicarboxylic acid is tert.-butyl isophthalic acid.
- alkylene polyamine is a polyamine of the formula wherein T is alkylene of from 2 to 3 carbon atoms and x is an integer of from 1 to 10.
- a composition according to claim 1 wherein said alkylene polyamine has the formula wherein T is alkylene of from 2 to 6 carbon atoms, and U and U4 are lower alkyl.
- composition according to claim 1 wherein said dicarboxylic acid is terephthalic acid and said alkylene polyamine is a polyamine of the formula wherein T is an alkylene of from 2 to 3 carbon atoms and x is an integer of from 1 to 10.
- composition according to claim 1 wherein said dicarboxylic acid is terephthalic acid and said alkylene polyamine has the formula wherein T is alkylene of from 2 to 6 carbon atoms, and U and U are lower alkyl.
- a composition according to claim 1 having from FOREIGN PATENTS 0.1 to 3 weight percent tricresyl phosphate. 208,447 6/1957 Australia References Cited by the Examiner 1367939 6/1964 France UNITED STATES PATENTS 5 DANIEL E. WYMAN, Primary Examiner.
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- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
United States Patent 3,287,271 COMBINED DETERGENT-CORROSION INIrHBITORS Frank A. Stuart, Orinda, and Warren Lowe, Berkeley,
Calif., assignors to Chevron Research Company, a corporation of Delaware No Drawing. Filed Jan. 21, 1965, Ser. No. 427,176
9 Claims. (Cl. 25249.9)
This application is a continuation-in-part of Frank A. Stuart and Warren Lowe, US. application Serial No. 220,573, filed August 30, 1962, now abandoned.
This invention concerns novel lubricating oil compositions containing a combined detergent-corrosion inhibitor. More particularly, this invention concerns novel lubricat ing oil compositions containing amine carboxylic acid products as detergent-corrosion inhibitors.
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 temperatures. 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 acidic in nature, tending to form deposits which corrosively attack the various operating parts of the engine, such as the pistons, piston ring bearings, etc. For the purpose of preventingsuch deposition and corrosivity by these prodnets on the various engine parts, it is necessary to incorporate detergents and corrosion inhibitors in the lubricating oil composition, thus keeping the corrosion products dispersed in a condition unfavorable for metals.
Al-so, when water is present, iron will corrode or rust. Frequently, corrosion inhibitors will protect lead or copper parts from corrosion, but are ineffective against rusting. Alternatively, rusting may be inhibited while other types of corrosion persist.
Numerous detergents added to crankcase oils .to reduce the formation of sludges and varnish, as well as corrosive attack on metal parts, are metal organic compounds, particularly those compounds in which the metal is linked to an organic group through an oxygen atom. Although these metal-containing organic compounds have corro sion inhibition capability as well as detergency, they form undesirable ash deposits in the engine. These ash deposit-s lower engine performance by fouling spark plugs in valves, and contribute to preignition.
Pursuant to this invention, novel compositions which provide both corrosion inhibition and detergency are provided which are obtained by combining a polyamine with a high molecular weight succinic anhydride and then contacting the resulting product with a dicarboxylic acid, having the carboxyl groups separated by at least three annular carbon atoms (3 to 4 annular carbon atoms). The product is obtained by combining at an elevated temperature an alkenyl succinic anhydride, wherein the alkenyl group has from about 30 to 200 carbon atoms, with a polyamine free of unsaturation (both aliphatic and aromatic) and having from 2 to carbon atoms and from 2 to 10 nitrogen atoms; then combining at elevated temperatures the above product with an aromatic dicarboxylic acid, characterized by having carboxyl groups bonded to annular carbons separated by at least one annular carbon .atom (the carboxylic groups are, therefore, separated by at least three annular carbon atoms) and having a total of from 8 to 16 carbon atoms.
3,287,271 Patented Nov. 22, 1966 The alkenyl succinic anhydride reactant has the following formula:
wherein R is a hydrocarbon radical having from 3010 200 carbon atoms, preferably from about 50 to about 200 carbon atoms.
The R radical of the above formula, that is, the alkenyl radical, is readily obtained by polymerizing olefins of from 2 to 5 carbons, such as propylene, ethylene, isobutylene, pentene, etc., and mixtures thereof. Methods of polymerization are well known in the art, e.g., US. Patents Nos. 3,024,237, 3,024,195 and 3,018,291.
The amine with which the alkenyl succinic anhydride is reacted .is a polyamine having from 1 to 2 primary amino groups, is of from 2 to 20 carbon atoms, has from 1 to 11 nitrogen atoms, preferably 1 to 6 nitrogen atoms (as its only heteroatoms) and is free of unsaturation. The nitrogen atoms will be joined by :alkylene groups of from 2 to 6 carbon atoms, more usually of from 2 to 3 carbon atoms and, except the primary amino groups, will be substituted with hydrogen or lower alkyl, i.e., l to 6 carbon atoms, more usually of from 1 to 3 carbon atoms.
The organic polyamines of this invention will, for the most part, come within the scope of the following formula:
wherein T is alkylene of from 2 to 6 carbon atoms, more usually of from 2 to 3 carbon atoms, x-l-y is an integer of from 1 to 10, y is a cardinal number of from 0 to 2, and x is a cardinal number of from 0 to 10, Y is either hydrogen, --TNU U or lower alkyl, U and U being either hydrogen or lower alkyl. Usually, the polyamines of the above formula will have from 2 to 20 carbon atoms, more usually from 4 to 16 carbon atoms.
A preferred subgenus has the following formula:
wherein T is :alkylene of from 2 to 3 carbon atoms and x is an integer of from 1 to 10, more usually from 1 to 5. Illustrative of various alkylene amines and polyalkylene amines of the following formula are diethylene triamine, triethylene tetramine, dipropylene triamine, tetraethylene pentamine, pentaethylene hexamine, no'naethylene deoamine, etc.
Another preferred sub-genus is the alkyl-substituted alkylene diamines of the following formula wherein T is alkylene of from 2 to 6 carbon atoms, preferably 2 to 3 carbon atoms, and U and U are lower alkyl, i.e., alkyl of from 1 to 6 carbon atoms. Exemplifying compounds included in the above formula are dimethylaminopropylamine, diet-hylaminopropylamine, diethylaminobutylamine, dipropylaminobutylamine, diethyl aminoethylamine, etc. The total number of carbon atoms will generally be in the range of about 4 to 12, more usually 5 to 10.
A further subgenus has the following formula:
wherein T is alkylene of from 2 to 6 carbon atoms and U is hydrogen or an alkyl radical of from 1 to 6 carbon atoms. Illustrative of compounds exemplifying the above formula are N-(2-aminoethyl)piperazine, N-rnethyl-N'- (2 aminoet-hyDpiperaZine, N (3 aminopropylene) piperazine, etc.
For purposes of brevity, the products obtained by reacting alkenyl succinic anhydrides and the polyamines described above will be termed N-substituted alkenyl succinimides. The N-substituted alkenyl succinimides are prepared by reacting at elevated temperatures an alkenyl succinic anhydride with the desired polyamine, generally in the presence of an inert medium. The polyamine-anhydride mole ratio will generally be in the range of from 0.5:1 to 1:1, more usually in the range of 0.821.
The temperature for the reaction will generally be from about 200 to 500 F., more usually from 225 to 400 F.
The concentration of the reactants in the inert medium may range from 1 to 90 weight percent, but will more usually be from about 25 to 75 weight percent of the total reaction mixture.
The time for the reaction will generally be from about one-half hour to 24 hours or more, more usually in the range of about 1 to 12 hours.
During the reaction, it may be desirable to distill off the water that is formed from the reaction between the amine and the succinic anhydride; however, this is not essential to the reaction. The removal of the water may be carried out by any means known in the art. Subatmospheric pressure may be used with advantage.
The inert medium may be any dispersant or solvent that permits sufiicient contact between the reactants to provide a reasonable rate of reaction. The solvent should be a liquid under the reaction conditions. Conveniently, an oil of lubricating viscosity, which is also a solvent, can be used, e.g., petroleum oils, such as paraffinic, aromatic and naphthenic oils.
As already indicated, the carboxylic acids which find use in this invention are dicarboxylic acids of from 8 to 16 carbon atoms having from to 2 alkyl substituents of from 1 to 8 carbon atoms and the carboxyl groups are separated by at least three annular carbon atoms. The compounds may be described by the following formula:
I COzII where the brace indicates the two positions to which the carboxyl may be bonded, U is lower alkyl, i.e., alkyl of from 1 to 6 carbon atoms and x is a cardinal number of from 0 to 3, preferably from 0 to 1. Illustrative of compounds included in the above formula are isophthalic acid, terephthalic acid, 4-methyl isophthalic acid, 4-isopropyl isophthalic acid, 2-(tert.-butyl)terephthalic acid, 5-(tert.-butyl)-isophthalic acid, 2,5-(dimethyl)tereph thalic acid, 2,5-di(tert.-butyl)terephthalic acid, 4,6-di- (methyl)isophthalic acid, etc.
Generally, about 1 mole of the dicarboxylic acid will be combined with 1 mole of the N-substituted alkenyl succinimide. With N-substituted alkenyl succinimides which have more than one basic titratable amino nitrogen atom, more than 1 mole of carboxylic acid per mole of succinimide may be used. Representing the number of basic titratable amine nitrogen atoms of the succinimide with x, the number of carboxylic acids which may be used will range from 1 to x, more usually from 1 to x1, but not less than about 1.
On a weight basis, the succinimide-dicarboxylic acid weight ratio in the finished lubricating oil composition will be less than 200:1, preferably less than 100:1, and more preferably in the range 50-1: 1.
The combining of the succinimide with the carboxylic acid is achieved by heating the carboxylic acid and succinimide in the presence of an inert medium, generally an oil of lubricating viscosity, to a temperaturein the range of about 200 to about 300 F., more usually from about 270 to 290 F. When an oil of lubricating viscosity is used as the medium, the composition may be prepared as a concentrate which may be diluted with other oils to form the final lubricating oil composition.
The compounds of this invention may be used with various base oils which find use as lubricating oils, such as petroleum oils, i.e., naphthenic base, paraffin base and mixed base lubricating olls; synthetic oils, e.g., alkylene polymers (such as polymers of butylene, l-decene, etc.), alkylene oxide type polymers (e.g., propylene oxide polymers); dicarboxylic acid esters; liquid esters of acids of phosphorus; alkyl benzenes; alkyl biphenyl ethers; alkyl or aryl silicon compounds, etc.
The above base oils may be used individually or in combination whenever miscible or made so by the use of mutual solvents.
The compounds of this invention can be used in oils of lubricating viscosity in amounts of from about 0.1 to weight percent. When the oil is used in an engine, usually the amount will be about 0.1 to 10 weight percent, more usually 0.25 to 5 weight percent. However, the oil compositions may be prepared as concentrates and diluted prior to use. As concentrates, the amount of the active compound may range from about 10 to 80 weight percent.
In the finished oil the oil to be used in the enginethe dicarboxylic acid will be present in amounts of 0.001 to 0.75 weight percent, preferably 0.005 to 0.25 weight percent.
The detergent-corrosion inhibitors of this invention are preferably used in conjunction with a metal salt of a phosphorodithioate, particularly zinc 0,0-di(hydrocarbyl)-phosphorodithioate, wherein the hydrocarbyl group is of from 4 to 36 carbon atoms. (By hydrocarbyl is intended a monovalent organic radical composed solely of carbon and hydrogen which may be aliphatic, aromatic, alicyclic, or combinations thereof, e.g., aralkyl.) Usually about 6 to 50 mM./ kg. of the metal thiophosphate is used in the engine oil.
A preferred composition is to include with the detergentcorrosion inhibitors of this invention tricresyl phosphate. The addition of the tricresyl phosphate imparts the extreme pressure characteristics necessary for oils operating under heavy loads to avoid valve lifter scufiing and camshaft scuffing. The amount of the tricresyl phosphate will generally be in the range of about 0.1 to 3 weight percent.
The following examples are offered by way of illustration and not by way of limitation.
Example A A mixture of 1000 g. (1 mole) of polyisobutylene (approximate molecular weight=1000) and 98 g. (1 mole) of maleic anhydride were heated at 410 F. in a nitrogen atmosphere with agitation for a period of 24 hours. The reaction mixture was cooled to 150 F. and 700 cc. of hexane added; after which, the mixture was filtered. The hexane was removed in vacuo and the residue heated at 350 F. at 10 mm. Hg for 1 hour to remove traces of maleic anhydride. The polybutenyl succinic anhydride thus prepared had a saponification number of 79 (meq. KOH/ 1 g. of sample).
A portion of the above product (702 g., 0.45 mole) and 84 g. (0.45 mole) of tetraethylene pentamine was blended with agitation at F. in a nitrogen atmosphere. The temperature was then increased to 400 F. for a period of 1 hour, after which time the absolute pressure was reduced to about 200 mm. Hg during a period of 30 minutes to facilitate the removal of water. The reaction mixture was allowed to cool at room temperature while maintaining the reduced pressure.
Example B Into a reaction flask was introduced 18 g. (0.4 mole) of N-(B-aminoethyl)piperazine and 200 g. (0.127 mole) of the polyisobutenyl succinic anhydride prepared as described in Example A and mixed with agitation in a nitrogen atmosphere. The mixture was heated for 1 hour at 500 F., the pressure was then reduced to about 200 mm. Hg and water and unreacted piperazine removed. The mixture was then allowed to cool. The infrared spectrum Was consistent with the succinimide structure. Analysis: percent N=2.59.
Example I A mixture of 36 -g. of terephathalic acid, 540 g. of a product prepared as in Example A (the polyisobutenyl radical contained 66 carbon atoms) and 756 g. of a California SAE 30 base oil was agitated at 295300 F. for 1.5 hours under a blanket of nitrogen.
An oil concentrate of the above product was formed by blending with agitation 1250 g. of the above product and 1250 g. of a California paraffinic base oil having a viscosity of 150 SSU at 100 F. by heating the mixture at 280 F. for minutes.
Example 11 A succinimide prepared as described in Example A (1970 g.) was charged to a reaction vessel and blanketed with nitrogen. The succinimide was then heated to 265 F. at which temperature 56.2 g. of terephthalic acid was then added. The temperature was then raised to 300 F. during a period of 1 hour and maintained for an additional 4 hours, then cooled to 250 F. and filtered.
Example Ill The procedure of Example II was repeated using tert.- butyl isophthalic acid in place of terephthalic acid.
Example IV The procedure of Example II was repeated using isophthalic acid in place of terephthalic acid.
The compositions of this invention were tested under numerous conditions to demonstrate their effectiveness as a combined detergent-corrosion inhibitor.
The following data were obtained in a L-38 test, using a l-cylinder CLR engine. The test was for 40 hours, with an engine speed of 3150 rpm. The results are reported as the bearing weight loss in milligrams. The base oil was a Mid-Continent SAE 30 base oil. The succinimides prepared as previously described were combined with the indicated acid as described in exemplary Examples 1-14. The following table indicates the results.
5.5 wt. percent of mixed 012-1: alkyl rnethaerylate-vinyl pyrrolidone copolymer of mol. wt. -475,000 and 0.1 wt. percent of cetyl methacrylate polymer of mol. wt. -220,000 was also added.
1 The succinimide is one prepared as described in Example A.
2 TPA-terephthalic acid. B-IPA-5-tert-.butyl isophthalio acid.
9 ZnO-butyl Opentyl phosphorodithioate.
4 Zn0,0-alkylphenyl phosphorodithioate (alkyl of from 12-15).
Repeating the L-38 test, using 2.0 weight percent of a succinimide prepared as described in Example A in a Mid-Continent SAE 30 oil, without the presence of phospercent.
6 phorodithioate, for a period of 40 hours, the following results were obtained.
TABLE II Dicarboxylic 1 Acid Wt. Percent Bearing Weight Loss, mg.
2 1, 267 IPA 0.05 253 1 IPA-isophthalic acid. TPAterephthalic acid. 2 The run was carried out for only 20 hours.
Copper and lead strips were immersed in oil formula tions using California paraflin base oil having a viscosity of about 500 SSU at F. at a temperature of 340 F. for 20 hours and the weight loss determined at the end of this time. The following table indicates the results. The succinimide and carboxylic acid were combined as described in exemplary Examples 14.
TABLE III Strip Weight Succinimide, Dicarboxylic Acid, Loss (mg) wt. percent wt. percent Copper Lead 1 A-1 succinimide prepared as described in Ex. A. Total N, 1.8 wt. A-2 succinimide prepared as described in Ex. A. Total N, 2.2 wt. percent. B-l succinimide prepared as in Ex. B.
TPA-terephthalic acid. IPA-isophthalic acid. BIPA5-tert.- butyl isophthalic acid.
The following data were obtained in an L-4 Chevrolet Engine Test after 36 hours. The base oil was a California parafiin base oil having a viscosity of about 500 SSU at 100 F. The succinimide and carboxylic acid were combined as described in exemplary Examples 14. The results were reported as bearing weight loss in milligrams.
TABLE IV Snccinimide, wt.
Dicarboxylic Acid, Percent TABLE V Oil 1 Containing Reference Oil GM Additive 6063 Lifter (avg) 8.5 6. 6 Push Rods". 5. 7 6.8 Engine (avg.)-. 7.9 6. 7
1 The oil contained 10 rnMJkg. of M 0,0-dialkyl phosphorodithioate (alkyl 0! from 4 to 6 carbon atoms), 2 rnM./kg. of M 0,0-dialkylphenyl phosphorodithioate (alkyl of from 12 to 15 carbon atoms). 2 wt. percent of a succinimide prepared as described in Example A and 0.15 wt. percent of tert.-butyl isophthalie acid.
The compounds of this invention were also tested in the Steel Ball Rust Test. The test comprises immersing clean steel balls-whioh are pre-soaked in test oils for one minute at 115-l20 F. and then allowed to drain for one minutein an emulsified test oil (The emulsified test oil is prepared by rapidly stirring 300 ml. of the test oil with a 9 ml. solution of equal parts by volume of cone. HCl, conc. H 50 and glacial acetic acid.) for 20 hours with stirring at 140 F. The steel ball is then removed from the bath, rinsed with acetone and rated on a to scale, 10 being no rust, 0 being heavy rust. The oil used was a Mid-Continent SAE oil, containing 10 mM./leg. of Zn 0,0-dialkyl dithiophosphate (alkyl of of from 46 carbon atoms) and 2 mM./k-g. of Zn 0,0-dialkylphenyl phosphorodithioate (alkyl of from 12l5 carbon atoms).
l ASuceinimidc prepared as in Example A. B-Suecinimido prepared as in Example B.
2 AIPAtert.-a1nyl isophthalic acid.
BIPAtert.butyl isophthalic acid.
The presence of small amounts of the dicarboxylic acids of this invention greatly inhibit rusting. The preferred dicarboxylic acids are those having alkyl substituents of from 4 to 8 carbon atoms, e.g., tert.-butyl terephthalic acid, tert.-hexyl isophthalic acid, octyl isophthalic acid, etc.
The following data demonstrate the effectiveness of the combination of tricresyl phosphate wit-h the compositions of this invention as extreme pressure additives. The following table presents data obtained in a Falex Extreme Pressure Load Test. The figures are by loads in pounds at which there was lubrication failure. The base oil used was California pa rafiin base oil having a viscosity of about 500 SSU at 100 F.
TABLE VII 1 One weight percent of commercial oxidation inhibitor was included in the composition.
To demonstrate the detergency of the compositions of this invention, 2 weight percent of the succinimide prepared as described in Example A was used with 0.05 Weight percent of terephthalic acid in a solvent refined base oil SAE and tested under L-l, Supp. 1 conditions (MILL2104B, Supp. 1 specifications). The test was carried out for 120 hours. 100 indicates a completely filled groove, while 0 indicates a completely clean groove. 800 indicates a completely coated land, while 0 indicates a completely clean land. For the base oil without additive, the groove numbers were 20, 20, 10, 7 and the land numbers were 755, 800, 800. For the same oil with the additive, the groove numbers were 14, 5, 2, 1 and the iand numbers were 240, 60.
It is evident from the prior data that by combining the succinimide detergents havin-g basic amines with dicarboxylic acids, as defined in this invention, at elevated temperatures, compositions :are obtained which not only provide good detergency, but excellent corrosion inhibition, including rust inhibition. Under a variety of conditions, as demonstrated by generally accepted testing procedures, the compositions of this invention have provided excellent protect-ion for the engines. Furthermore, when combined with tricresyl phosphate, good extreme pressure characteristics are demonstrated.
As will be evident to those skilled in the art, various modifications on this process can be made or followed, in the light of the foregoing disclosure and discussion,
without departing from the spirit or scope of the disclo-' sure or from the scope of the following claims.
We claim:
1. A lubricating oil composition comprising an oil of lubricating viscosity, and a product obtained by (1) reacting at a temperature in the range of from about 200 F. to 500 F:
(a) an alkenyl succinic anhydride having from 30 to 200 carbon atoms in the alkenyl radical, with (b) an alkylene polyamine having from 1 to 2 primary amino groups, from 2 to 20 carbon atoms and from 1 to 11 nitrogen atoms; wherein the mole ratio of the polyamine to the anhydride is from about 0.5:1 to about 1:1; followed by (2) reacting at a temperature in the range of about 200 to 300 F.,
(a) the product of (1) with (b) an aromatic dicarboxylic acid of from 8 to 14 carbon atoms having from 0 to 2 alkyl substitutuents and wherein the carboxyl groups are bonded to annular carbon atoms separated by at least one annular carbon atom;
such that the weight ratio of the product of (1) to the dicarboxylic acid of (2) is less than 200:1, the product of reaction (1) and (2) being present in said oil composition in amount of 0.001 to 0.75 weight percent based on dicarboxylic acid content.
2. A composition according to claim 1 wherein said dicarboxylic acid is terephthalic acid.
3. A composition according to claim 1 wherein said dicarboxylic acid is isophthalic acid.
4. A composition according to claim 1 wherein said dicarboxylic acid is tert.-butyl isophthalic acid.
5. A composition according to claim 1 wherein said alkylene polyamine is a polyamine of the formula wherein T is alkylene of from 2 to 3 carbon atoms and x is an integer of from 1 to 10.
6. A composition according to claim 1 wherein said alkylene polyamine has the formula wherein T is alkylene of from 2 to 6 carbon atoms, and U and U4 are lower alkyl.
7. A composition according to claim 1 wherein said dicarboxylic acid is terephthalic acid and said alkylene polyamine is a polyamine of the formula wherein T is an alkylene of from 2 to 3 carbon atoms and x is an integer of from 1 to 10.
8. A composition according to claim 1 wherein said dicarboxylic acid is terephthalic acid and said alkylene polyamine has the formula wherein T is alkylene of from 2 to 6 carbon atoms, and U and U are lower alkyl.
9 10 9. A composition according to claim 1 having from FOREIGN PATENTS 0.1 to 3 weight percent tricresyl phosphate. 208,447 6/1957 Australia References Cited by the Examiner 1367939 6/1964 France UNITED STATES PATENTS 5 DANIEL E. WYMAN, Primary Examiner.
3,216,936 11/1965 Le Suer 252-S1.5 X P. P. GARVIN, Assistant Examiner.
Claims (2)
1. A LUBRICATING OIL COMPOSITION COMPRISING AN OIL LIBRICATING VISCOSITY AND A PRODUCT OBTAINED BY (1) REACTING AT A TEMPERATURE IN THE RANGE OF FROM ABOUT 200* F. TO 500*F: (A) AN ALKENYL SUCCINIC ANHYDRIDE HAVING FROM 30 TO 200 CARBON ATOMS IN THE ALKENYL RADICAL, WITH (B) AN ALKYLENE POLYAMINE HAVING FROM 1 TO 2 PRIMARY AMINO GROUPS, FROM 2 TO 20 CARBON ATOMS AND FROM 1 TO 11 NITROGEN ATOMS; WHEREIN THE MOLE RATIO OF THE POLYAMINE TO THE ANHYDRIDE IS FROM ABOUT 0.5:1 TO ABOUT 1:1; FOLLOWED BY (2) REACTING AT A TEMPERATURE IN THE RANGE PF ABOUT 200* TO 300*F., (A) THE PRODUCT OF (1) WITH (B) AN AROMATIC DICARBOXYLIC ACID OF FROM 8 TO 14 CARBON ATOMS HAVING FROM 0 TO 2 ALKYL SUBSTITUENTS AND WHEREIN THE CARBOXYL GROUPS ARE BOND TO ANNULAR CARBON ATOMS SEPARATED BY AT LEAST ONE ANNULAR CARBON ATOM; SUCH THAT THE WEIGHT RATIO OF THE PRODUCT OF (1) TO THE DICARBOXYLIC ACID OF (2) IS LESS THAN 200:1, THE PRODUCT OF REACTION (1) AND (2) BEING PRESENT IN SAID OIL COMPOSITION IN AMOUNT OF 0.001 TO 0.75 WEIGHT PERCENT BASED ON DICARBOXYLIC ACID CONTENT.
9. A COMPOSITION ACCORDING TO CLAIM 1 HAVING FROM 0.1 TO 3 WEIGHT PERCENT TRICRESYL PHOSPHATE.
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Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3447916A (en) * | 1965-11-10 | 1969-06-03 | Exxon Research Engineering Co | Acylated polyesters,polyesteramides,or polyamides |
US3538000A (en) * | 1967-11-22 | 1970-11-03 | Chevron Res | Silyl esters of terephthalic acid as corrosion inhibitors |
EP0144922A2 (en) * | 1983-12-03 | 1985-06-19 | Mineralölwerke Wenzel und Weidmann Zweigniederlassung der Fuchs Mineralölwerke GmbH, Mannheim | Lubricant |
EP0213027A1 (en) * | 1985-08-14 | 1987-03-04 | Institut Français du Pétrole | Dispersant additive compositions for lubricating oils, and their preparation |
US4780111A (en) * | 1985-11-08 | 1988-10-25 | The Lubrizol Corporation | Fuel compositions |
EP0399764A1 (en) | 1989-05-22 | 1990-11-28 | Ethyl Petroleum Additives Limited | Lubricant compositions |
US5069684A (en) * | 1989-12-18 | 1991-12-03 | Mobil Oil Corporation | Fuel and lube additives from polyether derivatives of polyamine alkenyl succinimides |
EP0460309A1 (en) * | 1990-06-06 | 1991-12-11 | Ethyl Petroleum Additives Limited | Modified dispersant compositions |
WO1993009206A1 (en) * | 1991-10-30 | 1993-05-13 | Mobil Oil Corporation | Fuel and lube additives from polyether derivatives of polyamine alkenyl succinimides |
US5597785A (en) * | 1991-10-02 | 1997-01-28 | R. T. Vanderbilt Company, Inc. | Succinimide derivatives of 2,5-dimercapto-1,3,4-thiadiazole |
US6001780A (en) * | 1998-06-30 | 1999-12-14 | Chevron Chemical Company Llc | Ashless lubricating oil formulation for natural gas engines |
US20030224948A1 (en) * | 2002-02-14 | 2003-12-04 | Dam Willem Van | Lubricating oil additive comprising EC-treated succinimide, borated dispersant and corrosion inhibitor |
US20040235682A1 (en) * | 2003-05-22 | 2004-11-25 | Chevron Oronite Company Llc | Low emission diesel lubricant with improved corrosion protection |
WO2006091387A2 (en) | 2005-02-18 | 2006-08-31 | The Lubrizol Corporation | Multifunctional dispersants |
US20080248980A1 (en) * | 2005-02-18 | 2008-10-09 | The Lubrizol Corporation | Lubricant Additive Formulation Containing Multifunctional Dispersant |
US20090270531A1 (en) * | 2008-04-25 | 2009-10-29 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
US20100160192A1 (en) * | 2008-12-22 | 2010-06-24 | Chevron Oronite LLC | lubricating oil additive composition and method of making the same |
US7947636B2 (en) | 2004-02-27 | 2011-05-24 | Afton Chemical Corporation | Power transmission fluids |
EP2938713A4 (en) * | 2012-12-28 | 2016-01-27 | Chevron Oronite Co | Ultra-low saps lubricants for internal combustion engines |
US20220380658A1 (en) * | 2019-10-31 | 2022-12-01 | Chevron Oronite Company Llc | Functionalized olefin oligomers |
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FR1367939A (en) * | 1962-08-30 | 1964-07-24 | California Research Corp | Lubricating oils containing corrosion inhibitors |
US3216936A (en) * | 1964-03-02 | 1965-11-09 | Lubrizol Corp | Process of preparing lubricant additives |
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FR1367939A (en) * | 1962-08-30 | 1964-07-24 | California Research Corp | Lubricating oils containing corrosion inhibitors |
US3216936A (en) * | 1964-03-02 | 1965-11-09 | Lubrizol Corp | Process of preparing lubricant additives |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3447916A (en) * | 1965-11-10 | 1969-06-03 | Exxon Research Engineering Co | Acylated polyesters,polyesteramides,or polyamides |
US3538000A (en) * | 1967-11-22 | 1970-11-03 | Chevron Res | Silyl esters of terephthalic acid as corrosion inhibitors |
EP0144922A2 (en) * | 1983-12-03 | 1985-06-19 | Mineralölwerke Wenzel und Weidmann Zweigniederlassung der Fuchs Mineralölwerke GmbH, Mannheim | Lubricant |
EP0144922A3 (en) * | 1983-12-03 | 1987-01-07 | Uk-Mineralolwerke Wenzel & Weidmann Gmbh | Lubricant |
EP0213027A1 (en) * | 1985-08-14 | 1987-03-04 | Institut Français du Pétrole | Dispersant additive compositions for lubricating oils, and their preparation |
US4780111A (en) * | 1985-11-08 | 1988-10-25 | The Lubrizol Corporation | Fuel compositions |
EP0388991A1 (en) * | 1985-11-08 | 1990-09-26 | The Lubrizol Corporation | Fuel compositions |
EP0399764A1 (en) | 1989-05-22 | 1990-11-28 | Ethyl Petroleum Additives Limited | Lubricant compositions |
US5069684A (en) * | 1989-12-18 | 1991-12-03 | Mobil Oil Corporation | Fuel and lube additives from polyether derivatives of polyamine alkenyl succinimides |
EP0460309A1 (en) * | 1990-06-06 | 1991-12-11 | Ethyl Petroleum Additives Limited | Modified dispersant compositions |
US5597785A (en) * | 1991-10-02 | 1997-01-28 | R. T. Vanderbilt Company, Inc. | Succinimide derivatives of 2,5-dimercapto-1,3,4-thiadiazole |
WO1993009206A1 (en) * | 1991-10-30 | 1993-05-13 | Mobil Oil Corporation | Fuel and lube additives from polyether derivatives of polyamine alkenyl succinimides |
US6001780A (en) * | 1998-06-30 | 1999-12-14 | Chevron Chemical Company Llc | Ashless lubricating oil formulation for natural gas engines |
US20030224948A1 (en) * | 2002-02-14 | 2003-12-04 | Dam Willem Van | Lubricating oil additive comprising EC-treated succinimide, borated dispersant and corrosion inhibitor |
US20040235682A1 (en) * | 2003-05-22 | 2004-11-25 | Chevron Oronite Company Llc | Low emission diesel lubricant with improved corrosion protection |
US7947636B2 (en) | 2004-02-27 | 2011-05-24 | Afton Chemical Corporation | Power transmission fluids |
US8183187B2 (en) | 2005-02-18 | 2012-05-22 | The Lubrizol Corporation | Lubricant additive formulation containing multifunctional dispersant |
US20090054278A1 (en) * | 2005-02-18 | 2009-02-26 | The Lubrizol Corporation | Multifunctional Dispersants |
US7902130B2 (en) | 2005-02-18 | 2011-03-08 | The Lubrizol Corporation | Multifunctional dispersants |
US20080248980A1 (en) * | 2005-02-18 | 2008-10-09 | The Lubrizol Corporation | Lubricant Additive Formulation Containing Multifunctional Dispersant |
WO2006091387A2 (en) | 2005-02-18 | 2006-08-31 | The Lubrizol Corporation | Multifunctional dispersants |
US20090270531A1 (en) * | 2008-04-25 | 2009-10-29 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
US8455568B2 (en) | 2008-04-25 | 2013-06-04 | Chevron Oronite Company Llc | Lubricating oil additive composition and method of making the same |
US20100160192A1 (en) * | 2008-12-22 | 2010-06-24 | Chevron Oronite LLC | lubricating oil additive composition and method of making the same |
EP2938713A4 (en) * | 2012-12-28 | 2016-01-27 | Chevron Oronite Co | Ultra-low saps lubricants for internal combustion engines |
US20220380658A1 (en) * | 2019-10-31 | 2022-12-01 | Chevron Oronite Company Llc | Functionalized olefin oligomers |
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