CA1237725A - Copper complexes of oxazolines and lactone oxazolines as lubricating oil additives - Google Patents
Copper complexes of oxazolines and lactone oxazolines as lubricating oil additivesInfo
- Publication number
- CA1237725A CA1237725A CA000462036A CA462036A CA1237725A CA 1237725 A CA1237725 A CA 1237725A CA 000462036 A CA000462036 A CA 000462036A CA 462036 A CA462036 A CA 462036A CA 1237725 A CA1237725 A CA 1237725A
- Authority
- CA
- Canada
- Prior art keywords
- oxazoline
- copper
- lubricating oil
- composition
- bis
- 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
Links
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 26
- -1 lactone oxazolines Chemical class 0.000 title claims description 8
- 239000000654 additive Substances 0.000 title description 17
- 150000001879 copper Chemical class 0.000 title description 5
- 150000002918 oxazolines Chemical class 0.000 title description 2
- 239000002270 dispersing agent Substances 0.000 claims abstract description 38
- 239000000203 mixture Substances 0.000 claims abstract description 25
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical class C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910052802 copper Inorganic materials 0.000 claims abstract description 19
- 239000010949 copper Substances 0.000 claims abstract description 19
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003921 oil Substances 0.000 claims abstract description 16
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 13
- 239000002966 varnish Substances 0.000 claims abstract description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 11
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 11
- 150000002596 lactones Chemical class 0.000 claims abstract 5
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 239000005749 Copper compound Substances 0.000 claims description 3
- 150000001414 amino alcohols Chemical class 0.000 claims description 3
- 150000001880 copper compounds Chemical class 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical class [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- BQVVSSAWECGTRN-UHFFFAOYSA-L copper;dithiocyanate Chemical class [Cu+2].[S-]C#N.[S-]C#N BQVVSSAWECGTRN-UHFFFAOYSA-L 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 235000013350 formula milk Nutrition 0.000 claims 4
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000004699 copper complex Chemical class 0.000 claims 2
- 229940014800 succinic anhydride Drugs 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 abstract description 7
- 230000001747 exhibiting effect Effects 0.000 abstract description 2
- 230000003064 anti-oxidating effect Effects 0.000 abstract 1
- VKLVNVJAXJEXPT-RJMJUYIDSA-N 4,5-dihydro-1,3-oxazole (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol Chemical compound O1C=NCC1.OC1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O2)CO)[C@H](O1)CO VKLVNVJAXJEXPT-RJMJUYIDSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 229920000180 alkyd Polymers 0.000 description 7
- 239000008101 lactose Substances 0.000 description 7
- 239000002480 mineral oil Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000003599 detergent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002597 lactoses Chemical class 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000010802 sludge Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 241000282320 Panthera leo Species 0.000 description 2
- 208000037062 Polyps Diseases 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007866 anti-wear additive Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 2
- 229960004419 dimethyl fumarate Drugs 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000009434 Actinidia chinensis Nutrition 0.000 description 1
- 244000298697 Actinidia deliciosa Species 0.000 description 1
- 235000009436 Actinidia deliciosa Nutrition 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- AEKNYBWUEYNWMJ-QWOOXDRHSA-N Pramiconazole Chemical compound O=C1N(C(C)C)CCN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(CO3)C=3C(=CC(F)=CC=3)F)=CC=2)C=C1 AEKNYBWUEYNWMJ-QWOOXDRHSA-N 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PDZKZMQQDCHTNF-UHFFFAOYSA-M copper(1+);thiocyanate Chemical compound [Cu+].[S-]C#N PDZKZMQQDCHTNF-UHFFFAOYSA-M 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002751 molybdenum Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/18—Complexes with metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
-
- 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
- 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
-
- 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
- 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
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/30—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US529,391 | 1983-09-06 | ||
| US06/529,391 US4486326A (en) | 1983-09-06 | 1983-09-06 | Copper complexes of oxazolines and lactone oxazolines as lubricating oil additives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1237725A true CA1237725A (en) | 1988-06-07 |
Family
ID=24109719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000462036A Expired CA1237725A (en) | 1983-09-06 | 1984-08-29 | Copper complexes of oxazolines and lactone oxazolines as lubricating oil additives |
Country Status (5)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4683070A (en) * | 1985-08-21 | 1987-07-28 | Munsell Monroe W | Determination of metal source in used oil |
| US4954276A (en) * | 1986-10-07 | 1990-09-04 | Exxon Chemical Patents Inc. | Lactone modified adducts or reactants and oleaginous compositions containing same |
| US4954277A (en) * | 1986-10-07 | 1990-09-04 | Exxon Chemical Patents Inc. | Lactone modified, esterified or aminated additives useful in oleaginous compositions and compositions containing same |
| US4866141A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified, esterfied or aminated additives useful in oleaginous compositions and compositions containing same |
| US4866140A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified adducts or reactants and oleaginous compositions containing same |
| US4906394A (en) * | 1986-10-07 | 1990-03-06 | Exxon Chemical Patents Inc. | Lactone modified mono-or dicarboxylic acid based adduct dispersant compositions |
| US5032320A (en) * | 1986-10-07 | 1991-07-16 | Exxon Chemical Patents Inc. | Lactone modified mono- or dicarboxylic acid based adduct dispersant compositions |
| US4866139A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified, esterified dispersant additives useful in oleaginous compositions |
| US4886612A (en) * | 1987-07-31 | 1989-12-12 | The Nisshin Oil Mills, Ltd. | Lubricating oil |
| US5043083A (en) * | 1988-06-16 | 1991-08-27 | Exxon Chemical Patents, Inc. | Method for preparing salts of polyolefinic substituted dicarboxylic acids in oleaginous mixtures of reduced viscosity |
| JPH02100081U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1989-01-30 | 1990-08-09 | ||
| US5344467A (en) | 1991-05-13 | 1994-09-06 | The Lubrizol Corporation | Organometallic complex-antioxidant combinations, and concentrates and diesel fuels containing same |
| IL100669A0 (en) | 1991-05-13 | 1992-09-06 | Lubrizol Corp | Low-sulfur diesel fuel containing organometallic complexes |
| US5360459A (en) | 1991-05-13 | 1994-11-01 | The Lubrizol Corporation | Copper-containing organometallic complexes and concentrates and diesel fuels containing same |
| US5376154A (en) | 1991-05-13 | 1994-12-27 | The Lubrizol Corporation | Low-sulfur diesel fuels containing organometallic complexes |
| TW230781B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-05-13 | 1994-09-21 | Lubysu Co | |
| JPH0877678A (ja) * | 1994-09-01 | 1996-03-22 | Nec Corp | ディスク装置およびその情報処理方法 |
| US8077625B1 (en) * | 2005-06-30 | 2011-12-13 | National Semiconductor Corporation | Apparatus and method for using a communication resource for performing a timing operation |
| RU2339683C1 (ru) * | 2007-11-09 | 2008-11-27 | Федеральное Государственное Образовательное Учреждение Высшего Профессионального Образования "Южный Федеральный Университет" | Пластичная смазка |
| RU2374311C1 (ru) * | 2008-07-03 | 2009-11-27 | Федеральное Государственное Образовательное Учреждение Высшего Профессионального Образования "Южный Федеральный Университет" | Пластичная смазка |
| RU2381260C1 (ru) * | 2008-10-15 | 2010-02-10 | Федеральное Государственное Образовательное Учреждение Высшего Профессионального Образования "Южный Федеральный Университет" | Пластичная смазка |
| DE102010051310A1 (de) * | 2010-11-16 | 2012-05-16 | Thüringisches Institut für Textil- und Kunststoff-Forschung e.V. | Verfahren zur Herstellung von Polyamidzusammensetzungen mit verbesserten thermooxidativen, antibakteriellen, licht- oder energieaktiven Eigenschaften |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2587955A (en) * | 1947-04-28 | 1952-03-04 | Shell Dev | Corrosion preventive composition |
| US4169836A (en) * | 1974-03-27 | 1979-10-02 | Exxon Research & Engineering Co. | Oxazoline containing additive |
| US4035309A (en) * | 1975-03-24 | 1977-07-12 | Exxon Research And Engineering Company | Metal-containing oxazoline additives and lubricating oils containing said additives |
| US4062786A (en) * | 1976-09-24 | 1977-12-13 | Exxon Research And Engineering Company | Lactone oxazolines as oleaginous additives |
| US4116876A (en) * | 1977-01-28 | 1978-09-26 | Exxon Research & Engineering Co. | Borated oxazolines as varnish inhibiting dispersants in lubricating oils |
| US4176074A (en) * | 1978-09-18 | 1979-11-27 | Exxon Research & Engineering Co. | Molybdenum complexes of ashless oxazoline dispersants as friction reducing antiwear additives for lubricating oils |
| US4176073A (en) * | 1978-09-18 | 1979-11-27 | Exxon Research & Engineering Co. | Molybdenum complexes of lactone oxazoline dispersants as friction reducing antiwear additives for lubricating oils |
| US4253978A (en) * | 1979-10-01 | 1981-03-03 | Mobil Oil Corporation | Phosphorus-containing compounds and lubricants containing same |
| US4292186A (en) * | 1979-12-04 | 1981-09-29 | Mobil Oil Corporation | Metal complexes of alkylsuccinic compounds as lubricant and fuel additives |
-
1983
- 1983-09-06 US US06/529,391 patent/US4486326A/en not_active Expired - Lifetime
-
1984
- 1984-08-29 CA CA000462036A patent/CA1237725A/en not_active Expired
- 1984-08-30 DE DE8484305957T patent/DE3475410D1/de not_active Expired
- 1984-08-30 EP EP84305957A patent/EP0136820B1/en not_active Expired
- 1984-09-06 JP JP59185465A patent/JPS6072996A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4486326A (en) | 1984-12-04 |
| EP0136820A3 (en) | 1986-12-17 |
| EP0136820A2 (en) | 1985-04-10 |
| DE3475410D1 (en) | 1989-01-05 |
| EP0136820B1 (en) | 1988-11-30 |
| JPH058759B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-02-03 |
| JPS6072996A (ja) | 1985-04-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1237725A (en) | Copper complexes of oxazolines and lactone oxazolines as lubricating oil additives | |
| US4176074A (en) | Molybdenum complexes of ashless oxazoline dispersants as friction reducing antiwear additives for lubricating oils | |
| CA1090320A (en) | Lubricating oil composition containing a dispersing- varnish inhibiting combination of nitrogen-containing additives | |
| CA2189387C (en) | Lubricant containing molybdenum compound and secondary diarylamine | |
| US4176073A (en) | Molybdenum complexes of lactone oxazoline dispersants as friction reducing antiwear additives for lubricating oils | |
| US4116876A (en) | Borated oxazolines as varnish inhibiting dispersants in lubricating oils | |
| CA1299185C (en) | Borated reaction products of succinic compounds as lubricant dispersants and antioxidants | |
| CA2008258C (en) | Oil soluble dispersant additives modified with monoepoxy monounsaturated compounds | |
| US4153564A (en) | Nitrogen-containing compounds and lubricant compositions containing same | |
| EP0698657B1 (en) | Process for the production of a lubricating oil additive having anti-wear properties. | |
| US4201683A (en) | Alkanol solutions of organo molybdenum complexes as friction reducing antiwear additives | |
| EP0217591B1 (en) | Normally liquid c18 to c24 monoalkyl catechols | |
| JPS6327399B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| CA1171093A (en) | Fuel and lubricating compositions | |
| US4142980A (en) | Mannich reaction products made with alkyphenol substituted aliphatic unsaturated carboxylic acids | |
| US4292184A (en) | Thio-bis-(hydrocarbon-bisoxazolines) as oleaginous additives for lubricants and fuels | |
| US3390083A (en) | Polyester additives for hydrocarbon oil compositions and process of preparing the same | |
| CA1180320A (en) | Co-dispersant stabilized friction modifier lubricating oil composition | |
| US4906394A (en) | Lactone modified mono-or dicarboxylic acid based adduct dispersant compositions | |
| KR950011357B1 (ko) | 황-함유 붕산 에스테르 | |
| JP3650635B2 (ja) | モリブデン含有摩擦低減用添加剤 | |
| US5160649A (en) | Multifunctional ashless detergent additives for fuels and lubricants | |
| US5597785A (en) | Succinimide derivatives of 2,5-dimercapto-1,3,4-thiadiazole | |
| US4867892A (en) | Antiwear additives for lubricating oils | |
| US5154844A (en) | Lubricant additives and their production |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |