NO781339L - Antioksydasjonspreparater. - Google Patents
Antioksydasjonspreparater.Info
- Publication number
- NO781339L NO781339L NO781339A NO781339A NO781339L NO 781339 L NO781339 L NO 781339L NO 781339 A NO781339 A NO 781339A NO 781339 A NO781339 A NO 781339A NO 781339 L NO781339 L NO 781339L
- Authority
- NO
- Norway
- Prior art keywords
- nickel
- thiobis
- mixture according
- preparation
- coadditive
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 20
- 230000003064 anti-oxidating effect Effects 0.000 title claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 58
- 229910052759 nickel Inorganic materials 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 31
- 150000004982 aromatic amines Chemical class 0.000 claims description 20
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 18
- -1 2,5-bis-t-butyl-aminobenzoquinone Chemical compound 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000003078 antioxidant effect Effects 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000003921 oil Substances 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 229940031826 phenolate Drugs 0.000 claims description 7
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 239000012530 fluid Substances 0.000 claims description 6
- 230000001050 lubricating effect Effects 0.000 claims description 6
- 229950000688 phenothiazine Drugs 0.000 claims description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 5
- 239000002480 mineral oil Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- 150000002816 nickel compounds Chemical class 0.000 claims description 4
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 2
- FLSKKFALEYBSJE-UHFFFAOYSA-N 2,6-ditert-butyl-4-[1-(3,5-ditert-butyl-4-hydroxyphenyl)butyl]phenol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1C(CCC)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FLSKKFALEYBSJE-UHFFFAOYSA-N 0.000 claims description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 230000005540 biological transmission Effects 0.000 claims description 2
- 239000012208 gear oil Substances 0.000 claims description 2
- 239000004519 grease Substances 0.000 claims description 2
- 239000010720 hydraulic oil Substances 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- BIDXDCXNYXAQRR-UHFFFAOYSA-N 3-phenyl-4-sulfanylidenecyclohexa-2,5-dien-1-one Chemical compound O=C1C=CC(=S)C(C=2C=CC=CC=2)=C1 BIDXDCXNYXAQRR-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims 2
- OFGANEYOOWPTPZ-UHFFFAOYSA-N 2,5-bis(2,4,4-trimethylpentan-2-ylamino)cyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)(C)CC(C)(C)NC1=CC(=O)C(NC(C)(C)CC(C)(C)C)=CC1=O OFGANEYOOWPTPZ-UHFFFAOYSA-N 0.000 claims 1
- FIHHNVBNSUAJPS-UHFFFAOYSA-N 2,5-diphenyl-4-sulfanylidenecyclohexa-2,5-dien-1-one Chemical compound O=C1C=C(C=2C=CC=CC=2)C(=S)C=C1C1=CC=CC=C1 FIHHNVBNSUAJPS-UHFFFAOYSA-N 0.000 claims 1
- XLFVJRPJMOJTQG-UHFFFAOYSA-N 3-[2,5-di(octan-4-yl)phenyl]-4-sulfanylidenecyclohexa-2,5-dien-1-one Chemical compound CCCCC(CCC)C1=CC=C(C(CCC)CCCC)C(C=2C(C=CC(=O)C=2)=S)=C1 XLFVJRPJMOJTQG-UHFFFAOYSA-N 0.000 claims 1
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 claims 1
- XAXLGJQQVQQVBU-UHFFFAOYSA-N 4-sulfanyl-2,5-bis(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC(S)=C(C(C)(C)CC(C)(C)C)C=C1O XAXLGJQQVQQVBU-UHFFFAOYSA-N 0.000 claims 1
- 241001649081 Dina Species 0.000 claims 1
- 239000000295 fuel oil Substances 0.000 claims 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 description 8
- 150000002815 nickel Chemical class 0.000 description 7
- 150000004053 quinones Chemical class 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000010525 oxidative degradation reaction Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000010802 sludge Substances 0.000 description 3
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 2
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- ZLUHLPGJUZHFAR-UHFFFAOYSA-N n-[4-(2,4,4-trimethylpentan-2-yl)phenyl]naphthalen-1-amine Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1NC1=CC=CC2=CC=CC=C12 ZLUHLPGJUZHFAR-UHFFFAOYSA-N 0.000 description 2
- AEKBDRSZQRZRLL-UHFFFAOYSA-L nickel(2+);2-(2-oxidophenyl)sulfanylphenolate Chemical class [Ni+2].[O-]C1=CC=CC=C1SC1=CC=CC=C1[O-] AEKBDRSZQRZRLL-UHFFFAOYSA-L 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- QKHCUKLDPPXGFA-UHFFFAOYSA-N 1-phenoxy-2-(2-phenoxyphenoxy)benzene Chemical class C=1C=CC=C(OC=2C(=CC=CC=2)OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 QKHCUKLDPPXGFA-UHFFFAOYSA-N 0.000 description 1
- GQGTXJRZSBTHOB-UHFFFAOYSA-N 1-phenoxy-4-(4-phenoxyphenoxy)benzene Chemical class C=1C=C(OC=2C=CC(OC=3C=CC=CC=3)=CC=2)C=CC=1OC1=CC=CC=C1 GQGTXJRZSBTHOB-UHFFFAOYSA-N 0.000 description 1
- ZDXGQHXSMPGQRI-UHFFFAOYSA-N 2,6-ditert-butyl-3-[(2,4-ditert-butyl-3-hydroxyphenyl)methyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC=C1CC1=CC=C(C(C)(C)C)C(O)=C1C(C)(C)C ZDXGQHXSMPGQRI-UHFFFAOYSA-N 0.000 description 1
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 1
- IJVLHPVHEKQGKY-UHFFFAOYSA-N 4-(4-anilinonaphthalen-1-yl)sulfanyl-n-phenylnaphthalen-1-amine Chemical compound C=1C=C(SC=2C3=CC=CC=C3C(NC=3C=CC=CC=3)=CC=2)C2=CC=CC=C2C=1NC1=CC=CC=C1 IJVLHPVHEKQGKY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000012854 evaluation process Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical class [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
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- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
-
- 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
- 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
- C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- 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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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/08—Aldehydes; Ketones
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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Description
" Antioksydasjonspreparater".
Denne oppfinnelse angår blandinger som har utmerkede antioksydasjonsegenskaper og som omfatter organiske medier som vanligvis er mottagelige for oksydasjon, så som oljer og fett med smørende viskositet og forskjellige andre funksjonelle fluider innbefattet mineralske og syntetiske hydrokarbonfluider, også plast og gummier, hvilke inneholder en mengde som er tilstrekkelig til å gi antioksydative egenskaper dertil av en blanding av visse nikkel-organosvovel-holdige komplekser i kombinasjon med arylaminer og/eller hindrede fenoler og kinoner.
Det er kjent å anvende blandinger av svovelholdige forbindelser, f.eks. diestere av tiodikarboksylsyrer og hindrede fenoler, til å stabilisere organiske polymerer mot eksponering for lys og luft, se US-patentskrift nr. 3.644.282 og US-patentskrift nr. 3.652.495. Det er også kjent å anvende arylaminer så som fenylnaftylaminer som antioksydasjonsmidler for smøreoljer og for forskjellige polymerer, se US-patentskrift nr. 3.649.690og US-patentskrift nr. 3.781.361. Det er også kjent å anvende nikkel-forbindelser f.eks. bis(stilbenditiolato)nikkel, som antioksydasjonsmiddel for plastmaterialer, se britisk patentskrift nr. 1.263.910 (1972).
Denne søknad er imidlertid rettet mot den oppdagelse at preparater med forbedrede antioksyderende egenskaper blir til-veiebragt når en blanding av visse organonikkel-komplekser og/eller arylaminer*hindrede fenoler, kinoner eller blandinger derav blir kombinert i passende mengder.
Søknaden er derfor rettet mot preparater som omfatter en hoveddel av et organisk medium som vanligvis er mottagelig for oksydasjon, og en mindre del, som er tilstrekkelig til å gi anti-r* oksyderende egenskaper dertil, av en blanding som er løselig deri og vesentlig bestående av et organosvovelholdig nikkel-kompleks som beskrevet her i kombinasjon med et arylamin og/eller en hindret fenol og/eller et kinon.
Denne søknad er følgelig mer spesielt rettet mot en smøremiddelblanding som omfatter en hovedmengde med en smøremiddel-basis og en mindre mengde, som er effektiv til å stabilisere nevnte blanding mot oksydativ avbygning, av et nikkel-kompleks valgt fra gruppen bestående av nikkel-tiobis-alkylfenolater, nikkel-tiobis-alkylfenol-fenolater og amin-komplekser av nikkel-tiobis-alkylfenolater hvori alkylgruppene har fra 1 til ca. 30 karbonatomer i kombinasjon med de ovenfor omtalte koadditiver.
Nikkel-kompleksene i samsvar med den her åpenbarte oppfinnelse er spesielt effektive mot oksydativ avbygning i slike organiske medier som f.eks. oljer med smørende viskositet og andre smørende medier og/eller funksjonelle fluider så som hydrocrackede smøreoljer, hydrauliske oljer, mineralske eller syntetiske oljer eller fraksjoner derav, automobiloljer, gearoljer, overførings-væsker, vokser, fett og andre former for smøreblandinger som vanligvis behøver nærvær av et antioksydasjonsmiddel for å hindre og/eller inhibere den avbyggende virkning av oksydasjon.
De organosvovelholdige nikkel-komplekser og koadditivene*d.v»s. arylaminer, hindrede fenoler, kinoner eller blandinger derav, kan effektivt anvendes i hvilken som helst mengde som ;er tilstrekkelig til å gi de her omfattede blandinger den ønskede grad av antioksydativ beskyttelse. I mange tilfeller blir nikkel-komplekset effektivt anvendt i en mengde fra ca. 0,01 til ca. 5 vekt%, og fortrinnsvis i en mengde på fra ca. 0,1 til ca. 2 vekt%, av den totale vekt av f.eks. en smøremiddelblanding. Uttrykket "nikkel-kompleks" er når det anvendes her også ment å innbefatte nikkel-forbindelser som har en chelatring-dannelse. Arylaminene, de hindrede fenoler og kinoner kan hver effektivt anvendes i de samme vektforhold som nikkel-komplekset som er fra ca. o,Ol til ca. 5 vekt% av hver*og fortrinnsvis fra ca. 0,1 til ca. 2 vekt% av hver, basert på den totale vekt av de beskrevne blandinger.Blandingene kan følgelig i henhold til dette inneholde fra ca. 0,04 til ca. 20 vekt% av additiv-kombinasjonen av organonikkel-kompleks, arylamin, hindret fenol eller kinon og fra ca.0,04 til 10 vekt% av nikkel-komplekset og et arylamin, hindret fenol eller kinon.Blandingene inneholder imidlertid fortrinnsvis fra ca. 0,5 - 2,5 til 1 vekt% av nikkel-kompleks i forhold til arylamin, hindret fenol eller kinon på mol-basis, og fortrinnsvis fra 0,5 - 1,5 til 1.
Som angitt senere kan de organiske svovelholdige nikkel-komplekser inkorporeres i sraøremiddelmedier som innbefatter mineralske og syntetiske basisoljer med smørende viskositet og/eller fett, i hvilke hvilken som helst av de forannevnte oljer anvendes som hjelpemidler. Derfor kan også syntetiske oljer beskyttes effektivt mot oksydativ avbygning eller de kan også anvendes i kombinasjon med mineraloljer eller som fett-hjelpemidler. Typiske syntetiske hjelpemidler innbefatter polyisobutylen, polybutener, hydrogenerte polydecener, polypropylenglykol, polyetylenglykol, trimetylolpropanestere, neopentyl- og pentaerytritolestere, di (2-etylheksyl)sebacat, di(2-etylheksylJadipat, dibutylftalat, fluor-karboner*silikatestere, silaner, estere av fosforholdige syrer, flytende urinstoffer, ferrocenderivater, hydrogenerte mineraloljer, polyfenoler av kjede-type, siloksaner og silikoner (polysiloksaner) t alkyl-substituerte difenyletere så som typisk en butyl-substituert bis-(p-fenoksy-fenylJeter, fenoksy-fenyleter, etc.
Spesielt ønskede organiske svovelholdige nikkel-komplekser i henhold til foreliggende oppfinnelse innbefatter nikkel-tiobisfenolater, nikkel-tiobisfenol-fenolater, (tiobis-alkyl-fenolato)alkylamin-nikkel, (tiobis-alkyl-fenolato)arylamin-nikkel.
Det kan anvendes nikkel-tiobis-alkylfenolater som for eksempel har strukturens
i hvilkenR' er hydrogen eller en primær eller sekundær alkylgruppe med fra 1 til ca. 30 karbonatomer, og R er en alkylgruppe med fra 1 til ca. 30karbonatomer i hvilken hydrogenatomene i det ring-festede karbon er substituert med metyl (CH^J eller større alkylgrupper (f.eks. CgH^).
Representative for nikkel-tiobisfenolatene er et nikkel- tiobisalkylfenolat, nikkel-2,2 '-tiobis-(4-t-oktyl)-fenolat, som har nevnte struktur i hvilken R<*>er CgH^, 1,1,3,3-tetrametylbutyl eller annen 1,1-dimetylheksyl-isomer. Det kan her anvendes nikkel-tiobis-alkylfenol-fenolater som for eksempel har strukturen?
i hvilken R er en alkylgruppe med fra 1 tii '.ca.. 3.0. karbonatpmer.
Representativ . for nikkel-tiobis-alkylfenol-fenolatene er nikkel-2,2'-tiobis-(4-t-oktyl)fenol-fenolat med den ovenfor angitte struktur II i hvilken R er CgH^, 1,1,3,3-tetrametylbutyl eller annen 1,1-dimetylheksyl-alkylgruppe.
Struktur II kan omdannes i visse løsningsmidler, så som etanol, metanol, 2-propanol og aceton, til struktur I med ekstru-sjon av tiobis-alkylfenol.
Representativ for nikkel-tiobis-alkyl-fenolat og alkyl-arainer er [2,2*-tiobis-(4-tert-oktylfenolato) ]-n-butylamin-nikkel med strukturen:
og dens homolog [2,2'-tiobis-(4-tert-oktylfenolato) ]-n-oktylamin-nikkel og dens analog [2,2'-tiobis-(4-tert-oktylfenolato)]-pyridin-nikkel.Representativ for andre nikkel-tiobis-alkylfenolat-amin-komplekser er anilin-nikkel-tiobis-alkylfenolatet [2,2'-tiobis-(4-tert-oktylfenolato) ]-anilin med strukturen?
Arylaminene som anvendes her er fortrinnsvis valgt fra gruppen bestående av de følgende: N-fenyl-l-naftylamin, N-(4'-t-oktylfenyl)-l-naftylamin, N-fenyl-2-naftylamin, 4,4'-tiobis(W-fenyl-l-naftylamin)/1,1•-tiobis(W-fenyl-2-naftylamin), difenylamin, 4,4'-di-t-oktyldifenylamin, dinaftylamin, 4-decoksydifenylamin og fenotiazin. Spesielt foretrukket er fenyl-naftylaminer så som N-fenyl-l-naftylamin, N-(4-t-oktylfenyl)-l-naftylamin og H-fenyl-2-naftylamin. Det skal imidlertid forstås at dette er en ikke- begrensende liste og at ethvert arylamin som er passende i be-traktning av slike som er åpenbaret ovenfor, kan anvendes. For formålene med denne søknad skal det forstås at uttrykket arylaminer er ment å innbefatte arylaminokinoner t arylaminohydrokinoner og fenotiaziner.
Enhver egnet hindret fenolisk forbindelse kan anvendes her. Foretrukne er slike som er valgt fra den følgende ikke-uttømmende liste: 2,6-di-t-butyl-p-kresol, 4,4'-metylenbis-(2-6-di-t-butyl-m-kresol), 4,4'-butylidenbis(6-t-butyl-m-kresol, 4,4<*->metylenbis-(2,6-di-t-butylfenol), 2,6-di-t-butylfenol og 4,4'-butylidenbis-(2,6-di-t-butylfenol), 2,4,6-tri-t-butylfenol. Spesielt foretrukket er 4,4'-metylenbis-(2>6-di-t-butylfenol).
Egnede kinoner eller hydrokinoner innbefatter 2-fenyltiokinon, 2,5-bis-fenyltiokinon, alkyltiohydrokinoner beskrevet i US-patentskrift nr. 2.738.331, 2*5-bis-t-oktylaminobenzokinon, 2 t5-bis-dibutylamino<k>inonerog andre aminokinoner, naftokinoner eller substituerte derivater derav så som beskrevet i US-patentskrift nr. 3.445.391.
For å vurdere effektiviteten av preparater omfattende organosvovel-holdige nikkel-komplekser i kombinasjon med arylaminer og/eller hindrede fenoler eller kinoner som åpenbart ved foreliggende oppfinnelse, ble additivene angitt i tabellene neden-for testet i samsvar med de følgende vurderingsprosesser (aminene, de hindrede fenoler, kinoner og nikkel-kompleksene var generelt fra kommersielle kilder dersom ikke annet er angitt).
Katalytisk oksydasjbnstest
En prøve av basis-smøremidlet blir anbragt i en ovn ved en ønsket temperatur.Tilstede i prøven er de følgende metaller som enten er kjente for å katalysere organisk oksydasjon eller er vanlig anvendte konstruksjonsmaterialer.
a. 100,62 cm av sandblåst jerntråd,
b. 5,03 cm av polert kobbertråd,
c. 5,61 cm<2>av polert aluminiumtråd og
d. 1,08 etar av polert bly-overflate.
Tørr luft blir ført gjennom prøven med en hastighet på ca.
5 liter pr. time.
En gruppe med additiver (tabell 1) ble testet i en løsnings-middel -raf finert mineralolje. En annen gruppe (tabellene 2 og 3) ble testet i nærvær av et syntetisk smøremiddel omfattende en pentaerytritol-ester fremstilt fra en blanding av C5-Cg eller Cg og Cg monokarboksylsyrer. Den første gruppe (tabell 1) ble testet ved 162,8°C med en 40 timers luftbehandling og den annen gruppe (tabellene 2 og 3) ble testet ved 232,2°C med en 24 timers luftbehandling.<p>røvene ble undersøkt med hensyn til økning i surhet;(NN) og kinematisk viskositet (KV) før og etter behandlingen, vekt-tapet av blyprøvestykket og den relative mengde med synlig slam.Resultatene er oppført i de respektive tabeller 1, 2 og 3.
Resultatene ovenfor viser at additivene i henhold til denne oppfinnelse er nyttige til å hindre oksydativ nedbrytning av organiske fluider og andre organiske medier. Etter eksponering for høye temperaturer og luft i lange tidsperioder, er ikke-inhiberte mineraloljer spesielt mottagelige for oksydasjon. Tilsetningen av en liten mengde av de nye preparater i henhold
til denne oppfinnelse reduserer i betydelig grad deres forringelse. Dessuten virker nikkel-kompleksene som antislammidler, se tabell 3, eksemplene 6, 7 og 8 eller 24 og 25. PAN eller fenotiazin alene har synlig slam men PAN eller fenotiazin pluss et organisk nikkel-kompleks i samsvar med oppfinnelsen har lite om det i det hele tatt er noe. Disse preparater kan inneholde andre additiver som tilveiebringer en rekke ytterligere egenskaper, så som overflate-aktive midler, ekstreme trykk-midler, hellepunkt-nedsettende midler, ytterligere stabiliseringsmidler, viskositets-regulerende midler og lignende.
Denne oppfinnelse er beskrevet med hensyn til de spesi-fikke eksempler, men omfanget av oppfinnelsen er imidlertid ikke begrenset ved dette.
Claims (23)
1. Antioksydasjons-additivblanding, karakterisert ved at den omfatter (i) et svovelholdig nikkel-kompleks valgt fra nikkel-tiobis-alkylfenolater, nikkel-tiobis-alkylfenol-fenolater og atain-komplekser av nikkel-tiobis-alkylfenolater i hvilke alkylgruppene har fra 1 til 30 karbonatomer» i kombinasjon méd (ii) et koadditiv som er et arylamin, en hindret fenol og/eller et kinon, i hvilken vektforholdet mellom nikkel-koarplekset og arylaiainet, det hindrede fenol og/eller kinonet er fra 0,01 sl til 5,0sl.
2. Blanding i henhold til krav 1»karakterisert ved at koadditivet (ii) er et arylamin valgt fra N-fenyl-l-naftylamin, sr-fenyl-2-naf tylamin, N- (4-t-oktylf enyl) -1-na f tylamin, 4,4 •-tiobis-(N-fenyl-l-naftylamin), 1,1'-tiobis-(H-fenyl-2-naftylamin), 4.4 <*-> di-t-oktyl-difenylasain, difenylamin, tri fenylamin, dina f tylamin og fenotiazin.
3. Blanding i henhold til krav 2, karakterisert ved at arylaminet er N-fenyl-l-na ftylamin.
4. Blanding i henhold til krav 2, karakterisert ved at arylaminet er fenotiazin.
5. Blanding i henhold til krav 2, karakterisert ved at arylaminet er 4,4'-di-t-oktyldi fenylamin eller decoksydi-fenylarain.
6. Blanding i henhold til hvilket som helst av kravene 1 til 5, karakterisert ved at koadditivet (ii) er en hindret fenol valgt fra 2,6-di-t-butyl-p-kresol, 4,4 <*> -metylenbis-(2-6-di-t-butyl-m~ krGSol), 4,4 <*> -butylidenbis(6-t-butyl-ar-kresol), 4,4'-metylenbis(2,6-di-t-butylfenol), 2,S-di-t-butylfenol og 4,4 '-butylidenbis(2,6-di-t-butylfenol).
7. Blanding i henhold til krav 6, karakterisert ved at den hindrede fenol er 4,4 <*> -raetylenbis(2,6-di-t-butylfenol).
8. Blanding i henhold til hvilket som helst av kravene 1 til 7, karakterisert ved at koadditivet (ii) er et kinon valgt fra 2,5-bis-t-oktylaminobenzokinon, 2,5-bis-t-butyl-aminobenzokinon, 2-fenyltiobenzokinon, 2,5-bisfenyltiobenzokinon, 2,5-bis-4-oktylfenyltiobenzokinon og 2,5-bis-t-oktyltiohydrokinon.
9. preparat i henhold til krav 8, karakterisert ved at kinonet er 2-f enyltiobenzokinon.
10 . Preparat i henhold til krav 8, karakterisert ved at kinonet er 2,5-bis-t-oktylaarinobensokinon.
11. preparat i henhold til hvilket sora helst av kravene 1 til lo. karakterisert ved at nikkel-kompiekset (i) er nikkel-2,2'-tiobis-(4-t-oktyl)fenol-fenolat.
12. Blanding i henhold til hvilket som helst av kravene 1 til lo, karakterisert ved at nikkel-komplekset (i) er (2,2'-tiobis-(4-tert-oktylfenolato)-n-butylamin-nikkel.
13. Blanding i henhold til hvilket som helst av kravene 1 til 10 , karakterisert ved at nikkel-komplekset (i) er nikkel-2,2 *-tiobis(4-t-oktyl)fenolat.
14. Blanding i henhold til hvilket som helst av kravene 1 til lø, karakterisert ved at nikkel-koaplekset (i) er (2,2•-tiobis-(4-t-oktylf enolato))-n-oktylamin-nikkel.
15. Blanding i henhold til hvilket som helst av kravene 1 til 10, karakterisert ved at nikkel-koarplekset (i) er (2,2'-tiobis-(4-t-oktylfenolato))anilin-nikkel.
16. Blanding i henhold til hvilket som helst av kravene 1 til 10, karakterisert ved at nikkel-komplekset (i) er (2,2'-tiobis-(4-t-oktylfenolato))pyridin-nikkel.
17. Blanding i henhold til krav 1, karakterisert ved at nikkel-komplekset (i) er valgt fra nikkel-2,2'-tiobis-(4-t-oktyl)fenol-fenolat, (2,2'-tiobis-(4-t-oktyl-fenolato))anilin-nikkel og nikkel-2,2'-tiobis-(4-t-oktyl)fenolat og koadditivet (ii) er et arylamin valgt fra 51-f eny 1-1-na f tylamin, 4,4-di-t-oktyldifenylamin, H-(4, -t-oktylfenyl)-l-naftylarain og fenotiazin.
18. preparat omfattende en hoveddel av et organisk medium som vanligvis er mottagelig for oksydasjon, og en mindre del, tilstrekkelig til å gi antioksyderende egenskaper, av en blanding i henhold til hvilket som helst av kravene 1 til 17*
19. Preparat i henhold til krav 18, karakterisert ved at det organiske medium er en olje med smørende viskositet,
et fett, en brennstoff-olje, en hydrocracket olje, en hydraulisk olje, en mineralolje eller fraksjoner derav, en gearolje, et over-førings-fluidum eller en voks.
20 . Preparat i henhold til krav 18 eller 19, karakterisert ved at mengden av nikkel-komplekset (i) i preparatet er fra 0,0 1 til 5 vekt%
21. Preparat i henhold til krav 18 eller 19, karakterisert ved at mengden av nikkel-komplekset (i) i preparatet er fra0 ,1 til 2 vékt%.
22. Preparat i henhold til hvilket som helst av kravene 18 til 21, karakterisert ved at mengden av koadditivet (ii) i preparatet er fra0 ,0 1 til 5 vekt%.
23. preparat i henhold til hvilket som helst av kravene 18 til 21, karakterisert ved at mengden av koadditivet (ii) i preparatet er fra 0,1 til 2 vékt%.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/788,213 US4090970A (en) | 1977-04-18 | 1977-04-18 | Antioxidant compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO781339L true NO781339L (no) | 1978-10-19 |
Family
ID=25143794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO781339A NO781339L (no) | 1977-04-18 | 1978-04-17 | Antioksydasjonspreparater. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4090970A (no) |
| JP (1) | JPS53130287A (no) |
| AT (1) | AT366093B (no) |
| AU (1) | AU513994B2 (no) |
| BE (1) | BE865853A (no) |
| BR (1) | BR7802367A (no) |
| CA (1) | CA1103911A (no) |
| CS (1) | CS212271B2 (no) |
| DE (1) | DE2816653A1 (no) |
| DK (1) | DK166178A (no) |
| ES (1) | ES468339A1 (no) |
| FI (1) | FI780684A (no) |
| FR (1) | FR2388035A1 (no) |
| GR (1) | GR64220B (no) |
| IT (1) | IT1094918B (no) |
| NL (1) | NL7804063A (no) |
| NO (1) | NO781339L (no) |
| NZ (1) | NZ186523A (no) |
| PT (1) | PT67832B (no) |
| SE (1) | SE7803941L (no) |
| ZA (1) | ZA781738B (no) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4119548A (en) * | 1977-10-28 | 1978-10-10 | Mobil Oil Corporation | Reaction product of nickel thiobis(alkylphenolate) and thiobis(alkylphenol) and organic compositions containing the same |
| US4536192A (en) * | 1978-04-24 | 1985-08-20 | Mobil Oil Corporation | Additives for improving the research octane number of liquid hydrocarbon fuels |
| US4211663A (en) * | 1978-05-01 | 1980-07-08 | Mobil Oil Corporation | Alkali metal containing transition metal complexes of thiobis (alkylphenols) as stabilizers for various organic media |
| US4225448A (en) * | 1978-08-07 | 1980-09-30 | Mobil Oil Corporation | Copper thiobis(alkylphenols) and antioxidant compositions thereof |
| US4240958A (en) * | 1978-12-20 | 1980-12-23 | Mobil Oil Corporation | Process of preparing sulfurized olefins |
| US4217232A (en) * | 1978-12-21 | 1980-08-12 | Mobil Oil Corporation | Antioxidant compositions |
| US4243539A (en) * | 1979-08-06 | 1981-01-06 | Mobil Oil Corporation | Antioxidant stabilized lubricant compositions |
| US4370246A (en) * | 1981-04-27 | 1983-01-25 | Chevron Research Company | Antioxidant combinations of molybdenum complexes and aromatic amine compounds |
| US4534873A (en) * | 1983-09-28 | 1985-08-13 | Clark Gary G | Automotive friction reducing composition |
| US5344467A (en) * | 1991-05-13 | 1994-09-06 | The Lubrizol Corporation | Organometallic complex-antioxidant combinations, and concentrates and diesel fuels containing same |
| US6599865B1 (en) * | 2002-07-12 | 2003-07-29 | Ethyl Corporation | Effective antioxidant combination for oxidation and deposit control in crankcase lubricants |
| US20220033730A1 (en) * | 2018-11-28 | 2022-02-03 | Basf Se | Antioxidant mixture for low viscous polyalkylene glycol basestock |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734867A (en) * | 1956-02-14 | Additive for lubricants | ||
| US2738331A (en) * | 1952-03-18 | 1956-03-13 | Socony Mobil Oil Co Inc | Alkylthio hydroquinones and mineral oil compositions thereof |
| US2971941A (en) * | 1959-05-15 | 1961-02-14 | Ferro Corp | Nickel bis-(p-octylphenol) monosulphide stabilized polyethylene |
| US3398170A (en) * | 1964-05-21 | 1968-08-20 | Universal Oil Prod Co | Mixed chelates of a schiff base, an amine, and a transition series metal |
| US3445391A (en) * | 1966-10-31 | 1969-05-20 | Mobil Oil Corp | Organic compositions containing aminoquinones |
| US3557225A (en) * | 1969-02-17 | 1971-01-19 | Phillips Petroleum Co | Storage of dienes |
| US3636022A (en) * | 1969-04-09 | 1972-01-18 | American Cyanamid Co | Nickel amide complexes of bisphenol sulfides |
| US3692738A (en) * | 1971-04-08 | 1972-09-19 | Phillips Petroleum Co | Ultraviolet stabilizer system for polyolefins |
| US3816492A (en) * | 1972-04-03 | 1974-06-11 | American Cyanamid Co | Nickel cyclohexylamine complexes of 2,2'-thiobis(p-alkylphenol)and use in polyolefins |
-
1977
- 1977-04-18 US US05/788,213 patent/US4090970A/en not_active Expired - Lifetime
-
1978
- 1978-02-21 NZ NZ186523A patent/NZ186523A/xx unknown
- 1978-02-28 FI FI780684A patent/FI780684A/fi not_active Application Discontinuation
- 1978-03-10 GR GR55689A patent/GR64220B/el unknown
- 1978-03-21 CA CA299,418A patent/CA1103911A/en not_active Expired
- 1978-03-28 PT PT67832A patent/PT67832B/pt unknown
- 1978-03-28 ZA ZA00781738A patent/ZA781738B/xx unknown
- 1978-03-30 ES ES468339A patent/ES468339A1/es not_active Expired
- 1978-04-03 AU AU34682/78A patent/AU513994B2/en not_active Expired
- 1978-04-07 SE SE7803941A patent/SE7803941L/xx unknown
- 1978-04-10 BE BE186696A patent/BE865853A/xx unknown
- 1978-04-14 AT AT0263378A patent/AT366093B/de not_active IP Right Cessation
- 1978-04-17 BR BR787802367A patent/BR7802367A/pt unknown
- 1978-04-17 IT IT22392/78A patent/IT1094918B/it active
- 1978-04-17 DK DK166178A patent/DK166178A/da not_active IP Right Cessation
- 1978-04-17 CS CS782473A patent/CS212271B2/cs unknown
- 1978-04-17 DE DE19782816653 patent/DE2816653A1/de not_active Withdrawn
- 1978-04-17 NO NO781339A patent/NO781339L/no unknown
- 1978-04-17 JP JP4430578A patent/JPS53130287A/ja active Pending
- 1978-04-17 NL NL7804063A patent/NL7804063A/xx not_active Application Discontinuation
- 1978-04-18 FR FR7811374A patent/FR2388035A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES468339A1 (es) | 1982-06-01 |
| ATA263378A (de) | 1981-07-15 |
| SE7803941L (sv) | 1978-10-19 |
| BE865853A (fr) | 1978-10-10 |
| DK166178A (da) | 1978-10-19 |
| ZA781738B (en) | 1979-11-28 |
| AU513994B2 (en) | 1981-01-15 |
| NZ186523A (en) | 1979-12-11 |
| IT7822392A0 (it) | 1978-04-17 |
| IT1094918B (it) | 1985-08-10 |
| BR7802367A (pt) | 1979-02-13 |
| US4090970A (en) | 1978-05-23 |
| CA1103911A (en) | 1981-06-30 |
| CS212271B2 (en) | 1982-03-26 |
| FR2388035B1 (no) | 1984-05-04 |
| GR64220B (en) | 1980-02-12 |
| NL7804063A (nl) | 1978-10-20 |
| PT67832B (en) | 1979-09-28 |
| AU3468278A (en) | 1979-10-11 |
| AT366093B (de) | 1982-03-10 |
| FR2388035A1 (fr) | 1978-11-17 |
| PT67832A (en) | 1978-04-01 |
| JPS53130287A (en) | 1978-11-14 |
| DE2816653A1 (de) | 1978-10-19 |
| FI780684A (fi) | 1978-10-19 |
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