US3900410A - Lubricating oil compositions containing trialkyl-substituted phenols and benzotriazole - Google Patents
Lubricating oil compositions containing trialkyl-substituted phenols and benzotriazole Download PDFInfo
- Publication number
- US3900410A US3900410A US353394A US35339473A US3900410A US 3900410 A US3900410 A US 3900410A US 353394 A US353394 A US 353394A US 35339473 A US35339473 A US 35339473A US 3900410 A US3900410 A US 3900410A
- Authority
- US
- United States
- Prior art keywords
- tert
- lubricating oil
- butyl
- benzotriazole
- antioxidant
- 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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- 239000010687 lubricating oil Substances 0.000 title claims abstract description 19
- 239000000203 mixture Substances 0.000 title claims description 25
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title abstract description 11
- 239000012964 benzotriazole Chemical class 0.000 title abstract description 11
- 150000002989 phenols Chemical class 0.000 title 1
- SZATXRHXOOLEFV-UHFFFAOYSA-N 2,6-ditert-butyl-4-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SZATXRHXOOLEFV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 21
- 230000003078 antioxidant effect Effects 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000010688 mineral lubricating oil Substances 0.000 claims description 3
- QPKDVAYNINMEAS-UHFFFAOYSA-N 2,6-ditert-butyl-4-decylphenol Chemical compound CCCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 QPKDVAYNINMEAS-UHFFFAOYSA-N 0.000 claims description 2
- QPKNZTMDJWHXDC-UHFFFAOYSA-N 2,6-ditert-butyl-4-hexadecylphenol Chemical compound CCCCCCCCCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 QPKNZTMDJWHXDC-UHFFFAOYSA-N 0.000 claims description 2
- AXIWTRCDSODNIZ-UHFFFAOYSA-N 2,6-ditert-butyl-4-icosylphenol Chemical compound C(C)(C)(C)C1=C(C(=CC(=C1)CCCCCCCCCCCCCCCCCCCC)C(C)(C)C)O AXIWTRCDSODNIZ-UHFFFAOYSA-N 0.000 claims description 2
- VLXAWUXVAXHHLO-UHFFFAOYSA-N 2,6-ditert-butyl-4-octadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VLXAWUXVAXHHLO-UHFFFAOYSA-N 0.000 claims 1
- NICMVXRQHWVBAP-UHFFFAOYSA-N 2,6-ditert-butyl-4-octylphenol Chemical compound CCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NICMVXRQHWVBAP-UHFFFAOYSA-N 0.000 claims 1
- DCPPRPTWXOVKFR-UHFFFAOYSA-N 2,6-ditert-butyl-4-tetradecylphenol Chemical compound CCCCCCCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 DCPPRPTWXOVKFR-UHFFFAOYSA-N 0.000 claims 1
- 238000010525 oxidative degradation reaction Methods 0.000 abstract description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229960004643 cupric oxide Drugs 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- -1 2,6-di-tert-butyl-4-dodecyl anisole Chemical compound 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 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 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 150000001565 benzotriazoles Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- HXQHRUJXQJEGER-UHFFFAOYSA-N 1-methylbenzotriazole Chemical compound C1=CC=C2N(C)N=NC2=C1 HXQHRUJXQJEGER-UHFFFAOYSA-N 0.000 description 1
- UQQSNJSWRZYUQU-UHFFFAOYSA-N 4-(2,4,4-trimethylpentan-2-yl)-2H-benzotriazole Chemical compound C(C)(C)(CC(C)(C)C)C1=CC=CC=2NN=NC21 UQQSNJSWRZYUQU-UHFFFAOYSA-N 0.000 description 1
- RSQCFSMNFWQJPT-UHFFFAOYSA-N 5-butan-2-yl-2h-benzotriazole Chemical compound C1=C(C(C)CC)C=CC2=NNN=C21 RSQCFSMNFWQJPT-UHFFFAOYSA-N 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WIKSRXFQIZQFEH-UHFFFAOYSA-N [Cu].[Pb] Chemical group [Cu].[Pb] WIKSRXFQIZQFEH-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- ZASWJUOMEGBQCQ-UHFFFAOYSA-L dibromolead Chemical group Br[Pb]Br ZASWJUOMEGBQCQ-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- OSCBARYHPZZEIS-UHFFFAOYSA-N phenoxyboronic acid Chemical class OB(O)OC1=CC=CC=C1 OSCBARYHPZZEIS-UHFFFAOYSA-N 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
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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
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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
- C10M2205/026—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
- 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
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M2207/027—Neutral salts thereof
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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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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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- 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
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
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- 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
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/26—Amines
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/30—Heterocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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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- 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
- 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
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbased sulfonic acid salts
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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
- 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
- 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
Definitions
- ABSTRACT Lubricating oil is protected against oxidative degradation by inclusion of a 2,6-di-C -tert-alkyl-4-n-C alkylphenol,:.,e.g., 2,6-di-tert-butyl-4-n-dodecylphenol, and benzotriezole.
- the dodecyl group appears to be a branched-chain secondary or tertiary alkyl because there is no method given for the preparation of the 4-n-alkyl derivative.
- U.S. Pat. No. 3,717,611 the antioxidant use of 2,6-di-tert-butyl-4-dodecyl anisole and 2,6-di-trtbutyl-4-octadecyl anisole is disclosed.
- the anisole derivatives are made from the corresponding phenol.
- the dodecyl andoctadecyl groups appear to be secondary or tertiary since those compounds in which the alkyl is normal are so specified.
- mineral lubricating oils are stabilized against oxidative degradation by the addition of a small antioxidant amount of a 2,6-ditert-alkyl-4-C -n-alkylphenol and a small promoter amount of benzotriazole.
- 2 ,6-di-tert-eicosy-4-n-- groups These are represented by: 2,6-di-tert-butyl-4-ndecylphenol, 2,o-di-tert-butyl-4-n-dodecylphenol, 2,6- di-tert-butyl-4-n-tetradecylpheno], 2,6-di-tert-butyl-4- n-hexadecylphenol, 2,6-di-tert-butyl-4-noctadecylphenol, 2,6-di-tertbutyl-4-n-eicosylphenol, 2,6-di-tert-butyl-4-n-docosylphenol and 2,6-di-tertbutyl-4'n-tetracosylphenol.
- Additives of this invention are made by heating a 2,6- di-tert-alkylphenol with a straight chain primary alcohol of the desired chain length in the presence of potassium hydroxide and a cupric oxide catalyst.
- the alcohol is generally employed in stoichiometric excess. An amount of about 3-20 moles of alcohol per mole of phenol is satisfactory. Good results are obtained using about 0.5-0.2 mole of KOH per mole of alcohol. About 0.005-0.05 mole of cupric oxide per mole of 2,6-ditert-alkylphenol gives good results. Reaction temperatures of about 200250C. are preferred.
- Product can be recovered by distillation. In a highly preferred embodiment the reaction mixture is distilled to remove 2,6-di-tert-alkylphenol and other more volatile components and the residue used as the phenolic antioxidant of this invention.
- EXAMPLE 1 In a pressure reaction vessel was placed 326.] grams of 2,6-di-tert-butylphenol, 1000 grams of n-decanol, 32.8 grams of 86 per cent KOH and 0.95 gram of cupric oxide. This mixture was stirred and heated to 225C. and held at that temperature for 24 hours. Following this, the mixture was cooled, diluted with 250 ml toluene and washed with aqueous sodium bicarbonate. It was then washed with water until neutral and distilled under vacuum to isolate the product 2,6-di-tertbutyl-4-n-decylphenol (b.p. l55C., 0.250.3 mm Hg).
- additives can be similarly prepared by substituting different straight chain alcohols containing from 8-24 carbon atoms.
- the amount of antioxidant blended with the oil should be sufficient to impart the required degree of stability. Good results are achieved using about 0.01-3 weight per cent and, preferably, 0.05l.5 weight per cent.
- the amount of benzotriazole should be an amount such that when used with the 2,6-di-tert-alkyl- 4-C -n-alkylphenol good overall performance is obtained. A useful range is from about 0.0l0.5 weight per cent.
- simple lower alkyl-substituted benzotriazoles can be used such as the C alkylsubstituted benzotriazoles, e.g., 3-methylbenzotriazole, l,2,3-trimethylbenzotriazole, 6-sec-butylbenzotriazole, 4-tert-octylbenzotriazole, 4-sec-hexylbenzotriazole, and the like.
- additives normally included in oil compositions can be beneficially used together with the additives of this invention.
- These include zinc dialkyldithiophosphates, calcium aryl sulfonates, overbased calcium aryl sulfonates, magnesium aryl sulfonates, barium phenates, calcium phenates, barium polybutenyl ph phonates, V.l. improvers such as polybutene, ethylenepropylene copolymer, polylauryl mcthacrylate, dispersants such as polybutenyl kylenepolyamines, and the like.
- EXAMPLE 3 In a blending vessel place 10,000 pounds of SAE-30 neutral mineral oil. To this add 100 pounds of zinc dialkyldithiophosphate (7 weight per cent zinc), 50 pounds of 2,6-di-tert-butyl-4-n-dodecylphenol, 50 pounds calcium aryl sulfonate (overbased with colloidal calcium carbonate), 250 pounds ethylenepropylene copolymer and 400 pounds of a 50 per cent oil solution of a C polybutenyl succinimide of tetraethylenepentamine. Stir the mixture until homogenous to obtain an oil composition suitable for. use in internal combustion engines.
- Tests have been carried out to demonstrate the effectiveness of the present compositions. These are oxidationcorrosion tests in which oil samples are prepared containing the test additive, 0.1 per cent lead bromide and a copper-lead bearing. These are heated to 300F. and air bubbled through them for 48 hours at 48 liters per hour. Criteria of the additive effectiveness are the increase in acid number, increase in viscosity and bearing weight loss. The results obtained were as follows:
- R and R are tert alkyl groups containing 4 to 7 about 20 carbon atoms and R is a straight chain primary alkyl group containing S te about 24 carbon atoms and an antioxidant promoter amount of a benzo triazole.
- said antioxidant compounds are 2,6-di-tert-butyl-4-n- C8 -alkylphenols.
- the phenolic additives are effective in preventing oxidative degradation but cause a large increase in bearing weight loss.
- Inclusion of benzotriazole not only greatly reduces the bearing weight loss but, in addition, sharply reduces the acid number increase and viscosity increase, thus contributing to the overall effectiveness of the antioxidant.
- composition of claim 1 wherein UNITED STATES PATENT AND TRADEMARK OFFICE CERTIFICATE OF GORECTION PATENT NO. 5,900, i1o
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Abstract
Lubricating oil is protected against oxidative degradation by inclusion of a 2,6-di-C4-20-tert-alkyl-4-n-C8-24 alkylphenol, e.g., 2,6-di-tert-butyl-4-n-dodecylphenol, and benzotriazole.
Description
United States Patent Malec LUBRICATING OIL COMPOSITIONS CONTAINING TRIALKYL-SUBSTITUTED PIIENOLS AND BENZOTRIAZOLE Robert E. Malec, Birmingham,
Mich.
Assignee: Ethyl Corporation, Richmond, Va.
Filed: Apr. 23, 1973 Appl. No.: 353,394
Inventor:
US. Cl 252/5L5 R; 252/50; 252/392 Int. Cl C.10m 1/32 Field of Search 252/5l.5 R, 50, 42.7, 392
References Cited UNITED STATES PATENTS 6/1940 Stevens et al. 252/52 X 10/1957 Pruett 252/5l5 R 11] 3,900,410 Aug. 19, 1975 Primary Exaniinr-Delbert E. Gantz Assistant Examiner-Andrew H. Metz Attorney, Agrit, 0r FirmDonald L. Johnson; Robert A. Linn; Josepli D. Odenweller [57] ABSTRACT Lubricating oil is protected against oxidative degradation by inclusion of a 2,6-di-C -tert-alkyl-4-n-C alkylphenol,:.,e.g., 2,6-di-tert-butyl-4-n-dodecylphenol, and benzotriezole.
9 Claims, No Drawings LUBRICATING OIL COMPOSITIONS CONTAINING TRIALKYL-SUBSTITUTED PI-IENOLS AND BENZOTRIAZOLE BACKGROUND Alkylphenols have been used to provide antioxidant protection for a broad range of organic materials. For example, 2,6-di-tert-butyl-4-methylphenol is a known commercial antioxidant used in polymers, rubber and as a food additive. Polyolefin use of 2,6-di-tert-butyl-4- dodecylphenol is disclosed in Neth. PatfNo. 64/08010. The dodecyl group appears to be a branched-chain secondary or tertiary alkyl because there is no method given for the preparation of the 4-n-alkyl derivative. In U.S. Pat. No. 3,717,611 the antioxidant use of 2,6-di-tert-butyl-4-dodecyl anisole and 2,6-di-trtbutyl-4-octadecyl anisole is disclosed. The anisole derivatives are made from the corresponding phenol. The dodecyl andoctadecyl groups appear to be secondary or tertiary since those compounds in which the alkyl is normal are so specified.
Synthetic ester lubricants containing benzotriazole in addition to other constituents are disclosed in US. Pat. No. 2,971,912. Lubricating oils containing phenylborate esters are reported in Br. Pat. No. 1,287,444 to give increased undercrown and piston skirt deposit which is said to be largely eliminated by inclusion of a heterocycle such as benzotriazole.
, SUMMARY According to the present invention, mineral lubricating oils are stabilized against oxidative degradation by the addition of a small antioxidant amount of a 2,6-ditert-alkyl-4-C -n-alkylphenol and a small promoter amount of benzotriazole.
DESCRIPTION OF THE PREFERRED EMBODIMENTS The phenolic additives of this invention are compounds having the formula:
2 ,6-di-tert-eicosy-4-n-- groups. These are represented by: 2,6-di-tert-butyl-4-ndecylphenol, 2,o-di-tert-butyl-4-n-dodecylphenol, 2,6- di-tert-butyl-4-n-tetradecylpheno], 2,6-di-tert-butyl-4- n-hexadecylphenol, 2,6-di-tert-butyl-4-noctadecylphenol, 2,6-di-tertbutyl-4-n-eicosylphenol, 2,6-di-tert-butyl-4-n-docosylphenol and 2,6-di-tertbutyl-4'n-tetracosylphenol.
Additives of this invention are made by heating a 2,6- di-tert-alkylphenol with a straight chain primary alcohol of the desired chain length in the presence of potassium hydroxide and a cupric oxide catalyst. The alcohol is generally employed in stoichiometric excess. An amount of about 3-20 moles of alcohol per mole of phenol is satisfactory. Good results are obtained using about 0.5-0.2 mole of KOH per mole of alcohol. About 0.005-0.05 mole of cupric oxide per mole of 2,6-ditert-alkylphenol gives good results. Reaction temperatures of about 200250C. are preferred. Product can be recovered by distillation. In a highly preferred embodiment the reaction mixture is distilled to remove 2,6-di-tert-alkylphenol and other more volatile components and the residue used as the phenolic antioxidant of this invention.
The following example illustrates the manner by which the phenolic additives are prepared.
EXAMPLE 1 In a pressure reaction vessel was placed 326.] grams of 2,6-di-tert-butylphenol, 1000 grams of n-decanol, 32.8 grams of 86 per cent KOH and 0.95 gram of cupric oxide. This mixture was stirred and heated to 225C. and held at that temperature for 24 hours. Following this, the mixture was cooled, diluted with 250 ml toluene and washed with aqueous sodium bicarbonate. It was then washed with water until neutral and distilled under vacuum to isolate the product 2,6-di-tertbutyl-4-n-decylphenol (b.p. l55C., 0.250.3 mm Hg).
EXAMPLE 2 In a pressure reaction vessel was placed 247.5 grams of 2,6-di-tert-butylphenol, 894 grams of n-dodecanol,
26.9 grams 86 per cent KOH and 1.2 grams cupric oxide. The vessel was flushed with hydrogen and pressurized to 100 psig with hydrogen. While stirring, it was heated to 235C. and maintained at this temperature for 24 hours. Following this, it was cooled and discharged into dilute hydrochloric acid. Discharge was completed by adding 200 ml of toluene and 300 ml of hot water to the reaction vessel, which was combined with the discharged reaction mixture. The organic phase was washed with water until almost neutral (pH 6) and then dried over magnesium sulfate. Toluene and unreacted n-decanol was distilled from the reaction mixture, leaving 403 grams of residue which assayed per cent 2,6-di-tert-butyl-4-n-dodecylphenol by VPC.
Other additives can be similarly prepared by substituting different straight chain alcohols containing from 8-24 carbon atoms.
The amount of antioxidant blended with the oil should be sufficient to impart the required degree of stability. Good results are achieved using about 0.01-3 weight per cent and, preferably, 0.05l.5 weight per cent. The amount of benzotriazole should be an amount such that when used with the 2,6-di-tert-alkyl- 4-C -n-alkylphenol good overall performance is obtained. A useful range is from about 0.0l0.5 weight per cent. Optionally, simple lower alkyl-substituted benzotriazoles can be used such as the C alkylsubstituted benzotriazoles, e.g., 3-methylbenzotriazole, l,2,3-trimethylbenzotriazole, 6-sec-butylbenzotriazole, 4-tert-octylbenzotriazole, 4-sec-hexylbenzotriazole, and the like.
Other additives normally included in oil compositions can be beneficially used together with the additives of this invention. These include zinc dialkyldithiophosphates, calcium aryl sulfonates, overbased calcium aryl sulfonates, magnesium aryl sulfonates, barium phenates, calcium phenates, barium polybutenyl ph phonates, V.l. improvers such as polybutene, ethylenepropylene copolymer, polylauryl mcthacrylate, dispersants such as polybutenyl kylenepolyamines, and the like.
The following example illustrates the preparation of a typical oil composition of this invention.
EXAMPLE 3 In a blending vessel place 10,000 pounds of SAE-30 neutral mineral oil. To this add 100 pounds of zinc dialkyldithiophosphate (7 weight per cent zinc), 50 pounds of 2,6-di-tert-butyl-4-n-dodecylphenol, 50 pounds calcium aryl sulfonate (overbased with colloidal calcium carbonate), 250 pounds ethylenepropylene copolymer and 400 pounds of a 50 per cent oil solution of a C polybutenyl succinimide of tetraethylenepentamine. Stir the mixture until homogenous to obtain an oil composition suitable for. use in internal combustion engines.
Tests have been carried out to demonstrate the effectiveness of the present compositions. These are oxidationcorrosion tests in which oil samples are prepared containing the test additive, 0.1 per cent lead bromide and a copper-lead bearing. These are heated to 300F. and air bubbled through them for 48 hours at 48 liters per hour. Criteria of the additive effectiveness are the increase in acid number, increase in viscosity and bearing weight loss. The results obtained were as follows:
succinimidesof almula:
wherein R and R are tert alkyl groups containing 4 to 7 about 20 carbon atoms and R is a straight chain primary alkyl group containing S te about 24 carbon atoms and an antioxidant promoter amount of a benzo triazole. 2. A lubricating oil said antioxidant compounds are 2,6-di-tert-butyl-4-n- C8 -alkylphenols.
3. A lubricatingoil composition of claim 2 wherein As the above results show, the phenolic additives are effective in preventing oxidative degradation but cause a large increase in bearing weight loss. Inclusion of benzotriazole not only greatly reduces the bearing weight loss but, in addition, sharply reduces the acid number increase and viscosity increase, thus contributing to the overall effectiveness of the antioxidant.
I claim:
l. A mineral lubricating oil composition containing an antioxidant amount of a compound having the for- 7. A lubricating oil composition of claim 2 wherein said antioxidant compound is 2,6-di-tert-butyl-4-nhexadecylphenol.
8. A lubricating oil composition of claim 2 wherein said antioxidant compound is 2,6-di-tert-butyl-4-noctadecylphenol.
9. A lubricating oil composition of claim 2 wherein said antioxidant compound is 2,6-di-tert-butyl-4-neicosylphenol.
composition of claim 1 wherein UNITED STATES PATENT AND TRADEMARK OFFICE CERTIFICATE OF GORECTION PATENT NO. 5,900, i1o
DATED August 9 975 mv om 1 Robert E. Melee it is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:
Column i, in Claim 1, at lines 15-1 i, insert "about 0.01O.5 weight per cent of before "a benzoticietzole Signed and fiealed this fourteenth Day Of October 1975 [SEAL] Attest:
RUTH C. MASON C. MARSHALL DANN Arresting Officer Commissioner oj'Patents and Trademarks UNITED STATES PATENT AND TRADEMARK OFFICE CERTIFICATE OF CORRECTION PATENT NO. 3,9OOA1O DATED August 19, 1975 INVENTORQI): Robert E. Malec It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:
Column t, in Claim 1, art lines 151 t, insert "about 0.01O.5 weight per cent of" before e ioenzotriazole Signed and Sealed this fourteenth D ay Of October 1 9 75 [SEAL] A ttest:
RUTH C. MASON C. MARSHALL DANN Arresting Officer Commissioner ofParents and Trademarks UNITED STATES PATENT AND TRADEMARK OFFICE CERTIFICATE OF CORRECTION PATENT NO. 5,900,h10
DATED August 19, 1975 rNv ENT0R( s Robert E. Malec It is certified that error appears in the ab0ve-identified patent and that said Letters Patent are hereby corrected as shown below:
Column t, in Claim 1, at lines 15l t, insert about 0.01O.5 weight per cent of" before "a benzotriazole Signed and Scaled this fourteenth Day Of October 1975 [SEAL] A rtes t:
RUTH C. MASON C. MARSHALL DANN Arresting Officer Commissioner of Patents and Trademarks
Claims (9)
1. A MINERAL LUBRICATING OIL COMPOSITION CONTAINING AN ANTIOXIDANT AMOUNT OF A COMPOUND HAVING THE FORMULA:
2. A lubricating oil composition of claim 1 wherein said antioxidant compounds are 2,6-di-tert-butyl-4-n-C8-24 24-alkylphenols.
3. A lubricating oil composition of claim 2 wherein said antioxidant compound is 2,6-di-tert-butyl-4-n-octylphenol.
4. A lubricating oil composition of claim 2 wherein said antioxidant compound is 2,6-di-tert-butyl-4-n-decylphenol.
5. A lubricating oil composition of claim 2 wherein said antioxidant compound is 2,6-di-tert-butyl-4-n-dodecylphenol.
6. A lubricating oil composition of claim 2 wherein said antioxidant compound is 2,6-di-tert-butyl-4-n-tetradecylphenol.
7. A lubricating oil composition of claim 2 wherein said antioxidant compound is 2,6-di-tert-butyl-4-n-hexadecylphenol.
8. A lubricating oil composition of claim 2 wherein said antioxidant compound is 2,6-di-tert-butyl-4-n-octadecylphenol.
9. A lubricating oil composition of claim 2 wherein said antioxidant compound is 2,6-di-tert-butyl-4-n-eicosylphenol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US353394A US3900410A (en) | 1973-04-23 | 1973-04-23 | Lubricating oil compositions containing trialkyl-substituted phenols and benzotriazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US353394A US3900410A (en) | 1973-04-23 | 1973-04-23 | Lubricating oil compositions containing trialkyl-substituted phenols and benzotriazole |
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| Publication Number | Publication Date |
|---|---|
| US3900410A true US3900410A (en) | 1975-08-19 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US353394A Expired - Lifetime US3900410A (en) | 1973-04-23 | 1973-04-23 | Lubricating oil compositions containing trialkyl-substituted phenols and benzotriazole |
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| US (1) | US3900410A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55106297A (en) * | 1979-02-09 | 1980-08-14 | Toa Nenryo Kogyo Kk | Lubricating oil composition |
| US4233207A (en) * | 1979-07-09 | 1980-11-11 | Ciba-Geigy Corporation | Hydrolytically stable ortho-alkylated phenyl phosphonites and stabilized compositions |
| EP0028200A1 (en) * | 1979-10-29 | 1981-05-06 | The Goodyear Tire & Rubber Company | Alkylation of 2,6-di-tert.-alkylphenols with alkanediols |
| US4306985A (en) * | 1979-02-14 | 1981-12-22 | Atlantic Richfield Company | Stabilization of hydrocracked oils with certain nitrogen containing aromatic components and phenolic components |
| US4836943A (en) * | 1987-07-15 | 1989-06-06 | Texaco Inc. | Anti-oxidant system |
| US6121209A (en) * | 1994-12-09 | 2000-09-19 | Exxon Chemical Patents Inc | Synergistic antioxidant systems |
| JP2014091695A (en) * | 2012-11-02 | 2014-05-19 | Dic Corp | Method for producing hindered phenol |
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| US2202877A (en) * | 1937-04-12 | 1940-06-04 | Gulf Oil Corp | Antioxidants and petroleum oils containing the same |
| US2809164A (en) * | 1955-04-21 | 1957-10-08 | American Cyanamid Co | Oxidation inhibitors for lubricating oil |
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| US3173871A (en) * | 1961-06-08 | 1965-03-16 | Castrol Ltd | Lubricating oils containing benzalcyclohexylamine and bis-phenols |
| US3413227A (en) * | 1963-12-06 | 1968-11-26 | Geigy Chem Corp | Compositions containing substituted benzotriazoles |
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| US2202877A (en) * | 1937-04-12 | 1940-06-04 | Gulf Oil Corp | Antioxidants and petroleum oils containing the same |
| US2809164A (en) * | 1955-04-21 | 1957-10-08 | American Cyanamid Co | Oxidation inhibitors for lubricating oil |
| US2890170A (en) * | 1956-09-06 | 1959-06-09 | Dow Corning | Organosiloxane greases |
| US3032502A (en) * | 1959-08-17 | 1962-05-01 | Standard Oil Co | Lubricant compositions |
| US3173871A (en) * | 1961-06-08 | 1965-03-16 | Castrol Ltd | Lubricating oils containing benzalcyclohexylamine and bis-phenols |
| US3413227A (en) * | 1963-12-06 | 1968-11-26 | Geigy Chem Corp | Compositions containing substituted benzotriazoles |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55106297A (en) * | 1979-02-09 | 1980-08-14 | Toa Nenryo Kogyo Kk | Lubricating oil composition |
| JPH0152438B2 (en) * | 1979-02-09 | 1989-11-08 | Toa Nenryo Kogyo Kk | |
| US4306985A (en) * | 1979-02-14 | 1981-12-22 | Atlantic Richfield Company | Stabilization of hydrocracked oils with certain nitrogen containing aromatic components and phenolic components |
| US4233207A (en) * | 1979-07-09 | 1980-11-11 | Ciba-Geigy Corporation | Hydrolytically stable ortho-alkylated phenyl phosphonites and stabilized compositions |
| EP0028200A1 (en) * | 1979-10-29 | 1981-05-06 | The Goodyear Tire & Rubber Company | Alkylation of 2,6-di-tert.-alkylphenols with alkanediols |
| US4836943A (en) * | 1987-07-15 | 1989-06-06 | Texaco Inc. | Anti-oxidant system |
| US6121209A (en) * | 1994-12-09 | 2000-09-19 | Exxon Chemical Patents Inc | Synergistic antioxidant systems |
| JP2014091695A (en) * | 2012-11-02 | 2014-05-19 | Dic Corp | Method for producing hindered phenol |
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