US3014869A - Lubricating oil composition - Google Patents
Lubricating oil composition Download PDFInfo
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- US3014869A US3014869A US849453A US84945359A US3014869A US 3014869 A US3014869 A US 3014869A US 849453 A US849453 A US 849453A US 84945359 A US84945359 A US 84945359A US 3014869 A US3014869 A US 3014869A
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- United States
- Prior art keywords
- borate
- tri
- lubricating oil
- oil
- cyclohexyl
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 9
- 239000010687 lubricating oil Substances 0.000 title description 3
- -1 TRI(3,3,5-TRIETHYL CYCLOHEXYL)BORATE Chemical compound 0.000 claims description 16
- 239000010688 mineral lubricating oil Substances 0.000 claims description 9
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 6
- 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 5
- BOOITXALNJLNMB-UHFFFAOYSA-N tricyclohexyl borate Chemical compound C1CCCCC1OB(OC1CCCCC1)OC1CCCCC1 BOOITXALNJLNMB-UHFFFAOYSA-N 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 101000766253 Homo sapiens TLR4 interactor with leucine rich repeats Proteins 0.000 claims 1
- 102100026308 TLR4 interactor with leucine rich repeats Human genes 0.000 claims 1
- 239000002480 mineral oil Substances 0.000 description 10
- 235000010446 mineral oil Nutrition 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 5
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 230000001050 lubricating effect Effects 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical class CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 1
- NDVWOBYBJYUSMF-UHFFFAOYSA-N 2-methylcyclohexan-1-ol Chemical compound CC1CCCCC1O NDVWOBYBJYUSMF-UHFFFAOYSA-N 0.000 description 1
- BRRVXFOKWJKTGG-UHFFFAOYSA-N 3,3,5-trimethylcyclohexanol Chemical compound CC1CC(O)CC(C)(C)C1 BRRVXFOKWJKTGG-UHFFFAOYSA-N 0.000 description 1
- JTAXUBKTCAOMTN-UHFFFAOYSA-N Abietinol Natural products CC(C)C1=CC2C=CC3C(C)(CO)CCCC3(C)C2CC1 JTAXUBKTCAOMTN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241001327708 Coriaria sarmentosa Species 0.000 description 1
- DTGKSKDOIYIVQL-MRTMQBJTSA-N Isoborneol Natural products C1C[C@@]2(C)[C@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-MRTMQBJTSA-N 0.000 description 1
- CCAZWUJBLXKBAY-ULZPOIKGSA-N Tutin Chemical compound C([C@]12[C@@H]3O[C@@H]3[C@@]3(O)[C@H]4C(=O)O[C@@H]([C@H]([C@]32C)O)[C@H]4C(=C)C)O1 CCAZWUJBLXKBAY-ULZPOIKGSA-N 0.000 description 1
- GQRUHVMVWNKUFW-LWYYNNOASA-N abieta-7,13-dien-18-ol Chemical compound OC[C@]1(C)CCC[C@]2(C)[C@@H](CCC(C(C)C)=C3)C3=CC[C@H]21 GQRUHVMVWNKUFW-LWYYNNOASA-N 0.000 description 1
- 229930001565 abietol Natural products 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- QCRFMSUKWRQZEM-UHFFFAOYSA-N cycloheptanol Chemical class OC1CCCCCC1 QCRFMSUKWRQZEM-UHFFFAOYSA-N 0.000 description 1
- VEJFFUKFKNSOBD-UHFFFAOYSA-N cyclohepten-1-ol Chemical class OC1=CCCCCC1 VEJFFUKFKNSOBD-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- NWZXFAYYQNFDCA-UHFFFAOYSA-N cyclopenten-1-ol Chemical class OC1=CCCC1 NWZXFAYYQNFDCA-UHFFFAOYSA-N 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- SFCBPVBDIBWEJM-UHFFFAOYSA-N tris(2-cyclohexylcyclohexyl) borate Chemical compound C1CCCCC1C1C(OB(OC2C(CCCC2)C2CCCCC2)OC2C(CCCC2)C2CCCCC2)CCCC1 SFCBPVBDIBWEJM-UHFFFAOYSA-N 0.000 description 1
- GHMDTEDTNDZHTB-UHFFFAOYSA-N tris(2-phenylcyclohexyl) borate Chemical compound C1CCCC(C=2C=CC=CC=2)C1OB(OC1C(CCCC1)C=1C=CC=CC=1)OC1CCCCC1C1=CC=CC=C1 GHMDTEDTNDZHTB-UHFFFAOYSA-N 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
- 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
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/104—Aromatic fractions
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/106—Naphthenic fractions
-
- 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
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
-
- 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
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
-
- 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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/061—Esters derived from boron
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/16—Dielectric; Insulating oil or insulators
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/17—Electric or magnetic purposes for electric contacts
Definitions
- This invention relates-to improved lubricating oil compositions, and more particularly to mineral lubricating oil compositions which are resistantto oxidative deterioraatent tion under storage or use in equipment subjected to adverse operating conditions of temperature and pressure.
- Lubricating oils such as mineraloils in the lubricating viscosity range tend to deteriorate and break down due to oxidation both in storage and during use, particularly at extremely high temperatures, such as above 400 F. and higher, resulting in the formation of undesirable products such as gums, sludges, resins, acidic products and other I deleterious products which decrease the useful life of the oil or render it useless within a short period of time.
- Mineral oils of this type include aircraft, truck and automobile mineral lubricating oils, industrial oils such as gear oils, transformer oils, hydraulic oils and the like.
- oil-soluble aromatic "amines represented by Formula I includeldiphenyl, dinaphthyl, phenyl alphanaphthyl, phenyl beta-naphthyl amines and mixtures thereof.
- the tricycloalkyl borates represented by Formula II 1 (RO) B- are prepared by any suitable'means such as by reacting under reflux conditions boric acid with a desired cycloalkanol in a suitable solvent such as a liquid hydrocarbon, e.g., benzene, toluene or the like;
- heptanols', etc Representative specific compounds are 3,3,5 trimethylcyclohexanol, 4,6 4 diter tiarybutyl 2 methyl-cyclohexanol, borneol, isoborneol, abietyl alcohol,
- cycloalkyl borates useful in lubricating compositions of the present invention, are tricyclohexyl borate, tri(3,3,S-triethylcyclohexyl)borate, tri(4,6'- ditertbutyl 3 methylcyclohexyl)borate, tri(2- cyclohexylcyclohexyl)borate, tri(2 phenylcyclohexyl)- borate, tri(2 chlorocyclohexyl)borate, phenyl dicyclohexyl borate, tri(2,3 dimethylcyclopentyl)borate, tri(2- butylcycloheptyl)borate, dicyclohexylcyclopentyl borate and the like.
- the additive combination of this invention effectively stabilizes a variety of petroleum lubricating stocks such as parafiinic, naphthenic and mixed base mineral oils having a viscosity range of from 50 SUS at F. to 250 SUS at 210 F.
- a typical useful oil is a refined mineral lubricating oil (X) having the following properties:
- Another typical useful oil (Y) is an Oklahoma neutral petroleum fraction having the following properties:
- compositions were prepared and evaluated in a micro-oxidation test of the MIL-L- 7808 oxidation test under the following testcondition: solid metal catalyst (Ag, Ti, Cu, Mg, Fe), with the results as shown in Table I.
- compositions of this invention which would be expected to give comparable results to composition 6, Table I of this invention, include:
- a mineral lubricating oil containing from about 0.05% to about 2% each of phenyl-alpha-naphthylamine and tricyclohexyl borate.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
free
i] t d St t I 3,014,869 I LUBRICATING ()IL CONHOSITIQN William W. Reynolds and Hans Low, East Alton, 'Iil assignors to ShellOil Company, a corporation of Delawere No Drawing. tutu news, 1959', Ser. No. 349,453
- 2 Claims. ((1252- 196) 7 r This invention relates-to improved lubricating oil compositions, and more particularly to mineral lubricating oil compositions which are resistantto oxidative deterioraatent tion under storage or use in equipment subjected to adverse operating conditions of temperature and pressure. Lubricating oils such as mineraloils in the lubricating viscosity range tend to deteriorate and break down due to oxidation both in storage and during use, particularly at extremely high temperatures, such as above 400 F. and higher, resulting in the formation of undesirable products such as gums, sludges, resins, acidic products and other I deleterious products which decrease the useful life of the oil or render it useless within a short period of time. Mineral oils of this type include aircraft, truck and automobile mineral lubricating oils, industrial oils such as gear oils, transformer oils, hydraulic oils and the like.
It is known that certain aromatic amines are useful as oxidation inhibitors for 'mineral oils. However, their application is limited because of their tendency to discolor mineral oils and form deposits, particularly at or prevent deterioration, discoloration and deposit formation in mineral oil during storage and use over a wide temperature range, particularly at elevated temperatures. Other objects of the invention will be apparent from the following description of the invention.
Specific gravity 0.876 Pour point, F. +10 Viscosity at 100 F., cs 56.88 V.I 93.9 Flash point, COC, F 450 Fire point, F 490 Aromatics, percent 23.7
It has now been discovered that various types of mineral lubricating oil including those which contain substantial amounts of aromatics (530%) can be effectively stabilized even at temperatures above 400 F. without undesirable side effects by addition 'thcreto of small amounts (0.054%, preferably 0.11% by weight.) each of an oil-soluble aromatic amine having the Formula I RR NH, wherein the Rs are the same or different monoor diaromatic radicals, and an oil-soluble boron ester having the Formula II (RO) B, wherein R is an alicyclic group, preferably monocyclic group of non-aromatic carbyl radicals, or polar radicals such as halogenihydroxyl, amino, nitro, or carboxylate radicals. Boron esters represented .by Formula. II in which at least one and preferably two Rs of cyclohexyl groups are preferred.
The, oil-soluble aromatic "amines represented by Formula I includeldiphenyl, dinaphthyl, phenyl alphanaphthyl, phenyl beta-naphthyl amines and mixtures thereof.
' character which may contain substituent C C hydro- The tricycloalkyl borates represented by Formula II 1 (RO) B- are prepared by any suitable'means such as by reacting under reflux conditions boric acid with a desired cycloalkanol in a suitable solvent such as a liquid hydrocarbon, e.g., benzene, toluene or the like;
Suitable alicyclic alcohols for use as starting materials in the preparation of compounds of this invention'include cycloalkanols, such as cycloperitanols, cyclopentenols,
heptanols', etc, Representative specific compounds are 3,3,5 trimethylcyclohexanol, 4,6 4 diter tiarybutyl 2 methyl-cyclohexanol, borneol, isoborneol, abietyl alcohol,
cyclohexanols, cycloheptanols, cycloheptenols, bicyclo air flow of 1 liter/hour oxidizing agent, 400 F.,
cycloalkanols produced by hydrogenation of isophorone and isophorone bottoms as described in Adelson U. S. Patents 2,481,487 and 2,502,408 as well as cycloalkenols described in US. Patents 2,433,008, 2,467,451, 2,493,733, 2,497,349, 2,574,077 and 2,597,843.
Specific representative cycloalkyl borates useful in lubricating compositions of the present invention, are tricyclohexyl borate, tri(3,3,S-triethylcyclohexyl)borate, tri(4,6'- ditertbutyl 3 methylcyclohexyl)borate, tri(2- cyclohexylcyclohexyl)borate, tri(2 phenylcyclohexyl)- borate, tri(2 chlorocyclohexyl)borate, phenyl dicyclohexyl borate, tri(2,3 dimethylcyclopentyl)borate, tri(2- butylcycloheptyl)borate, dicyclohexylcyclopentyl borate and the like.
The additive combination of this invention effectively stabilizes a variety of petroleum lubricating stocks such as parafiinic, naphthenic and mixed base mineral oils having a viscosity range of from 50 SUS at F. to 250 SUS at 210 F. A typical useful oil is a refined mineral lubricating oil (X) having the following properties:
Pour point, F 29-31 Flash point, F. (COC) Min. 420 Viscosity SUS, 100 F 345-355 Unsulfonated residue Min. 98
Another typical useful oil (Y) is an Oklahoma neutral petroleum fraction having the following properties:
To illustrate the pronounced superiority of the additive combination in stabilizing and preventing oxidation of mineral oil, the following compositions were prepared and evaluated in a micro-oxidation test of the MIL-L- 7808 oxidation test under the following testcondition: solid metal catalyst (Ag, Ti, Cu, Mg, Fe), with the results as shown in Table I.
Table I [Eraser-refined mineral lubricating oil X,'amou11t 0t Inhibitor=0.02 M'=0.002 mole/100 g.]
Other compositions of this invention which would be expected to give comparable results to composition 6, Table I of this invention, include:
(7) Mineral oil+0.02 M phenylalpha-naphthylamine +0.02 M tri(3,3,5-triethy1 cyclohexyl)borate,
(8) 'Mineral oil+0.02 M phenyl-alpha-naphthylarnine +0.02 M tri(4,6-ditertbutyl-3methyl cyclohexyl)borate,
(9) Mineral oil}0.02 M beta,beta-dinaphthylamine+0.02 M tricyclohexyl borate, I t (10.) lvfineral oil+0.05 M phenyl-alpha-naphthylamine +0.03 M tri(Z-butylcy'ciloheptyl)borate.
' PatentedDec. 2c, 1961 sentially of a major amount of mineral lubricating oil and from about 0.05% to about 2% each, of (1) an oilsoluble aromatic amine selected from the group consisting of phenyl-alpha-naphthylamine and beta-beta-dinaphthylamine and (2) an oil-soluble cycloalkyl borate selected from the group consisting of tri(cyclohexyl)borate, tri- (3,3,5 triethyl cyclohexyDborate, tri(4,6 ditertbutyl 3- methyl cyclohexyl)borate, and tri(2-butylcycloheptyl)- borate.
2. A mineral lubricating oil containing from about 0.05% to about 2% each of phenyl-alpha-naphthylamine and tricyclohexyl borate.
References Cited in the file of this patent UNITED STATES PATENTS 2,084,472 Wiezevich June 22, 1937 2,160,917 Shoemaker et a1 June 6, 1939 2,312,208 Clayton et al. Feb. 26, 1943 2,452,319 Patterson et a1 Oct. 26, 1948 2,721,181 Lawrence et al. Oct. 18, 1955 FOREIGN PATENTS 748.430 Great Britain May 2, 1956
Claims (1)
1. A MINERAL LUBRICATING OIL COMPOSITION CONSISTING ESSENTIALLY OF A MAJOR AMOUNT OF MINERAL LUBRICATING OIL AND FROM ABOUT 0.05% TO ABOUT 2% EACH, OF (1) AN OILSOLUBLE AROMATIC AMINE SELECTED FROM THE GROUP CONSISTING OF PHENYL-ALPHA-NAPHTHYLAMINE AND BETA-BETA-DINAPHTHYLAMINE AND (2) AN OIL-SOLUBLE CYCLOALKYL BORATE SELECTED FROM THE GROUP CONSISTING OF TRI(CYCLOHEXYL)BORATE, TRI(3,3,5-TRIETHYL CYCLOHEXYL)BORATE, TRIL(4,6-DITERBUTYL - 3METHYL CYCLOHEXYL)BORATE, AND TRI(2-BUTYLCLOHEPTYL)BORATE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US849453A US3014869A (en) | 1959-10-29 | 1959-10-29 | Lubricating oil composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US849453A US3014869A (en) | 1959-10-29 | 1959-10-29 | Lubricating oil composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3014869A true US3014869A (en) | 1961-12-26 |
Family
ID=25305787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US849453A Expired - Lifetime US3014869A (en) | 1959-10-29 | 1959-10-29 | Lubricating oil composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3014869A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4328113A (en) * | 1980-01-14 | 1982-05-04 | Mobil Oil Corporation | Friction reducing additives and compositions thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2084472A (en) * | 1934-07-14 | 1937-06-22 | Standard Oil Dev Co | Lubricating and insulating compound |
| US2160917A (en) * | 1937-06-10 | 1939-06-06 | Standard Oil Co | Lubricant |
| US2312208A (en) * | 1941-04-12 | 1943-02-23 | Standard Oil Co California | Compounded hydrocarbon oil |
| US2452319A (en) * | 1943-12-08 | 1948-10-26 | Texas Co | Rust and oxidation inhibited lubricating compositions |
| US2721181A (en) * | 1952-10-09 | 1955-10-18 | Kendall Refining Company | Lubricant |
| GB748430A (en) * | 1953-11-07 | 1956-05-02 | Gulf Research Development Co | Hydrocarbon oil compositions and processes for preparing the same |
-
1959
- 1959-10-29 US US849453A patent/US3014869A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2084472A (en) * | 1934-07-14 | 1937-06-22 | Standard Oil Dev Co | Lubricating and insulating compound |
| US2160917A (en) * | 1937-06-10 | 1939-06-06 | Standard Oil Co | Lubricant |
| US2312208A (en) * | 1941-04-12 | 1943-02-23 | Standard Oil Co California | Compounded hydrocarbon oil |
| US2452319A (en) * | 1943-12-08 | 1948-10-26 | Texas Co | Rust and oxidation inhibited lubricating compositions |
| US2721181A (en) * | 1952-10-09 | 1955-10-18 | Kendall Refining Company | Lubricant |
| GB748430A (en) * | 1953-11-07 | 1956-05-02 | Gulf Research Development Co | Hydrocarbon oil compositions and processes for preparing the same |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4328113A (en) * | 1980-01-14 | 1982-05-04 | Mobil Oil Corporation | Friction reducing additives and compositions thereof |
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