US3173871A - Lubricating oils containing benzalcyclohexylamine and bis-phenols - Google Patents
Lubricating oils containing benzalcyclohexylamine and bis-phenols Download PDFInfo
- Publication number
- US3173871A US3173871A US197571A US19757162A US3173871A US 3173871 A US3173871 A US 3173871A US 197571 A US197571 A US 197571A US 19757162 A US19757162 A US 19757162A US 3173871 A US3173871 A US 3173871A
- Authority
- US
- United States
- Prior art keywords
- percent
- weight
- composition
- bis
- phenol
- 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
Links
- QKSQEJXIILKPDX-UHFFFAOYSA-N n-cyclohexyl-1-phenylmethanimine Chemical compound C1CCCCC1N=CC1=CC=CC=C1 QKSQEJXIILKPDX-UHFFFAOYSA-N 0.000 title claims description 10
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 title description 2
- 229930185605 Bisphenol Natural products 0.000 title description 2
- 239000010687 lubricating oil Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 28
- 230000001050 lubricating effect Effects 0.000 claims description 9
- 239000010688 mineral lubricating oil Substances 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- -1 alkyl phenol Chemical compound 0.000 description 13
- 239000000654 additive Substances 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 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 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000010727 cylinder oil Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- RNVMVSMBLWJDDQ-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol;2,4-ditert-butylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1.CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 RNVMVSMBLWJDDQ-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
-
- 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
- C10M2203/108—Residual fractions, e.g. bright stocks
-
- 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
-
- 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
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
-
- 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
- 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
- C10M2215/044—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
Definitions
- the invention relates to lubricating compositions and in particular to compositions based on mineral lubricating oils containing additives to impart oxidation resistance and anti-corrosion properties.
- a lubricating or anti-corrosive composition may contain small proportions of a compound obtained by the action of an aldehyde or ketone on a non-aromatic basic water-soluble primary or secondary monoamine.
- the present invention relates to compositions containing specifically one such additive together with a certain class of antioxidants which have been found to be specifically suitable for use therewith.
- a lubricating composition comprising a major proportion of a mineral lubricating oil, from 0.3 to 2.0 percent by weight of (a) benzal cyclohexylamine and from 0.25 to 2.0 percent by weight of (b) an alkyl phenol having at least one secondary or tertiary alkyl substituent in the ortho position to the hydroxyl group.
- the additive benzal cyclohexylamine appears to function in a lubricating composition not only as a corrosion inhibitor but also as a sludge dispersant; it may also be used with advantage in marine cylinder oils where, in some cases, this additive may be efiective as a dispersant and/or an inhibitor of varnish formation on pistons, as well as in some cases reducing cylinder liner wear.
- alkyl phenol of this invention may be represented by the general formula:
- R is a branched chain alkyl group of 3 to 8 carbon atoms attached to the benzene nucleus at a carbon atom at which branching occurs;
- R R and R are hydrogen, or methyl groups or are the same as R and
- X is hydrogen, or is the same as R or is one of the following two groups:
- Preferred compounds having the above general formula are those in which R; is the same as R i.e. is a branched tertiary alkyl group of 4 to 8 carbon atoms with no hydrogen atoms attached to the carbon atom adjacent to the benzene nucleus.
- additive (a) is present in the composition in amounts of from 0.5 to 1.0 percent by weight on the weight of the composition and that additive (b) is employed in amounts of from 0.3 to 1.0 percent by weight on the weight of the composition.
- a preferred composition according to the invention comprises a major proportion of a mineral lubricating oil comprising 0.5 percent by weight of benzal cyclohexylamine and from 0.3 to 0.5 percent by weight of methylene bis (2,6 di-t-butyl phenol).
- Mineral oil A is a blend consisting of 88% of a solvent refined mineral oil of viscosity about 145 seconds Redwood I at F. with 12% of a solvent refined brightstock of viscosity about 600 seconds Redwood I at 140 F.
- test data demonstrate that a lubricating composition suitable for lubricating marine crankcases which is based upon a mineral lubricating oil and contains benzal cyclohexylarnine is improved by the conjoint use therewith of antioxidants consisting of certain phenolic materials.
- Table I demonstrates that, as assessed by the total acid number and the demulsification value, a synergistic effect exists in those blends containing between 0.25 percent and 2.0 percent of the phenolic material in conjunction with between 0.3 percent and 2.0 percent of benzal cyclohexylamine. Further Table II demonstrates that a synergistic effect is present in the compositions containing benzal cyclohexylamine and mono or binuclear phenols.
- a lubricating composition comprising a major proportion of a mineral lubricating oil, from 0.3 to 2.0 percent by weight of (a) benzal cyclohexylamine and from 0.25 to 2.0 percent by weight of (b) an alkyl phenol having the following formula:
- R is a tertiary butyl group; R is selected from the group consisting of methyl and tertiary butyl groups, and
- X is selected from the group consisting of methyl, tertiary butyl and and where R and R are as defined above.
- composition as claimed in claim 1 wherein the alkyl phenol is 4,4 methylene bis(2,6 di-t-butyl phenol).
- a composition as claimed in claim 1 wherein the alkyl phenol is 2,6 di-t-butyl-4-methyl phenol 4.
- a composition as claimed in claim 1 wherein the alkyl phenol is 12,6 di-t-butyl phenol.
- composition as claimed in claim 1 wherein the alkyl phenol is 4,4 bis(2,6-cli-t-butyl phenol).
- composition as claimed in claim 1 wherein the alkyl phenol is 2,4 dimethyl 6t-butyl phenol.
- a lubricating composition comprising a major proportion of a mineral lubricating oil about 0.5 percent by weight of benzal cyclohexylamine and from 0.3 to 0.5 percent by weight of methylene bis (2,6 di-t-butyl phenol).
Landscapes
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB20819/61A GB976970A (en) | 1961-06-08 | 1961-06-08 | Improvements in or relating to lubricating oils having anticorrosive properties |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3173871A true US3173871A (en) | 1965-03-16 |
Family
ID=10152229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US197571A Expired - Lifetime US3173871A (en) | 1961-06-08 | 1962-05-25 | Lubricating oils containing benzalcyclohexylamine and bis-phenols |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3173871A (en)) |
| BE (1) | BE618661A (en)) |
| DE (1) | DE1271879B (en)) |
| GB (1) | GB976970A (en)) |
| NL (2) | NL279407A (en)) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3250713A (en) * | 1964-05-29 | 1966-05-10 | Shell Oil Co | Lubricant composition |
| US3839210A (en) * | 1971-12-01 | 1974-10-01 | Gaf Corp | Antioxidant composition comprising a synergistic mixture of a phenol, amine and sulfone |
| US3900410A (en) * | 1973-04-23 | 1975-08-19 | Ethyl Corp | Lubricating oil compositions containing trialkyl-substituted phenols and benzotriazole |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2060138A (en) * | 1935-09-16 | 1936-11-10 | Merrimac Chemical Co | Corrosion inhibitor |
| US2225533A (en) * | 1938-07-26 | 1940-12-17 | Gulf Research Development Co | Transformer oil composition |
| US2303819A (en) * | 1940-01-31 | 1942-12-01 | Gulf Oil Corp | Stabilizing solution of tetra-alkyl lead compounds |
| US2308282A (en) * | 1937-12-28 | 1943-01-12 | Us Rubber Co | Corrosion inhibitor |
| GB618083A (en) * | 1946-10-17 | 1949-02-16 | Elliott Alfred Evans | Improvements in or relating to lubricating and protective oil compositions |
| US2809164A (en) * | 1955-04-21 | 1957-10-08 | American Cyanamid Co | Oxidation inhibitors for lubricating oil |
| US2900417A (en) * | 1955-03-21 | 1959-08-18 | Ethyl Corp | 3,3' - diisopropyl - 5,5' - di - tert - butyl-4,4'-dihydroxydiphenyl, its preparation and use |
| US2923745A (en) * | 1957-10-21 | 1960-02-02 | Shell Dev | Ortho alkylation of phenols |
| US2944086A (en) * | 1955-09-23 | 1960-07-05 | Ethyl Corp | 1, 1-bis(3, 5-dialkyl-4-hydroxyphenyl) methanes |
| US3032502A (en) * | 1959-08-17 | 1962-05-01 | Standard Oil Co | Lubricant compositions |
| US3043775A (en) * | 1959-07-24 | 1962-07-10 | Thomas H Coffield | Organic material containing a 4, 4'-methylenebis phenol |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB824405A (en) * | 1957-03-19 | 1959-12-02 | Exxon Research Engineering Co | Improved oil compositions |
| US3018248A (en) * | 1960-01-20 | 1962-01-23 | California Research Corp | Oxidation inhibited mineral oil compositions |
-
0
- NL NL132017D patent/NL132017C/xx active
- NL NL279407D patent/NL279407A/xx unknown
- BE BE618661D patent/BE618661A/xx unknown
-
1961
- 1961-06-08 GB GB20819/61A patent/GB976970A/en not_active Expired
-
1962
- 1962-05-25 US US197571A patent/US3173871A/en not_active Expired - Lifetime
- 1962-06-05 DE DEP1271A patent/DE1271879B/de active Pending
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2060138A (en) * | 1935-09-16 | 1936-11-10 | Merrimac Chemical Co | Corrosion inhibitor |
| US2308282A (en) * | 1937-12-28 | 1943-01-12 | Us Rubber Co | Corrosion inhibitor |
| US2225533A (en) * | 1938-07-26 | 1940-12-17 | Gulf Research Development Co | Transformer oil composition |
| US2303819A (en) * | 1940-01-31 | 1942-12-01 | Gulf Oil Corp | Stabilizing solution of tetra-alkyl lead compounds |
| GB618083A (en) * | 1946-10-17 | 1949-02-16 | Elliott Alfred Evans | Improvements in or relating to lubricating and protective oil compositions |
| US2900417A (en) * | 1955-03-21 | 1959-08-18 | Ethyl Corp | 3,3' - diisopropyl - 5,5' - di - tert - butyl-4,4'-dihydroxydiphenyl, its preparation and use |
| US2809164A (en) * | 1955-04-21 | 1957-10-08 | American Cyanamid Co | Oxidation inhibitors for lubricating oil |
| US2944086A (en) * | 1955-09-23 | 1960-07-05 | Ethyl Corp | 1, 1-bis(3, 5-dialkyl-4-hydroxyphenyl) methanes |
| US2923745A (en) * | 1957-10-21 | 1960-02-02 | Shell Dev | Ortho alkylation of phenols |
| US3043775A (en) * | 1959-07-24 | 1962-07-10 | Thomas H Coffield | Organic material containing a 4, 4'-methylenebis phenol |
| US3032502A (en) * | 1959-08-17 | 1962-05-01 | Standard Oil Co | Lubricant compositions |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3250713A (en) * | 1964-05-29 | 1966-05-10 | Shell Oil Co | Lubricant composition |
| US3839210A (en) * | 1971-12-01 | 1974-10-01 | Gaf Corp | Antioxidant composition comprising a synergistic mixture of a phenol, amine and sulfone |
| US3900410A (en) * | 1973-04-23 | 1975-08-19 | Ethyl Corp | Lubricating oil compositions containing trialkyl-substituted phenols and benzotriazole |
Also Published As
| Publication number | Publication date |
|---|---|
| NL132017C (en)) | |
| GB976970A (en) | 1964-12-02 |
| NL279407A (en)) | |
| DE1271879B (de) | 1968-07-04 |
| BE618661A (en)) |
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