US2665254A - Oxidation inhibited mineral oil - Google Patents
Oxidation inhibited mineral oil Download PDFInfo
- Publication number
- US2665254A US2665254A US170059A US17005950A US2665254A US 2665254 A US2665254 A US 2665254A US 170059 A US170059 A US 170059A US 17005950 A US17005950 A US 17005950A US 2665254 A US2665254 A US 2665254A
- Authority
- US
- United States
- Prior art keywords
- oil
- oxidation
- temperature conditions
- lubricating oil
- mineral oil
- 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
- 230000003647 oxidation Effects 0.000 title claims description 22
- 238000007254 oxidation reaction Methods 0.000 title claims description 22
- 239000002480 mineral oil Substances 0.000 title description 2
- 235000010446 mineral oil Nutrition 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 10
- 230000001050 lubricating effect Effects 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 239000010688 mineral lubricating oil Substances 0.000 claims description 3
- 239000003921 oil Substances 0.000 description 17
- 239000003112 inhibitor Substances 0.000 description 12
- 239000010687 lubricating oil Substances 0.000 description 11
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 8
- -1 ethyl radicals Chemical class 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 150000005840 aryl radicals Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- MMTOSBCMFDNOIY-UHFFFAOYSA-N 2-(chloromethyl)-3-methyloxirane Chemical compound CC1OC1CCl MMTOSBCMFDNOIY-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- VGTRHVDJGLVLEY-UHFFFAOYSA-N 6-butyl-1-methylcyclohexa-2,4-dien-1-ol Chemical compound CCCCC1C=CC=CC1(C)O VGTRHVDJGLVLEY-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
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006388 chemical passivation reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/042—Epoxides
-
- 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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
-
- 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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/20—Containing nitrogen-to-oxygen bonds
- C10M2215/202—Containing nitrogen-to-oxygen bonds containing nitro groups
Definitions
- oxidation inhibitors have been proposed for lubricating oil.
- certain alkylated phenols particularly tertiary butyl sub-stituted phenols such as 2,6-ditertiary butyl-imethyl phenol.
- Such alkylated phenols are generally effective to inhibit oxidative deterioration of lubricating oil under ordinary conditions of use.
- Lubricating oil suitable for use under severe temperature conditions is required to have certain general specifications. For example, it must 'have relatively high flash point (A. S. T. M. D92- 46), e. g. 350 F. or above, and preferably above the highest temperature to which the oil is to be subjected; otherwise the oil will be too volatile for effective use under severe temperature conditions.
- Lubricating oil for certain specific applications involving severe temperature conditions must have additional specifications.
- lubricating oil for use in automotive fluid couplings Where temperatures of about 400 F. must be withstood, are generally required to have an U. viscosity at 100 F. within the ap roximate range 170-190, and S. U. viscosity at 210 F. not substantially less than 45.
- the present invention relates to the inhibition against oxidation of such lubricating oil and other lubricating oil suitable for use under severe temperature conditions.
- Oxidation inhibitors for use according to the invention should be substantially non-volatile at the temperature at which the oil is used, i. e. they should have normal boiling points higher than the temperature of use of the oil.
- Phenoxy propylene oxide (1,2-epoxy-3-phenoxy propane, boiling point 452 F.) is an additive compound according to the invention which has high enough boiling point for severe temperature uses ordinarily encountered.
- Phenoxy propylene oxide is particularly advantageous for use according to the invention; for although phen-oxy propylene oxide, as an oxidation inhibitor for oil under ordinary temperature conditions of use, is inferior to at least one Widely used alkylated phenol oxidation inhibitor of the prior art, it has been found that on the other hand phenoxy propylene oxide is distinctly superior to that same alkylated phenol oxidation inhibitor as an inhibitor for oil under severe temperature conditions of use.
- the amount of additive compound according to the invention used in a given amount of lubricating oil will Vary according to the degree'of oxidation inhibition desi1 'ed. Generally, satisfactory results are'obtained with 0.01-2100weight percent of additive.
- the oil tested in this example was a solvent-refined, dewaxed, acid-treated, and clay-treated distillate from mixed-base crude petroleum, the distillate having an S. U. viscosity at F. of about 185 and a viscosity index of about 90.
- Two samples of this oil were tested for oxidation stability under severe temperature conditions by subjecting each to a temperature of 400 F. in an oven for hours, air being passed through the sample during this period at the rate of two bubbles per second. Before and after the oxidation period, the amount of naphtha-insoluble material in each sample and the S. U. viscosity at 210 F. of each sample were determined.
- Sample No. 1 contained one weight percent of 2,6-ditertiary butyll-methyl phenol as oxidation inhibitor, and Sample No. 2 contained one Weight 3 percent 01 phenoxy propylene oxide as oxidation inhibitor.
- the following table shows the increase in naphtha-insoluble content and in 210 F. viscosity for each sample during the oxidation 4, major proportion of mineral lubricating oil suitable for use under severe temperature conditions; and a minor proportion constituting an oxidation inhibiting quantity of a compound having period 6 the formula R-OCH:CH-CHR' Percent Percent Increase in Increase in Sample i qggwhere R is an aryl radical and R' is selected from Materials 210 F. the group consisting of hydrogen and methyl and ethyl radicals. 1.
- composition according to claim 1 wherein 2 said oil has a flash point of at least about 350 F. 3.
- Composition according to claim 1 wherein The above results Show lubrlcatlng O11 lIlpercent of said aroxy epoxy alka ne in hibited with 2,6-ditertiary butyl-4-methyl phenol the composition is about undergoes greater oxidative deterioration under Composition according to claim 1 wherein severe temperature conditions than does the same said aroxy epoxy alkane is 1,2 epoXy 3 phenoXy oil inhibited with phenoxy propylene oxide. propane On the other hand, lubricating Oi].
- the method of lubricating metal parts with fi- Y butyl-l-methyl phenol which comprises: contacting such parts with erally undergoes less oxidative deterioration unmineral lubricating oil at a temperature in the der ordinary temperature conditions of use than range fro to F" Said 011 containing do the S Oil inhibited With p 'l y P a minor proportion constituting an oxidation inpylene oxide.
- an oil havm pr hibiting quantity of a compound having the forerties generally like those of the oil tested inltl'ae, mula, example above, but having S. U. viscosity at 0 F.
- a lubricating composition comprising: a
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)
Description
Patented Jan. 5, 1954 OXIDATION INHIBITED MINERAL OIL Walter J. Coppock, Ridley Park, Pa... assignor to Sun Oil Company, Philadelphia, Pa., a corporation of New Jersey No Drawing. Application June 23, 1950, Serial No. 170,059
chemical compounds having the desired inhibiting effect.
Many oxidation inhibitors have been proposed for lubricating oil. Among the best such inhibitors that have been proposed are certain alkylated phenols, particularly tertiary butyl sub-stituted phenols such as 2,6-ditertiary butyl-imethyl phenol. Such alkylated phenols are generally effective to inhibit oxidative deterioration of lubricating oil under ordinary conditions of use.
Certain types of lubricating oil, however, are used under unusually severe temperature conditions, e. g. 250-450" F.; and oxidation irmibitors which are suitable at ordinary temperature conditions of LISQ'E. g. 100-250 F., are frequently much less effective and therefore unsuitable when used in such lubricating oilunder such. severe temperature conditions.
Lubricating oil suitable for use under severe temperature conditions is required to have certain general specifications. For example, it must 'have relatively high flash point (A. S. T. M. D92- 46), e. g. 350 F. or above, and preferably above the highest temperature to which the oil is to be subjected; otherwise the oil will be too volatile for effective use under severe temperature conditions. Lubricating oil for certain specific applications involving severe temperature conditions must have additional specifications. For example, lubricating oil for use in automotive fluid couplings, Where temperatures of about 400 F. must be withstood, are generally required to have an U. viscosity at 100 F. within the ap roximate range 170-190, and S. U. viscosity at 210 F. not substantially less than 45. The present invention relates to the inhibition against oxidation of such lubricating oil and other lubricating oil suitable for use under severe temperature conditions.
. 6 Claims. (Cl. 25252) I have discovered that compounds having the formula where R is an aryl radical and R is selected from the group consisting of hydrogen, methyI, and ethyl radicals, are efiective oxidation inhibitors for lubricating oil used under severe temperature conditions.
Oxidation inhibitors for use according to the invention should be substantially non-volatile at the temperature at which the oil is used, i. e. they should have normal boiling points higher than the temperature of use of the oil. Phenoxy propylene oxide (1,2-epoxy-3-phenoxy propane, boiling point 452 F.) is an additive compound according to the invention which has high enough boiling point for severe temperature uses ordinarily encountered. Phenoxy propylene oxide is particularly advantageous for use according to the invention; for although phen-oxy propylene oxide, as an oxidation inhibitor for oil under ordinary temperature conditions of use, is inferior to at least one Widely used alkylated phenol oxidation inhibitor of the prior art, it has been found that on the other hand phenoxy propylene oxide is distinctly superior to that same alkylated phenol oxidation inhibitor as an inhibitor for oil under severe temperature conditions of use.
The amount of additive compound according to the invention used in a given amount of lubricating oil will Vary according to the degree'of oxidation inhibition desi1 'ed. Generally, satisfactory results are'obtained with 0.01-2100weight percent of additive.
The following example illustrates the invention:
The oil tested in this example was a solvent-refined, dewaxed, acid-treated, and clay-treated distillate from mixed-base crude petroleum, the distillate having an S. U. viscosity at F. of about 185 and a viscosity index of about 90. Two samples of this oil were tested for oxidation stability under severe temperature conditions by subjecting each to a temperature of 400 F. in an oven for hours, air being passed through the sample during this period at the rate of two bubbles per second. Before and after the oxidation period, the amount of naphtha-insoluble material in each sample and the S. U. viscosity at 210 F. of each sample were determined.
Sample No. 1 contained one weight percent of 2,6-ditertiary butyll-methyl phenol as oxidation inhibitor, and Sample No. 2 contained one Weight 3 percent 01 phenoxy propylene oxide as oxidation inhibitor. The following table shows the increase in naphtha-insoluble content and in 210 F. viscosity for each sample during the oxidation 4, major proportion of mineral lubricating oil suitable for use under severe temperature conditions; and a minor proportion constituting an oxidation inhibiting quantity of a compound having period 6 the formula R-OCH:CH-CHR' Percent Percent Increase in Increase in Sample i qggwhere R is an aryl radical and R' is selected from Materials 210 F. the group consisting of hydrogen and methyl and ethyl radicals. 1. 1.3 78 '2. Composition according to claim 1 wherein 2 said oil has a flash point of at least about 350 F. 3. Composition according to claim 1 wherein The above results Show lubrlcatlng O11 lIlpercent of said aroxy epoxy alka ne in hibited with 2,6-ditertiary butyl-4-methyl phenol the composition is about undergoes greater oxidative deterioration under Composition according to claim 1 wherein severe temperature conditions than does the same said aroxy epoxy alkane is 1,2 epoXy 3 phenoXy oil inhibited with phenoxy propylene oxide. propane On the other hand, lubricating Oi]. 5 The method of lubricating metal parts with fi- Y butyl-l-methyl phenol which comprises: contacting such parts with erally undergoes less oxidative deterioration unmineral lubricating oil at a temperature in the der ordinary temperature conditions of use than range fro to F" Said 011 containing do the S Oil inhibited With p 'l y P a minor proportion constituting an oxidation inpylene oxide. For example, an oil havm pr hibiting quantity of a compound having the forerties generally like those of the oil tested inltl'ae, mula, example above, but having S. U. viscosity at 0 F. of about 160, was found to be more stable in R o CH2 R the turbine oil oxidation stability test (A. S. T. M. 0 I D943-4'7T), which is conducted at 203 F., when where R is an aryl radical and R is selected from inhibited with 2,6 ditertiary butyl--methyl the group consisting of hydrogen and methyl phenol than when inhibited with phenoxy pro13Y1- and ethyl radicals.
ene oxide. 6. A composition consisting essentially of a Thus, it iS seen that the efiectiveness Of lubrimajor proportion of mineral lubricating oil and eating oil oxidation inhibitors depends on the i o prgportion constituting an oxidation conditions to which the oil is subjected during hibiting quantity of a compound having the foruse, and that phenoxy propylene oxide gives sul perior results in oil used under severe temperature conditions, as compared with a prior art oxidation inhibitor, such as 2,6-ditertiary butyl-l- 4O 0 methyl h l, where R is an aryl radical and R is selected from Although, in the preceding example a phenoxy the group c nsi tin f y n n m hyl n epoxy propane is used as an example of the adethyl radicals. ditive employed, similar results may be obtained WALTER J. COPPOCK. when other additive compounds within the scope of the invention are used. Such compounds may References clted m the file of this Patent be prepared by any suitable method, e. g., by re- UNITED STATES PATENTS acting at about 100 C. an excess of an epoxy chloro alkane such as epichlorohydrin, or 1- g ggz fii Jan 5 chloro-2,3-epoxy butane, etc. with an aqueous 1 6 Myer 1939 solution of an alkali metal salt of phenol or other 2221818 slagh Nov 1940 aryl hydroxy compound such as cresol, methyl 2263664 Wassol; Nov 1941 isopropyl phenol, bromophenol, nitrophenol, 2362516 Wasson 1944 ggfiy 2,438,468 Wasson Mar. 23, 1948 1. A lubricating composition comprising: a
Claims (1)
1. A LUBRICATING COMPOSITION COMPRISING: A MAJOR PROPORTION OF MINERAL LUBRICATING OIL SUITABLE FOR USE UNDER SEVERE TEMPERATURE CONDITIONS; AND A MINOR PROPORTION CONSTITUTING AN OXIDATION INHIBITING QUANTITY OF A COMPOUND HAVING THE FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US170059A US2665254A (en) | 1950-06-23 | 1950-06-23 | Oxidation inhibited mineral oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US170059A US2665254A (en) | 1950-06-23 | 1950-06-23 | Oxidation inhibited mineral oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2665254A true US2665254A (en) | 1954-01-05 |
Family
ID=22618380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US170059A Expired - Lifetime US2665254A (en) | 1950-06-23 | 1950-06-23 | Oxidation inhibited mineral oil |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2665254A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734032A (en) * | 1956-02-07 | Lubricants | ||
| US3127353A (en) * | 1958-07-15 | 1964-03-31 | Lubricating compositions | |
| US3425814A (en) * | 1963-05-03 | 1969-02-04 | Exxon Research Engineering Co | Stabilized oil |
| US9410105B2 (en) | 2012-11-16 | 2016-08-09 | Basf Se | Lubricant compositions comprising epoxide compounds |
| US20210095177A1 (en) * | 2004-12-21 | 2021-04-01 | Honeywell International Inc | Stabilized iodocarbon compositions |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2067960A (en) * | 1937-01-19 | Ethers of dihydric phenols | ||
| US2166604A (en) * | 1932-04-22 | 1939-07-18 | Ig Farbenindustrie Ag | Stable compositions comprising chlorinated substances |
| US2221818A (en) * | 1938-08-17 | 1940-11-19 | Dow Chemical Co | Ethers of alkyl-phenols |
| US2263664A (en) * | 1941-11-25 | Mineeal | ||
| US2362516A (en) * | 1942-05-02 | 1944-11-14 | Standard Oil Dev Co | Antioxidant |
| US2438468A (en) * | 1942-12-31 | 1948-03-23 | Standard Oil Dev Co | Oil composition |
-
1950
- 1950-06-23 US US170059A patent/US2665254A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2067960A (en) * | 1937-01-19 | Ethers of dihydric phenols | ||
| US2263664A (en) * | 1941-11-25 | Mineeal | ||
| US2166604A (en) * | 1932-04-22 | 1939-07-18 | Ig Farbenindustrie Ag | Stable compositions comprising chlorinated substances |
| US2221818A (en) * | 1938-08-17 | 1940-11-19 | Dow Chemical Co | Ethers of alkyl-phenols |
| US2362516A (en) * | 1942-05-02 | 1944-11-14 | Standard Oil Dev Co | Antioxidant |
| US2438468A (en) * | 1942-12-31 | 1948-03-23 | Standard Oil Dev Co | Oil composition |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734032A (en) * | 1956-02-07 | Lubricants | ||
| US3127353A (en) * | 1958-07-15 | 1964-03-31 | Lubricating compositions | |
| US3425814A (en) * | 1963-05-03 | 1969-02-04 | Exxon Research Engineering Co | Stabilized oil |
| US20210095177A1 (en) * | 2004-12-21 | 2021-04-01 | Honeywell International Inc | Stabilized iodocarbon compositions |
| US9410105B2 (en) | 2012-11-16 | 2016-08-09 | Basf Se | Lubricant compositions comprising epoxide compounds |
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