US2295179A - Lubricating composition and modified addition agent therefor - Google Patents
Lubricating composition and modified addition agent therefor Download PDFInfo
- Publication number
- US2295179A US2295179A US363025A US36302540A US2295179A US 2295179 A US2295179 A US 2295179A US 363025 A US363025 A US 363025A US 36302540 A US36302540 A US 36302540A US 2295179 A US2295179 A US 2295179A
- Authority
- US
- United States
- Prior art keywords
- addition agent
- phosphatides
- lubricants
- lubricating composition
- reaction product
- 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
- 239000000203 mixture Substances 0.000 title description 6
- 230000001050 lubricating effect Effects 0.000 title 1
- 239000003795 chemical substances by application Substances 0.000 description 23
- 239000000314 lubricant Substances 0.000 description 18
- 239000000463 material Substances 0.000 description 16
- 239000007795 chemical reaction product Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 8
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 5
- 239000000787 lecithin Substances 0.000 description 5
- 229940067606 lecithin Drugs 0.000 description 5
- 235000010445 lecithin Nutrition 0.000 description 5
- 239000010687 lubricating oil Substances 0.000 description 5
- 230000003472 neutralizing effect Effects 0.000 description 5
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000003973 alkyl amines Chemical class 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010685 fatty oil Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910001092 metal group alloy Inorganic materials 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- -1 amine salts Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/08—Ammonium or amine salts
-
- 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
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2221/041—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds involving sulfurisation of macromolecular compounds, e.g. polyolefins
-
- 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
-
- 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
- C10M2223/042—Metal salts thereof
-
- 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
- C10M2223/10—Phosphatides, e.g. lecithin, cephalin
Definitions
- the present invention relates to lubricating oils containing addition agents for use in automotive engines, and to methods for modifying certain addition agents sothat their undesirable qualities may be removed, thereby gaining the full benefit of the desirable qualities.
- An object of the present invention is to improve the properties of the oils by modifying the addition agents ither before addition to the lubricant or in situ.
- the present invention relates to such addition agents as phosphatides and commercial mixtures of the same.
- the former include, for example, lecithin and cephalin. while the latter usually comprises a mixture of the two along with residual fatty oil and free fatty acids.
- the commercial products frequently contain about 65%. phosphatides, based on phosphorus content, and about 35% of fatty 011 plus fatty acid; Whenever the term phosphatides appears herein it is to be understood that not only the pure compounds such as lecithin and cephalin, but also the commercial mixtures of lecithin, cephalin, oil, etc. are intended.
- the modified phosphatides are better suited for use as addition agents to lubricating oils.
- the neutralization may be carried out by various neutralizing agents such as ammonia or by the use of amines, including the alkylamines, the alkylol amines and aromatic amines such as pyridine, quinoline and their derivatives. It is believed that the ammonium or amine salts of the commercial phosphatides are formed.
- the amount of or-' ganic base used in the neutralization may be varied from 50% to 100%, or even an excess of organic base, ranging up to 200% of the acidity of the phosphatlde, may be used.
- the phosphatides ar neutralized simply by mixing them with one of the aforementioned neutralizing agents for several hours either at room temperature or at temperatures from F. to about 300 F. If desired, the phosphatide or neutralizing agent may be added to the oil first and then the other added so the reaction will take place in situ.
- ammonia, ammonium hydroxide, pyridine or pyridine derivatives may be used, it is preferred to use an organic base such as the tetra alkyl ammonium hydroxides, hydroxylamines, primary, secondary and tertiary amines or the amines prepared from various oils such as cocoanut oil.
- the amines may have the following general formulae RANCH, RaN, RzNH, RNHz, (OHRMN, RNHR or R'NRz wherein Rand R represent an alkyl, alkylene, aryl, or aralkyl radioal.
- a small quantity preferably from about 0.01% to about 5% is added to the oil with the result that the oxidation stability and the detergent properties of the oil are improved, at least as sullurized olefin polymers. organic phosphites, etc. to the oil.
- a process for neutralizing phosphatides to improve their value as addition agents for lubricants comprising treating the phosphatide with 3.
- a process for neutralizing phosphatides to improve their value as addition agents for lubricants comprising treating the phosphatide with an amine at temperatures below about 300 F.
- An addition agent for lubricants comprising the reaction product of a phosphatidic material and an alkyl amine at temperatures below about 300 F.
- An addition agent for lubricants comprising the reaction product of a phosphatidic material and an aromatic amine at temperatures below about 300 F.
- An addition agent for lubricants comprising the reaction product of a phosphatidic material -and an alkylolamine at temperatures below about 8.
- a lubricant comprising a lubricating oil and the reaction product of a phosphatidic material and an aromatic amine at temperatures below about 300 F.
- a lubricant comprising a lubricating oil and the reaction product of a phosphatidic material and an alkylolamine at temperatures below about 300 F.
- the phosphatidic material comprises lecithin.
- a lubricant comprising a lubricating oil and from about 0.01% to about 5% of the reaction product of a hosphatidic material and an osganic amine at temperatures below about 3 0 F.
- An addition agent for lubricants comprising the reaction product of a phosphatidic material and an organic amine at temperatures within the approximate range of F. to 300 F.
- An addition agent for lubricants comprising the reaction product of a phosphatidic material and an alkyl amine at temperatures within the approximate range of 90 F. to 300 F.
- An addition agent for lubricants comprising the reaction product of a phosphatidic material and an aromatic amine at temperatures within the approximate range of 90 F. to 300 F.
- An addition agent for lubricants comprising the reaction product oi a phosphatidic material and an alkylolamineat temperatures within the approximate range of 90 F. to 300 F.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
the neutralizationstep is not clear.
Patented Sept. 8, 1942- LUBBICATING COMPOSITION AND MODI- FIED ADDITION AGENT THEREFOR Clarence M. Loane, Hammond, Ind., assignor to Standard Oil Company, Chicago, 11]., a corporation of Indiana NorDrawing. Application October 26, 1940, Serial No. 363,025
19 Claims.
The present invention relates to lubricating oils containing addition agents for use in automotive engines, and to methods for modifying certain addition agents sothat their undesirable qualities may be removed, thereby gaining the full benefit of the desirable qualities.
An object of the present invention is to improve the properties of the oils by modifying the addition agents ither before addition to the lubricant or in situ.
More particularly the present invention relates to such addition agents as phosphatides and commercial mixtures of the same. The former include, for example, lecithin and cephalin. while the latter usually comprises a mixture of the two along with residual fatty oil and free fatty acids. The commercial products frequently contain about 65%. phosphatides, based on phosphorus content, and about 35% of fatty 011 plus fatty acid; Whenever the term phosphatides appears herein it is to be understood that not only the pure compounds such as lecithin and cephalin, but also the commercial mixtures of lecithin, cephalin, oil, etc. are intended.
It is known that theaddition of phosphatides to oils improves the quality thereof by preventing ring sticking and by acting as detergents and antioxidants. It .has been found, however, that while certain qualities of the lubricant are improved by these addition agents, certain other undesirable properties appear. In the case of the phosphatides it has been found that early sludge is often formed and that certain metal alloy bearing surfaces are corroded, particularly lead-containing bearings. These adverse effects are believed to be caused by the acidic properties of the phosphatides, or the fatty oils occurrin in the commercial mixture of phosphatides.
In order to overcome the above-mentioned undesirable effects of the phosphatides they may be neutralized. After such treatment the modified phosphatides are better suited for use as addition agents to lubricating oils.
The exact nature of the reactions involved in The fact that the unmodified phosphatides cause corrosion of various metal alloy bearing surfaces is probably due to the fact that the phosphatides exhibit acidic properties. The neutralization may be carried out by various neutralizing agents such as ammonia or by the use of amines, including the alkylamines, the alkylol amines and aromatic amines such as pyridine, quinoline and their derivatives. It is believed that the ammonium or amine salts of the commercial phosphatides are formed. The amount of or-' ganic base used in the neutralization may be varied from 50% to 100%, or even an excess of organic base, ranging up to 200% of the acidity of the phosphatlde, may be used.
In order to facilitate handling of the phosphatide during the neutralization step it is sometimes desirable to dilute the phosphatidic material with mineral oil, preferably in the proportion of 1 part material to 1 part or more of mineral oil. g
The phosphatides ar neutralized simply by mixing them with one of the aforementioned neutralizing agents for several hours either at room temperature or at temperatures from F. to about 300 F. If desired, the phosphatide or neutralizing agent may be added to the oil first and then the other added so the reaction will take place in situ.
While ammonia, ammonium hydroxide, pyridine or pyridine derivatives may be used, it is preferred to use an organic base such as the tetra alkyl ammonium hydroxides, hydroxylamines, primary, secondary and tertiary amines or the amines prepared from various oils such as cocoanut oil. The amines may have the following general formulae RANCH, RaN, RzNH, RNHz, (OHRMN, RNHR or R'NRz wherein Rand R represent an alkyl, alkylene, aryl, or aralkyl radioal.
have been found to be satisfactory.
After the phosphatidic material has been-neutralized, a small quantity, preferably from about 0.01% to about 5% is added to the oil with the result that the oxidation stability and the detergent properties of the oil are improved, at least as sullurized olefin polymers. organic phosphites, etc. to the oil.
I claim:
1. A process for neutralizing phosphatides to improve their value as addition agents for lubricants comprising treating the phosphatide with 3. A process for neutralizing phosphatides to improve their value as addition agents for lubricants comprising treating the phosphatide with an amine at temperatures below about 300 F.
4. An addition agent (or lubricants comprising the reaction product of a phosphatidic material and an organic amine at temperatures below about 300 F; I I
5. An addition agent for lubricants comprising the reaction product of a phosphatidic material and an alkyl amine at temperatures below about 300 F.
6. An addition agent for lubricants comprising the reaction product of a phosphatidic material and an aromatic amine at temperatures below about 300 F.
'7. An addition agent for lubricants comprising the reaction product of a phosphatidic material -and an alkylolamine at temperatures below about 8. An addition agent for lubricants as claimed in claim 4 wherein the phosphatidic material comprises lecithin and cephalin.
9. An addition agent for lubricants as claimed terial and an alkyl amine at temperatures below about 300 F.
13. A lubricant comprising a lubricating oil and the reaction product of a phosphatidic material and an aromatic amine at temperatures below about 300 F.
14. A lubricant comprising a lubricating oil and the reaction product of a phosphatidic material and an alkylolamine at temperatures below about 300 F.
in claim 4 wherein the phosphatidic material comprises lecithin.
10. An addition agent for lubricants as 15. A lubricant comprising a lubricating oil and from about 0.01% to about 5% of the reaction product of a hosphatidic material and an osganic amine at temperatures below about 3 0 F.
16. An addition agent for lubricants comprising the reaction product of a phosphatidic material and an organic amine at temperatures within the approximate range of F. to 300 F.
1'7. An addition agent for lubricants comprising the reaction product of a phosphatidic material and an alkyl amine at temperatures within the approximate range of 90 F. to 300 F.
18. An addition agent for lubricants comprising the reaction product of a phosphatidic material and an aromatic amine at temperatures within the approximate range of 90 F. to 300 F.
19. An addition agent for lubricants comprising the reaction product oi a phosphatidic material and an alkylolamineat temperatures within the approximate range of 90 F. to 300 F.
CLAREIICE M. LOANE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US363025A US2295179A (en) | 1940-10-26 | 1940-10-26 | Lubricating composition and modified addition agent therefor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US363025A US2295179A (en) | 1940-10-26 | 1940-10-26 | Lubricating composition and modified addition agent therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2295179A true US2295179A (en) | 1942-09-08 |
Family
ID=23428469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US363025A Expired - Lifetime US2295179A (en) | 1940-10-26 | 1940-10-26 | Lubricating composition and modified addition agent therefor |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2295179A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2434790A (en) * | 1944-03-27 | 1948-01-20 | Nopco Chem Co | Stabilizing fatty materials |
| US2511428A (en) * | 1947-05-27 | 1950-06-13 | Nopco Chem Co | Antioxidants |
| US2511427A (en) * | 1947-05-27 | 1950-06-13 | Nopco Chem Co | Stabilized oleaginous materials |
| US2987527A (en) * | 1959-02-16 | 1961-06-06 | Central Soya Co | Treating compound and method |
| US2987385A (en) * | 1959-02-16 | 1961-06-06 | Standard Oil Co | Anti-stalling gasoline composition |
| US3078177A (en) * | 1959-12-28 | 1963-02-19 | Phillips Petroleum Co | Fluidized bed coating process, article, and composition |
| US5503866A (en) * | 1995-01-17 | 1996-04-02 | Mallet And Company, Inc. | Releasing compositions for food contact surfaces |
-
1940
- 1940-10-26 US US363025A patent/US2295179A/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2434790A (en) * | 1944-03-27 | 1948-01-20 | Nopco Chem Co | Stabilizing fatty materials |
| US2511428A (en) * | 1947-05-27 | 1950-06-13 | Nopco Chem Co | Antioxidants |
| US2511427A (en) * | 1947-05-27 | 1950-06-13 | Nopco Chem Co | Stabilized oleaginous materials |
| US2987527A (en) * | 1959-02-16 | 1961-06-06 | Central Soya Co | Treating compound and method |
| US2987385A (en) * | 1959-02-16 | 1961-06-06 | Standard Oil Co | Anti-stalling gasoline composition |
| US3078177A (en) * | 1959-12-28 | 1963-02-19 | Phillips Petroleum Co | Fluidized bed coating process, article, and composition |
| US5503866A (en) * | 1995-01-17 | 1996-04-02 | Mallet And Company, Inc. | Releasing compositions for food contact surfaces |
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