GB717039A - Improvements in or relating to method of preparing a lubricating oil additive and the new lubricating oil additive resulting from said method - Google Patents
Improvements in or relating to method of preparing a lubricating oil additive and the new lubricating oil additive resulting from said methodInfo
- Publication number
- GB717039A GB717039A GB17387/51A GB1738751A GB717039A GB 717039 A GB717039 A GB 717039A GB 17387/51 A GB17387/51 A GB 17387/51A GB 1738751 A GB1738751 A GB 1738751A GB 717039 A GB717039 A GB 717039A
- Authority
- GB
- United Kingdom
- Prior art keywords
- barium
- phosphorus
- phospho
- salt
- hydroxide
- 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
Links
- 239000000654 additive Substances 0.000 title abstract 8
- 230000000996 additive effect Effects 0.000 title abstract 6
- 239000010687 lubricating oil Substances 0.000 title abstract 4
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 18
- 239000000194 fatty acid Substances 0.000 abstract 18
- 229930195729 fatty acid Natural products 0.000 abstract 18
- 150000004665 fatty acids Chemical class 0.000 abstract 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 13
- 239000011574 phosphorus Substances 0.000 abstract 13
- 229910052698 phosphorus Inorganic materials 0.000 abstract 13
- 239000000047 product Substances 0.000 abstract 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 8
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 abstract 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 8
- 229910052751 metal Inorganic materials 0.000 abstract 8
- 239000002184 metal Substances 0.000 abstract 8
- 230000003472 neutralizing effect Effects 0.000 abstract 8
- 229910052788 barium Inorganic materials 0.000 abstract 7
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 7
- 239000003921 oil Substances 0.000 abstract 7
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 6
- ZUDYPQRUOYEARG-UHFFFAOYSA-L barium(2+);dihydroxide;octahydrate Chemical compound O.O.O.O.O.O.O.O.[OH-].[OH-].[Ba+2] ZUDYPQRUOYEARG-UHFFFAOYSA-L 0.000 abstract 6
- 239000000463 material Substances 0.000 abstract 6
- 150000003839 salts Chemical class 0.000 abstract 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 5
- 229910001863 barium hydroxide Inorganic materials 0.000 abstract 5
- 229910052791 calcium Inorganic materials 0.000 abstract 5
- 239000011575 calcium Substances 0.000 abstract 5
- 235000019388 lanolin Nutrition 0.000 abstract 5
- 239000011133 lead Substances 0.000 abstract 5
- 239000000203 mixture Substances 0.000 abstract 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 4
- 239000005642 Oleic acid Substances 0.000 abstract 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 4
- 159000000009 barium salts Chemical class 0.000 abstract 4
- 239000003599 detergent Substances 0.000 abstract 4
- -1 fatty acid salt Chemical class 0.000 abstract 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 4
- 229910052749 magnesium Inorganic materials 0.000 abstract 4
- 239000011777 magnesium Substances 0.000 abstract 4
- 229910052759 nickel Inorganic materials 0.000 abstract 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 4
- 229910052712 strontium Inorganic materials 0.000 abstract 4
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 abstract 4
- 239000011135 tin Substances 0.000 abstract 4
- 229910052718 tin Inorganic materials 0.000 abstract 4
- 229910052725 zinc Inorganic materials 0.000 abstract 4
- 239000011701 zinc Substances 0.000 abstract 4
- 239000011787 zinc oxide Substances 0.000 abstract 4
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 abstract 2
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 abstract 2
- 240000002791 Brassica napus Species 0.000 abstract 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 240000006240 Linum usitatissimum Species 0.000 abstract 2
- 235000004431 Linum usitatissimum Nutrition 0.000 abstract 2
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 abstract 2
- 230000003078 antioxidant effect Effects 0.000 abstract 2
- BHDOPTZJCSDVJE-CVBJKYQLSA-L barium(2+);(z)-octadec-9-enoate Chemical compound [Ba+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O BHDOPTZJCSDVJE-CVBJKYQLSA-L 0.000 abstract 2
- 150000007514 bases Chemical class 0.000 abstract 2
- ZCZLQYAECBEUBH-UHFFFAOYSA-L calcium;octadec-9-enoate Chemical compound [Ca+2].CCCCCCCCC=CCCCCCCCC([O-])=O.CCCCCCCCC=CCCCCCCCC([O-])=O ZCZLQYAECBEUBH-UHFFFAOYSA-L 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000004359 castor oil Substances 0.000 abstract 2
- 150000001868 cobalt Chemical class 0.000 abstract 2
- 229910017052 cobalt Inorganic materials 0.000 abstract 2
- 239000010941 cobalt Substances 0.000 abstract 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 2
- 235000004426 flaxseed Nutrition 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 150000004715 keto acids Chemical class 0.000 abstract 2
- 229910044991 metal oxide Inorganic materials 0.000 abstract 2
- 239000003208 petroleum Substances 0.000 abstract 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 abstract 2
- 229960003656 ricinoleic acid Drugs 0.000 abstract 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 abstract 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract 2
- 150000003751 zinc Chemical class 0.000 abstract 2
- 229910021511 zinc hydroxide Inorganic materials 0.000 abstract 2
- 229940007718 zinc hydroxide Drugs 0.000 abstract 2
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 abstract 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 abstract 1
- 239000000920 calcium hydroxide Substances 0.000 abstract 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003925 fat Substances 0.000 abstract 1
- 229910000000 metal hydroxide Inorganic materials 0.000 abstract 1
- 150000004706 metal oxides Chemical class 0.000 abstract 1
- 239000010688 mineral lubricating oil Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000013112 stability test Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003505 terpenes Chemical class 0.000 abstract 1
- 235000007586 terpenes Nutrition 0.000 abstract 1
- 238000012360 testing method Methods 0.000 abstract 1
- 239000001993 wax Substances 0.000 abstract 1
- 150000003752 zinc compounds Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus 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
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/08—Groups 4 or 14
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/14—Group 7
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/16—Groups 8, 9, or 10
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Lubricants (AREA)
Abstract
A product suitable for use as a lubricating oil additive (see Group III) is obtained by reacting a zinc, barium, calcium, strontium, magnesium, tin, lead, nickel, or cobalt salt of a fatty acid having from 12 to 30 carbon atoms in the molecule and containing a group reactive with a sulphide of phosphorus, with a sulphide of phosphorus and then neutralizing the phospho-sulphurized material with a basic compound of zinc, barium, calcium, strontium, magnesium, tin, lead, nickel, or cobalt, the weight per cent of metal in the neutralized material being substantially greater than that in said salt. The metal introduced into the phospho-sulphurized fatty acid salt may be the same as or different from the metal present in the salt. The fatty acid containing a group reactive with a sulphide of phosphorus may be a hydroxy fatty acid, an olefinically unsaturated fatty acid, or an oxidized petroleum fraction containing hydroxy, olefinic and/or keto acids, specified fatty acids being hydroxy stearic acid, oleic acid, ricinoleic acid, wool grease fatty acids and fatty acid mixtures derived from natural oils such as cornseed, rapeseed, linseed, sperm and castor oils. The fatty acid metal salt starting material may be prepared from the fatty acid or from the oils, fats or waxes which are the sources of the fatty acids; oleic acid may, for example, be neutralized with a metal or a metallic oxide or hydroxide. The product after phospho-sulphurization is then neutralized with the same or a different metal oxide or hydroxide. An additive having good detergent and anti-oxidant properties can be made by neutralizing the fatty material with barium oxide or hydroxide, phospho-sulphurizing with a phosphorus sulphide, e.g. phosphorus sesquisulphide or pentasulphide and then neutralizing with zinc oxide or hydroxide. In examples (1) oleic acid dissolved in a hydrocarbon oil and heated to 275-300 DEG F. is neutralized by the addition of calcium hydroxide and phosphorus sesquisulphide is then added, and reaction effected at 250 DEG F. whilst passing air into the reaction mixture; the temperature is then raised to 275 DEG to 300 DEG F. and barium hydroxide octahydrate then added to the solution and the mixture heated and filtered to yield a product containing phosphorus, sulphur, calcium and barium; (2) calcium oleate is prepared as in (1) and then reacted with phosphorus pentasulphide for two hours at 300 DEG F., barium hydroxide octahydrate is then added and reaction effected as in (1); (3) wool grease is heated to 300 DEG to 325 DEG F. and saponified with barium hydroxide octahydrate, phosphorus sesquisulphide is then added and air passed into the mixture to maintain the temperature at 240 DEG F. A hydrocarbon oil is added to the reaction product which is then reacted with barium hydroxide octahydrate at 275 DEG to 300 DEG F. and the mixture filtered to yield a product containing a high percentage of barium. Instead of using barium hydroxide to neutralize the phospho-sulphurized barium salt a basic zinc compound may be used. Other products referred to are the barium salt of the phospho-sulphurized zinc salt of wool grease fatty acids, the products obtained by neutralizing phospho-sulphurized barium oleate with barium oxide or hydroxide or with zinc oxide, and the barium salt of phospho-sulphurized zinc oleate. Reference is also made to the double lead salts.ALSO:A lubricating oil additive is obtained by reacting a zinc, barium, calcium, strontium, magnesium, tin, lead, nickel, or cobalt salt of a fatty acid having from 12 to 30 carbon atoms in the molecule and containing a group reactive with a sulphide of phosphorus, with a sulphide of phosphorus and subsequently neutralizing the phospho-sulphurized material with a basic compound of zinc, barium, calcium, strontium, magnesium, tin, lead, nickel or cobalt, the weight per cent. of metal in the neutralized material being substantially greater than that in said salt (see Group IV (b)). The products are useful as additives to enhance detergent properties of mineral lubricating oils. The metal introduced into the phospho-sulphurized fatty acid salt may be the same as or different from the metal present in the salt. The fatty acid containing a group reactive with a sulphide of phosphorus may be a hydroxy fatty acid, an olefinically unsaturated fatty acid, or an oxidized petroleum fraction containing hydroxy, olefinic and/or keto acids, specified fatty acids being hydroxy stearic acid, oleic acid, ricinoleic acid, wool grease, fatty acids and fatty acid mixtures derived from natural oils such as cornseed, rapeseed, linseed, sperm and castor oils. An additive having good detergent and antioxidant properties can be made by neutralizing the fatty material with barium oxide or hydroxide, phospho-sulphurizing with a phosphorus sulphide, e.g. phosphorus sesquisulphide or pentasulphide and then neutralizing with zinc oxide or hydroxide. Stability tests are described for a mid-continent solvent refined oil containing the product obtained by reacting barium hydroxide octahydrate with that obtained by reacting calcium oleate with phosphorus sesquisulphide and with phosphorus pentasulphide respectively, and tests for the detergent qualities of a mid-continent solvent refined oil containing a small amount of a phosphosulphurized terpene together with (a) the barium salt of phospho-sulphurized zinc oleate; or (b) and (c) the product obtained by reacting the barium and zinc salts respectively of wool grease with phosphorus sesquisulphide and then with barium hydroxide octahydrate. Other additives referred to are the products obtained by neutralizing phospho-sulphurized barium oleate with barium oxide or hydroxide or with zinc oxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17387/51A GB717039A (en) | 1951-07-23 | 1951-07-23 | Improvements in or relating to method of preparing a lubricating oil additive and the new lubricating oil additive resulting from said method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17387/51A GB717039A (en) | 1951-07-23 | 1951-07-23 | Improvements in or relating to method of preparing a lubricating oil additive and the new lubricating oil additive resulting from said method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB717039A true GB717039A (en) | 1954-10-20 |
Family
ID=10094303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17387/51A Expired GB717039A (en) | 1951-07-23 | 1951-07-23 | Improvements in or relating to method of preparing a lubricating oil additive and the new lubricating oil additive resulting from said method |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB717039A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2945810A (en) * | 1956-12-31 | 1960-07-19 | California Research Corp | Lubricating oil compositions containing bi-metal dithiophosphates |
| WO1989006237A1 (en) * | 1988-01-04 | 1989-07-13 | The Lubrizol Corporation | Basic metal dihydrocarbylphosphorodithioates |
| US5015402A (en) * | 1986-11-07 | 1991-05-14 | The Lubrizol Corporation | Basic metal dihydrocarbylphosphorodithioates |
-
1951
- 1951-07-23 GB GB17387/51A patent/GB717039A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2945810A (en) * | 1956-12-31 | 1960-07-19 | California Research Corp | Lubricating oil compositions containing bi-metal dithiophosphates |
| US5015402A (en) * | 1986-11-07 | 1991-05-14 | The Lubrizol Corporation | Basic metal dihydrocarbylphosphorodithioates |
| WO1989006237A1 (en) * | 1988-01-04 | 1989-07-13 | The Lubrizol Corporation | Basic metal dihydrocarbylphosphorodithioates |
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