US2689220A - Lubricating oil compositions of mixed diester dithiophosphates - Google Patents
Lubricating oil compositions of mixed diester dithiophosphates Download PDFInfo
- Publication number
- US2689220A US2689220A US218282A US21828251A US2689220A US 2689220 A US2689220 A US 2689220A US 218282 A US218282 A US 218282A US 21828251 A US21828251 A US 21828251A US 2689220 A US2689220 A US 2689220A
- Authority
- US
- United States
- Prior art keywords
- alcohols
- oil
- zinc
- alcohol
- zinc salts
- 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
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- 239000000203 mixture Substances 0.000 title description 22
- 239000010687 lubricating oil Substances 0.000 title description 11
- 150000005690 diesters Chemical class 0.000 title description 9
- 239000002253 acid Substances 0.000 claims description 34
- 150000001298 alcohols Chemical class 0.000 claims description 33
- 150000007513 acids Chemical class 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000000314 lubricant Substances 0.000 claims description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
- 230000001050 lubricating effect Effects 0.000 claims description 7
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 235000019441 ethanol Nutrition 0.000 description 39
- 239000003921 oil Substances 0.000 description 29
- 150000003751 zinc Chemical class 0.000 description 26
- 150000002148 esters Chemical class 0.000 description 23
- -1 2-ethyl amyl Chemical group 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 229910052725 zinc Inorganic materials 0.000 description 7
- 239000011701 zinc Substances 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 239000002199 base oil Substances 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ISTJMQSHILQAEC-UHFFFAOYSA-N 2-methyl-3-pentanol Chemical compound CCC(O)C(C)C ISTJMQSHILQAEC-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- CLPFFLWZZBQMAO-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 CLPFFLWZZBQMAO-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
- GTBPDKIKDFFCBC-UHFFFAOYSA-N CC(CCCCC)SP(O)(O)=S Chemical compound CC(CCCCC)SP(O)(O)=S GTBPDKIKDFFCBC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- NXEUTNOJLUEESD-UHFFFAOYSA-L P(OCCCCCCCCCCCCCCCC)([O-])=S.[Ca+2].C(CCCCCCCCCCCCCCC)OP([O-])=S Chemical compound P(OCCCCCCCCCCCCCCCC)([O-])=S.[Ca+2].C(CCCCCCCCCCCCCCC)OP([O-])=S NXEUTNOJLUEESD-UHFFFAOYSA-L 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- WIKSRXFQIZQFEH-UHFFFAOYSA-N [Cu].[Pb] Chemical group [Cu].[Pb] WIKSRXFQIZQFEH-UHFFFAOYSA-N 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001669 calcium Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DZQISOJKASMITI-UHFFFAOYSA-N decyl-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound CCCCCCCCCCP(O)(O)=O DZQISOJKASMITI-UHFFFAOYSA-N 0.000 description 1
- 229940100539 dibutyl adipate Drugs 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- OJXOOFXUHZAXLO-UHFFFAOYSA-M magnesium;1-bromo-3-methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC(Br)=C1 OJXOOFXUHZAXLO-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- DCHRWDODMXBBQG-UHFFFAOYSA-L zinc;butan-2-yloxy-butan-2-ylsulfanyl-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCC(C)OP([O-])(=S)SC(C)CC.CCC(C)OP([O-])(=S)SC(C)CC DCHRWDODMXBBQG-UHFFFAOYSA-L 0.000 description 1
- YZKRIHZCXGPZGB-UHFFFAOYSA-L zinc;oxido-propan-2-yloxy-propan-2-ylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CC(C)OP([O-])(=S)SC(C)C.CC(C)OP([O-])(=S)SC(C)C YZKRIHZCXGPZGB-UHFFFAOYSA-L 0.000 description 1
Classifications
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- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/17—Esters of thiophosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
-
- 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
- C10M137/10—Thio derivatives
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/024—Propene
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
-
- 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
- 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
- C10M2207/027—Neutral 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- 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
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- 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
- C10M2207/40—Fatty vegetable or animal oils
-
- 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
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
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Definitions
- This invention pertains to a new composition of matter; that is, a lubricating oil composition comprising an oil of lubricating viscosity and zinc salts of mixed diesters of dithiophosphoric acids (i. e., wherein the organic portions of the acids are derived from two different alcohols e. g., butyl alcohol and hexyl alcohol).
- this invention pertains to lubricants containing zinc salts of mixed diesters of dithiophosphoric acids wherein the alcohols used in the preparation of the dithiophosphoric acids are of low molecular weight.
- zinc salts of dialkyldithiophosphoric acids inhibit oxidation of lubricating oil compositions.
- the alkyl groups of these zinc dialkyldithiophosphates may be of high molecular weight or low molecular weight.
- the lubricants considered herein comprise, in particular, oils of lubricating viscosity and zinc salts of mixed esters of dithiophosphoric acids.
- the zinc salts of mixed esters of diothiophosphoric acids incorporated in the lubricating compositions of this invention are zinc salts of products obtained by reacting phosphorus pentasulfide with two different alcohols.
- One of the alcohols used in preparing the mixed ester of dithiophosphoric acids contains not more than 4 carbon atoms; for example, methyl alcohol, ethyl alcohol, propyl alcohol, isopropyl alcohol, butyl alcohol, sec-butyl alcohol and tertiary butyl alcohol.
- this group of alcohols will hereinafter be called the R1 alcohols.
- the other alcohols used in the preparation of mixed esters of dithiophosphoric acids contain from 6 to 18 carbon atoms. These include the following alcohols: hexyl, methylisobutylcarbinol, ethylisopropylcarbinol, heptyl, isoheptyl, 2-ethyl amyl, octyl, isooctyl, 3-ethyl hexyl, 2- propyl amyl, decyl, undecyl, dodecyl, hexadecyl, octadecyl, etc.
- this group of alcohols will hereinafter be known as the R2 alcohols.
- the R1 and R2 alcohols need not be present in the reaction mixture in equal molar amounts.
- the mole ratio of R1 alcohols to R2 alcohols be from 1 to 5. It is particularly preferred to use a mole ratio of R1 alcohols to R2 alcohols from 2 to 4.
- Suitable oils of lubricating viscosity include a wide variety of lubricating oils such as naphthenic base, parailin base, and mixed base mineral oils, other hydrocarbon lubricants, e. g., alkylene polymers (such as polymers of propylene, butylene, etc., and mixtures thereof), alkylene oxide type polymers, dicarboxylic acid esters and liquid esters of acids of phosphorus.
- Synthetic oils of the alkylene oxide type polymer which may be used include those exemplified by alkylene oxide polymers (e. g., propylene oxide polymers) and derivatives, including alkylene oxide polymers prepared by polymerizing alkylene oxides (e.
- propylene oxide in the presence of water or alcohols, e. g., ethyl alcohol, and esters of alkylene oxide-type olymers, e. g., acetylated propylene oxide polymers prepared by acetylating the propylene oxide polymers containing hydroxyl groups.
- alcohols e. g., ethyl alcohol
- esters of alkylene oxide-type olymers e. g., acetylated propylene oxide polymers prepared by acetylating the propylene oxide polymers containing hydroxyl groups.
- Synthetic oils of the dicarboxylic acid ester type include those which are prepared by esterifying such 'di'carboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alxenyl succinic acid, fumaric acid, maleic acid, etc., with alcohols such as butyl alcohol, hexyl alcohol, Z-ethylhexyl alcohol, dodecyl alcohol, etc.
- Examples of dicarboxylic acid ester synthetic oils include dibutyl adipate, dihexyl adipate, di-2-ethylhexyl sebacat'e, di-n-hexyl fumarate polymer, etc.
- Synthetic oils of the type of liquid esters of acids of phopshorus include the esters of phosphoric acid, e. g., tricresyl phosphate; the esters of phosphonic acid, e. g., diethyl ester of decane phosphonic acid, or other such esters as obtained by reacting alkyl phosphonyl chlorides with hydroxyl-containing compounds, such as phenols and aliphatic alcohols, and with olefin oxides such as propylene oxide, as described in Jensen et al., U. S. application Serial No. 86,856, filed April 11, 19 9, now abandoned.
- the zinc salts of this invention that is, the zinc salts of mixed esters of dithiophosphoric acids are normally used in lubricating oil compositions in amounts su'fiicient to inhibit oxida tion of the base oil. Although it is preferred to use from 0.05% to 2.0% by weight, based on the final oil composition, lubricating oil concentrates containing as much as 50% or more by weight may be prepared.
- the zinc salts of this invention are formed from mixed esters of dithiophospho'ric acids prepared by reacting phosphorus pentasulfide (P285) with a mixture of two different alcohols at temperatures ranging from about 120 F. to 200 F.
- P285 phosphorus pentasulfide
- 4 moles of the desired alcohols e. g., 3 moles of methyl alcohol and 1 mole of hexyl alcohol, wherein the mol ratio of methyl alcohol to hexyl alcohol is 3:1
- PzSs e. g., 3 moles of methyl alcohol and 1 mole of hexyl alcohol, wherein the mol ratio of methyl alcohol to hexyl alcohol is 3:1
- the mixed dialkyldithiophosphoric acids e. g., zinc methyl hexyl dithiophosphate
- the mixed dialkyldithiophoshphoric acids are reacted with zinc oxide at temperatures ranging from 70 F. to 170 F.
- Example 1 Zinc salt of reactionproduct of isopropyl alcohol, methylisobutylcarbinol and P285
- a mixture of 252 parts by weight (67 mole per cent) of isopropyl alcohol and 206 parts by weight (33 mole per cent) of methylisobutylcarbinol was placed in a glass reaction vessel.
- To this mixture was added 333 partsby weight of P265.
- the whole mixture was heated at 170 F. for 2 hours, after which the reaction mixture was cooled, and the product filtered to remove a small amount of unreacted P2S5.
- Example 2 --Zinc salt of reaction product of butyl alcohol, methylisobutylcarbinol and PzSs
- a mixture of 237 parts by weight (77 mol per cent) of sec-butyl alcohol, 98 parts by weight (23 mole per cent) of methylisobutylcarbinol and 222 parts by weight of P285 was charged to a reaction vessel and agitated at F. for a period of 2 hours.
- the reaction mixture was cooled and filtered to remove a small amount of unreacted P285.
- the resulting butylmethylisobutylcarbinol dithiophosphate was a dark red green liquid having a neutralization number of 193 (mgs. KOH/gram) a viscosity of 35.7 SSU at 100 F., a specific gravity of 1.04 (60/60), and contained 24.0% sulfur and 11.9% phosphorus.
- the oil solubility of mixed diester dithiophosphoric acids is considerably greater than the same mole ratio of a mixture of two diester dithiophosphoric acids (wherein the ester groups in each acid are the same; that is, each acid contains only one of the ester radicals of the above mixed diester dithiophosphoric acid).
- a 35% petroleum oil solution of a mixture of zinc di(sec-butyl) dithiophosphate and zinc di(methylisobutylcarbinol) dithiophosphate (mole ratio of 3.35:1) began to crystallize from solution within a period of 2 days at -20 F.
- the table below presents data concerning the effectiveness of zinc salts of mixed esters of dithiophosphoric acids in reducing corrosion of metal parts due to oxidation of lubricating oils during operation of internal combustion engines.
- a stock Chevrolet engine was used. Instead of the normal babbitt bearings of the Chevrolet engine, two of the connecting rods were modified to accommodate copper-lead bearing inserts, Which were weighed before being assembled in the engine.
- the Chevro et engine was operated at 3150 R. P. M., the engine jacket temperature was maintained at 200 F., the crankcase oil temperature was maintained at 280 F., and the engine was operated for a period of 36 hours before being disassembled and the bearing inserts weighed. Before weighing, the bearing inserts were carefully washed with solvents to remove the oil therefrom.
- This reference 011 was a Mid-Continent SAE 30 oil.
- Tests were also run to determine the effectiveness of the zinc salts of mixed diesters of dithiophosphoric acids for increasing the inhibition period of lubricating oils.
- a medicinal white oil was the base oil.
- the inhibition period (the time in hours before 100 grams of oil sample utilizes 1000 cubic centimeters of oxygen at 340 F.) of medicinal white oil was zero hours.
- the inhibition period of the same base oil containing 0.19% of the zinc salt of Example 2 above was 4.2 hours.
- zinc salts of mixed esters of this invention also include phenates (e. g'., calcium cetyl phenate), sulfonates (e. g., calcium petroleum sulfonate), phenols (e. g., 2,6-di-tertiary butyl-4-methyl phenol), phosphonates (e. g., calcium white oil phosphonate), thiophosphonates (e. g., calcium cetyl thiophosphonate), sulfur-containing parafiins (e. g., sulfurized diparaffin sulfide), etc.
- phenates e. g'., calcium cetyl phenate
- sulfonates e. g., calcium petroleum sulfonate
- phenols e. g., 2,6-di-tertiary butyl-4-methyl phenol
- phosphonates e. g., calcium white oil phosphonate
- thiophosphonates
- a lubricant consisting essentially of a major proportion of an oil of lubricating viscosity and from 0.05% to 2.0% of zinc salts of mixed esters of dithiophosphoric acids produced by reacting phosphorus pentasulfide with a blend of 2 aliphatic monohydric alcohols at temperatures from F. to 200 F., one of said alcohols containing not more than 4 carbon atoms, the other of said alcohols containing from 6 to 18 carbon atoms, the ratio of the lower molecular weight alcohol to the higher molecular weight alcohol being from 1.0 to 5.0.
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and from 0.05% to 2.0% of zinc salts of mixed esters of dithiophosphoric acids produced by reacting phosphorus pentasulfide with a blend of 2 aliphatic monohydric alcohols at temperatures from 120 F. to 200 F., one of said alcohols containing not more than 4 carbon atoms, the other of said alcohols containing from 6 to 10 carbon atoms, the ratio of the lower molecular weight alcohol to the higher molecular weight of alcohol being from 1.0 to 5.0.
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- Lubricants (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US218282A US2689220A (en) | 1951-03-29 | 1951-03-29 | Lubricating oil compositions of mixed diester dithiophosphates |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US218282A US2689220A (en) | 1951-03-29 | 1951-03-29 | Lubricating oil compositions of mixed diester dithiophosphates |
| US218281A US2680123A (en) | 1951-03-29 | 1951-03-29 | Zinc salt of mixed ester thiophosphates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2689220A true US2689220A (en) | 1954-09-14 |
Family
ID=22814481
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US218282A Expired - Lifetime US2689220A (en) | 1951-03-29 | 1951-03-29 | Lubricating oil compositions of mixed diester dithiophosphates |
| US218281A Expired - Lifetime US2680123A (en) | 1951-03-29 | 1951-03-29 | Zinc salt of mixed ester thiophosphates |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US218281A Expired - Lifetime US2680123A (en) | 1951-03-29 | 1951-03-29 | Zinc salt of mixed ester thiophosphates |
Country Status (6)
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2837549A (en) * | 1955-05-12 | 1958-06-03 | American Cyanamid Co | Zinc dialkyl dithiophosphates |
| DE1042807B (de) * | 1955-01-27 | 1958-11-06 | Lubrizol Corp | Dithiophosphorsaeurederivate und organische Polysulfide enthaltender fluessiger Schmiermittelzusatz |
| DE1112067B (de) * | 1957-04-18 | 1961-08-03 | American Cyanamid Co | Verfahren zur Herstellung von Zinksalzen gemischter Dithiophosphorsaeuredialkylester |
| US3000822A (en) * | 1957-01-22 | 1961-09-19 | Lubrizol Corp | Phosphorodithioate inhibitors |
| US3013970A (en) * | 1955-01-27 | 1961-12-19 | Lubrizol Corp | Gear lubricant improving agents |
| US3013969A (en) * | 1955-01-27 | 1961-12-19 | Lubrizol Corp | Gear lubricant improving agents |
| US3013971A (en) * | 1955-01-27 | 1961-12-19 | Lubrizol Corp | Gear lubricant improving agents |
| DE1119854B (de) * | 1958-01-07 | 1961-12-21 | Exxon Research Engineering Co | Verfahren zur Herstellung von Metallsalzen von O, O-Dialkyldithio-phosphorsaeuren von verbesserter Bestaendigkeit |
| US3018247A (en) * | 1960-03-15 | 1962-01-23 | California Research Corp | Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends |
| US3073781A (en) * | 1960-07-07 | 1963-01-15 | Standard Oil Co | Demulsifiable lubricant compositions |
| US3074990A (en) * | 1958-12-29 | 1963-01-22 | Universal Oil Prod Co | Alkylthiophosphoric acid salt of polymeric condensation product and use thereof |
| US3087950A (en) * | 1959-01-22 | 1963-04-30 | Exxon Research Engineering Co | Extreme pressure lubricant additive |
| US3112271A (en) * | 1959-04-13 | 1963-11-26 | Shell Oil Co | Liquid hydrocarbon composition |
| US3293181A (en) * | 1965-10-15 | 1966-12-20 | Chevron Res | Dialkyl dithiophosphates and lubricants containing them |
| US3318808A (en) * | 1963-10-15 | 1967-05-09 | Standard Oil Co | Extreme pressure lubricants |
| US3390082A (en) * | 1967-09-19 | 1968-06-25 | Lubrizol Corp | Lubricants containing metal-free dispersants and inhibitors |
| US3442804A (en) * | 1967-01-19 | 1969-05-06 | Lubrizol Corp | Lubricating composition containing a phosphorodithioate inhibitor |
| US3511780A (en) * | 1966-02-09 | 1970-05-12 | Exxon Research Engineering Co | Oil-soluble ashless dispersant-detergent-inhibitors |
| US4092341A (en) * | 1976-02-27 | 1978-05-30 | Edwin Cooper And Company Limited | Process of making an oil solution of zinc dihydrocarbyldithiophosphates |
| US4377527A (en) * | 1981-03-09 | 1983-03-22 | Standard Oil Company (Indiana) | Ammonia catalyzed preparation of zinc dihydrocarbyl dithiophosphates |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2838555A (en) * | 1951-10-12 | 1958-06-10 | Lubrizol Corp | Group ii metal salts of a mixture of simple diesters of dithiophosphoric acids |
| US3341633A (en) * | 1955-01-27 | 1967-09-12 | Lubrizol Corp | Reaction of o, o-dihydrocarbyl phosphorodithioic acids with epoxides |
| US2925398A (en) * | 1957-02-11 | 1960-02-16 | Monsanto Chemicals | Composition comprising solid polyolefin and a hydrogenated polyphenyl |
| US2932614A (en) * | 1958-01-07 | 1960-04-12 | Exxon Research Engineering Co | Manufacture of metal salts of dialkyl dithiophosphoric acids and concentrate in oil solution |
| GB1565961A (en) * | 1976-02-25 | 1980-04-23 | Orobis Ltd | Composition comprising a mixture of the zinc salts of o,o'-dialkyl dithiophosphoric acids |
| DE3048087A1 (de) * | 1980-12-19 | 1982-07-15 | Bayer Ag, 5090 Leverkusen | Zinkkomplexe, ein verfahren zu ihrer herstellung und ihre verwendung als verschleissschutz-additive |
| US4577037A (en) * | 1984-02-10 | 1986-03-18 | Chevron Research | Methods for preventing the precipitation of mixed zinc dialkyldithiophosphates which contain high percentages of a lower alkyl group |
| US4495075A (en) * | 1984-05-15 | 1985-01-22 | Chevron Research Company | Methods and compositions for preventing the precipitation of zinc dialkyldithiophosphates which contain high percentages of a lower alkyl group |
| GB8729963D0 (en) * | 1987-12-23 | 1988-02-03 | Exxon Chemical Patents Inc | Dithiophosphates |
| US6884855B2 (en) | 2003-01-30 | 2005-04-26 | Chevron Oronite Company Llc | Sulfurized polyisobutylene based wear and oxidation inhibitors |
| US7368596B2 (en) * | 2003-11-06 | 2008-05-06 | Afton Chemical Corporation | Process for producing zinc dialkyldithiophosphates exhibiting improved seal compatibility properties |
| US8211840B2 (en) * | 2008-12-09 | 2012-07-03 | Afton Chemical Corporation | Additives and lubricant formulations for improved antiwear properties |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2334393A (en) * | 1940-02-26 | 1943-11-16 | Union Oil Co | Determination of magnetic and electrical anisotropy of formation core samples |
| US2342432A (en) * | 1941-12-22 | 1944-02-22 | Gulf Oil Corp | Mineral oil lubricating composition and an improvement agent therefor and its methodof preparation |
| US2368000A (en) * | 1941-12-04 | 1945-01-23 | American Cyanamid Co | Lubricating compositions |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1939951A (en) * | 1929-06-26 | 1933-12-19 | American Cyanamid Co | Seed disinfection |
| US2063629A (en) * | 1935-02-19 | 1936-12-08 | Du Pont | Esters of the thio acids of phosphorus |
| USRE22829E (en) * | 1939-05-06 | 1947-01-14 | Compounded hydrocarbon oil | |
| US2261047A (en) * | 1941-07-28 | 1941-10-28 | Lubri Zol Corp | Lubricant |
| US2343213A (en) * | 1942-04-10 | 1944-02-29 | American Cyanamid Co | Preparation of barium salts of dithiophosphoric acid esters |
| US2361746A (en) * | 1943-04-12 | 1944-10-31 | American Cyanamid Co | Crankcase lubricating oil composition |
| US2466408A (en) * | 1946-01-26 | 1949-04-05 | American Cyanamid Co | Lubricating composition |
| US2540084A (en) * | 1947-05-14 | 1951-02-06 | Lubrizol Corp | Metallic salt of reaction product of phosphorus sulfide and alkylated cycloaliphatic alcohol |
| GB626251A (en) * | 1947-06-30 | 1949-07-12 | Shell Refining & Marketing Co | Improvements in or relating to mineral lubricating oil compositions |
| NL70344C (US07223432-20070529-C00017.png) * | 1947-12-09 |
-
0
- BE BE510012D patent/BE510012A/xx unknown
- NL NL85589D patent/NL85589C/xx active
-
1951
- 1951-03-29 US US218282A patent/US2689220A/en not_active Expired - Lifetime
- 1951-03-29 US US218281A patent/US2680123A/en not_active Expired - Lifetime
-
1952
- 1952-03-04 GB GB5686/52A patent/GB716343A/en not_active Expired
- 1952-03-13 DE DEC5529A patent/DE1097606B/de active Pending
- 1952-03-14 FR FR1057074D patent/FR1057074A/fr not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2334393A (en) * | 1940-02-26 | 1943-11-16 | Union Oil Co | Determination of magnetic and electrical anisotropy of formation core samples |
| US2368000A (en) * | 1941-12-04 | 1945-01-23 | American Cyanamid Co | Lubricating compositions |
| US2342432A (en) * | 1941-12-22 | 1944-02-22 | Gulf Oil Corp | Mineral oil lubricating composition and an improvement agent therefor and its methodof preparation |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1042807B (de) * | 1955-01-27 | 1958-11-06 | Lubrizol Corp | Dithiophosphorsaeurederivate und organische Polysulfide enthaltender fluessiger Schmiermittelzusatz |
| US3013970A (en) * | 1955-01-27 | 1961-12-19 | Lubrizol Corp | Gear lubricant improving agents |
| US3013969A (en) * | 1955-01-27 | 1961-12-19 | Lubrizol Corp | Gear lubricant improving agents |
| US3013971A (en) * | 1955-01-27 | 1961-12-19 | Lubrizol Corp | Gear lubricant improving agents |
| US2837549A (en) * | 1955-05-12 | 1958-06-03 | American Cyanamid Co | Zinc dialkyl dithiophosphates |
| US3000822A (en) * | 1957-01-22 | 1961-09-19 | Lubrizol Corp | Phosphorodithioate inhibitors |
| DE1112067B (de) * | 1957-04-18 | 1961-08-03 | American Cyanamid Co | Verfahren zur Herstellung von Zinksalzen gemischter Dithiophosphorsaeuredialkylester |
| DE1119854B (de) * | 1958-01-07 | 1961-12-21 | Exxon Research Engineering Co | Verfahren zur Herstellung von Metallsalzen von O, O-Dialkyldithio-phosphorsaeuren von verbesserter Bestaendigkeit |
| US3074990A (en) * | 1958-12-29 | 1963-01-22 | Universal Oil Prod Co | Alkylthiophosphoric acid salt of polymeric condensation product and use thereof |
| US3087950A (en) * | 1959-01-22 | 1963-04-30 | Exxon Research Engineering Co | Extreme pressure lubricant additive |
| US3112271A (en) * | 1959-04-13 | 1963-11-26 | Shell Oil Co | Liquid hydrocarbon composition |
| US3018247A (en) * | 1960-03-15 | 1962-01-23 | California Research Corp | Lubricating oil compositions containing metal dithiophosphate-nu-dialkylaminoalkyl alkenyl succinimide blends |
| US3073781A (en) * | 1960-07-07 | 1963-01-15 | Standard Oil Co | Demulsifiable lubricant compositions |
| US3318808A (en) * | 1963-10-15 | 1967-05-09 | Standard Oil Co | Extreme pressure lubricants |
| US3293181A (en) * | 1965-10-15 | 1966-12-20 | Chevron Res | Dialkyl dithiophosphates and lubricants containing them |
| US3511780A (en) * | 1966-02-09 | 1970-05-12 | Exxon Research Engineering Co | Oil-soluble ashless dispersant-detergent-inhibitors |
| US3442804A (en) * | 1967-01-19 | 1969-05-06 | Lubrizol Corp | Lubricating composition containing a phosphorodithioate inhibitor |
| US3390082A (en) * | 1967-09-19 | 1968-06-25 | Lubrizol Corp | Lubricants containing metal-free dispersants and inhibitors |
| US4092341A (en) * | 1976-02-27 | 1978-05-30 | Edwin Cooper And Company Limited | Process of making an oil solution of zinc dihydrocarbyldithiophosphates |
| US4377527A (en) * | 1981-03-09 | 1983-03-22 | Standard Oil Company (Indiana) | Ammonia catalyzed preparation of zinc dihydrocarbyl dithiophosphates |
Also Published As
| Publication number | Publication date |
|---|---|
| GB716343A (en) | 1954-10-06 |
| BE510012A (US07223432-20070529-C00017.png) | |
| NL85589C (US07223432-20070529-C00017.png) | |
| US2680123A (en) | 1954-06-01 |
| FR1057074A (fr) | 1954-03-04 |
| DE1097606B (de) | 1961-01-19 |
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