US3210275A - Lubricating composition containing metal salts of hindered phosphorodithioates - Google Patents
Lubricating composition containing metal salts of hindered phosphorodithioates Download PDFInfo
- Publication number
- US3210275A US3210275A US269799A US26979963A US3210275A US 3210275 A US3210275 A US 3210275A US 269799 A US269799 A US 269799A US 26979963 A US26979963 A US 26979963A US 3210275 A US3210275 A US 3210275A
- Authority
- US
- United States
- Prior art keywords
- lubricating oil
- metal
- phosphorodithioates
- carbon atoms
- phosphorodithioate
- 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 claims description 41
- 230000001050 lubricating effect Effects 0.000 title claims description 11
- 229910052751 metal Inorganic materials 0.000 title description 41
- 239000002184 metal Substances 0.000 title description 41
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 title description 18
- 150000003839 salts Chemical class 0.000 title description 14
- 239000010687 lubricating oil Substances 0.000 claims description 32
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 claims description 19
- 239000002199 base oil Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- -1 monosubstituted methanol Chemical class 0.000 description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 10
- 229910052698 phosphorus Inorganic materials 0.000 description 10
- 239000011574 phosphorus Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 229910052788 barium Inorganic materials 0.000 description 5
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000010688 mineral lubricating oil Substances 0.000 description 3
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 3
- 150000003138 primary alcohols Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-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
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229960005335 propanol Drugs 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-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
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000010689 synthetic lubricating oil Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 229910052718 tin Inorganic materials 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
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- QTOMCRXZFDHJOL-UHFFFAOYSA-N 2,2-dimethylpentan-1-ol Chemical compound CCCC(C)(C)CO QTOMCRXZFDHJOL-UHFFFAOYSA-N 0.000 description 1
- RNAMYOYQYRYFQY-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-n-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine Chemical compound N1=C(N2CCC(F)(F)CC2)N=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1NC1CCN(C(C)C)CC1 RNAMYOYQYRYFQY-UHFFFAOYSA-N 0.000 description 1
- HLVYTWAZPRTCMW-UHFFFAOYSA-N 2-cyclohexyl-2-methylpropan-1-ol Chemical compound OCC(C)(C)C1CCCCC1 HLVYTWAZPRTCMW-UHFFFAOYSA-N 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- ZVSCENGNXWPDPL-UHFFFAOYSA-N 2-methyl-2-phenylpropan-1-ol Chemical compound OCC(C)(C)C1=CC=CC=C1 ZVSCENGNXWPDPL-UHFFFAOYSA-N 0.000 description 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-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
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 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
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000004074 biphenyls Chemical class 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- AHMZKMOWTURMQK-UHFFFAOYSA-N hexyl-(4-methylpentan-2-yloxy)-silyloxysilane Chemical compound CCCCCC[SiH](O[SiH3])OC(C)CC(C)C AHMZKMOWTURMQK-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005461 lubrication Methods 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 239000002966 varnish 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
- 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
- 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
-
- 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
-
- 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
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
-
- 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
- C10M2207/08—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
- 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
- C10M2207/283—Esters of polyhydroxy 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
- C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl 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
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
-
- 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
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral 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
- 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
- C10M2223/045—Metal containing 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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/02—Esters of silicic 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
-
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
-
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
-
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
-
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/045—Siloxanes with specific structure containing silicon-to-hydroxyl bonds
-
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/046—Siloxanes with specific structure containing silicon-oxygen-carbon bonds
-
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/047—Siloxanes with specific structure containing alkylene oxide 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/048—Siloxanes with specific structure containing carboxyl groups
-
- 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
- C10N2010/02—Groups 1 or 11
-
- 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
- C10N2010/06—Groups 3 or 13
-
- 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
Definitions
- This invention relates to improved lubricating oil compositions which contain metal phosphorodithioates. More particularly this invention relates to improved lubricating oil compositions containing metal phosphorodithioates which are derived from primary alcohols which contain no hydrogen atoms on the beta carbon atom.
- the use of the metal salts of dialkylphosphorodithioic acids as oxidation inhibitors in lubricating oil compositions is well known. As such, they are able to increase the useful life of lubricating oil compositions which are susceptible to oxidation.
- the metal salts of dialkylphosphorodithioic acids have performed well as oxidation inhibitors.
- Recent trends in automotive design have imposed additional demands on the lubricants used for these engines. The newer engines subject the lubricant to higher temperatures than encountered in the past. It is foreseeable that in the future these temperatures will go even higher. Under these conditions, thermal stability will be a primary consideration in the choice of an oxidation inhibitor.
- the present invention concerns lubricating oil compositions containing metal salts of phosphorodithioic acids derived from a monosubstituted methanol in which the substituent group is a hydrocarbon radical attached to a tertiary carbon atom.
- the metal phosphorodithioates, which are present in the lubricating composition have the following formula:
- R R and R are selected from the group consisting of alkyl, aryl, alkaryl, aralkyl, and cyclic alkyl; M is a metal; and x is the valence of the metal.
- A is a hydrocarbon radical which can have any of the formulas:
- R and R are alkyl groups having from 1 to 5 carbon atoms each, and may be alike or unlike, and R is an alkyl group having from 2 to 18 carbon atoms;
- R and R are alkyl groups having from 1 to 18 carbon atoms each, and may be alike or unlike, and R is an aryl group containing from 6 to 10 carbon atoms;
- R and R are alkyl groups containing from 1 to 18 carbon atoms each, and may be alike or unlike, and R is an alkaryl group containing from 7 to 20 carbon atoms;
- R12 wherein R and R are alkyl groups having from 1 to 18 carbon atoms each, and may be alike or unlike, and R is a cyclic alkyl group having from 6 to 12 carbon atoms; M is a metal; and x is the valence of the metal.
- the monosubstituted methanols used in the preparation of the novel phosphorodithioates of this invention may also be referred to as primary alcohols having no hydrogen atoms on the beta carbon atom.
- suitable materials for use in preparing the phosphorodithioates of this invention include the following:
- All substituents on the beta carbon atom are alkyl groups 2,2-dimethyl-1-pentanol 2,2-diethyl-l-pentanol 2,2-dimethyl-l-hexanol 2,2-diethyl-1-butanol 2,2,4-trirnethyll-pentanol 2,2-diisobutyll-dodecanol 2,2-diamyl-1-eicosanol 2,2-ditertiarybutyl-l-hexadecanol 2-methyl-2-ethyll-pentanol 2-methyl-2-propyl-l-pentanol 2-ethyl-2-propyl-l -hexanol B.
- the substituents on the beta carbon atom include aryl groups 2,2-dimethyl-2-phenyl ethanol 2,2-diethyl-2-(p-p'ropy1phenyl) ethanol 2,2-dimethyl-3-phenyll-prop anol C.
- the substituents on the beta carbon atom include cyclo-alkyl groups 2,2-dimethyl-2-cyclohexyl ethanol 2-cyclohexyl-2-methyll-hexanol 2,2-dicyclohexyll-propanol
- the materials listed under A wherein all substituents on the beta carbon atom are alkyl groups, are preferred.
- Metals which may be used to prepare the salts of the phosphorodithioic acids used in my lubricating composition include metals which will give oil-soluble salts and also metals which give oil-dispersible salts. These metals can be any of the following: zinc, barium, magnesium, aluminum, calcium, lithium, lead, tin, copper, cadmium, cobalt, strontium, and nickel. The preferred metal is 21116.
- the usual method of preparing phosphorodithioates is by reacting four moles of alcohol with one mole of a sulfide of phosphorus (preferably, phosphorus pentasulfide). The resulting secondary phosphorodithioic acid ester is then converted to the metal salt.
- esters which contain only alkyl or other than hydrogen groups in the six position cannot undergo thermal degradation to yield acids and olefins by this mechanism.
- Alcohols previously disclosed for use in preparing the phosphorodithioates used in prior art lubricating compositions have at least one hydrogen atom on the carbon beta to the hydroxy group. Since the corresponding monovalent metal phosphorodithioates contain two alkyl groups, the number of hydrogen atoms in the six positions, counting from the covalent sulfur atom, are at least two. As all of these hydrogens are subject to thermal elimination, their replacement with alkyl or other non-hydrogen groups will increase the thermal stability of the molecules. Since the number of the six position hydrogen (the six number) in the metal salts may vary quite widely, depending upon the starting alcohol structure, their thermal stabilities will be quite different. Those having the highest six number will be the least stable and those having the lowest, the most stable.
- Novel metal salts of phosphorodithioic acids in which the acid is prepared from completely beta substituted alcohols, e.g., Z-Z-dimethyl-l-pentanol, have no available hydrogen atoms in the six position as described above and are consequently extremely stable thermally. This improvement is reflected in lubricating oil compositions containing hindered metal phosphorodithioates in that the compositions are more stable thermally.
- Alcohols having groups other than hydrogen on the beta carbon atom are referred to as hindered.
- phosphorodithioic acids and salts in which there are no available hydrogen atoms in the six position are referred to as hindered.
- the lubricating oils which can be used as base oils for my lubricating oil compositions can be any of the oils of lubricating viscosity which are normally used. More specifically, the lubricating oil can be either a mineral oil or a synthetic oil. have a viscosity of about 50 to 2500 seconds, preferably, 75 to 400 seconds, Saybolt Universal at F. The choice of the particular base oil will be determined by the use intended for the lubricant. Since mineral lubricating oils are presently more economical and readily available, they are preferred.
- the mineral oil may be a petroleum distillate or residuum oil or mixtures thereof, or may be a synthetic hydrocarbon oil falling within the above-described viscosity range. Also, the oil may be treated in various ways, such as by acid treating, but preferably, is a solvent refined oil.
- the synthetic lubricating oil can be any of the following:
- Alkylene polymers such as polymers of propylene, butylene, et cetera
- Alkylene oxide-type polymers prepared by polymerizing an alkylene oxide (e.g., propylene oxide) in the presence of water or alcohols;
- esters include the so-called complex esters prepared from the aforementioned representative acids and polyhydroxy alcohols.
- Dicarboxylic acid esters prepared by esterifying a dicarboxylic acid, such as adipic acid, azelaic acid, suberic acid, sebacic acid, alkanol succinic acid, fumaric acid, maleic acid, et cetera, with alcohols, such as butyl alcohol, hexyl alcohol, Z-ethylhexyl alcohol, dodecyl alcohol, et cetera;
- a dicarboxylic acid such as adipic acid, azelaic acid, suberic acid, sebacic acid, alkanol succinic acid, fumaric acid, maleic acid, et cetera
- alcohols such as butyl alcohol, hexyl alcohol, Z-ethylhexyl alcohol, dodecyl alcohol, et cetera;
- the base oil may contain, in addition to the metal phosphorodithioate, other additives such as detergents, over-based detergents, pour point depressants, anti-foam agents, antioxidants, and viscosity index improvers.
- other additives such as detergents, over-based detergents, pour point depressants, anti-foam agents, antioxidants, and viscosity index improvers.
- the metal phosphorodithioate content of my lubricating compositions is expressed on the basis of the phosphorus content of the lubricating oil.
- a suitable amount of metal phosphorodithioate is that amount which contributes a phosphorus content in the lubricating 'oil in the range of about 0.005 to about 0.5 percent by weight.
- a more suitable amount of metal phosphorodithioate is that amountwhich will contribute a phosphorus content in the lubricating 'oil in the range of about 0.01 to about 0.25 percent by weight.
- the metal phosphorodithioate contributes a phosphorus content in the lubricating oil in the range of 0.04 to 0.10 percent by weight. More preferably, the metal phosphorodithioate contributes a phosphorus content of about 0.065 percent by weight.
- EXAMPLE III The product of Examples I and II were incorporated in lubricating oil blends and tested in a Caterpillar engine under CRC L-l conditions. These conditions were as The compositions of the lubricating oil blends were as follows:
- Blend A 4.8 percent detergent (barium alkaryl sulfonate overbased with barium carbonate), 0.77 percent Example I (E0065 percent P), balance SAE 30 mineral oil
- Blend B 4.8 percent detergent (same as above), 0.69 percent Example II (0.065 percent P), balance SAE 30 mineral oil
- a lubricating oil containing a hindered phosphorodithioate is superior to a lubricating oil containing a conventional phosphorodithioate.
- R and R are alkyl groups having from 1 to 5 carbon atoms each and R is an alkyl group having from 2 to 18 carbon atoms;
- R and R are alkyl groups having from 1 to 18 carbon atoms each, and R is an aryl group containing from 6 to 10 carbon atoms;
- R and R are alkyl groups containing from 1 to 18 carbon atoms each, and R is an alkaryl group containing from 7 to 20 carbon atoms;
- R and R are alkyl groups having from 1 to 18 carbon atoms each, and R is a cyclic alkyl group having from 6 to 12 carbon atoms;
- M is a metal selected from the group consisting of zinc, barium, magnesium, aluminum, calcium, lithium, lead, tin, copper, cadmium, cobalt, strontium and nickel; and
- x is the valence of the metal, said metal phosphorodithioate being present in an amount which will contribute an amount of phosphorus in the range of about 0.005 weight percent to about 0.5 weight percent in the lubricating oil composition.
- R and R are alkyl groups having from 1 to carbon atoms each, and R is an alkyl group having from 2 to 18 carbon atoms; and M and x are as defined in claim 1.
- a lubricating oil composition as defined in claim 1 wherein the metal phosphorodithioate has the formula:
- R and R are alkyl groups having from 1 to 18 carbon atoms each, and R is an aryl group containing from 6 to 10 carbon atoms; and M and x are as defined in claim 1.
- a lubricating oil composition as defined in claim 1 wherein the metal phosphorodithioate has the formula:
- R and R are alkyl groups containing from 1 to 18 carbon atoms each, and R is an alkaryl group containing from 7 to 20 carbon atoms; and M and x are as defined in claim 1.
- R and R are alkyl groups having from 1 to 18 carbon atoms each, and R is a cyclic alkyl group having from 6 to 12 carbon atoms; and M and x are as defined in claim 1.
- a lubricating oil composition comprising a base oil of a lubricating viscosity and a zinc phosphorodithioate having the formula:
- said zinc phosphorodithioate being present in an amount which will contribute about 0.065 percent by weight phosphorus to the composition.
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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Description
United States Patent of Delaware No Drawing. Filed Apr. 1, 1963,. Ser. No. 269,799
12 Claims. (Cl. 25232.7)
This application is a continuation-in-part of application Serial Number 751,880, filed July 30, 195 8, and now abandoned.
This invention relates to improved lubricating oil compositions which contain metal phosphorodithioates. More particularly this invention relates to improved lubricating oil compositions containing metal phosphorodithioates which are derived from primary alcohols which contain no hydrogen atoms on the beta carbon atom.
The use of the metal salts of dialkylphosphorodithioic acids as oxidation inhibitors in lubricating oil compositions is well known. As such, they are able to increase the useful life of lubricating oil compositions which are susceptible to oxidation. In general, the metal salts of dialkylphosphorodithioic acids have performed well as oxidation inhibitors. Recent trends in automotive design have imposed additional demands on the lubricants used for these engines. The newer engines subject the lubricant to higher temperatures than encountered in the past. It is foreseeable that in the future these temperatures will go even higher. Under these conditions, thermal stability will be a primary consideration in the choice of an oxidation inhibitor.
It is an object of the present invention to provide improved lubricating oil compositions.
It is another object of the present invention to provide lubricating oil compositions having improved thermal stability.
provide lubricating oil compositions containing novel and improved metal phosphorodithioates.
The present invention concerns lubricating oil compositions containing metal salts of phosphorodithioic acids derived from a monosubstituted methanol in which the substituent group is a hydrocarbon radical attached to a tertiary carbon atom. The metal phosphorodithioates, which are present in the lubricating composition, have the following formula:
where R R and R are selected from the group consisting of alkyl, aryl, alkaryl, aralkyl, and cyclic alkyl; M is a metal; and x is the valence of the metal.
The suitable metal phosphorodithioates which are used in this invention have the following formula:
where A is a hydrocarbon radical which can have any of the formulas:
wherein R and R are alkyl groups having from 1 to 5 carbon atoms each, and may be alike or unlike, and R is an alkyl group having from 2 to 18 carbon atoms;
It is still another object of the present invention to 3,21%,275 Patented Oct. 5, 1965 wherein R and R are alkyl groups having from 1 to 18 carbon atoms each, and may be alike or unlike, and R is an aryl group containing from 6 to 10 carbon atoms;
I la
wherein R and R are alkyl groups containing from 1 to 18 carbon atoms each, and may be alike or unlike, and R is an alkaryl group containing from 7 to 20 carbon atoms;
Ru I
R12 wherein R and R are alkyl groups having from 1 to 18 carbon atoms each, and may be alike or unlike, and R is a cyclic alkyl group having from 6 to 12 carbon atoms; M is a metal; and x is the valence of the metal.
The monosubstituted methanols used in the preparation of the novel phosphorodithioates of this invention may also be referred to as primary alcohols having no hydrogen atoms on the beta carbon atom. Examples of suitable materials for use in preparing the phosphorodithioates of this invention include the following:
A. All substituents on the beta carbon atom are alkyl groups 2,2-dimethyl-1-pentanol 2,2-diethyl-l-pentanol 2,2-dimethyl-l-hexanol 2,2-diethyl-1-butanol 2,2,4-trirnethyll-pentanol 2,2-diisobutyll-dodecanol 2,2-diamyl-1-eicosanol 2,2-ditertiarybutyl-l-hexadecanol 2-methyl-2-ethyll-pentanol 2-methyl-2-propyl-l-pentanol 2-ethyl-2-propyl-l -hexanol B. The substituents on the beta carbon atom include aryl groups 2,2-dimethyl-2-phenyl ethanol 2,2-diethyl-2-(p-p'ropy1phenyl) ethanol 2,2-dimethyl-3-phenyll-prop anol C. The substituents on the beta carbon atom include cyclo-alkyl groups 2,2-dimethyl-2-cyclohexyl ethanol 2-cyclohexyl-2-methyll-hexanol 2,2-dicyclohexyll-propanol Of the suitable materials listed above, the materials listed under A, wherein all substituents on the beta carbon atom are alkyl groups, are preferred.
' Metals which may be used to prepare the salts of the phosphorodithioic acids used in my lubricating composition include metals which will give oil-soluble salts and also metals which give oil-dispersible salts. These metals can be any of the following: zinc, barium, magnesium, aluminum, calcium, lithium, lead, tin, copper, cadmium, cobalt, strontium, and nickel. The preferred metal is 21116.
The usual method of preparing phosphorodithioates is by reacting four moles of alcohol with one mole of a sulfide of phosphorus (preferably, phosphorus pentasulfide). The resulting secondary phosphorodithioic acid ester is then converted to the metal salt.
While I do not wish to be bound by any particular theory as to the mechanism of the function of these particular phospohordithioates, when used in my lubricating com-position, I believe the correct explanation is as follows:
Pyrolysis or thermal degradation of esters made from conventional straight-chain primary, secondary, and tertiary alcohols and aliphatic monoand dicarboxylic acids is initiated at the carbonyl oxygen and results in the formation of olefin and acid. This degradation arises from electron migration after formation of an unstable ring structure. To form this intermediate ring there must be hydrogen atoms in the alcohol portion of the ester which are in the sixth atom position from the carbonyl oxygen. These hydrogen atoms must also be coplanar to the carbonyl group or must have rotational freedom if ring formation is to occur. The action is indicated by the following diagram:
(DR-C (50-11(6) (")(1) Original state showing numbering system H H--O Intermediate ring formation 0 R' C H Products after electron I migration Obviously, esters which contain only alkyl or other than hydrogen groups in the six position cannot undergo thermal degradation to yield acids and olefins by this mechanism.
Similarly, by extending this principle, the metal salts of conventional secondary dialkyl phosphorodithioic acid esters were predicted to yield olefins and complex thioacids upon thermal decomposition as illustrated:
Confirmation was obtained by heating a sample of a conventional zinc dialkyl phosphorodithioate at atmospheric pressures. Infrared analysis of the distillate indicated a predominance of olefin.
Alcohols previously disclosed for use in preparing the phosphorodithioates used in prior art lubricating compositions have at least one hydrogen atom on the carbon beta to the hydroxy group. Since the corresponding monovalent metal phosphorodithioates contain two alkyl groups, the number of hydrogen atoms in the six positions, counting from the covalent sulfur atom, are at least two. As all of these hydrogens are subject to thermal elimination, their replacement with alkyl or other non-hydrogen groups will increase the thermal stability of the molecules. Since the number of the six position hydrogen (the six number) in the metal salts may vary quite widely, depending upon the starting alcohol structure, their thermal stabilities will be quite different. Those having the highest six number will be the least stable and those having the lowest, the most stable. It should be noted, however, that only one hydrogen atom is required in this position to allow thermal decomposition. An increased number of these only affects the degree of instability. For illustration, the six number of monovalent metal phosphorodithioates derived from conventionally used commercial alcohols are tabulated below:
Alcohol: Monovalent salt six number n-Hexanol 4 Mixed amyl (Pentasols) *2 2-ethyl-l-hexanol 2 2-ethyl-l-butanol 2 Isooctyl 4 4-methyl-2-pentan0l (methyl amyl) l0 Capryl 10 Isopropyl 12 *Or more.
Commercially, both individual and mixtures of alcohols are used for phosphorodithioate preparations. For example, blends of isopropyl and 4-methyl-2-pentanol are used for economic and solubility reasons. To illustrate further a conventional structure, a graphic formula of the salt derived from the commonly used 4-methyl-2-penta- 1101 is given with the six position hydrogens starred.
The instability of this molecule, when used as a lubricant oxidation inhibitor, is evidenced in internal combustion engines by the formation of excessive piston varnish. This is illustrated under the Caterpillar L-l tests (Example III).
Novel metal salts of phosphorodithioic acids, in which the acid is prepared from completely beta substituted alcohols, e.g., Z-Z-dimethyl-l-pentanol, have no available hydrogen atoms in the six position as described above and are consequently extremely stable thermally. This improvement is reflected in lubricating oil compositions containing hindered metal phosphorodithioates in that the compositions are more stable thermally.
Alcohols having groups other than hydrogen on the beta carbon atom are referred to as hindered. Similarly, phosphorodithioic acids and salts in which there are no available hydrogen atoms in the six position are referred to as hindered.
The lubricating oils which can be used as base oils for my lubricating oil compositions can be any of the oils of lubricating viscosity which are normally used. More specifically, the lubricating oil can be either a mineral oil or a synthetic oil. have a viscosity of about 50 to 2500 seconds, preferably, 75 to 400 seconds, Saybolt Universal at F. The choice of the particular base oil will be determined by the use intended for the lubricant. Since mineral lubricating oils are presently more economical and readily available, they are preferred.
The mineral oil may be a petroleum distillate or residuum oil or mixtures thereof, or may be a synthetic hydrocarbon oil falling within the above-described viscosity range. Also, the oil may be treated in various ways, such as by acid treating, but preferably, is a solvent refined oil.
In general, the oil will I The synthetic lubricating oil can be any of the following:
Alkylene polymers-such as polymers of propylene, butylene, et cetera;
Alkylene oxide-type polymersprepared by polymerizing an alkylene oxide (e.g., propylene oxide) in the presence of water or alcohols;
Carboxylic acid esters-prepared by esterifying a monobasic acid, such as butyric acid, octanoic acid, decan'oic acid, nonanoic acid, 2-ethyl-hexanoic acid, et
cetera, with glycols, such as ethylene glycol, neopentyl glycol, 1,3-propanediol, et cetera; These esters include the so-called complex esters prepared from the aforementioned representative acids and polyhydroxy alcohols.
Dicarboxylic acid esters-prepared by esterifying a dicarboxylic acid, such as adipic acid, azelaic acid, suberic acid, sebacic acid, alkanol succinic acid, fumaric acid, maleic acid, et cetera, with alcohols, such as butyl alcohol, hexyl alcohol, Z-ethylhexyl alcohol, dodecyl alcohol, et cetera;
Liquid esters of acids of phosphorus, alkyl benzenes, polyphenyls (e.g., biphenyls and terphenyls), and alkyl biphenyl ethers;
Polymers of silicon-such as tetraethyl silicate, tetraisopropyl silicates, tetra (4-methyl-2-tetraethyl) silicate, hexyl (4-methyl-2-pentoxy) disiloxane, poly(methyl) siloxane, and poly(methylphenyl) siloxane.
The base oil may contain, in addition to the metal phosphorodithioate, other additives such as detergents, over-based detergents, pour point depressants, anti-foam agents, antioxidants, and viscosity index improvers.
The metal phosphorodithioate content of my lubricating compositions is expressed on the basis of the phosphorus content of the lubricating oil. A suitable amount of metal phosphorodithioate is that amount which contributes a phosphorus content in the lubricating 'oil in the range of about 0.005 to about 0.5 percent by weight. A more suitable amount of metal phosphorodithioate is that amountwhich will contribute a phosphorus content in the lubricating 'oil in the range of about 0.01 to about 0.25 percent by weight. Preferably, the metal phosphorodithioate contributes a phosphorus content in the lubricating oil in the range of 0.04 to 0.10 percent by weight. More preferably, the metal phosphorodithioate contributes a phosphorus content of about 0.065 percent by weight.
In order todisclose the nature of the present invention still more clearly and to more fully illustrate the practical application, the following examples will be given. It is to be understood that the invention is not to be limited to the specific conditions or details set forth in the examples except insofar as such limitations are specified in the appended claims.
EXAMPLE I Apparatus A two-liter, three-necked flask was fitted with a thermometer, stirrer, dropping funnel, Barrett water trap, reflux condenser, and bubble counter.
Procedure To the reaction flask was charged 222.26 grams (1.0 mole) of phosphorus pentasulfide and 500 milliliters of benzene. This slurry was stirred and heated to benzene reflux temperature (81 C.). Dropwise, 500 grams (4.3 moles) of 2,2-dimethyl-1-pentanol was added over 1.2 hours. Hydrogen sulfide was evolved, and after 2 hours at reflux all of the solid was dissolved. After an additional 30 minutes at reflux (95 C.) hydrogen sulfide gas evolution ceased. This mixture was cooled and added from a dropping funnel to a stirred, heated slurry of 93.59 grams (1.15 moles) of zinc oxide in 500 milliliters of benzene contained in the apparatus as above described.
Water (17.8 milliliters) was separated over a six-hour period. Benzene (968 milliliters) was stripped off up to 87 C. at house vacuum. The partially stripped solution was filtered through Filter Cel filter aid to remove excess zinc oxide. The filtrate was stripped by heating to C. at 0.4 millimeter Hg pressure. A yield of 660 grams of syrupy product was obtained. The product was soluble in SAE 30 grade base oil at 0 C. and to a 10 percent by weight level at room temperature (about 18 C.). Also, it was soluble in a detergent consisting of barium -alk-aryl sulmonate overbased with barium carbonate.
Analyses Theory Percent P=8.45 8.65 Percent S=17.74 17.96 Percent Zn=8.71 9.13
EXAMPLE II To provide a sample prepared from an unhindered alcohol, a product was prepared from methyl amyl alcohol in the same manner as described in Example I.
Materials Grams Moles Methyl amyl alcohol 968. 44 8. 5 Phosphorus pentasulfide 444. 52 2. 0 Zinc oxide 179. 03 2.0 Benzene (solvent) 1 1, 500
1 Milliliters.
A yield of 1,250 grams of syrupy product was obtained. It yielded a bright blend at 0.68 weight percent concentration with a detergent consisting of a barium sulfonate overbased with barium carbonate in SAE 30 grade base oil.
Analyses Theory Percent P=9.48 9.47 Percent S=18.5 19.6 Percent Zn=9.8 9.99
EXAMPLE III The product of Examples I and II were incorporated in lubricating oil blends and tested in a Caterpillar engine under CRC L-l conditions. These conditions were as The compositions of the lubricating oil blends were as follows:
Blend A: 4.8 percent detergent (barium alkaryl sulfonate overbased with barium carbonate), 0.77 percent Example I (E0065 percent P), balance SAE 30 mineral oil Blend B: 4.8 percent detergent (same as above), 0.69 percent Example II (0.065 percent P), balance SAE 30 mineral oil The results of the engine tests are shown in the following table:
CATERPILLAR L-l TESTS Blend A Blend B Lacquer rating 49.7 (excellent) O verall rating P 42.8 (unsatisfactory). ass Fail.
*50=perfectly clean.
Thus, it is apparent that a lubricating oil containing a hindered phosphorodithioate is superior to a lubricating oil containing a conventional phosphorodithioate.
While particular embodiments of the invention have where A is a hydrocarbon radical having a formula selected from the group consisting of:
Ra I
wherein R and R are alkyl groups having from 1 to 5 carbon atoms each and R is an alkyl group having from 2 to 18 carbon atoms;
wherein R and R are alkyl groups having from 1 to 18 carbon atoms each, and R is an aryl group containing from 6 to 10 carbon atoms;
wherein R and R are alkyl groups containing from 1 to 18 carbon atoms each, and R is an alkaryl group containing from 7 to 20 carbon atoms;
wherein R and R are alkyl groups having from 1 to 18 carbon atoms each, and R is a cyclic alkyl group having from 6 to 12 carbon atoms; M is a metal selected from the group consisting of zinc, barium, magnesium, aluminum, calcium, lithium, lead, tin, copper, cadmium, cobalt, strontium and nickel; and x is the valence of the metal, said metal phosphorodithioate being present in an amount which will contribute an amount of phosphorus in the range of about 0.005 weight percent to about 0.5 weight percent in the lubricating oil composition.
2. A lubricating oil composition as defined in claim 1 wherein the metal phosphorodithioate has the formula:
wherein R and R are alkyl groups having from 1 to carbon atoms each, and R is an alkyl group having from 2 to 18 carbon atoms; and M and x are as defined in claim 1.
3. A lubricating oil composition as defined in claim 1 wherein the metal phosphorodithioate has the formula:
R4 H i [(R.=. J+O)zPs].M
I ia H wherein R and R are alkyl groups having from 1 to 18 carbon atoms each, and R is an aryl group containing from 6 to 10 carbon atoms; and M and x are as defined in claim 1.
4. A lubricating oil composition as defined in claim 1 wherein the metal phosphorodithioate has the formula:
wherein R and R are alkyl groups containing from 1 to 18 carbon atoms each, and R is an alkaryl group containing from 7 to 20 carbon atoms; and M and x are as defined in claim 1.
5. A lubricating oil composition as defined in claim 1 wherein the metal phosphorodithioate has the formula:
wherein R and R are alkyl groups having from 1 to 18 carbon atoms each, and R is a cyclic alkyl group having from 6 to 12 carbon atoms; and M and x are as defined in claim 1.
6. A lubricating oil composition as defined in claim 2 wherein the metal phosphorodithioate is present in an amount which will contribute an amount of phosphorus in the range of about 0.01 weight percent to about 0.25 weight percent in the lubricating oil composition.
7. A lubricating oil composition as defined in claim 6 wherein the base oil is a mineral lubricating oil.
8. A lubricating oil composition as defined in claim 6 wherein the base oil is a synthetic lubricating oil.
9. A lubricating oil composition as defined in claim 7 wherein the metal phosphorodithioate is a Zinc phosphorodithioate.
10. A lubricating oil composition as defined in claim 8 wherein the metal phosphorodithioate is a zinc phosphorodithioate.
11. A lubricating oil composition comprising a base oil of a lubricating viscosity and a zinc phosphorodithioate having the formula:
said zinc phosphorodithioate being present in an amount which will contribute about 0.065 percent by weight phosphorus to the composition.
12. A lubricating oil composition of claim 11 where the base oil is a mineral lubricating oil having a viscosity of about to 400 seconds, Saybolt Universal at F.
References Cited by the Examiner UNITED STATES PATENTS 2,552,570 5/51 McNab et al. 252-32.7 2,889,354 6/59 Blake et al. 25256 X 2,891,084 6/59 Alm et al 25256 X 3,000,822. 9/61 Higgins et al. 2523.7
OTHER REFERENCES Barnes et al., Synthetic Ester Lubricants, Lubrication Engineering (August 1957), page 454 pertinent.
DANIEL E. WYMAN, Primary Examiner.-
Claims (1)
1. A LUBRICATING OIL COMPOSITION COMPRISING A BASE OIL OF LUBRICATING VISCOSITY AND A METAL PHOSPHORODITHIOATE HAVING THE FORMULA:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US269799A US3210275A (en) | 1963-04-01 | 1963-04-01 | Lubricating composition containing metal salts of hindered phosphorodithioates |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US269799A US3210275A (en) | 1963-04-01 | 1963-04-01 | Lubricating composition containing metal salts of hindered phosphorodithioates |
Publications (1)
Publication Number | Publication Date |
---|---|
US3210275A true US3210275A (en) | 1965-10-05 |
Family
ID=23028695
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US269799A Expired - Lifetime US3210275A (en) | 1963-04-01 | 1963-04-01 | Lubricating composition containing metal salts of hindered phosphorodithioates |
Country Status (1)
Country | Link |
---|---|
US (1) | US3210275A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4383931A (en) * | 1981-12-02 | 1983-05-17 | Gulf Research & Development Company | Lubricating oils containing molybdenyl chelates |
US4867890A (en) * | 1979-08-13 | 1989-09-19 | Terence Colclough | Lubricating oil compositions containing ashless dispersant, zinc dihydrocarbyldithiophosphate, metal detergent and a copper compound |
WO1989009812A1 (en) * | 1988-04-11 | 1989-10-19 | The Lubrizol Corporation | Lubricating oil additives |
US5013465A (en) * | 1987-12-23 | 1991-05-07 | Exxon Chemical Patents, Inc. | Dithiophosphates |
US5739089A (en) * | 1987-11-24 | 1998-04-14 | Exxon Chemical Patents Inc. | Dihydrocarbyl dithiophosphates |
US20030119576A1 (en) * | 2001-12-20 | 2003-06-26 | Mcclintic Monica A. | Gaming devices and methods incorporating interactive physical skill bonus games and virtual reality games in a shared bonus event |
US20040127291A1 (en) * | 2001-09-28 | 2004-07-01 | Jeffrey George | System and method for retrieving remote device information |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2552570A (en) * | 1947-11-28 | 1951-05-15 | Standard Oil Dev Co | Oxidation resisting hydrocarbon products |
US2889354A (en) * | 1955-10-06 | 1959-06-02 | Monsanto Chemicals | Dicarboxylate esters of alcohol containing a quaternary carbon in the beta-position |
US2891084A (en) * | 1959-06-16 | Method of preparing same | ||
US3000822A (en) * | 1957-01-22 | 1961-09-19 | Lubrizol Corp | Phosphorodithioate inhibitors |
-
1963
- 1963-04-01 US US269799A patent/US3210275A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2891084A (en) * | 1959-06-16 | Method of preparing same | ||
US2552570A (en) * | 1947-11-28 | 1951-05-15 | Standard Oil Dev Co | Oxidation resisting hydrocarbon products |
US2889354A (en) * | 1955-10-06 | 1959-06-02 | Monsanto Chemicals | Dicarboxylate esters of alcohol containing a quaternary carbon in the beta-position |
US3000822A (en) * | 1957-01-22 | 1961-09-19 | Lubrizol Corp | Phosphorodithioate inhibitors |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4867890A (en) * | 1979-08-13 | 1989-09-19 | Terence Colclough | Lubricating oil compositions containing ashless dispersant, zinc dihydrocarbyldithiophosphate, metal detergent and a copper compound |
US4383931A (en) * | 1981-12-02 | 1983-05-17 | Gulf Research & Development Company | Lubricating oils containing molybdenyl chelates |
US5739089A (en) * | 1987-11-24 | 1998-04-14 | Exxon Chemical Patents Inc. | Dihydrocarbyl dithiophosphates |
US5013465A (en) * | 1987-12-23 | 1991-05-07 | Exxon Chemical Patents, Inc. | Dithiophosphates |
WO1989009812A1 (en) * | 1988-04-11 | 1989-10-19 | The Lubrizol Corporation | Lubricating oil additives |
US20040127291A1 (en) * | 2001-09-28 | 2004-07-01 | Jeffrey George | System and method for retrieving remote device information |
US20030119576A1 (en) * | 2001-12-20 | 2003-06-26 | Mcclintic Monica A. | Gaming devices and methods incorporating interactive physical skill bonus games and virtual reality games in a shared bonus event |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2680123A (en) | Zinc salt of mixed ester thiophosphates | |
US3544463A (en) | Overbased oil-soluble metal salts | |
US3224971A (en) | Borate esters and lubricant compositions containing said esters | |
US2736706A (en) | Lubricant containing a phosphorus acid ester-aldehyde condensation product | |
US3451933A (en) | Formamido-containing alkenylsuccinates | |
US2591577A (en) | Lubricating oil containing disulfide derivatives of organo-substituted thiophosphoric acids | |
US3277133A (en) | Phosphorus-, sulfur-, and metal-containing composition | |
US3259579A (en) | Esters of dithiophosphoric acids and lubricating oil compositions containing same | |
US3210275A (en) | Lubricating composition containing metal salts of hindered phosphorodithioates | |
US2723237A (en) | Phosphoric acid esters of diethylene glycol ethers and lubricants containing the same | |
US2756213A (en) | Amate-dicarboxylate-thickened grease | |
US2785128A (en) | Metal salts of organic acids of phosphorus | |
US2543735A (en) | Lubricating composition | |
US3068259A (en) | Molybdenum and tungsten halides and sulfides of organic substituted dithiophosphoricacids | |
US3609077A (en) | Lubricant compositions | |
US2409726A (en) | Lubricant composition | |
US2766291A (en) | Metal salts of alkyl phenol sulfides | |
US2760937A (en) | Phosphorus-containing lubricant additives | |
US2599341A (en) | New phosphorus containing compounds | |
US3240704A (en) | Lubricating compositions having oilsoluble phosphorus-containing condensation products | |
US2783203A (en) | Corrosion preventing agent | |
US2809162A (en) | Corrosion inhibited lubricant composition | |
US3257321A (en) | 3, 5-dialkyl-4-hydroxybenzyl chloride | |
US3245979A (en) | Phosphorus phenol condensation compounds | |
US3125524A (en) | Lubricating greases containing salts of |