US2451345A - Compounded lubricating oil - Google Patents
Compounded lubricating oil Download PDFInfo
- Publication number
- US2451345A US2451345A US560192A US56019244A US2451345A US 2451345 A US2451345 A US 2451345A US 560192 A US560192 A US 560192A US 56019244 A US56019244 A US 56019244A US 2451345 A US2451345 A US 2451345A
- Authority
- US
- United States
- Prior art keywords
- phosphorus
- sulfide
- phenol
- metal
- oil
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000010687 lubricating oil Substances 0.000 title description 29
- 229910052751 metal Inorganic materials 0.000 description 86
- 239000002184 metal Substances 0.000 description 86
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 75
- 229910052698 phosphorus Inorganic materials 0.000 description 75
- 239000011574 phosphorus Substances 0.000 description 75
- 239000000203 mixture Substances 0.000 description 57
- 239000000047 product Substances 0.000 description 56
- 229910052717 sulfur Inorganic materials 0.000 description 56
- 239000011593 sulfur Substances 0.000 description 55
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 54
- 239000000654 additive Substances 0.000 description 51
- 239000003921 oil Substances 0.000 description 50
- -1 aromatic sulfides Chemical class 0.000 description 47
- 150000003839 salts Chemical class 0.000 description 47
- 239000012141 concentrate Substances 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 35
- 230000000996 additive effect Effects 0.000 description 34
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 32
- 229910052788 barium Inorganic materials 0.000 description 31
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 31
- LJKQIQSBHFNMDV-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical class C1=CC=CC2(O)C1S2 LJKQIQSBHFNMDV-UHFFFAOYSA-N 0.000 description 30
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 27
- 239000010688 mineral lubricating oil Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical class S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 18
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 17
- 239000000376 reactant Substances 0.000 description 17
- 239000007795 chemical reaction product Substances 0.000 description 16
- 150000001298 alcohols Chemical class 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 150000002989 phenols Chemical class 0.000 description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
- 229910052791 calcium Inorganic materials 0.000 description 13
- 239000011575 calcium Substances 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 11
- 239000002480 mineral oil Substances 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000000314 lubricant Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 159000000009 barium salts Chemical class 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000001993 wax Substances 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 8
- 239000002199 base oil Substances 0.000 description 8
- 235000010446 mineral oil Nutrition 0.000 description 8
- 230000000737 periodic effect Effects 0.000 description 8
- 230000000087 stabilizing effect Effects 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 239000003599 detergent Substances 0.000 description 5
- 230000006866 deterioration Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 238000007664 blowing Methods 0.000 description 4
- 239000010685 fatty oil Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 230000001050 lubricating effect Effects 0.000 description 4
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 4
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- 241000158728 Meliaceae Species 0.000 description 3
- FQNGWRSKYZLJDK-UHFFFAOYSA-N [Ca].[Ba] Chemical compound [Ca].[Ba] FQNGWRSKYZLJDK-UHFFFAOYSA-N 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 229910001863 barium hydroxide Inorganic materials 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000005077 polysulfide Substances 0.000 description 3
- 229920001021 polysulfide Polymers 0.000 description 3
- 150000008117 polysulfides Polymers 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical group CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004264 Petrolatum Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- WIKSRXFQIZQFEH-UHFFFAOYSA-N [Cu].[Pb] Chemical compound [Cu].[Pb] WIKSRXFQIZQFEH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000006079 antiknock agent Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- ZUDYPQRUOYEARG-UHFFFAOYSA-L barium(2+);dihydroxide;octahydrate Chemical compound O.O.O.O.O.O.O.O.[OH-].[OH-].[Ba+2] ZUDYPQRUOYEARG-UHFFFAOYSA-L 0.000 description 2
- 229910052728 basic metal Inorganic materials 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000005608 naphthenic acid group Chemical group 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 229940066842 petrolatum Drugs 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 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 2
- 239000000126 substance Substances 0.000 description 2
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- DGBNNVRFDHMFJL-UHFFFAOYSA-N 1,2-dipentyl-3,8-dithiatricyclo[5.1.0.02,4]oct-5-en-4-ol Chemical compound C(CCCC)C12C3(C(C=CC1S2)(O)S3)CCCCC DGBNNVRFDHMFJL-UHFFFAOYSA-N 0.000 description 1
- MRWSNXVEXZNROC-UHFFFAOYSA-N 1-(2,4,4-trimethylpentan-2-yl)-7-thiabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical compound C1=CC=CC2(C(C)(C)CC(C)(C)C)C1(O)S2 MRWSNXVEXZNROC-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- STMRWVUTGPZZER-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=CC(O)=C1CC(C)C STMRWVUTGPZZER-UHFFFAOYSA-N 0.000 description 1
- PTMRDOLOEDPHLB-UHFFFAOYSA-N 2,3-dipentylphenol Chemical compound CCCCCC1=CC=CC(O)=C1CCCCC PTMRDOLOEDPHLB-UHFFFAOYSA-N 0.000 description 1
- DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 description 1
- GKPNMUZVXNHWPX-UHFFFAOYSA-N 2,4-dipentylphenol Chemical compound CCCCCC1=CC=C(O)C(CCCCC)=C1 GKPNMUZVXNHWPX-UHFFFAOYSA-N 0.000 description 1
- URRHKOYTHDCSDA-UHFFFAOYSA-N 2,5,8,11-tetramethyldodec-2-ene Chemical group CC(C)CCC(C)CCC(C)CC=C(C)C URRHKOYTHDCSDA-UHFFFAOYSA-N 0.000 description 1
- NCIAZCLIFWUDPR-UHFFFAOYSA-N 2-butyl-3,4,5,6-tetramethylphenol Chemical compound CCCCC1=C(C)C(C)=C(C)C(C)=C1O NCIAZCLIFWUDPR-UHFFFAOYSA-N 0.000 description 1
- HMWIHOZPGQRZLR-UHFFFAOYSA-N 2-hexadecylphenol Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1O HMWIHOZPGQRZLR-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- VUBOQPNQIMKEKI-UHFFFAOYSA-N 3,8-dithiatricyclo[5.1.0.02,4]oct-5-en-4-ol Chemical compound C12SC2C=CC2(O)C1S2 VUBOQPNQIMKEKI-UHFFFAOYSA-N 0.000 description 1
- XENCZPMACKCGLJ-UHFFFAOYSA-N 5,6-dipentyl-7-thiabicyclo[4.1.0]hepta-2,4-dien-1-ol Chemical compound C(CCCC)C=1C2(C(C=CC1)(O)S2)CCCCC XENCZPMACKCGLJ-UHFFFAOYSA-N 0.000 description 1
- 244000226021 Anacardium occidentale Species 0.000 description 1
- 229910015900 BF3 Inorganic materials 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
- SHIMVYYQZCXMAD-UHFFFAOYSA-N C(CCCC)C=1C2(C(C=CC1)(O)S2)CCCCC.[Ba] Chemical compound C(CCCC)C=1C2(C(C=CC1)(O)S2)CCCCC.[Ba] SHIMVYYQZCXMAD-UHFFFAOYSA-N 0.000 description 1
- CQVGJDHNDCIUSL-UHFFFAOYSA-N C(CCCCCCCCC(C)C)C12C(C=CC=C1)(O)S2 Chemical compound C(CCCCCCCCC(C)C)C12C(C=CC=C1)(O)S2 CQVGJDHNDCIUSL-UHFFFAOYSA-N 0.000 description 1
- FYTFYXHLJDZBHV-UHFFFAOYSA-N C(CCCCCCCCCCCCC(C)C)C12C(C=CC=C1)(O)S2 Chemical compound C(CCCCCCCCCCCCC(C)C)C12C(C=CC=C1)(O)S2 FYTFYXHLJDZBHV-UHFFFAOYSA-N 0.000 description 1
- SVGNAECMIAIXBU-UHFFFAOYSA-N CC(C)=C.CC(C)=C.S(Cl)Cl Chemical group CC(C)=C.CC(C)=C.S(Cl)Cl SVGNAECMIAIXBU-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 240000003550 Eusideroxylon zwageri Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000005139 Lycium andersonii Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-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
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
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- 229910052712 strontium Inorganic materials 0.000 description 1
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Classifications
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- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
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- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/123—Reaction products obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/30—Refrigerators lubricants or compressors lubricants
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/32—Wires, ropes or cables lubricants
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/34—Lubricating-sealants
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/36—Release agents or mold release agents
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/38—Conveyors or chain belts
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- C10N2040/40—Generators or electric motors in oil or gas winning field
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/42—Flashing oils or marking oils
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- C10N2040/44—Super vacuum or supercritical use
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- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
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- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Definitions
- This invention relates to lubricants and other organic materials subject to deterioration in the presence of oxygen, and it relates more particularly to mineral lubricating oil compositions for use as crankcase lubricants for internal combustion engines and to addition agents suitable for retarding the deterioration of such oils and for improving other properties of the same.
- metal organic compounds improves various properties thereof, such as their oillness characteristics and their detergent action in engines, particularly manifested in the maintenance of a clean engine condition during operation.
- Various metal compounds which have been used for such purposes include the metal derivatives of such organic compounds as fatty acids, naphthenic acids, sulfonic acids, alcohols, phenols and ketones.
- these various metal compounds generally have the disadvantage of tending to corrode alloy bearings, such as those of cadmium-silver and copper-lead, now so widely used in automotive engines; and this is especially true in engines which operate at relatively high speeds and high temperatures.
- the new class of products which have now been found to be highly satisfactory as addition agents are the products obtained by the reaction of the elements sulfur and phosphorus with metal salts of hydroxy and mercapto substituted aromatic sulfides.
- these compounds When these compounds are to be used as additives for mineral oils, they should contain as a substituent in each aromatic nucleus at least one alkvl group, the total number or carbon atoms in such groups being at least live. It has been found that such products are usually satisfactory in inhibiting bearing corrosion, and in being adaptable to use with a wide variety of petroleum lubricating oil base stocks.
- the elements sulfur and phosphorus may be introduced into the metallic salt molecule by reacting the latter with both elemental sulfur and elemental phosphorus, or by reacting the same with a sulfide of phosphorus.
- the reaction may generally be brought about in a solution of lubricating oil or other petroleum oil, whereby concentrates may be prepared which may be conveniently stored or shipped and added to lubricating oils when required.
- the new sulfur and phosphorus containing compositions herein described are also useful as antioxidants for other purposes when incorporated in organic materials other than lubricating oils, as will be more fully explained hereinafter, and in some cases it may not be necessary to have alkyl groups present to impart sufficient solubility.
- the invention also includes the reaction products of phosphorus sulfides or phosphorus and sulfur with compounds analogous to the salts of phenol sulfides and thiophenol sulfides, but containing selenium and tellurlum in place of oxygen or sulfur, and with compounds in which aromatic nuclei other than benzene nuclei are present.
- Some of the more preferred products to be used in accordance with the present invention are those obtained by reaction or a sulfide oi phosphorus or a combination of the elements sulfur and phosphorus with the following compounds:
- Barium tert.-octyl phenol sulfide Barium di-tert.-amyl phenol sulfide Calcium isohexadecyl phenol sulfide 'lin wax alkylated salicylic acid sulfide Magnesium tert.-amyl phenol sulfide
- The, invention includes the reaction of phosphorus and sulfur or sulfides of phosphorus with not only the normal metal salts of phenol sultides, thiophenol sulfides and the like, but the basicmetalsaltsaswell. manormalphenol sulfide salt or a divalent metal the mo! ratio of metal to phenol sulfide is 1:1, as in the following formula:
- the new class of addition agents employed in a cordance with the present invention may he defined in its broadest scope is the reaction prodnets of any combination of the elements sulfur and phosphorwswith a metal salt oi a compound having the formula inwhichlirisanaromationuoleusandmamtor illustration, be a benzene nucleus. or it may consistofapiuralityotrinealsinbiphenyhorfi may be a condensed nucleus, exemplified by naphthalene, anthracene and the like. R in the formulaishydroeenoratleastone p di prei'erabh'analkylsroup.
- xinthetormul-a is a non-metal of zroup VI oi the periodic table: Yisamemberoi'thesuliurfamilnzis anint s'eri'romltoi; audit isanomaniclrcup which may be either and. elbl. aralkyl. or alkylaryl. and which may contain substituent atoms or hydrogeninthe-Xfleroupoi'theaboniornmiaini'ormingsaitsorsuchcompoundsmay be any metalathe most important for the Purposes of the present invention -lacing calcium, barium, strontium.
- M is oxygen or sulfur.
- M is a divalent metal or group tehleandcisaninteeerirom It should be understood that the above general iormulas include compounds in which various substituent atoms or groups may be attached to the aromatic nucleus. such as alkyl. cycloalkyl, aralkyl, aryl, carboxyl, hydroxyl, alkoxy,
- Different types of atoms or groups may be attached to the same aromatic nucleus.
- Alkyl radicals attached to the nucleus may have a total of five .to twentyfive carbon atoms in all of such groups, and in some cases as many as sixteen to twenty or more carbon atoms in a single group, as in a wax chain group, or in a plurality or groups, may be prei'erred. If more than one alkyl group is present in a single molecule, whether or not attached to the same and nucleus, such groups may be alike or difi'erent. Such alkyl or other hydrocarbon groups may'contain substituent groups, such as those named above as substituents in the aromatic nucleus. The various groups or atoms attached to the aromatic nucleus may be in any positions relative to one another.
- Alkyl phenol sulfides whose metal salts may be used to prepare the reaction products of the present invention, may be illustrated by the following general classes of compounds:
- Alkyl phenol thioethers 3. Polmers of alkyl phenol sulfides on [on on R- s @s-- -R l. R .4: and
- R represents an alkyl group containing preferably at least four carbon atoms, and z is a small whole number not greater than about six.
- metal salts or alkyl phenol sulfides having Clo-Can branched chain alkyl groups can be conveniently prepared from phenols which have been allwlated with suitable branched chain polymers obtained by polymerizing low boiling olefins such as propylene, butylenes, or amylenes, or mixtures 01' these olefins.
- alkyl phenol sulfide is meant to include not only the monosulfides but also the diand polysulfides and polymers of alkyl phenol sulfides as well.
- reaction of two mols 01' an alkylated phenol with one moi of sulfur dichloride (801:) will give essentially an alkyl phenol monosulfide, small amounts of polysulfides and of polymeric materials will also be formed.
- R is used to represent an alkyl radical
- such radicals may be illustrated by the following species, which are radicals particularly preferred in the compounds, it being understood that the list is merely illustrative and does not restrict the scope or the groups or the formulas. These include n'-butyi, isobutyl, tort.- butyl. n-amyl. isoamyl. cyclohexyl, n-oetyi, isopreparing the alkyl phenol octadecyi. wax chain radicals.
- hvdroxyaryl sulfide s p acidic organic groups such as carboxy, aroxy, alkoxy, organo-substituted inorganic acid groups such as phosphoric, phosphorous, thiophosphoric, thiophosphorous, phosphonic, phosphinic, sulionic, sulfinic, and the like.
- the present invention also includes reaction products oi phosphorus sulfides with such compounds as:
- Aluminum mixed salt of tert.-octyl phenol sulfide and stearic acid Tin mixed salt of di-tert.-amyl phenol sulfide and naphthenic acids some 01' them may be satisfied by other Barium mixed salt of tert.-octyl phenol sulfide and petroleum mahogany sulionic acids
- the metal salts or alkylated phenol sulfides have been preferably prepared irom phenolic compounds readily obtained by synthetic alkylation of the simple phenols. followed by treatment with a sulfur chloride. and then neutralization with a metallic base.
- Suitable synthetic alkyl phenols for preparing the desired phenol sulfide salts are preferably those containing secondary or tertiary alkyl radicals. Because alkyiation oiia simple phenol occurs more readily with branched chain aliphatic reactants. Commonly, the aikylation reaction involves a condensation of olefins with the simple phenols, the reaction being catalyzed by anhydrous metal halides, boron fluoride, hydrofluoric acid, stannic chloride with hydrogen chloride, suliuric acid. phosphoric acid. or certain activated clays. As olefinic reactants, refinery gases containing propylene.
- butylenes, amylenes, etc. are economically useful, although individual olefins or olefin-containing mixtures derived from other sources may be used.
- Preferred individual olefins are the butenes, amylenes and olefin polymers. such as diisobutylene or triisobutyiene or normal olefln polymers or wpolymers or normal and secondary or tertiary oleilns or copolymers, of olefins and diolefins.
- the reaction temperature is usually controlled to avoid side reactions. In employing sulfuric acid, a liquid phase reaction at relatively low temperature is preferre while with phosphoric acid th reaction may be carried out in the vapor phase.
- Suitable alkylated phenols for conversion to phenol sulfides may be thus prepared by alkylating phenol, cresol, naphthol or other phenolic compounds.
- High molecular weight alkylated phenols may also be used, for example, those prepared by condensing phenols with chlorinated petrolatum or chlorinated paraflln wax or with a chlorinated kerosene or gas oil.
- Naturally occurring phenols such as those obtained by alkaline extraction of certain petroleum stocks or those obtained from cashew nut shell lliquid or those obtained from other vegetable all sources may likewise be used.
- Halogenated or nitrated phenols will also find application in this invention, particularly if the final additive is to be employed in extreme pressure lubricants.
- alkyl phenols which are particularly preferred are those which have been prepared by alkylation of phenol with an olefin polymer such as diisobutylene or a refinery butene polymer oil.
- Alkyl-atlon of phenol with about an equal molar proportion of diisobutyiene gives p-tert.-octyl phenol, also known as diisobutyl phenol or tetramethyl butyl phenol.
- This phenolic material is especially desirable because of the ease oi its preparation and because products made from it.are highly satisiactory tor the present invention.
- phenol may be alkylated with as much as two molecular equivalents of diisobutylene to give. under proper conditions, essentially di-tert.-octyl phenol; or it may be alkylated with other olefin polymers such as triisobutylene or other isobutylene polymers.
- alkylated phenols having branched alkyl groups of from 16 to 30 carbon atoms.
- Suitable products may be prepared by alkylating phenol with certain of the polymeric materials obtained as by-products in the manufacture of butyl alcohol from petroleum refinery butenes.
- the phenol is reacted with sulfur dichloride to produce essentially a phenol monosulfide having a thioether linkage, while sulfur monochloride may be used to produce essentially the phenol disulfide.
- sulfur dichloride may be used to produce essentially the phenol disulfide.
- About one-half to one mol of sulfur halide is used with each mol of phenol, and the reaction is preferably carried out in a solvent such as dichlorethane, chloroform, petroleum naphtha, benzol, xylol, toluol, and the like.
- barium salts of alkylated phenol sulfides are prepared by reacting the sulfide with barium hydroxide, preferably in the form of the hydrate, Ba(OH)2.8I-I2O. In some instances it may be preferable to prepare heavy metal salts from the alkali metla salt by double decomposition.
- the calcium salts are conveniently prepared by reacting alkyl phenol sulfides with calcium methylate or other calcium alcoholate.
- metal aikyl phenol sulfide prepared by neutralizing with a metal hydroxide may occur as a hydrated salt.
- Use of hydrated salts prepared in this manner or by any other method is also contemplated in the processes of the present invention.
- the metallic salt of a phenol sulfide or other metallic derivative of a hydroxy or mercapto aromatic sulfide is caused to react with the elements sulfur and phosphorus.
- This may be accomplished by adding a mixture of the substances in elemental form. or first one element and then the other, to the heated metallic compound, or by adding a sulfide of phosphorus, such as P255, P483, P481, or the like, or by treatment with sulfur and/or phosphorus and a sulfide of phosphorus, or by treatment with any other subtance or substances containing essentially only the elements phosphorus and sulfur.
- the phosphorus may be used either in the white (yellow) or red allotropic form, and the sulfur may likewise be used in any of its allotropic forms.
- reaction can be brought about by fusing the metal salt with hosphorus and sulfur, or with a phosphorus sulfide, it is more convenient to carry out the reaction with the aid of solvents, particularly high boiling hydrocarbon solvents, such as xylol or a petroleum fraction.
- solvents particularly high boiling hydrocarbon solvents, such as xylol or a petroleum fraction.
- a particularly preferred reaction medium is a lubricating oil fraction, since the final reaction products can thus be obtained as a mineral oil concentrate of the desired additive, which may be conveniently shipped or stored as such and then readily blended with the lubricating oil base stock in the desired concentration to form a finished lubricating oil blend.
- the additives may generally be prepared by first dissolving an alkylated phenol sulfide in a mineral oil or other suitable solvent and treating the same with a metal hydroxide, e. g., Ba 0H):.8H-.-O, at about -200 0., preferably -l50 C. After a further period of heating, free sulfur and free phosphorus, or a sulfide of phosphorus, or other mixture or combination of the elements, is added, heating being continued at 100-200 0., preferably at l50-l80 0., to complete the reaction. The period of heating will be at least 10 minutes and generally at least 1 hour, although in some cases a longer period may be required. The product is then filtered, giving a concentrate of the desired additive.
- a metal hydroxide e. g., Ba 0H
- free sulfur and free phosphorus, or a sulfide of phosphorus, or other mixture or combination of the elements is added, heating being continued at 100-200 0.,
- the products are found to have a slight odor of hydrogen sulfide, this can be substantially eliminated by blowing the products with a suitable gas such as dry or moist air or nitrogen or superheated steam at temperatures of 80-l50 C., or by treating with a neutralizing 'agent such as barium or calcium hydroxide or calcium oxide.
- a suitable gas such as dry or moist air or nitrogen or superheated steam at temperatures of 80-l50 C.
- a neutralizing 'agent such as barium or calcium hydroxide or calcium oxide.
- a combination of these treating steps may also be employed. For example, satisfactory results have been obtained by treating the products with 2-5% of barium hydroxide at C. before the filtering step, followed by nitrogen blowing at 100-120" C. after filtration. If the blowing step is found to be necessary in commercial operation.
- one convenient method is to treat the material with the gas in countercurrent flow in a suitable tower.
- the metal phenol sulfide salt may be subjected to a heat-treating step, e. g.. for 8-10 hours at 150-180" C., or it may be blown with dry or moist carbon dioxide, before adding the sulfide of phosphorus, in order to render the final product non-sensitive to the presence of water when blended in lubricating oil.
- a heat-treating step e. g.. for 8-10 hours at 150-180" C.
- this step will not be necessary, inasmuch as the products of the present invention are substantially non-water-sensitive, as will be demonstrated hereinafter.
- the additives oi the present invention are most advantageously blended with lubricating oil base stocks in concentrations between the approximate limits of 0.02% and 5.0% and preferably from 0.1% to 2.0%, although larger amounts may be used for some purposes.
- concentrations between the approximate limits of 0.02% and 5.0% and preferably from 0.1% to 2.0%, although larger amounts may be used for some purposes.
- EXAMPLEI Tertiary octyl phenol was prepared by alkylating phenol with diisobutylene in the presence of *SnCh-HCl catalyst substantially as described in 12 fur dichloride was added to this solution in the ratio 1.0 mole of 801: to each 2 mole of tertsoctyl phenol, the temperature being maintained at 25-35 C. After maintaining the same temperature for an additional half hour the reaction mixture was heated to C. and the solvent stripped oil under vacuum, leaving the tert.-octyl phenol sulfide as a residue.
- EXALIPLE 2 As starting material for the preparation of a reaction product of a barium salt, there was used a concentrate containing 40% by weight of barium tert.-octyl phenol sulfide. 6% cl stearyl alcohol. and 54% of a refined mineral oil of 52 seconds viscosity Saybolt at 210 E, prepared as described in Example 1. 30.3 kg. of this concentrate was treated with 2.81 kg. 01 Pass by heating the concentrate to C. and adding the phosphorus sulfide gradually with agitation over a period oi 1 hour, during which the temperature rose to -190 C. The temperature was then held at 160-180 C. for an additional 2 hour period and the final product filtered. The resulting additive concentrate contained 8.10% barium, 2.12% phosphorus, and 7.93% sulfur.
- Example 8 To demonstrate the reproducibility of the preparation of the present invention, Example 2 was repeated, using 29.95 kg. of the concentrate oi Exampl 1 and 2.3 kg. of P285, and the same reaction times andtemperatures. The filtered concentrate analyzed 8.14% barium, 2.08% phosphorus, and 7.96% sulfur.
- EXAIHPLE4 This example demonstrates the preparation 01' an additive concentrate of the present invention on a plant scale.
- an oil solution of ten.- octyl phenol sulfide and stearyl alcohol was treated with Ba(OH)r.8H2O, but the reaction product was not filtered.
- EXAMPLE In this example a mol ratio of phosphorus sulfide to metal phenol sulfide of 0.2 to l was employed. 2470 g. of an oil concentrate of 40% barium tert.-octyl phenol sulfide, 6% stearyl al-' EXAMPLE 6 This example demonstrates the preparation of an additive similar to that of Example 2, but employing P481 instead of Past.
- the starting material was an additive concentrate prepared in the same manner as that described in Example 1, containing 40% barium tert.-octyl' phenol sulfide, 6% stearyl alcohol and 54% mineral oil. Analysis of the concentrate showed it to contain 8.97% barium and 3.51% sulfur.
- EXAMPLE 8 A reaction product of the present invention emplaying a mixed calcium-barium alkyl phenol suiride was prepared as grams of tert.-octyl phenol sulfide. 1620 grams of S. A. E. 20 grade mineral lubricating oil, 180 grams of commercial stearyl alcohol, and 205 grams of calcium hydroxide was placed in a 12-liter reaction fiask equipped with a stirrer and water trap reflux condenser and heated at -425 C. for 10 hours, at the end of which time 83% of the theoretical amount of water from the reaction had been removed through the water trap. The mixture was then heated to 150 C. and filtered, employing Hyfio filter aid. The oil concentrate of calcium tert.-octyl phenol sulfide contained 2.82% calcium and and 4.13% sulfur.
- diamyl phenol disulfide was prepared from 1404 grams of 2.4-diamyl phenol and 608 grams of sulfur monochloride, this being 1.5 mols of 81012 per 2 mols of alkyl phenol.
- the product contained 16.55% sulfur.
- the tests were conducted as follows: 500 cc. of in a. glass oxidation oil to be tested was placed tube (13" long and 2%" diameter) fitted at the bottom with a V4" bore air inlet tube perforated to facilitate air distribution. The oxidation tube four hour period and then polished and reweighed before continuing for another four hour period.
- Lubricating oil blends were prepared by adding to separate portions of an S. A. E. 20 grade extracted Mid-Continent oil 2.5% by weight of the additive concentrates prepared as described in Example 1 and as described in Example 5. Each oil was tested for water sensitivity, i. e., the tendency of the additive to separate from the oil in the presence of water. This test was conducted as follows: 600 cc. of the oil blend is emulsified with 1% water by means of a motordriven eggbeater-type mixer operated at maximum speed for minutes. After stirring. 500 cc. of the emulsion is poured into a 500 cc. graduated cylinder and allowed to stand for 24 hours. At the end of this period the amount of emulsion layer separated from the oil is noted. The smaller the amount of separation the better the water resistant qualities of the additive.
- additives of the present invention will oi themselves impart sufncient improvement to lubricating oils to give very satisfactory results, still greater improvement may often be obtained by employing these addition agents in conJunction with other additives of the detergent type, such as metal soaps, metal phenates, metal alcoholates, metal phenol sulfides, metal organs phosphates, thiophosphates, phosphites and thiophosplntes, metal sulionates, metal thiocarbamates, metal xanthates and thioxanthates, and the like.
- detergent type such as metal soaps, metal phenates, metal alcoholates, metal phenol sulfides, metal organs phosphates, thiophosphates, phosphites and thiophosplntes, metal sulionates, metal thiocarbamates, metal xanthates and thioxanthates, and the like.
- addition agents of our invention may be used in mineral lubricating oils in conjunction with one or more 01' the following representative materials:
- lubricant compositions in which the additives of the present invention are employed in conjunction with metal salts of petroleum mahogany suifonlc acids.
- oils may be refined by conventional methods using acid, alkali, and/or clay or other agents such as aluminum chloride, or they may be extracted oils produced, for example, by solvent extraction with type of phenol, ethyl ether, nitrobenzene, crotonaldehyde, etc.
- the oil must possess the viscosity and volatility characteristics known to be required for the service contemplated.
- the oil must be a satisfactory solvent for the additive, although in some cases auxiliary solvent agents may be used.
- the lubricating oils may have been produced, may vary considerably in viscosity and other properties depending upon the particular use for which they are desired. but they usually range from about 40 to 150 seconds Saybolt viscosity at 210 F.
- the general practice has often been to use a lubricating oil base stock prepared from naphthenic or aromatic crudes and having a Saybolt viscosity at 210 F.
- oils of higher viscosity index are often pre-' ferred, for example, up to '15 to 100, or even higher, viscosity index.
- agents may also be used such as dyes, pour depressors, heat thickened fatty oils, sulfurized fatty oils, organo metallic compounds, metallic or other soaps, sludge dispersers, antioxidants, thickeners, viscosity index improvers, oiliness agents, resins, rubber, olefin polymers, voltolized fatty oils or fats, voltolized mineral oils, and/or voltolized waxes and colloidal solids such as graphite or zinc oxide, etc.
- additives such as dyes, pour depressors, heat thickened fatty oils, sulfurized fatty oils, organo metallic compounds, metallic or other soaps, sludge dispersers, antioxidants, thickeners, viscosity index improvers, oiliness agents, resins, rubber, olefin polymers, voltolized fatty oils or fats, voltolized mineral oils, and/or voltolized waxes and colloidal solids such as graphite or zinc oxide, etc.
- Such other agents include phenyl alpha naphthylamine, voltolized sperm oil, 2,6-di-tert.-butyl-4-methyl phenol, sulfurlzed sperm oil, p-tert.-amyl phenol sulfide, dibenzyl disulfide, polyisobutylene, sulfurized wax oleflns, tricresyl phosphate, dlamyl trisulflde, and the condensation product of phenol with a sulfur chloride-diisobutylene reaction product.
- Solvents and assisting agents such as esters, ketones, alcohols, aldehydes, halogenated or nitrated compounds, and the like, may also be employed.
- Assisting agents which are particularly desirable are the higher alcohols having eight or more carbon atoms and preferably 12 to 20 carbon atoms
- the alcohols may be saturated straight and branched chain aliphatic alcohols such as octyl alcohol (CaHnOH) lauryl alcohol (CuHasOH) cetyl alcohol (CmI-IaaOI-I), stearyl alcohol, sometimes referred to as octadecyl alcohol (C1aHa7OH) heptadecyl alcohol (CnHasOI-I) and the like; the corresponding olefinic alcohols such as oleyl alcohol; cyclic alcohols, such as naphthenic alcohols; and aryl substituted alkyl alcohols, for instance, phenyl octyl alcohol, or octadecyl benzyl alcohol, or mixtures of these various alcohols, which may be pure or substantially pure synthetic alcohols.
- Products prepared synthetically by chemical processes may also be used, such as alcohols prepared by th oxidation of petroleum hydrocarbons. e. g., parafiin wax, petrolatum, etc.
- These assisting agents serve to enhance the detergent and sludge dispersive qualities and aid the solubility of the metal-containing additives and at the same time impart some oiliness properties to the lubricating oil compositions.
- the additives or the present invention may also be used in extreme pressure lubricants, engine flushing oils, industrial oils, general machinery oils, process oils, rust preventive compositions and greases. Also their use inmotor fuels, Diesel fuels and kerosene is contemplated. A particular application in this regard i their use in r motor fuels containing tetraethyl lead or other anti-knock agents, the additives of the present invention serving not only as antioxidants for the fuel but also as stabilizers for the anti-knock agent itself.
- these additives exhibit antioxidant properties and are believed also to pos- -sess ability to modify surface activity, they may be employed in asphalts, road oils, waxes, fatty oils of animal or vegetable origin, soaps, and plastics. Similarly, they may be used in natural and synthetic rubber compounding both as vulcanizm tion assistants and as anti-oxidants, and generally they may be used in any organic materials subject to deterioration by atmospheric oxygen.
- a hydrocarbon product subject to deterioration by atmospheric oxygen containing a stabilizing amount of a product obtained by reacting a sulfide of phosphorus with a divalent group 11 metal salt of a compound having the characterizing structure bilizing amount of a product obtained by react- 23 log a sulfide oi phbsphorus with a compound of the formula M x x agnng.
- R is an alkyl radical of 4-24 carbon atoms
- X is an element of the group consisting of oxygen and sulfur.
- M is a divalent metal of group II of the periodic table, and a: is an integer from 1 to 4, at a temperature of IUD-200 C. for a period of at least 10 minutes, the proportions of reactants being such that 0.03-2 atomic proportions of phosphorus are present for each atomic proportion of metal.
- a mineral lubricating 011 containing a stabilizing quantity of a product obtained by reacting a sulfide of phosphorus with a divalent group II metal salt, of a compound having the characterizing structure in which the groups R. KB and Y R are all connected to the aromatic nucleus Ar and in which It represents at least one alkyl group of 4 to 24 carbon atoms and R represents an aryl group, X is an element of the group consisting of oxygen and sulfur, Y is a member of the sulfur family of elements, and :r is an integer from 1 to 4, at a temperature of 100-200 C. for a period of at least ten minutes, the proportions of reactants being such that 0.03-2 atomic proportions of phosphorus are present for each atomic proportion of metal.
- a mineral lubricating oil containing a stabilizing quantity of a product obtained by reacting a sulfide of phosphorus with a metal salt of an alkylated phenol sulfide in which the alkyl groups attached to each benzene nucleus contain a total of at least carbon atoms, and in which the metal of the salt is a divalent metal of group II of the periodic table, at a temperature of 100-200" C. for a period of at, least minutes, the proportions of reactants being such that 0.03-2 atomic proportions of phosphorus are present for each atomic proportion of metal.
- each benzene nucleus oi the metal salt contains a substituent tert.-octy1 radical.
- a mineral lubricating oil containing a stabilizing quantity of a product obtained by reacting a. sulfide of phosphorus with a barium salt of a tert.-octyl phenol sulfide, at a temperature of -180" C. for a period of at least 1 hour, the proportions of reactants being such that 0.06- 0.75 atomic proportion of phosphorus is present for each atomic proportion of barium.
- a mineral lubricating oil containing a stabilizing quantity of a product obtained by reacting about 0.06 to about 0.75 molecular proportion or phosphorus pentasulflde with one molecular proportion of the barium salt of a tert.-octyl phenol sulfide, at a. temperature of 150-180 C. for a period of at least 1 hour.-
- a mineral lubricating oil containing a stabilizing quantity or a product obtained by heating a concentrated mineral lubricating oil solution containing about 40% of barium tert.-octyl phenol sulfide, about 6% of stearyl alcohol, and about 54% of a refined mineral lubricating oil to about ISO-180 C., gradually adding about 0.4 molecular proportion 01' phosphorus pentasulflde for each molecular proportion of the barium salt while maintaining the temperature not higher than about 190 C., further maintaining the temperature at about to about C. for at least 2 hours, and filtering the final product.
- a mineral lubricating oil containing a stabilizing quantity of a product obtained by heating a concentrated mineral lubricating oil solution containing about 40% of'barium tert.-octyl phenol sulfide, about 6% or stearyl alcohol. and about 54% of a refined mineral lubricating oil to about 150-180 C., gradually adding about 0.2 molecular proportion of phosphorus pentasulflde for each molecular proportion of the barium salt while maintaining the temperature not higher than about (2., further maintaining the temperature at about 160 to about 180 C. for at least 2 hours, and filtering the final product.
- a sulfur and phosphorus containing product obtained by reacting a sulfide of phosphorus with a divalent group II metal salt of a compound having the characterizing structure where Ar is an aromatic nucleus, R is an alkyl radical of 4-24 carbon atoms, X is an element of the group consisting of ongen and sulfur, Y is a member of the sulfur family of elements, and a: is an integer from 1 to 4, at a. temperature of 100-200 C. for a. period of at least 10 minutes, the proportions of reactants being such that 0.03-2 atomic proportions of phosphorus are present for each atomic proportion of metal.
- an oil-soiuble sulfur and phosphorus containing product obtained by reacting a sulfide of phosphorus with a metal salt of an alkylated phenol sulfide in which the 'alkyl groups contain 4-24 carbon atoms and in which the metal is a divalent metal of group II of the periodic table, at a temperature of 100-200 C. for a period or at least 10 minutes, the proportions of reactants being such that 0.03-2 atomic proportions of phosphorus are present for each atomic proportion of metal.
- a concentrate consisting essentially of a mineral lubricating oil containing 25-75% of the product obtained by reacting a divalent group II metal salt of an alkyl phenol sulfide with a sulfide of phosphorus at a temperature of 100- 200' C. for a period of at least ten minutes, the proportion oi reactants being such that 0.03-2 atomic proportions of phosphorus are present for each atomic proportion of metal.
- the method 01' preparing an oil-soluble sulfur and phosphorus containing product having tal of 4-24 carbon atoms and in which the metalis a divalent metal Of group II of the periodic table, at a. temperature of -200 C. for a period of at least 10 minutes. the proportions of reactants being such that 0.03-2 atomic proportionst of phosphorus are present for each atomic proportion of metal.
- a mineral lubricating oil additive concentrate containing about 54% of mineral lubricating oil, about 6% of stearyl alcohol, and about 40% of the product obtained by reacting barium tert.-octyl phenol sulfidv with phosphorus pentasulfide at a temperature of -180 C, for a period of at least 1 hour. the proportions of reactants being such that 0.06-0.75 atomic proportion of phosphorus is present for each atomic proportion of barium.
Description
Patented Oct. 12, 1948 2,451,345 COMPOUNDED LUBBICATING OIL John G. McNab,
Cranford, and Dllworth '1.
Rogers, Summit, N. J., assignors to Standard Oil Development Company,
Delaware a corporation of No Drawing. Application October 24, 1944, Serial No. 560,192
(Cl. 25232.'I]
24 Claims.
This invention relates to lubricants and other organic materials subject to deterioration in the presence of oxygen, and it relates more particularly to mineral lubricating oil compositions for use as crankcase lubricants for internal combustion engines and to addition agents suitable for retarding the deterioration of such oils and for improving other properties of the same.
This is a continuation-in-part of our co-pending application Serial Number 493,734, filed July 7, 1943, which issued October 22, 1946, as Patent Number 2,409,686. 7
It is known that the addition of certain types of metal organic compounds to lubricating oils improves various properties thereof, such as their oillness characteristics and their detergent action in engines, particularly manifested in the maintenance of a clean engine condition during operation. Various metal compounds which have been used for such purposes include the metal derivatives of such organic compounds as fatty acids, naphthenic acids, sulfonic acids, alcohols, phenols and ketones. However, these various metal compounds generally have the disadvantage of tending to corrode alloy bearings, such as those of cadmium-silver and copper-lead, now so widely used in automotive engines; and this is especially true in engines which operate at relatively high speeds and high temperatures.
It, is an object of the present invention to provide a new class of addition agents for oils which are to be used as crankcase lubricants for internal combustion engines and which exhibit the desirable properties of promoting general engine cleanliness, improving film strength properties, reducing ring sticking, piston skirt varnish formation and the like, and which not only do not exhibit the corrosion promoting tendencies char.- acteristic of the above metal compounds, but also inhibit the corrosiveness of oils to which they are added.
The new class of products which have now been found to be highly satisfactory as addition agents are the products obtained by the reaction of the elements sulfur and phosphorus with metal salts of hydroxy and mercapto substituted aromatic sulfides. When these compounds are to be used as additives for mineral oils, they should contain as a substituent in each aromatic nucleus at least one alkvl group, the total number or carbon atoms in such groups being at least live. It has been found that such products are usually satisfactory in inhibiting bearing corrosion, and in being adaptable to use with a wide variety of petroleum lubricating oil base stocks. The elements sulfur and phosphorus may be introduced into the metallic salt molecule by reacting the latter with both elemental sulfur and elemental phosphorus, or by reacting the same with a sulfide of phosphorus. The reaction may generally be brought about in a solution of lubricating oil or other petroleum oil, whereby concentrates may be prepared which may be conveniently stored or shipped and added to lubricating oils when required.
The new sulfur and phosphorus containing compositions herein described are also useful as antioxidants for other purposes when incorporated in organic materials other than lubricating oils, as will be more fully explained hereinafter, and in some cases it may not be necessary to have alkyl groups present to impart sufficient solubility. The invention also includes the reaction products of phosphorus sulfides or phosphorus and sulfur with compounds analogous to the salts of phenol sulfides and thiophenol sulfides, but containing selenium and tellurlum in place of oxygen or sulfur, and with compounds in which aromatic nuclei other than benzene nuclei are present.
In our co-pending application Serial Number 493,734 we have described the preparation of reaction products of phosphorus and sulfur or phosphorus sulfides with metal phenates and the use of such products in lubricating oil compositions. It was there shown that the sulfur and phosphorus atoms were probably linked directly to the metal atoms in the molecules or the reaction product. It is believed that the same type of reaction occurs when metal salts of phenol sulfides and the like are treated with phosphorus sulfides or with phosphorus and sulfur, giving compounds in which the phosphorus and sulfur atoms are linked together in the molecule to form a group which is attached directly to the metal atom.
Although the exact structures of the compounds formed by the processes of the present invention have not been established, there is evidence to show that they are not metal salts of alkyl phenol sulfide esters of thio-ac'ids of phosphorus. It is possible to prepare metal salts inwhichnrepresentsanalkylatedaromatio However, it is believed metal salts of this type donotresultwhentheelkylphenolsulfideisflrst converted to a metal salt and then treated with a sulfide of phosphorus or with any other combination of sulfur and phosphorus. One basis for this belietisthatinthereactionnoinoraanicmetal sulfideistormeiwhichwouldbethecaseita thiophosiliate salt was produced in the reaction.
In addition, there is no appreciable loss 0! metaleontentin theoraanicmaterialduringthe reaction with the sulfide oi the metal content of the filtered product being in the same orderotmagnitudeasthatoitheoriainalmetal phenol sulfide. It the mechanism or the reaction were the conversion of the metal phenol sulfide to a metal omano thiophosphate oi the type shown above, approximately 50% of the metal content wouldbeloshhutthishasbeeni'ound nottobe the case. Furthermore, there is an evolution oi! H18 during the treatment of the metal phenol sulfides with phosphorus sulfides, and it is not expected that such H evolution would occur if the reaction were the conversion of the metal phenol sulfide to a metal salt of an alkyl phenol sulfide ester of a thio-acid of phosphorus.
Some of the more preferred products to be used in accordance with the present invention are those obtained by reaction or a sulfide oi phosphorus or a combination of the elements sulfur and phosphorus with the following compounds:
Barium tert.-octyl phenol sulfide Barium di-tert.-amyl phenol sulfide Calcium isohexadecyl phenol sulfide 'lin wax alkylated salicylic acid sulfide Magnesium tert.-amyl phenol sulfide The, invention includes the reaction of phosphorus and sulfur or sulfides of phosphorus with not only the normal metal salts of phenol sultides, thiophenol sulfides and the like, but the basicmetalsaltsaswell. manormalphenol sulfide salt or a divalent metal the mo! ratio of metal to phenol sulfide is 1:1, as in the following formula:
MOB MOE 0 egg- . 4 In thecaseoialjzlratiotheiormuiambe OM08 0ll o OIIOH Inthecaseoi'atintlotheiorluulamayhe ouou OIOH ll. anomsary to form the normal salts. Reaction 7 not: of phosphorus sulfides with basic metal salts ofalkyiphenolsulfidesareparticuiarlyusei'ulin extreme pressure lubricants. and are especially :dvantaaeous for imparting color stability to luricants.
The new class of addition agents employed in a cordance with the present invention may he defined in its broadest scope is the reaction prodnets of any combination of the elements sulfur and phosphorwswith a metal salt oi a compound having the formula inwhichlirisanaromationuoleusandmamtor illustration, be a benzene nucleus. or it may consistofapiuralityotrinealsinbiphenyhorfi may be a condensed nucleus, exemplified by naphthalene, anthracene and the like. R in the formulaishydroeenoratleastone p di prei'erabh'analkylsroup. xinthetormul-a is a non-metal of zroup VI oi the periodic table: Yisamemberoi'thesuliurfamilnzis anint s'eri'romltoi; audit isanomaniclrcup which may be either and. elbl. aralkyl. or alkylaryl. and which may contain substituent atoms or hydrogeninthe-Xfleroupoi'theaboniornmiaini'ormingsaitsorsuchcompoundsmay be any metalathe most important for the Purposes of the present invention -lacing calcium, barium, strontium. maenesi .andsinaaithouzh for some corresponding compounds containingtimlead, aluminummobaltornickclwill alsoheioundtobeespecially Compounds perticularlysmiedtorthepurposes ottheprcsentinventionaieiormedhyrcacting salonand or a phosphorus sulfide withacomponmdottheiormuia x-M -x where it represents at least one elkyl radical attached to the nucleusithe total number ot carbon atoms in all oi such radicals attached to each benzene nucleus being at least live when the compound is to be dissolved in hydrocarbon oils. 1:
is oxygen or sulfur. M is a divalent metal or group tehleandcisaninteeerirom It should be understood that the above general iormulas include compounds in which various substituent atoms or groups may be attached to the aromatic nucleus. such as alkyl. cycloalkyl, aralkyl, aryl, carboxyl, hydroxyl, alkoxy,
aroxy, sulihydryl, nitro, ester (organic and/or inorganic), keto, amino, aldehydo, chlormethyl, aminomethyl, alkyl thlomethyi, alkyl xanthomethyl. metal substituted carboxyl, metal substituted sulio, metal substituted hydroxyi or n. hydryl groups, halogen atoms, etc. Different types of atoms or groups may be attached to the same aromatic nucleus. Alkyl radicals attached to the nucleus may have a total of five .to twentyfive carbon atoms in all of such groups, and in some cases as many as sixteen to twenty or more carbon atoms in a single group, as in a wax chain group, or in a plurality or groups, may be prei'erred. If more than one alkyl group is present in a single molecule, whether or not attached to the same and nucleus, such groups may be alike or difi'erent. Such alkyl or other hydrocarbon groups may'contain substituent groups, such as those named above as substituents in the aromatic nucleus. The various groups or atoms attached to the aromatic nucleus may be in any positions relative to one another.
Alkyl phenol sulfides, whose metal salts may be used to prepare the reaction products of the present invention, may be illustrated by the following general classes of compounds:
1. Alkyl phenol thioethers 3. Polmers of alkyl phenol sulfides on [on on R- s @s-- -R l. R .4: and
OH [on OH R- I 41,- R
In all of the above formulas under the headlngs l to 3, R represents an alkyl group containing preferably at least four carbon atoms, and z is a small whole number not greater than about six.
When the products are to be employed as additives i'or lubricating oils, exceptionally good results can be obtained by employing metal salts or alkyl phenol sulfides having Clo-Can branched chain alkyl groups. These can be conveniently prepared from phenols which have been allwlated with suitable branched chain polymers obtained by polymerizing low boiling olefins such as propylene, butylenes, or amylenes, or mixtures 01' these olefins.
It should be understood that generally throughout the specification the term alkyl phenol sulfide is meant to include not only the monosulfides but also the diand polysulfides and polymers of alkyl phenol sulfides as well. Thus, although the reaction of two mols 01' an alkylated phenol with one moi of sulfur dichloride (801:) will give essentially an alkyl phenol monosulfide, small amounts of polysulfides and of polymeric materials will also be formed.
This is even more usually the result when more than the theoretically required proportion of sulfur halide is used in sulfide, as for example when 2 mols of alkyl phenol are treated with 1.5 mols of sulfur dichloride. Similarly, the alkyl phenols may be treated with more than theoretical quantities oi suliul monochloride ($2012) or with mixtures of sulfur monoand dichloride or with first one halide and then the other.
Other compounds whose metal salts may be used in accordance with this'invention are illustrated by the following:
In all or the above described type formulas, both general and specific, where R is used to represent an alkyl radical, such radicals may be illustrated by the following species, which are radicals particularly preferred in the compounds, it being understood that the list is merely illustrative and does not restrict the scope or the groups or the formulas. These include n'-butyi, isobutyl, tort.- butyl. n-amyl. isoamyl. cyclohexyl, n-oetyi, isopreparing the alkyl phenol octadecyi. wax chain radicals.
the following:
on on sKu unit (b) on on En inn (t) 0H 0H ciulocgsoeoolm in a in (0 on on c-nmocQsOooocm: sHn sHu Specific examples of compounds which may be treated with a phosphorus sulfide in accordance with the present invention include the following, which are not to be construed as limitins the invention in any manner:
when the salts employed are those of polyvalent metals, it is not essential that all or the valences be satisfied by hvdroxyaryl sulfide s p acidic organic groups such as carboxy, aroxy, alkoxy, organo-substituted inorganic acid groups such as phosphoric, phosphorous, thiophosphoric, thiophosphorous, phosphonic, phosphinic, sulionic, sulfinic, and the like.
Thus, for example, the present invention also includes reaction products oi phosphorus sulfides with such compounds as:
Calcium mixed salt oi tert.-amyl phenol sulfide and iso-octyl sallcylate Aluminum mixed salt of tert.-octyl phenol sulfide and stearic acid Tin mixed salt of di-tert.-amyl phenol sulfide and naphthenic acids some 01' them may be satisfied by other Barium mixed salt of tert.-octyl phenol sulfide and petroleum mahogany sulionic acids Nickel mixed salt 01 tert.-amyl phenol sulfide and amyl xanthic acid Zinc mixed salt of isododecyl phenol sulfide and methyl cyclohexyl thiophosphoric acid Nickel mixed salt or tert.-amyl phenol sulfide and oieic acid Magnesium mixed salt of tert-octyl phenol sulfide and cetyl phenol Ashasbcenmentionedpreviousiyinthisspecification. the term phenol sulfide is meant to include not only the monosulfide but also disulfides, polysulfides, or polymers, or mixtures oi any oi these in any proportion.
For the objects stated, the metal salts or alkylated phenol sulfides have been preferably prepared irom phenolic compounds readily obtained by synthetic alkylation of the simple phenols. followed by treatment with a sulfur chloride. and then neutralization with a metallic base.
L Suitable synthetic alkyl phenols for preparing the desired phenol sulfide salts are preferably those containing secondary or tertiary alkyl radicals. because alkyiation oiia simple phenol occurs more readily with branched chain aliphatic reactants. Commonly, the aikylation reaction involves a condensation of olefins with the simple phenols, the reaction being catalyzed by anhydrous metal halides, boron fluoride, hydrofluoric acid, stannic chloride with hydrogen chloride, suliuric acid. phosphoric acid. or certain activated clays. As olefinic reactants, refinery gases containing propylene. butylenes, amylenes, etc., are economically useful, although individual olefins or olefin-containing mixtures derived from other sources may be used. Preferred individual olefins are the butenes, amylenes and olefin polymers. such as diisobutylene or triisobutyiene or normal olefln polymers or wpolymers or normal and secondary or tertiary oleilns or copolymers, of olefins and diolefins. The reaction temperature is usually controlled to avoid side reactions. In employing sulfuric acid, a liquid phase reaction at relatively low temperature is preferre while with phosphoric acid th reaction may be carried out in the vapor phase.
Suitable alkylated phenols for conversion to phenol sulfides may be thus prepared by alkylating phenol, cresol, naphthol or other phenolic compounds. High molecular weight alkylated phenols may also be used, for example, those prepared by condensing phenols with chlorinated petrolatum or chlorinated paraflln wax or with a chlorinated kerosene or gas oil. Naturally occurring phenols, such as those obtained by alkaline extraction of certain petroleum stocks or those obtained from cashew nut shell lliquid or those obtained from other vegetable all sources may likewise be used. Halogenated or nitrated phenols will also find application in this invention, particularly if the final additive is to be employed in extreme pressure lubricants.
One class of alkyl phenols which are particularly preferred are those which have been prepared by alkylation of phenol with an olefin polymer such as diisobutylene or a refinery butene polymer oil. Alkyl-atlon of phenol with about an equal molar proportion of diisobutyiene gives p-tert.-octyl phenol, also known as diisobutyl phenol or tetramethyl butyl phenol. This phenolic material is especially desirable because of the ease oi its preparation and because products made from it.are highly satisiactory tor the present invention. In many instances, however, a higher degree of alkylation may be advantageous, and for this reason the phenol may be alkylated with as much as two molecular equivalents of diisobutylene to give. under proper conditions, essentially di-tert.-octyl phenol; or it may be alkylated with other olefin polymers such as triisobutylene or other isobutylene polymers. For many purposes it is preferable to employ alkylated phenols having branched alkyl groups of from 16 to 30 carbon atoms. Suitable products may be prepared by alkylating phenol with certain of the polymeric materials obtained as by-products in the manufacture of butyl alcohol from petroleum refinery butenes. These consist essentially of polymers of n-butene with small percentages of isobutene and other olefins and give alkylated phenols having branched chain alkyl groups of 16-20 or 20-24 carbon atoms depending on the polymeric material used in the alkylation. It should be understood that in many cases the allrylation products may be mixtures of various compounds rather than entirely one specific alkyl phenol and that it is intended to use such mixtures in practicing this invention.
For conversion of phenols to phenol sulfides, the phenol is reacted with sulfur dichloride to produce essentially a phenol monosulfide having a thioether linkage, while sulfur monochloride may be used to produce essentially the phenol disulfide. About one-half to one mol of sulfur halide is used with each mol of phenol, and the reaction is preferably carried out in a solvent such as dichlorethane, chloroform, petroleum naphtha, benzol, xylol, toluol, and the like.
For converting the phenol sulfides to metal salts it is usually sufficient merely to add a metal or a metallic oxide, hydroxide, sulfide, alkoxide, hydride or carbide to a mineral oil solution or other solution of the phenol sulfide at an elevated temperature. Thus, barium salts of alkylated phenol sulfides are prepared by reacting the sulfide with barium hydroxide, preferably in the form of the hydrate, Ba(OH)2.8I-I2O. In some instances it may be preferable to prepare heavy metal salts from the alkali metla salt by double decomposition. The calcium salts are conveniently prepared by reacting alkyl phenol sulfides with calcium methylate or other calcium alcoholate.
In many cases the metal aikyl phenol sulfide prepared by neutralizing with a metal hydroxide may occur as a hydrated salt. Use of hydrated salts prepared in this manner or by any other method is also contemplated in the processes of the present invention.
In accordance with the present invention, the metallic salt of a phenol sulfide or other metallic derivative of a hydroxy or mercapto aromatic sulfide is caused to react with the elements sulfur and phosphorus. This may be accomplished by adding a mixture of the substances in elemental form. or first one element and then the other, to the heated metallic compound, or by adding a sulfide of phosphorus, such as P255, P483, P481, or the like, or by treatment with sulfur and/or phosphorus and a sulfide of phosphorus, or by treatment with any other subtance or substances containing essentially only the elements phosphorus and sulfur. The phosphorus may be used either in the white (yellow) or red allotropic form, and the sulfur may likewise be used in any of its allotropic forms.
However, it is ordinarily more convenient to use a sulfide of phosphorus. In carrying out 10 the reactions described above the proportions of phosphorus sulfide and metal salt of phenol sulfide are so chosen that from 0.03 to 2 atomic proportions of phosphorus are reacted with 1 atomic proportion of polyvalent metal, the preferred ratio being within the limits of about 0.06 to 0.75 molecular proportions of the phosphorus sulfide for each atomic proportion of metal, when the phosphorus sulfide contains 2 atoms of phosphorus per molecule. This preferred ratio gives the products the optimum content of phosphorus and sulfur to impart to them the maximum amount of inhibiting power and detergent action. In general, these same ratios will be employed when the reaction is conducted with elemental sulfur and elemental phosphorus.
Although the reaction can be brought about by fusing the metal salt with hosphorus and sulfur, or with a phosphorus sulfide, it is more convenient to carry out the reaction with the aid of solvents, particularly high boiling hydrocarbon solvents, such as xylol or a petroleum fraction. A particularly preferred reaction medium is a lubricating oil fraction, since the final reaction products can thus be obtained as a mineral oil concentrate of the desired additive, which may be conveniently shipped or stored as such and then readily blended with the lubricating oil base stock in the desired concentration to form a finished lubricating oil blend.
The additives may generally be prepared by first dissolving an alkylated phenol sulfide in a mineral oil or other suitable solvent and treating the same with a metal hydroxide, e. g., Ba 0H):.8H-.-O, at about -200 0., preferably -l50 C. After a further period of heating, free sulfur and free phosphorus, or a sulfide of phosphorus, or other mixture or combination of the elements, is added, heating being continued at 100-200 0., preferably at l50-l80 0., to complete the reaction. The period of heating will be at least 10 minutes and generally at least 1 hour, although in some cases a longer period may be required. The product is then filtered, giving a concentrate of the desired additive. If the products are found to have a slight odor of hydrogen sulfide, this can be substantially eliminated by blowing the products with a suitable gas such as dry or moist air or nitrogen or superheated steam at temperatures of 80-l50 C., or by treating with a neutralizing 'agent such as barium or calcium hydroxide or calcium oxide. A combination of these treating steps may also be employed. For example, satisfactory results have been obtained by treating the products with 2-5% of barium hydroxide at C. before the filtering step, followed by nitrogen blowing at 100-120" C. after filtration. If the blowing step is found to be necessary in commercial operation. one convenient method is to treat the material with the gas in countercurrent flow in a suitable tower.
If desired, the metal phenol sulfide salt may be subjected to a heat-treating step, e. g.. for 8-10 hours at 150-180" C., or it may be blown with dry or moist carbon dioxide, before adding the sulfide of phosphorus, in order to render the final product non-sensitive to the presence of water when blended in lubricating oil. In general, however, this step will not be necessary, inasmuch as the products of the present invention are substantially non-water-sensitive, as will be demonstrated hereinafter.
It has been found that good results are obtained when preparing these additives in mineral oil if a minor proportion of a higher alcohol, such as accuses 1 1 stearyl, lauryl or cetyl alcoh'ol. or wool tat alcohol or the lilie, is added to thereaction mixture in which the compounds of the present invention are prepared. This alcohol reduces foaming during the process and acts as an auxiliary solvent for the final product. The best results are obtained by adding a sufilcient quantity or alcohol to give a concentration of about 3% to about 15% of the final additive concentrate.
Although some of the alcohol present will be found to react with the phosphorus sulfide, this will in no way impair the efilciency oi the additive and may in some cases enhance its desirable qualities. Should it be desired to have the higher alcohol present in substantially unchanged form, it can be added to the reaction mixture just prior to the filtration step. Other materials which may be used instead of the higher alcohols to serve as plasticizers, foam reducing agents, etc. include the high molecular weight amines and nitriles, such as stearonitrile or lauronitrile. The products obtained by condensing phenol with the reaction products of sulfur halides and diisobutylene have also been found to be efilcient agents for this purpose.
It has also been found that products of better oil solubility can often be obtained when carrying out the reaction with phosphorus sulfides in the presence of a small proportion of an oiefinic material, such as a tetraisobutylene, cracked wax or an unsaturated alcohol.
Generally, the additives oi the present invention are most advantageously blended with lubricating oil base stocks in concentrations between the approximate limits of 0.02% and 5.0% and preferably from 0.1% to 2.0%, although larger amounts may be used for some purposes. The
exact amount of addition agent required for a maximum improvement depends to a certain extent on the particular products used, the nature of the lubricating oil base stock and the general operating conditions of the engine in which the lubricant is to be employed. This same general range of concentration will also be effective when the additives are to be used in greases and in extreme pressure lubricants, although in the latter instance greater amounts, up to may also be employed.
As has been pointed out elsewhere in this specification, it is often convenient to prepare concentrates or the additives in oil, containing. say, to 75% of efi'ective addition agent, the concentrate later being added to a suitable lubricating 011 base stock to give -a finished blend containing the desired percentage of additive. Thus, when using a 40% concentrate, 2.5% of this material may be blended with a suitable base stock to give a finished oil containing 1% of efiective addition agent.
In the following examples are described various preparations of products in accordance with this invention and the results obtained on testing the same in various lubricating oil blends. It is to be understood that these examples, given for illustrative purposes only, are not to be construed as limiting the scope of the invention in any way.
EXAMPLEI Tertiary octyl phenol was prepared by alkylating phenol with diisobutylene in the presence of *SnCh-HCl catalyst substantially as described in 12 fur dichloride was added to this solution in the ratio 1.0 mole of 801: to each 2 mole of tertsoctyl phenol, the temperature being maintained at 25-35 C. After maintaining the same temperature for an additional half hour the reaction mixture was heated to C. and the solvent stripped oil under vacuum, leaving the tert.-octyl phenol sulfide as a residue.
201'? pounds of tert.-octyl phenol sulfide prepared in the above manner was dissolved in 4580 pounds of S. A. E. 20 grade mineral lubricating all together with 512 pounds or commercial stearyl alcohol and the solution heated to 0. Over a 3 hour period 1952 pounds or BMOH) 2.8H2O
was added gradually, the mixture being well stirred and the temperature being maintained at 120 C. The temperature was raised to 0., 1% by weight of a filter aid added, and the mixture filtered, giving about 1000 gallons of an additive concentrate containing approximately 40% of barium tert.-octyl phenol sulfide, 8% stearyi alcohol, and 54% mineral lubricating oil. Analysis of concentrate: 8.92% Ba; 8.40% B.
EXALIPLE 2 As starting material for the preparation of a reaction product of a barium salt, there was used a concentrate containing 40% by weight of barium tert.-octyl phenol sulfide. 6% cl stearyl alcohol. and 54% of a refined mineral oil of 52 seconds viscosity Saybolt at 210 E, prepared as described in Example 1. 30.3 kg. of this concentrate was treated with 2.81 kg. 01 Pass by heating the concentrate to C. and adding the phosphorus sulfide gradually with agitation over a period oi 1 hour, during which the temperature rose to -190 C. The temperature was then held at 160-180 C. for an additional 2 hour period and the final product filtered. The resulting additive concentrate contained 8.10% barium, 2.12% phosphorus, and 7.93% sulfur.
EXAMPLE 8 To demonstrate the reproducibility of the preparation of the present invention, Example 2 was repeated, using 29.95 kg. of the concentrate oi Exampl 1 and 2.3 kg. of P285, and the same reaction times andtemperatures. The filtered concentrate analyzed 8.14% barium, 2.08% phosphorus, and 7.96% sulfur.
EXAIHPLE4 This example demonstrates the preparation 01' an additive concentrate of the present invention on a plant scale. In essentially the same manner as described in Example 1, an oil solution of ten.- octyl phenol sulfide and stearyl alcohol was treated with Ba(OH)r.8H2O, but the reaction product was not filtered. (A portion of the reaction product which was filtered to prepare a finished additlve concentrate contained 0.97% barium and 3.51% sulfur.) 1231 pounds of the unfiltered reaction product was placed in a reactor and heated to 180 C. Then, over a five hour period 72.5 pounds of Pass was gradually added, the mixture being agitated and kept at the 180 C. temperature. (Moi ratio Pass to barium tert.-octyl phenol sulfide=0.4/1.) Heating and agitation were then continued at the same temperature for an additional four hour period, after which time the temperature was lowered to 140 6. and the reaction mixture blown with inert gas for five hours to remove Has. 20 lbs. of Hyfio filter aid was dded and the mixture then filtered to give 13 the final desired additive concentrate. Analysis of this concentrate showed it to contain 8.37% barium. 1.70% phosphorus, and 6.98% sulfur.
EXAMPLE In this example a mol ratio of phosphorus sulfide to metal phenol sulfide of 0.2 to l was employed. 2470 g. of an oil concentrate of 40% barium tert.-octyl phenol sulfide, 6% stearyl al-' EXAMPLE 6 This example demonstrates the preparation of an additive similar to that of Example 2, but employing P481 instead of Past. The starting material was an additive concentrate prepared in the same manner as that described in Example 1, containing 40% barium tert.-octyl' phenol sulfide, 6% stearyl alcohol and 54% mineral oil. Analysis of the concentrate showed it to contain 8.97% barium and 3.51% sulfur.
1200 grams of this concentrate was heated to 180 C. Then over a one hour period 73 grams of P481 was added in small portions. of P487 to metal phenol sulfide=0.4/1.) The mixture was heated for an additional 3 hour period at 180 C. and was then filtered, using I-lyfio filter aid. The filtered product was blown with nitrogen for hours at 100 C. to remove residual HaS. The finished additive concentrate contained 8.54% barium. 6.78% sulfur. and 2.19% phosphorus.
EXAMPLE "I The preparation oi a product of the present invention employing a basic metal salt of an alkYl phenol sulfide is shown in this example. Tertiary octyl phenol. prepared by aikylation of phenol with diisobutylene using BF: catalyst, was converted to the sulfide by essentially the same procedure as described in Example 1, employing a ratio of 1.6 mols of SC]: to 2 mols of tert.-octyl phenol. 7740 grams of this tert.-octyl phenol suifide and 1500 grams of stearyl alcohol were dissolved in 13,500 grams of refined paraflinic mineral lubricating oil (52 seconds Saybolt viscosity at 210' R). The mixture was heated with stirring to 120-125 C. under an atmosphere of nitrogen, and then over a 6 hour period 11,990 grams of Ba(0H)2.8H2O was added. The temperature was then raised to 135-140" C. and heating and stirring were continued for an additional 2 hours. 1% by weight of filter aid was added and the mixture filtered, giving a concentrate containing approximately 42% of basic barium tert.-octyl phenol sulfide, slightly less than 6% stearyl alcohol and slightly more than 52% mineral lubricating oil. Analysis of the concentrate showed it to contain 12.97% barium and 2.99% suliur.
2000 grams of this concentrate was heated to 180 C. and to it was added 129 g. of P185 over a period of 1 hour. Heating was continued for an additional 3 hour period and the product filtered and blown with nitrogen for 6 hours at 100 C. The final additive concentrate contained (Moi ratio mixture was stirred for 11.70% barium, 1.8% phosphorus, and 6.56% sulfur.
EXAMPLE 8 A reaction product of the present invention emplaying a mixed calcium-barium alkyl phenol suiride was prepared as grams of tert.-octyl phenol sulfide. 1620 grams of S. A. E. 20 grade mineral lubricating oil, 180 grams of commercial stearyl alcohol, and 205 grams of calcium hydroxide was placed in a 12-liter reaction fiask equipped with a stirrer and water trap reflux condenser and heated at -425 C. for 10 hours, at the end of which time 83% of the theoretical amount of water from the reaction had been removed through the water trap. The mixture was then heated to 150 C. and filtered, employing Hyfio filter aid. The oil concentrate of calcium tert.-octyl phenol sulfide contained 2.82% calcium and and 4.13% sulfur.
1500 grams oi the concentrate obtained in the above manner was heated to 120 C. and over a 1% hour period 476 grams of barium hydroxide octahydrate was added with constant stirring. Heating was continued for two additional hours at C., a stream of nitrogen being blown through the mixture during the entire reaction period. The product was then filtered, giving an oil concentrate containing approximately 40% calcium-barium tert.-octyl phenol sulfide, 6% stearyl alcohol, and 54% mineral lubricating oil. Analysis: 2.26% calcium: 7.53% barium; 3.66% sulfur.
1000 grams of the calcium-barium tert-octlilv was placed in an iron 1 C. with stirring and nitrogen blowing. Then over a period oi 30 phenol sulfide concentrate kettle and heated to 100 minutes 00 grams of P285 was added, the temperature rising to 195 C. during the first 15 minutes and then returning to 180 C. Heating was continued for an additional 30 minutes, the mixture then being cooled to C. and filtered. The filtered product was blown with nitrogen for 4 hours at C. to ensure the removal of any residual 1118 that may have been present. The final additive concentrate contained 7.11% barium. 2.21% calcium, 1.76% phosphorus, and 6.94% sulfur. and for blending purposes was considered to contain 40% by weight of effective additive.
EXAMPLE 9 The preparation of a reaction product from barium diamyl phenol sulfide is described.
(a) 1404 grams (6 mols) of 2,4-diamyl phenol was dissolved in 4212 grams of a petroleum solvent naphtha (200-285 F. boiling range; 65-70% aromatics) and placed in a reaction vessel equipped with a stirrer and reflux condenser. Over a period of 2 hours 464 grams (4.5 mols) of sulfur dichloride was added to the stirred solution, the temperature being maintained at 20-25 C. The an additional hour and was then heated at reflux temperature for 2 hours. after which time the solvent was stripped of! at a maximum temperature of 300 F. in a stream of nitrogen. The resulting diarnyl phenol sulfide contained 10.05% sulfur.
(b) In the same manner as described in part (a) diamyl phenol disulfide was prepared from 1404 grams of 2.4-diamyl phenol and 608 grams of sulfur monochloride, this being 1.5 mols of 81012 per 2 mols of alkyl phenol. The product contained 16.55% sulfur.
(c) 170 grams of diamyl phenol sulfide (from part (0.)) and grams of diamyl phenol disuiflde (from part (0)) were dissolved in 550 follows: A mixture of 1110' mineral lubricating. oil of no grams of commercial stearyl alcohol was added and the temperature to 110 0. Over a period of 1% hours 273 grams of barium hydroxide octahydrate was Innis oi refined 8. A. E. grade.
concentrate containing barium diamyi phenol sulhde-disulnde, 10% stearyl alcohol. and mineral lubricating oil. Analysis: 5.96% barium: 3.44% sulfur.
827 grams of the oil concentrate of barium diamyl phenol sulflde-disuliide was heated with This example demonstrates the preparation of present invention in so-called not as an additive concentrate in mineral oil solution.
(a) 2000 grams (10 molsl of tert.-octyl phenol was dissolved in approximately 0 liters oi chloroform in a lit-liter reaction flask stirrer and reflux condenser. 8% hours 800 grams (7.6 mols plus 10% excess) suliur dichloride was added. the reaction mixture being maintained at 25-86 0. Following this at 05' C. for 6 hours The flnai product was 0420 ml. oi chloroform solution which contained 3306 grams of tert.-octyl phenol 'sulilde. Analysis of a portion of solvent-tree product showed it to contain 11.38% sulfur, which would correspond to a product having on the average about 1.6 atoms oi suliur for each pair of aromatic nuclei.
(b) 2490 ml. of the chloroform solution obtained in part (a). containing 922 grams of the tert.-octyl phenol sulfide. was placed in a 5 liter flask fitted with a water trap condenser and about 75% of the chloroform removed under vacuum. Then 2 liters of pure xylene was added and the temperature raised to 140 (2., causing the remaining chloroform to distill over into the water trapJi-om which it was removed. Over a period of 14 hours 651 grains of BaiOHlnBHsO was added with stirring. the temperature being maintained at 140 0.. and water of reaction being removed through the water trap. After an additional 8-hour heating period no additional water 'uum at 140' C. The
solid, containing 20.65 95 140 C. Over a period 01 Pass was gradually added with stirring. and heating at 140' C. was continued for an additional 3 XAMPLEII product was not an additive concentrate but was "pure" additive. A comparative test was made with a sample oi unblended oil base.
The tests were conducted as follows: 500 cc. of in a. glass oxidation oil to be tested was placed tube (13" long and 2%" diameter) fitted at the bottom with a V4" bore air inlet tube perforated to facilitate air distribution. The oxidation tube four hour period and then polished and reweighed before continuing for another four hour period.
. The results show the cumulative weight loss at the end of each four hour period. The results are shown in Table 1.
Tuna I 0|] Blond Cumulative Bearing Weight Loss (Mg.l25 sq. cm.)
4 Hrs.
collected in the trap. The mixture was then filtered and most of the xylene removed by heating the filtrate on the steam bath. The remain- EXAMPLE 12 In the following tests. a lubricating oil blend ing solvent was removed by heating under vaccontaining an additive of the present invention and an unblended oil were tested in a single cylinder 0., F. R. engine run under the following conditions: 1800 R. P. M., 265 F. oil temperature, and 200 F. waterjacket temperature for 55 hour periods. After each testewas completed the engine parts were examined and given demerit ratings based on their condition. The individual ratings were weighted according to their relative rating the more satisfactory the performance or the oil. The results of these tests are presented in Table III. It will be observed that a reaction product of the present invention, prepared by reaction 01' a metal alkyl phenol sulfide with a phosphorus sulfide (blend 2) was more satisfactory in this test than the metal alkyl phenol sulfide itseli (blend 1). It should also be noted that importance and an overall rating calculated even better results were obtained with an oil from them. It should be pointed out that the in blend containing both a, metal sulionate and an lower the demerit rating the better the engine additive of the present invention (blend 8). It condition and hence the better the oil performed should likewise be noted that the capacity of the i in the engine. In these tests the base oil was a additive to inhibit corrosiveness, as indicated by solvent extracted Mid-Continent paraflinic oil laboratory tests, was borne out by the results of 46 Se Viscosity 37 1? t 210 F-. t wh c the tests in actual engine operations.
Team III Chevrolet engine tests [so hours-30 B. H. P.-3iii0 n. I. new zso F.-water jacket 2m" F.l
Engine Damerit Ratings (1 -Pb-B on mud tit? 51 a ri s X 2.
6 S, ra zone Varnish u g per Bear- Base oil 1.93 a. 41 2.33 1.41 4.09 Blend l-Base Oil +2.5 Wt. percent of Concentrate oi Example 1 0. 44 0.01 0. 38 0. 16 0.07 Blend 2-Buse Oil-+2.5 Wt. percent oi Concentrate oi Example ii 0. 31 0. 20 0. 0. 09 0. 04 Blend 3-Bsse Oil+i .6 percent oi Basic Calcium Sultanate +2.13
percent of concentrate of Example 4' 0.28 0.19 0.08 0.03 0.07
! Equals 1 percent of eflective additive. i Contained 33 percent excess calcium over tbeoretiml. l Equals 0.85 percent of eiiectiva additive in addition to the metal sulionste. had been added a small amount of polybutene to EXAMPL 14 give a lubricating oil of 52 seconds viscosity at 210 F. Results of these tests are shown in the following table.
TABLE 11.
Engine Demerits Oil Blend Piston Ring Rmg Skirt Slick Slud g5 an zone Varnish ing Base Oil 2.78 3.3 4.0 2.75 1.7 Base Oil+2.5% Product of ELZ 0.68 1.4 (1.5 0.0 0.1
It may be readily seen that the performance of the base oil in the engine was materially improved by the incorporation of the agent of the present invention.
EXAMPLE 13 Lubricating oil blends of various of the additives whose preparations have been described in the foregoing examples were prepared with the same base oil as described in Example 12. The base oil and each of the various blends were tested in a Chevrolet engine run for 36 hours under the following conditions: brake horsepower, 3150 R. P. M., 280 F. oil temperature, and 200 F. water jacket temperature.
In order to measure the corrosiveness of each oil blend, two of the connecting rods of the engine were equipped with copper-lead bearings. At the end of each test the various parts of the engine were examined and given demerit ratings based on their appearance. The various demerit ratings were then employed to calculate an overall demerit rating for the engine, this serving as a measure of the performance of the lubricating oil in the test As before, the lower the demerit A further series of engine tests were made in a test being run for 126 hours under the following conditions: 19.8 brake horsepower, 1000 R. P. NL, F. oil temperature, F. water jacket temperature. The oil blends tested contained additives of the present invention in an S. A. E. 30 grade solvent extracted Mid-Continent lubricating oil.
In the same manner as described in Example 13, the engine condition was rated on a demerit basis with the results shown in Table IV. It will be seen that here again, where a different lubri eating oil base stock engine test employed, an additive of the present invention (blend 2) gave greater improvement than an untreated metal alkyl phenol sulfide (blend 1) and that superior results were obtained with a combination of a metal petroleum suitonate and an additive of the present invention (blend 3).
TABLE IV Caterpillar Diesel engine tests we hours-19.8 B. H. P.l 000 R. P. M.-180 r. oil temp-180 F.
l Contained about 40% excess calcium over theoretical.
was used and a difierent.
- EXAMPLE 1s Lubricating oil blends were prepared by adding to separate portions of an S. A. E. 20 grade extracted Mid-Continent oil 2.5% by weight of the additive concentrates prepared as described in Example 1 and as described in Example 5. Each oil was tested for water sensitivity, i. e., the tendency of the additive to separate from the oil in the presence of water. This test was conducted as follows: 600 cc. of the oil blend is emulsified with 1% water by means of a motordriven eggbeater-type mixer operated at maximum speed for minutes. After stirring. 500 cc. of the emulsion is poured into a 500 cc. graduated cylinder and allowed to stand for 24 hours. At the end of this period the amount of emulsion layer separated from the oil is noted. The smaller the amount of separation the better the water resistant qualities of the additive.
The results obtained in this test are shown in Table V.
Additive in on Blond Water minary Itwill readily be seen that the phosphorus sulfide treated metal alkyl phenol suliide was substantially non-water-sensitive, whereas the untreated metal alkyl phenol sulfide was appreciably sensitive to the presence of water.
Although in most instances the additives of the present invention will oi themselves impart sufncient improvement to lubricating oils to give very satisfactory results, still greater improvement may often be obtained by employing these addition agents in conJunction with other additives of the detergent type, such as metal soaps, metal phenates, metal alcoholates, metal phenol sulfides, metal organs phosphates, thiophosphates, phosphites and thiophosplntes, metal sulionates, metal thiocarbamates, metal xanthates and thioxanthates, and the like. f
Thus, the addition agents of our invention may be used in mineral lubricating oils in conjunction with one or more 01' the following representative materials:
product of amyl isohexadecyl Particularly advantageous are lubricant compositions in which the additives of the present invention are employed in conjunction with metal salts of petroleum mahogany suifonlc acids.
The advantageous properties of lubricating oil blends containing both metal mahogany sulfonates and additives addition to being highly desirable crankcase lubricating oils these additive blends also possess rust preventive properties. For example, an S. A. E. 10 grade lubricating oil containing 1.5% calcium sulfonates and 0.85% of the reaction product of barium tert.-octyl phenol sulflde and P285 (0.4:1 mol ratio P285 to phenol sulfide salt) was found to be a satisfactory rust salt water immersion test. Panels coated with the above composition remained in the humidity cabinet humidity at 100 F.) for 200 hours without rusting. Other panels similarly coated NazSOd for 20 hours without The lubricating oil base stocks used in the com- The oils may be refined by conventional methods using acid, alkali, and/or clay or other agents such as aluminum chloride, or they may be extracted oils produced, for example, by solvent extraction with type of phenol, ethyl ether, nitrobenzene, crotonaldehyde, etc.
of oxides of carbon with hydrogen or by the hydrogenation of coal or its products. instances cracking coil tar fractions and coal tar or shale oil distillates may also be used. Also, for special applications, animal, vegetable or fish oils. or their hydrogenated or voltolized products, may be employed, either alone or in admixture with mineral oils.
For the best can be laid down for the choice of the base stock. Certain essentials must of course be observed. The oil must possess the viscosity and volatility characteristics known to be required for the service contemplated. The oil must be a satisfactory solvent for the additive, although in some cases auxiliary solvent agents may be used. The lubricating oils, however they may have been produced, may vary considerably in viscosity and other properties depending upon the particular use for which they are desired. but they usually range from about 40 to 150 seconds Saybolt viscosity at 210 F. For the lubrication of certain low and medium speed Diesel engines the general practice has often been to use a lubricating oil base stock prepared from naphthenic or aromatic crudes and having a Saybolt viscosity at 210 F. of 45 to 90 seconds and a viscosity index of to 50. However, in certain. types of 'Diesel service, particularly with high speed Diesel engines, and in aviation engine and other gasoline engine service, oils of higher viscosity index are often pre-' ferred, for example, up to '15 to 100, or even higher, viscosity index.
In addition to the materials to be added according to the present invention, other agents may also be used such as dyes, pour depressors, heat thickened fatty oils, sulfurized fatty oils, organo metallic compounds, metallic or other soaps, sludge dispersers, antioxidants, thickeners, viscosity index improvers, oiliness agents, resins, rubber, olefin polymers, voltolized fatty oils or fats, voltolized mineral oils, and/or voltolized waxes and colloidal solids such as graphite or zinc oxide, etc. Specific examples of such other agents include phenyl alpha naphthylamine, voltolized sperm oil, 2,6-di-tert.-butyl-4-methyl phenol, sulfurlzed sperm oil, p-tert.-amyl phenol sulfide, dibenzyl disulfide, polyisobutylene, sulfurized wax oleflns, tricresyl phosphate, dlamyl trisulflde, and the condensation product of phenol with a sulfur chloride-diisobutylene reaction product. Solvents and assisting agents, such as esters, ketones, alcohols, aldehydes, halogenated or nitrated compounds, and the like, may also be employed.
Assisting agents which are particularly desirable are the higher alcohols having eight or more carbon atoms and preferably 12 to 20 carbon atoms, The alcohols may be saturated straight and branched chain aliphatic alcohols such as octyl alcohol (CaHnOH) lauryl alcohol (CuHasOH) cetyl alcohol (CmI-IaaOI-I), stearyl alcohol, sometimes referred to as octadecyl alcohol (C1aHa7OH) heptadecyl alcohol (CnHasOI-I) and the like; the corresponding olefinic alcohols such as oleyl alcohol; cyclic alcohols, such as naphthenic alcohols; and aryl substituted alkyl alcohols, for instance, phenyl octyl alcohol, or octadecyl benzyl alcohol, or mixtures of these various alcohols, which may be pure or substantially pure synthetic alcohols. One may also use mixed naturally occurring alcohols such as those found in wool fat which is known to contain a substantial percentage of alcohols having about 16 to 18 carbon atoms) and in sperm oil (which contains a high percentage of cetyl alcohol) and although it is preferable to isolate the alcohols from those materials, for some purposes, the wool fat, sperm oil or other natural products rich in alcohols may be used per se. Products prepared synthetically by chemical processes may also be used, such as alcohols prepared by th oxidation of petroleum hydrocarbons. e. g., parafiin wax, petrolatum, etc.
These assisting agents serve to enhance the detergent and sludge dispersive qualities and aid the solubility of the metal-containing additives and at the same time impart some oiliness properties to the lubricating oil compositions.
In addition to being employed in crankcase lubricants the additives or the present invention may also be used in extreme pressure lubricants, engine flushing oils, industrial oils, general machinery oils, process oils, rust preventive compositions and greases. Also their use inmotor fuels, Diesel fuels and kerosene is contemplated. A particular application in this regard i their use in r motor fuels containing tetraethyl lead or other anti-knock agents, the additives of the present invention serving not only as antioxidants for the fuel but also as stabilizers for the anti-knock agent itself. Since these additives exhibit antioxidant properties and are believed also to pos- -sess ability to modify surface activity, they may be employed in asphalts, road oils, waxes, fatty oils of animal or vegetable origin, soaps, and plastics. Similarly, they may be used in natural and synthetic rubber compounding both as vulcanizm tion assistants and as anti-oxidants, and generally they may be used in any organic materials subject to deterioration by atmospheric oxygen.
The present invention is not to be considered as limited by any of the examples described herein which are given by way of illustration only, but it is to be limited solely by the terms of the appended claims.
We claim:
1. A hydrocarbon material subject to deterioration by atmospheric oxygen .cdntainlng a stabil zing amount of a product obtained by reacting a sulfide of phosphorus with a divalent group II metal salt ofa compound having the characterizing structure in which the groups R, XH and YPR' are all connected to the aromatic nucleus Ar, and in which R represents at least one alkyl group of 4 to 24 carbon atoms and R represents an aryl group, X is an element of the group consisting of oxygen and sulfur, Y is a member of the sulfur family of elements, and :c is an integer from 1 to 4, at a temperature of -200 C. for ,a period of at least 10 minutes, the proportions of reactants being such that from 0.03-2 atomic proportions of phosphorus are present for each atomic proportion of metal.
2. A hydrocarbon product subject to deterioration by atmospheric oxygen containing a stabilizing amount of a product obtained by reacting a sulfide of phosphorus with a divalent group 11 metal salt of a compound having the characterizing structure bilizing amount of a product obtained by react- 23 log a sulfide oi phbsphorus with a compound of the formula M x x agnng.
where R is an alkyl radical of 4-24 carbon atoms, X is an element of the group consisting of oxygen and sulfur. M is a divalent metal of group II of the periodic table, and a: is an integer from 1 to 4, at a temperature of IUD-200 C. for a period of at least 10 minutes, the proportions of reactants being such that 0.03-2 atomic proportions of phosphorus are present for each atomic proportion of metal.
4. A mineral lubricating 011 containing a stabilizing quantity of a product obtained by reacting a sulfide of phosphorus with a divalent group II metal salt, of a compound having the characterizing structure in which the groups R. KB and Y=R are all connected to the aromatic nucleus Ar and in which It represents at least one alkyl group of 4 to 24 carbon atoms and R represents an aryl group, X is an element of the group consisting of oxygen and sulfur, Y is a member of the sulfur family of elements, and :r is an integer from 1 to 4, at a temperature of 100-200 C. for a period of at least ten minutes, the proportions of reactants being such that 0.03-2 atomic proportions of phosphorus are present for each atomic proportion of metal.
5. A mineral lubricating oil according to claim 4 in which Ar 01' the formula represents a. henzene nucleus and X represents oxygen.
6. A mineral lubricating oil containing a stabilizing amount of a product obtained by reacting a sulfide of phosphorus with a compound of the formula M x x where R is an alkyl radical of 4-24 carbon atoms, X is a member of the group consisting of oxygen and sulfur, M is a divalent metal of group It the periodic table, and a: is an integer from 1 to 4, at a temperature of 100-200 C. for a. period of at least 10 minutes, the proportions of reactants being such that 0.03-2 atomic proportions of phosphorus are present for each atomic proportion of metal.
7. A mineral lubricating oil containing a stabilizing quantity of a product obtained by reacting a sulfide of phosphorus with a metal salt of an alkylated phenol sulfide in which the alkyl groups attached to each benzene nucleus contain a total of at least carbon atoms, and in which the metal of the salt is a divalent metal of group II of the periodic table, at a temperature of 100-200" C. for a period of at, least minutes, the proportions of reactants being such that 0.03-2 atomic proportions of phosphorus are present for each atomic proportion of metal.
8. A mineral lubricating oil according to claim 7 in which each benzene nucleus oi the metal salt contains a substituent tert.-octy1 radical.
9. A mineral lubricating oil containing a stabilizing quantity of a product obtained by reacting a. sulfide of phosphorus with a barium salt of a tert.-octyl phenol sulfide, at a temperature of -180" C. for a period of at least 1 hour, the proportions of reactants being such that 0.06- 0.75 atomic proportion of phosphorus is present for each atomic proportion of barium.
10. A mineral lubricating oil containing a stabilizing quantity of a product obtained by reacting about 0.06 to about 0.75 molecular proportion or phosphorus pentasulflde with one molecular proportion of the barium salt of a tert.-octyl phenol sulfide, at a. temperature of 150-180 C. for a period of at least 1 hour.-
11. A mineral lubricating oil according to claim 10 in which the additive was obtained by reacting the sulfide of phosphorus with the metal salt in the presence or a mineral oil as a. reaction medium and a small proportion 01' a higher fatty alcohol.
12. A mineral lubricating oil containing a stabilizing quantity or a product obtained by heating a concentrated mineral lubricating oil solution containing about 40% of barium tert.-octyl phenol sulfide, about 6% of stearyl alcohol, and about 54% of a refined mineral lubricating oil to about ISO-180 C., gradually adding about 0.4 molecular proportion 01' phosphorus pentasulflde for each molecular proportion of the barium salt while maintaining the temperature not higher than about 190 C., further maintaining the temperature at about to about C. for at least 2 hours, and filtering the final product.
13. A mineral lubricating oil containing a stabilizing quantity of a product obtained by heating a concentrated mineral lubricating oil solution containing about 40% of'barium tert.-octyl phenol sulfide, about 6% or stearyl alcohol. and about 54% of a refined mineral lubricating oil to about 150-180 C., gradually adding about 0.2 molecular proportion of phosphorus pentasulflde for each molecular proportion of the barium salt while maintaining the temperature not higher than about (2., further maintaining the temperature at about 160 to about 180 C. for at least 2 hours, and filtering the final product.
14. As a new composition of matter a sulfur and phosphorus containing product obtained by reacting a sulfide of phosphorus with a divalent group II metal salt of a compound having the characterizing structure where Ar is an aromatic nucleus, R is an alkyl radical of 4-24 carbon atoms, X is an element of the group consisting of ongen and sulfur, Y is a member of the sulfur family of elements, and a: is an integer from 1 to 4, at a. temperature of 100-200 C. for a. period of at least 10 minutes, the proportions of reactants being such that 0.03-2 atomic proportions of phosphorus are present for each atomic proportion of metal.
15. As a new composition of matter an oil-soluble sulfur and phosphorus containing product obtained by reacting a sulfide of phosphorus with a compound of the formula where R is an alkyl radical of 4-24 carbon atoms, X is an element of the group consisting of oxygen and sulfur, M is a divalent metal of group II of 25 the periodic table, and :r is an integer from 1 to 4, at a temperature of 100-200 C. for a period of at least minutes. the proportions of reactants being such that 0.03-2 atomic proportions of phosphorus are present for each atomic proportlon of metal.
10. As a new composition of matter an oil-soiuble sulfur and phosphorus containing product obtained by reacting a sulfide of phosphorus with a metal salt of an alkylated phenol sulfide in which the 'alkyl groups contain 4-24 carbon atoms and in which the metal is a divalent metal of group II of the periodic table, at a temperature of 100-200 C. for a period or at least 10 minutes, the proportions of reactants being such that 0.03-2 atomic proportions of phosphorus are present for each atomic proportion of metal.
17. A new composition of matter according to claim 10 in which the metal of the metal salt is barium.
18. As a new composition of matter an oil-soluble product obtained by reacting phosphorus pentasulfide with the barium salt of a p-tert.- octyl phenol sulfide at a temperature of 150- 180 C. for a period of at least 1 hour, the proportions of reactants being such that 0.06-0.75 atomic proportion of prosphorus is present for each atomic proportion of barium.
10. A concentrate consisting essentially of a mineral lubricating oil containing 25-75% of the product obtained by reacting a divalent group II metal salt of an alkyl phenol sulfide with a sulfide of phosphorus at a temperature of 100- 200' C. for a period of at least ten minutes, the proportion oi reactants being such that 0.03-2 atomic proportions of phosphorus are present for each atomic proportion of metal.
20. The method of preparing an oil-soluble sulfur and phosphorus containing product having antioxidant properties in the presence of organic materials which comprises reacting a sulfide of phosphorus with a compound or the formula M x x where R is an alkyl radical of 4-24 atoms, X is an element of the group consisting of oxygen and sulfur, M is a divalent metal of the group II of the periodic table and :r: is an integer from 1 to 4, at a temperature of 100-200 C. for a period of at least 10 minutes, the proportions of reactants being such that 0.03-2 atomic-proportions of phosphorus are present for each atomic proportion of metal.
21. The method 01' preparing an oil-soluble sulfur and phosphorus containing product having tal of 4-24 carbon atoms and in which the metalis a divalent metal Of group II of the periodic table, at a. temperature of -200 C. for a period of at least 10 minutes. the proportions of reactants being such that 0.03-2 atomic proportionst of phosphorus are present for each atomic proportion of metal.
22. The method of preparing an oil-soluble sulfur and phosphorus containing product having antioxidant properties in the presence of organic material which comprises reacting phosphorus pentasulflde with the barium salt of a tert.-octyl phenol sulfide. at a temperature of 150-180 C. of a period of at least 1 hour. the proportions of reactants being such that 0.06-0.75 atomic proportion of phosphorus is present for each atomic proportion of barium.
23. The method of preparing an oil-soluble sulfur and phosphorus containing product which imparts detergent and anti-corrosion properties to mineral lubricating oils which comp-rises reacting about 0.06 to about 0.75 molecular pro portion of phosphorus pentasulfldc with l molecular proportion of the barium salt of p-tert.- octyl phenol sulfide in the presence of a mineral lubricating oil solvent and a small quantity of stearyl alcohol at a temperature of about to about 190 C. for a period of at least one hour.
24. A mineral lubricating oil additive concentrate containing about 54% of mineral lubricating oil, about 6% of stearyl alcohol, and about 40% of the product obtained by reacting barium tert.-octyl phenol sulfidv with phosphorus pentasulfide at a temperature of -180 C, for a period of at least 1 hour. the proportions of reactants being such that 0.06-0.75 atomic proportion of phosphorus is present for each atomic proportion of barium.
JOHN G. McNAB. DILWORTH T. ROGERS.
REFERENCES CITED The following references are oi record in the file of this patent:
UNITED STATES PATENTS Number Name Date 1,813,344 Derby July 7, 1931 2,242,260 Prutton May 20, 1941 2,331,448 Winning at al Oct. 12, 1943 2,335,017 McNab et ai. No 23, 1943 2,360,302 Etzler et al Oct. 10, 1944 2,362,624 Gaynor et a] Nov. 14, 1944 2,365,938 Cook et al Dec. 26, 1944
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US560192A US2451345A (en) | 1944-10-24 | 1944-10-24 | Compounded lubricating oil |
DEST76A DE924472C (en) | 1944-10-24 | 1949-10-26 | Additive to mineral lubricating oils, petrol, diesel oils, kerosene and greases |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US560192A US2451345A (en) | 1944-10-24 | 1944-10-24 | Compounded lubricating oil |
Publications (1)
Publication Number | Publication Date |
---|---|
US2451345A true US2451345A (en) | 1948-10-12 |
Family
ID=24236747
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US560192A Expired - Lifetime US2451345A (en) | 1944-10-24 | 1944-10-24 | Compounded lubricating oil |
Country Status (2)
Country | Link |
---|---|
US (1) | US2451345A (en) |
DE (1) | DE924472C (en) |
Cited By (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2636858A (en) * | 1951-06-07 | 1953-04-28 | Standard Oil Dev Co | Mineral oil additive |
US2670383A (en) * | 1950-06-30 | 1954-02-23 | Monsanto Chemicals | Compound selected from the group consisting of thio bis [3-methyl-6-(1, 1, 3, 3-tetramethyl butyl)phenol] and thio bis |
US2689223A (en) * | 1951-06-22 | 1954-09-14 | Standard Oil Dev Co | Viscosity index improvers |
US2716090A (en) * | 1950-08-30 | 1955-08-23 | Exxon Research Engineering Co | Plasticizing agent for mineral oil solutions |
US2731418A (en) * | 1952-08-26 | 1956-01-17 | Exxon Research Engineering Co | Hydraulic transmission fluid |
US2739051A (en) * | 1951-03-31 | 1956-03-20 | Exxon Research Engineering Co | Production of stable fuel oil |
US2768953A (en) * | 1952-08-26 | 1956-10-30 | Exxon Research Engineering Co | Hydraulic transmission fluid |
US2769782A (en) * | 1953-10-26 | 1956-11-06 | Exxon Research Engineering Co | Lubricating oil additive having improved copper corrosion properties |
US2785131A (en) * | 1955-02-21 | 1957-03-12 | Exxon Research Engineering Co | Process for preparing alkyl phenol sulfides |
US2794716A (en) * | 1953-08-13 | 1957-06-04 | Ethyl Corp | Fuel antiknock |
US2808320A (en) * | 1950-11-13 | 1957-10-01 | Exxon Research Engineering Co | Hydrocarbon oil stabilization |
US2938776A (en) * | 1955-04-26 | 1960-05-31 | Standard Oil Co | Distillate fuel composition |
US2964474A (en) * | 1956-12-31 | 1960-12-13 | Standard Oil Co | Lubricating oil resistant to cold sludge formation |
US2964473A (en) * | 1956-12-24 | 1960-12-13 | Standard Oil Co | Additive for minimizing cold sludge formation and lubricating oil containing the same |
US2966461A (en) * | 1958-04-17 | 1960-12-27 | Gulf Research Development Co | Antifriction bearing grease |
DE2161121A1 (en) * | 1970-12-11 | 1972-07-06 | Chevron Research Co., San Francisco, Calif. (V.StA.) | Alkylphenoxides containing basic alkylenamine and sulfur bridges as additives for lubricating oils |
US4115287A (en) * | 1976-04-22 | 1978-09-19 | Exxon Research And Engineering Company | Lubricating compositions |
FR2645168A1 (en) * | 1989-03-30 | 1990-10-05 | Inst Francais Du Petrole | NOVEL THIOPHOSPHORUS COMPOUNDS, THEIR PREPARATION AND THEIR USE AS LUBRICANT ADDITIVES |
US5256319A (en) * | 1989-03-30 | 1993-10-26 | Institut Francais Du Petrole | New thiophosphoretted compounds, their preparation and their use as additives for lubricants |
US20050250656A1 (en) * | 2004-05-04 | 2005-11-10 | Masahiro Ishikawa | Continuously variable transmission fluid |
US20060214381A1 (en) * | 2003-04-04 | 2006-09-28 | Claudio Zampieri | In-line roller-skate, particularly for racing |
US20080015130A1 (en) * | 2006-07-14 | 2008-01-17 | Devlin Mark T | Lubricant compositions |
US20080051304A1 (en) * | 2006-08-28 | 2008-02-28 | Devlin Mark T | Lubricant compositions |
US7737094B2 (en) | 2007-10-25 | 2010-06-15 | Afton Chemical Corporation | Engine wear protection in engines operated using ethanol-based fuel |
WO2010147993A1 (en) | 2009-06-16 | 2010-12-23 | Chevron Phillips Chemical Company Lp | Oligomerization of alpha olefins using metallocene-ssa catalyst systems and use of the resultant polyalphaolefins to prepare lubricant blends |
WO2011102836A1 (en) | 2010-02-19 | 2011-08-25 | Infineum International Limited | Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of borated detergents |
WO2011102835A1 (en) | 2010-02-19 | 2011-08-25 | Toyota Jidosha Kabushiki Kaisha | Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of sodium detergents |
US20110237476A1 (en) * | 2010-03-25 | 2011-09-29 | Afton Chemical Corporation | Lubricant compositions for improved engine performance |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1813344A (en) * | 1928-11-17 | 1931-07-07 | Peter C Reilly | Froth flotation of ores |
US2242260A (en) * | 1937-01-22 | 1941-05-20 | Lubri Zol Dev Corp | Lubricating composition |
US2331448A (en) * | 1940-10-05 | 1943-10-12 | Standard Oil Dev Co | Chemical process |
US2335017A (en) * | 1941-12-31 | 1943-11-23 | Standard Oil Dev Co | Lubricating composition |
US2360302A (en) * | 1940-08-02 | 1944-10-10 | Standard Oil Co California | Compounded hydrocarbon oil |
US2362624A (en) * | 1943-01-21 | 1944-11-14 | Standard Oil Co | Lubricant |
US2365938A (en) * | 1941-10-17 | 1944-12-26 | American Cyanamid Co | Wax substituted diaryl dithiophosphoric acids and salts thereof |
-
1944
- 1944-10-24 US US560192A patent/US2451345A/en not_active Expired - Lifetime
-
1949
- 1949-10-26 DE DEST76A patent/DE924472C/en not_active Expired
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1813344A (en) * | 1928-11-17 | 1931-07-07 | Peter C Reilly | Froth flotation of ores |
US2242260A (en) * | 1937-01-22 | 1941-05-20 | Lubri Zol Dev Corp | Lubricating composition |
US2360302A (en) * | 1940-08-02 | 1944-10-10 | Standard Oil Co California | Compounded hydrocarbon oil |
US2331448A (en) * | 1940-10-05 | 1943-10-12 | Standard Oil Dev Co | Chemical process |
US2365938A (en) * | 1941-10-17 | 1944-12-26 | American Cyanamid Co | Wax substituted diaryl dithiophosphoric acids and salts thereof |
US2335017A (en) * | 1941-12-31 | 1943-11-23 | Standard Oil Dev Co | Lubricating composition |
US2362624A (en) * | 1943-01-21 | 1944-11-14 | Standard Oil Co | Lubricant |
Cited By (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2670383A (en) * | 1950-06-30 | 1954-02-23 | Monsanto Chemicals | Compound selected from the group consisting of thio bis [3-methyl-6-(1, 1, 3, 3-tetramethyl butyl)phenol] and thio bis |
US2716090A (en) * | 1950-08-30 | 1955-08-23 | Exxon Research Engineering Co | Plasticizing agent for mineral oil solutions |
US2808320A (en) * | 1950-11-13 | 1957-10-01 | Exxon Research Engineering Co | Hydrocarbon oil stabilization |
US2739051A (en) * | 1951-03-31 | 1956-03-20 | Exxon Research Engineering Co | Production of stable fuel oil |
US2636858A (en) * | 1951-06-07 | 1953-04-28 | Standard Oil Dev Co | Mineral oil additive |
US2689223A (en) * | 1951-06-22 | 1954-09-14 | Standard Oil Dev Co | Viscosity index improvers |
US2731418A (en) * | 1952-08-26 | 1956-01-17 | Exxon Research Engineering Co | Hydraulic transmission fluid |
US2768953A (en) * | 1952-08-26 | 1956-10-30 | Exxon Research Engineering Co | Hydraulic transmission fluid |
US2794716A (en) * | 1953-08-13 | 1957-06-04 | Ethyl Corp | Fuel antiknock |
US2769782A (en) * | 1953-10-26 | 1956-11-06 | Exxon Research Engineering Co | Lubricating oil additive having improved copper corrosion properties |
US2785131A (en) * | 1955-02-21 | 1957-03-12 | Exxon Research Engineering Co | Process for preparing alkyl phenol sulfides |
US2938776A (en) * | 1955-04-26 | 1960-05-31 | Standard Oil Co | Distillate fuel composition |
US2964473A (en) * | 1956-12-24 | 1960-12-13 | Standard Oil Co | Additive for minimizing cold sludge formation and lubricating oil containing the same |
US2964474A (en) * | 1956-12-31 | 1960-12-13 | Standard Oil Co | Lubricating oil resistant to cold sludge formation |
US2966461A (en) * | 1958-04-17 | 1960-12-27 | Gulf Research Development Co | Antifriction bearing grease |
DE2161121A1 (en) * | 1970-12-11 | 1972-07-06 | Chevron Research Co., San Francisco, Calif. (V.StA.) | Alkylphenoxides containing basic alkylenamine and sulfur bridges as additives for lubricating oils |
US4115287A (en) * | 1976-04-22 | 1978-09-19 | Exxon Research And Engineering Company | Lubricating compositions |
FR2645168A1 (en) * | 1989-03-30 | 1990-10-05 | Inst Francais Du Petrole | NOVEL THIOPHOSPHORUS COMPOUNDS, THEIR PREPARATION AND THEIR USE AS LUBRICANT ADDITIVES |
US5080812A (en) * | 1989-03-30 | 1992-01-14 | Institut Francais Du Petrol | Thiophosphoretted compounds, their preparation and their use as additives for lubricants |
US5256319A (en) * | 1989-03-30 | 1993-10-26 | Institut Francais Du Petrole | New thiophosphoretted compounds, their preparation and their use as additives for lubricants |
US20060214381A1 (en) * | 2003-04-04 | 2006-09-28 | Claudio Zampieri | In-line roller-skate, particularly for racing |
US20050250656A1 (en) * | 2004-05-04 | 2005-11-10 | Masahiro Ishikawa | Continuously variable transmission fluid |
US20080015130A1 (en) * | 2006-07-14 | 2008-01-17 | Devlin Mark T | Lubricant compositions |
US7906465B2 (en) | 2006-07-14 | 2011-03-15 | Afton Chemical Corp. | Lubricant compositions |
US7833952B2 (en) | 2006-08-28 | 2010-11-16 | Afton Chemical Corporation | Lubricant compositions |
US20080051304A1 (en) * | 2006-08-28 | 2008-02-28 | Devlin Mark T | Lubricant compositions |
US7737094B2 (en) | 2007-10-25 | 2010-06-15 | Afton Chemical Corporation | Engine wear protection in engines operated using ethanol-based fuel |
WO2010147993A1 (en) | 2009-06-16 | 2010-12-23 | Chevron Phillips Chemical Company Lp | Oligomerization of alpha olefins using metallocene-ssa catalyst systems and use of the resultant polyalphaolefins to prepare lubricant blends |
EP3587458A1 (en) | 2009-06-16 | 2020-01-01 | Chevron Phillips Chemical Company LP | Compositions comprising polyalphaolefins |
WO2011102836A1 (en) | 2010-02-19 | 2011-08-25 | Infineum International Limited | Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of borated detergents |
WO2011102835A1 (en) | 2010-02-19 | 2011-08-25 | Toyota Jidosha Kabushiki Kaisha | Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of sodium detergents |
US9365794B2 (en) | 2010-02-19 | 2016-06-14 | Infineum International Limited | Wet friction clutch—lubricant systems providing high dynamic coefficients of friction through the use of borated detergents |
US20110237476A1 (en) * | 2010-03-25 | 2011-09-29 | Afton Chemical Corporation | Lubricant compositions for improved engine performance |
EP2371935A1 (en) | 2010-03-25 | 2011-10-05 | Afton Chemical Corporation | Lubricant compositions for improved engine performance |
US9725673B2 (en) | 2010-03-25 | 2017-08-08 | Afton Chemical Corporation | Lubricant compositions for improved engine performance |
Also Published As
Publication number | Publication date |
---|---|
DE924472C (en) | 1955-03-03 |
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