US3108959A - Lubricant additive and composition containing same - Google Patents
Lubricant additive and composition containing same Download PDFInfo
- Publication number
- US3108959A US3108959A US778583A US77858358A US3108959A US 3108959 A US3108959 A US 3108959A US 778583 A US778583 A US 778583A US 77858358 A US77858358 A US 77858358A US 3108959 A US3108959 A US 3108959A
- Authority
- US
- United States
- Prior art keywords
- reaction product
- product
- hydrocarbon
- phosphorus
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 51
- 239000003879 lubricant additive Substances 0.000 title claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 38
- 239000000047 product Substances 0.000 claims description 34
- 239000004215 Carbon black (E152) Substances 0.000 claims description 28
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 27
- 229910052698 phosphorus Inorganic materials 0.000 claims description 27
- 239000011574 phosphorus Substances 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- 229920000768 polyamine Polymers 0.000 claims description 25
- 229930195733 hydrocarbon Natural products 0.000 claims description 24
- 150000002430 hydrocarbons Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 13
- 239000000376 reactant Substances 0.000 claims description 11
- 239000012141 concentrate Substances 0.000 claims description 6
- 239000003599 detergent Substances 0.000 claims description 6
- 239000010688 mineral lubricating oil Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 description 29
- 239000010687 lubricating oil Substances 0.000 description 23
- 230000000996 additive effect Effects 0.000 description 22
- -1 amine compound Chemical class 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 125000001931 aliphatic group Chemical group 0.000 description 16
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 11
- 229910052796 boron Inorganic materials 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 150000001336 alkenes Chemical class 0.000 description 9
- 239000002966 varnish Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 230000003301 hydrolyzing effect Effects 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 5
- 230000001050 lubricating effect Effects 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- 235000019271 petrolatum Nutrition 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 229940031439 squalene Drugs 0.000 description 3
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- UPCIBFUJJLCOQG-UHFFFAOYSA-L ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium;dibromide Chemical compound [Br-].[Br-].CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC UPCIBFUJJLCOQG-UHFFFAOYSA-L 0.000 description 2
- 125000003916 ethylene diamine group Chemical group 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 235000019809 paraffin wax Nutrition 0.000 description 2
- 150000003017 phosphorus Chemical class 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000010689 synthetic lubricating oil Substances 0.000 description 2
- 229960001124 trientine Drugs 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910001502 inorganic halide Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical class ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/04—Reaction products of phosphorus sulfur compounds with hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
- C10M2225/041—Hydrocarbon polymers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/09—Complexes with metals
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/06—Groups 3 or 13
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Definitions
- This invention relates to additive compositions for use in lubricating oils, the use of such additive compositions, and improved lubricating compositions containing such additive compositions and intended for use in internal combustion engines such as diesel engines and automobile engines. More particularly the invention relates to additive compositions which impart detergency and anti-rust properties to lubricating oils and suppress excess varnish formation and octane requirement increase when used in lubricating oils.
- Straight petroleum lubrican s are effective within certain defined limits of engine operating conditions and when these limits are exceeded, such lubricants frequently fail to give the desired periormance demanded of them. Since, in modern engines designed to give increased performance, these limits are frequently exceeded, the use of straight mineral oils as lubricants produce undesirable conditions within the engine; thus varnish formation, corrosion, preignition and octane requirement are all excessive in modern engines using mineral oils alone.
- a hydrolyzed phosphorus sulfide-hydrocarbon reaction product may be reacted with an amine compound and a borophosphoric acid to form a new composition of matter with desirable characteristics for use as an additive composition in a lubricating oil.
- the boron and amine-containing additive composition of our present invention overcomes the problems of the mineral lubricating oil in its use without additives by imparting to the lubricating oil high detergency properties and eliminating excessive varnish formation and corrosion, while suppressing octane requirement increase.
- the new composition may also be used in an additive concentrate in amounts of from to 50 weioht percent or more for addition to lubricating oils.
- our present invention provides an additive composition for lubricating oils formed by reacting a hydrolyzed phosphorus sulfide-hydrocarbon reaction prodami. e comthe resulting neutralized reaction product with boroph'osphoric acid.
- Our invention also provides an improved mineral oil containing an effective amount of our additive composition toimpart improved properties to the lubricating oil.
- the amine compound used in preparing the additive composition of our present invention may be any aliphatic or substituted aliphatic compound having 1 or more basic amine groups.
- Preferred amine compounds particularly suited for use in the preparation of the additive composition of our present invention are the hydroxy aliphatic amines such as monohydroxy, dihydroxy, and
- polyhydroxy aliphatic amines and particularly preferred are the aliphatic polyamines such as diamines, triamines, etc., having two or more carbon atoms in the alipha ic ohain.
- Polyhydroxy aliphatic polyamines are includable in either group.
- Particularly suitable aliphatic polyamines are ailkylene polyamines containing at least two primary amino nitrogen atoms.
- alkylene polyamines suitable for the hereindescribed purpose are ethylene diamine, propylene diamine, diethylene-triamine, diamylene triamine, triethylene tetramine, tripropylene tetramine, diethylene propylene tetramine, tetraethylene pcntamine, tetrabutylene pentamine, diethylendipropylcue pentamine, butylene diamine, dihexylene triamine, and the like, or mixtures thereof.
- a suitable polyamine product is a crude diethylene triamine containing minor amounts :of ethylene diamine and triethylene tetramine.
- Other suitable aliphatic polyamines include those having the general formula nnmcnpmn,
- R is preferably a C to C aliphatic chain, and which are obtained by condensing the suitable amine with acrylonitrile and hydrogenating to the corresponding diamine.
- aliphatic polyamines of this type are those marketed by Armour and Company as Duomeens, which are prepared by the condensation of a dodecyl (coco) amine or an octadecyl (tallow) amine with acrylonitrile followed by hydrogenation to the corresponding diamine product; these products are marketed as Du-omeen C and Duomeen T, respectively.
- Borophosphoric acid a dry nonhygroscopic powder
- Borophosphoric acid a dry nonhygroscopic powder
- the hydrolyzed phosphorus, sulfide-hydrocarbon reaction product may be prepared by any method known to the prior art. Vie prefer to react a hydrocarbon with from about 1% to about 50%, and preferably from about 5% to about 25% of phosphorus sulfide at .a temperature of from about 200 'F. to about 600 F. in a nonoxidizing atmosphere, as, for example, in a nitrogen atmosphere. The reaction is carried out for from about one to about ten hours or more, and preferably for about five hours. The reaction may be carried out in the presence of a sulfurizing agent such as sulfur, sulfur chlorides, etc., if desired. The product is hydrolyzed at a temperature of from about 200 F.
- the hydrolyzed product may be solvent extracted to remove salts of inorganic phosphorus acids and low molecular weight organic phosphorus acids formed during hydrolysis. Solvent extraction may be accomplished in accordance with the method described by Norman E. Lemmon et al. in U.S. 2,843,579, issued luly 15, 1958.
- any phosphorus sulfides such as P 5 P 8 P 8 or other phosphorus sulfides and preferably phosphorus pentasulide, P 5 may be reacted with a hydrocarbon.
- the hydrocarbons used in the phosphorus sulfidehydrocarbon reaction may be polymers such as monooletin polymers, copolymers, graft polymers, etc. and may also be unpolymerized or unpolymerizable hydrocarbons such as olefins, parafiins, cycloparaflins, aromatic hydrocarbons, etc.
- the mono-olefin polymer to be treated may be the polymer resulting from the polymerization of low molecular weight mono-olefins preferably the isomonoolefins, such as isobutylene and isoamylene and/or the copolymers obtained by the polymerization of hydrocarbon mixtures containing isomono-olefins and mono-olcfins of less than six carbon atoms and preferably those of four carbon atoms.
- the polymer may be obtained by the polymerization of these olefins or mixed olefins in the presence of catalysts such as sulfuric acid, phosphoric acid, or boron fluoride, aluminum chloride or other similar halide catalysts of the Friedel-Crafts type.
- the polymers advantageously have molecular weights ranging from about 150 to about 50,000 or more, and preferably from about 500 to about 10,000.
- a starting material there can be used the polymer or synthetic lubricating oil obtained by polymerizing the unsaturated hydrocarbons resulting from the vapor phase cracking of paraifin waxes in the presence of aluminum chloride which is fully described in U.S. patents Nos. 1,955,260; 1,970,402; and 2,091,398.
- Still another type of olefin polymer which may be employed is the polymer resulting from the treatment of vapor phase cracked gasoline and/or gasoline fractions with sulfuric acid or solid adsorbents, such as fullers earth, whereby the unsaturated polymerized hydrocarbons are removed.
- the treatment with phosphorus sulfide of the polymers resulting from the voltolization of hydrocarbons as described for example in US. Patents Nos. 2,197,768 and 2,191,787.
- hydrocarbons which we can use as reactants in the preparation of the phosphorus sulfide reaction product are paraflins, olefins, aromatics or alkyl aromatics, cyclic aliphatics, petroleum fractions, such as lubricating oil fractions, petrolatums, waxes, cracking cycle stocks, condensation products of the foregoing hydrocarbons, solvent extracts of petroleum extracts, etc.
- paraffin hydrocarbons can be those obtained from petroleum oils such as bright stock residuums, lubricating oil distillates, petrolatums, or paraffin waxes. We may also halogenate any of the foregoing parafiins and condense the same with aromatic hydrocarbons in the presence of anhydrous inorganic halides such as aluminum chloride, zinc chloride, boron fluoride and the like.
- high molecular weight olefinic hydrocarbons which we may employ as reactants are cetene (C cerotene (C melene (C and mixed high molecular weight alkenes obtained by cracking petroleum oils.
- olefins suitable for the preparation of the herein described phosphorus sulfide reaction products are olefins having at least 20 carbon atoms in the molecule of which from about 13 carbon atoms to about 18 carbon atoms, md preferably at least 15 carbon atoms are in a long chain.
- Such olefins can be obtained by the dehydrogenation of parafiins, such as by the cracking of paraffin Waxes or by the dehalogena-tion of alkyl halides, preferably long chain alkyl halides, particularly halo genated parafiin waxes.
- any of the hydrocarbons recited as useable by Norman E. Lernmon et al. in US. 2,843,579, issued July 15, 1958, may be employed herein.
- the additive composition concentrates of our present invention are formed by neutralizing a hydrolyzed phosphorus sulfide-hydrocarbon reaction product, formed, for example, as indicated above and preferably solvent extracted, with an amine compound having 2 or more carbon atoms and preferably an aliphatic polyamine as defined above.
- the neutralized product is then reacted with borophosphoric acid, preferably in amounts corresponding to from about 1 to about 3 moles boron per mole of neutralized product.
- the borophosphoric acid reaction may be carried out in the resence of a suitable solvent for the borophosphoric acid such as alcohol, acetone, water, or other suitable solvent to increase solubility of the reactants.
- a suitable solvent for the borophosphoric acid such as alcohol, acetone, water, or other suitable solvent to increase solubility of the reactants.
- the reaction mixture is then heated to a temperature above C.
- reaction mixture should not be heated to a temperature at which the amine is driven from the mixture. If temperatures higher than the boiling point of the amine are used means for retaining the amine, such as, for example, refluxing, should be employed.
- An alternative method of forming the boron and phosphorus-containing amine-neutralized reaction products which we have found acceptable is by first reacting the borophosphoric acid with the amine compound and then reacting the resulting product with the phosphorus sulfide-hydrocarbon reaction product.
- the reaction mixture is treated for removal of solvent by placing the mixture in a vacuum or by passing nitrogen gas or other inert gases through the reaction mixture at a temperature sufficient to strip solvent therefrom.
- One to six hours is generally sutficient to strip the solvent out; however, this period of time is dependent on the amount and temperature of the stripping gas used as well as the nature of the solvent.
- a lower boiling solvent such as acetone or methanol
- the nitrogen blowing generally results in the formation of a clear product having dispersed impurities essentially removed.
- the product should be hazy due to the presence of impurities, for example the presence of excess borophosphoric acid which has not reacted with the neutralized phosphorus sulfide hydrocarbon reaction product or has not dissolved therein, it may be desirable to filter the product through diatomaceous earth to obtain a suitably clear product.
- the products formed in the above reaction contain chemically bonded boron and phosphorus.
- the additive composition may be used in lubricating oils in varying amounts constituting minor proportions of the total lubricating composition.
- the amount of additive used should be in excess of 0.1 weight percent.
- the additive is effective in imparting improved detergcncy to lubricating oils even when used in such small amounts as range from about 0.1 weight percent.
- HYDROLYZED INTERMEDIATE about five hours for product formation.
- the product had a phosphorus content of about 4.3% and a sulfur content of about 7.5%.
- the reaction product formed is then hydrolyzed with steam at a temperature of about 300 F. to about 400 F.
- the hydrolyzed product was diluted, for ease of handling, to about a 60% concentrate with a solvent extracted Mid-Continent mineral oil having a viscosity of about 38 SSU at 210 F. This product was used as a starting material for the preparation of additives in subsequent examples.
- Example 2000 grams of the solvent extracted hydrolyzed intermediate were reacted with 73 grams (one mole per mole of intermediate) of ethylenediainine and a basic salt was formed.
- the basic salt was treated with 151 grams (1.22 moles per mole of intermediate) of borophosphoric acid with stirring at 100 C. for six hours.
- the reaction mixture was blown with nitrogen; 1255 grams of solvent extracted Mid-Continent 5 weight mineral oil having a viscosity of about 38 SSU at 210 F. were added and the mixture was filtered through Celite.
- the filtrate was a bright, brown, oil-soluble product which had a boron content of 0.16 Wt. percent, a nitrogen content of 0.58 wt. percent and a phosphorus content of 1.38 wt. percent.
- the commercial-type oil used was a mixture of SW and 10W solvent extracted base stock containing a polyisobutylene polymer viscosity improver and having a viscosity of about 62 SSU at 210 F. having 0.75% by weight sulfurized dipentene corrosion inhibitor.
- a run was also made on the commercial-type oil Without the product additive prepared in the above example and the comparative results are shown in Table I, below.
- Concentrates of a suitable oil base containing more than 10 percent, for example up to 50 percent or more, of the additives of this invention alone or in combination with other additives can be used for blending with hydrocarbon oils or other oils in the proportions desired for the particular conditions of use to give a finished lubricating product containing the additives of this invention.
- an oil-soluble detergent neutralized reaction product prepared by the process comprising: reacting a phosphorus sulfide With a hydrocarbon; hydrolyzing the resulting phosphorus sulfidehydrocarbon reaction product; and reacting the hydrolyzed product with borophosphoric acid in an amount corresponding to from about one to about three moles of boron per mole of reaction product and with an aliphatic polya-rnine having from 2 to 21 carbon atoms in the aliphatic group in an amount corresponding to from about one to about 1.1 moles of polyarnine per mole of acid phosphorus, at a temperature below the temperature at which said polyarnine is driven "from the mixture of reactants.
- a lubricating composition comprising a major amount of a hydrocarbon lubricating oil and from about 0.1 to about 20 weight percent of the composition of claim 1.
- composition of claim 1 wherein the aliphatic polyamine is ethylene diamine.
- an oil-soluble detergent neutralized reaction product prepared by the process comprising the steps of: reacting a phosphorus sulfide with a hydrocarbon; hydrolyzing the resultant phosphorus sulfide-hydrocarbon reaction product; neutralizing the hydrolyzed product with an aliphatic polyamine having from 2 to 21 carbon atoms in the aliphatic group in an amount corresponding to from about one to about 1.1 moles of polyamine per mole of acid phosphorus; and reacting the neutralize-d product with borophos-phoric acid in an amount corresponding to from about one to about three moles of boron per mole of reaction product at a temperature below the temperature at which said polyamine is driven from the mixture of reactants.
- a lubricating composition comprising a major amount of hydrocarbon lubricating oil and from about 0.1 to about 20 weight percent of the composition of claim 4.
- composition of claim 4 wherein the aliphatic polyamine is ethylene diamine.
- an oil-soluble detergent neutralized reaction product prepared by the process comprising the steps of: reacting a phosphorus sulfide with a hydrocarbon; hydrolyzing the resultant phosphorus sulfide-hydrocarbon reaction product; reacting boro-phosphoric acid in an amount corresponding to from about one to about three moles of boron per mole of reaction product with an alkylene polyamine having from 2 to 21 carbon atoms in the alkylene group and containing at least two primary amino nitrogen atoms in an amount corresponding to from about one to about 1.1 moles of greases polyamine per mole of acid phosphorus; and reacting the resulting reaction product with the hydrolyzed phosphorus sulfide-hydrocarbon reaction product at a temperature below the temperature at which the polyaminc is driven from the mixture of reactants.
- an oil-soluble detergent neutralized reaction product prepared by the process comprising the steps of: reacting phosphorus sulfide with a hydrocarbon; hydrolyzing the resulting phosphorus sulfide-hydrocarbon reaction product; neutralizing the resulting hydrolyzed product with from about one to about 1.1 moles per mole of hydnolyzed reaction product of ethylene diamine; and reacting the resulting neutralized product with from about one to about three moles based on boron of borophosphoric acid per mole of neutralized product at a temperature below the temperature at Which the polyamine is driven from the mixture of reactants.
- an oil-soluble detergent neutralized reaction product prepared by the process comprising the steps of: reacting phosphorus sulfide with a butene polymer at a temperature of from about 200 to about 600 F.; hydrolyzing the resulting phosphorus sulfide-butene polymer reaction product; neutralizing the resulting hydrolyzed product with from about one to about 1.1 moles per mole of hydrolyzed reaction product of an alkylene polyamine having the formula wherein R is a C to C aliphatic hydrocarbon chain; reacting the resulting neutralized product With from about one to about three moles based on boron of borophosi2.
- phoric acid per mole of neutralized product at a temperature below the tempenature at which the polyamine is driven from the mixture of reactants; and heating the reactants to a temperature above 100 C. whereby water is stripped from the reaction mixture.
- a lubricant additive concentrate consisting essentially of a mineral lubricating oil containing more than about 10% of an oil-soluble detergene neutralized reaction product prepared by the process comprising: reacting a phosphorus sulfide With a hydrocarbon; hydrolyzing the resulting phosphorus sulfide-hydrocarbon reaction product; and reacting the hydrolyzed product with borophosphoric acid in an amount corresponding to from about one to about three moles of boron per mole of reaction product and with an aliphatic polyamine having from 2 to 21 carbon atoms in the aliphatic group in an amount corresponding to from about one to about 1.1 moles of polyamine per mole of acid phosphorus, at a temperature beiow the tempenature at which the polyamine driven from the mixture of reactants.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Lubricants (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL246131D NL246131A (enrdf_load_html_response) | 1958-12-08 | ||
FR812272A FR1246407A (fr) | 1958-12-08 | 1958-12-07 | Additif pour lubrifiants |
US778583A US3108959A (en) | 1958-12-08 | 1958-12-08 | Lubricant additive and composition containing same |
US778576A US3108958A (en) | 1958-12-08 | 1958-12-08 | Lubricant additive and composition containing same |
US778606A US3089851A (en) | 1958-12-08 | 1958-12-08 | Lubricant additive and composition containing same |
DEST15883A DE1255221B (de) | 1958-12-08 | 1959-12-08 | Schmieroel |
GB41612/59A GB930504A (en) | 1958-12-08 | 1959-12-08 | Boron and nitrogen-containing phosphor-sulphurized products, their preparation and their use as lubricant additives |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US778583A US3108959A (en) | 1958-12-08 | 1958-12-08 | Lubricant additive and composition containing same |
US778576A US3108958A (en) | 1958-12-08 | 1958-12-08 | Lubricant additive and composition containing same |
US778606A US3089851A (en) | 1958-12-08 | 1958-12-08 | Lubricant additive and composition containing same |
Publications (1)
Publication Number | Publication Date |
---|---|
US3108959A true US3108959A (en) | 1963-10-29 |
Family
ID=27419742
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US778583A Expired - Lifetime US3108959A (en) | 1958-12-08 | 1958-12-08 | Lubricant additive and composition containing same |
US778606A Expired - Lifetime US3089851A (en) | 1958-12-08 | 1958-12-08 | Lubricant additive and composition containing same |
US778576A Expired - Lifetime US3108958A (en) | 1958-12-08 | 1958-12-08 | Lubricant additive and composition containing same |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US778606A Expired - Lifetime US3089851A (en) | 1958-12-08 | 1958-12-08 | Lubricant additive and composition containing same |
US778576A Expired - Lifetime US3108958A (en) | 1958-12-08 | 1958-12-08 | Lubricant additive and composition containing same |
Country Status (5)
Country | Link |
---|---|
US (3) | US3108959A (enrdf_load_html_response) |
DE (1) | DE1255221B (enrdf_load_html_response) |
FR (1) | FR1246407A (enrdf_load_html_response) |
GB (1) | GB930504A (enrdf_load_html_response) |
NL (1) | NL246131A (enrdf_load_html_response) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3185728A (en) * | 1960-06-20 | 1965-05-25 | Texaco Inc | Ethylene diamine salts of thiophosphonic acids |
US4438013A (en) | 1983-05-27 | 1984-03-20 | Olin Corporation | Phosphorylated and thiophosphorylated poly(oxyalkylated) hydrazines and selected adducts and their use as corrosion inhibitors |
US5652201A (en) * | 1991-05-29 | 1997-07-29 | Ethyl Petroleum Additives Inc. | Lubricating oil compositions and concentrates and the use thereof |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3294684A (en) * | 1963-07-11 | 1966-12-27 | Standard Oil Co | Lubricant compositions containing detergency additives |
US5026493A (en) * | 1989-08-03 | 1991-06-25 | Ethyl Petroleum Additives, Inc. | Reduced ash content lubricants |
CN115820329B (zh) * | 2022-12-30 | 2023-10-31 | 太原理工大学 | 层状硼磷酸胺化合物作为添加剂的润滑油及其制备方法 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2053474A (en) * | 1934-12-11 | 1936-09-08 | Du Pont | Higher alkyl borates and silicates and process for preparing same |
US2160917A (en) * | 1937-06-10 | 1939-06-06 | Standard Oil Co | Lubricant |
US2346156A (en) * | 1942-02-16 | 1944-04-11 | Standard Oil Co | Compounded lubricant |
US2636258A (en) * | 1949-02-23 | 1953-04-28 | Jones Allen | Fluid can punch and opener |
US2798045A (en) * | 1954-09-27 | 1957-07-02 | Shell Dev | Lubricating compositions |
US2809934A (en) * | 1953-10-01 | 1957-10-15 | Standard Oil Co | Detergent lubricants and lubricating oil additives and process of making the same |
US2900376A (en) * | 1955-10-31 | 1959-08-18 | Standard Oil Co | Hydrolysis of phosphorus sulfide-hydrocarbon reaction product |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2316082A (en) * | 1941-03-24 | 1943-04-06 | Standard Oil Co | Lubricant |
BE581744A (enrdf_load_html_response) * | 1950-12-22 | |||
US2636858A (en) * | 1951-06-07 | 1953-04-28 | Standard Oil Dev Co | Mineral oil additive |
US3002924A (en) * | 1958-05-26 | 1961-10-03 | Standard Oil Co | Lubricant additive and composition containing same |
-
0
- NL NL246131D patent/NL246131A/xx unknown
-
1958
- 1958-12-07 FR FR812272A patent/FR1246407A/fr not_active Expired
- 1958-12-08 US US778583A patent/US3108959A/en not_active Expired - Lifetime
- 1958-12-08 US US778606A patent/US3089851A/en not_active Expired - Lifetime
- 1958-12-08 US US778576A patent/US3108958A/en not_active Expired - Lifetime
-
1959
- 1959-12-08 DE DEST15883A patent/DE1255221B/de active Pending
- 1959-12-08 GB GB41612/59A patent/GB930504A/en not_active Expired
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2053474A (en) * | 1934-12-11 | 1936-09-08 | Du Pont | Higher alkyl borates and silicates and process for preparing same |
US2160917A (en) * | 1937-06-10 | 1939-06-06 | Standard Oil Co | Lubricant |
US2346156A (en) * | 1942-02-16 | 1944-04-11 | Standard Oil Co | Compounded lubricant |
US2636258A (en) * | 1949-02-23 | 1953-04-28 | Jones Allen | Fluid can punch and opener |
US2809934A (en) * | 1953-10-01 | 1957-10-15 | Standard Oil Co | Detergent lubricants and lubricating oil additives and process of making the same |
US2798045A (en) * | 1954-09-27 | 1957-07-02 | Shell Dev | Lubricating compositions |
US2900376A (en) * | 1955-10-31 | 1959-08-18 | Standard Oil Co | Hydrolysis of phosphorus sulfide-hydrocarbon reaction product |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3185728A (en) * | 1960-06-20 | 1965-05-25 | Texaco Inc | Ethylene diamine salts of thiophosphonic acids |
US4438013A (en) | 1983-05-27 | 1984-03-20 | Olin Corporation | Phosphorylated and thiophosphorylated poly(oxyalkylated) hydrazines and selected adducts and their use as corrosion inhibitors |
US5652201A (en) * | 1991-05-29 | 1997-07-29 | Ethyl Petroleum Additives Inc. | Lubricating oil compositions and concentrates and the use thereof |
Also Published As
Publication number | Publication date |
---|---|
US3089851A (en) | 1963-05-14 |
DE1255221B (de) | 1967-11-30 |
US3108958A (en) | 1963-10-29 |
NL246131A (enrdf_load_html_response) | |
FR1246407A (fr) | 1960-10-10 |
GB930504A (en) | 1963-07-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3131150A (en) | Lubricating oil compositions containing n-substituted alkenyl succinimides in combination with polyamines | |
US3216936A (en) | Process of preparing lubricant additives | |
US3390086A (en) | Sulfur containing ashless disperant | |
US2910439A (en) | Corrosion inhibited compositions | |
US3351552A (en) | Lithium compounds as rust inhibitors for lubricants | |
US2316082A (en) | Lubricant | |
US3779928A (en) | Automatic transmission fluid | |
JP2997057B2 (ja) | 動力伝達用組成物中において有用な低圧誘導混成燐―及び硫黄含有反応生成物並びにそれらの製造法 | |
US4056531A (en) | Polymonoolefin quaternary ammonium salts of triethylenediamine | |
JPH0141196B2 (enrdf_load_html_response) | ||
US3287271A (en) | Combined detergent-corrosion inhibitors | |
US2367468A (en) | Lubricants | |
US4108858A (en) | Polyolefin quaternary pyridinium salts | |
CA1038851A (en) | Dispersant-detergent libricant and fuel additives | |
US4094802A (en) | Novel lubricant additives | |
US3108959A (en) | Lubricant additive and composition containing same | |
US2316078A (en) | Lubricant | |
US2507731A (en) | Process of reacting phosphorus sulfide and olefinic hydrocarbon | |
US2759894A (en) | Rust inhibitor | |
US3218264A (en) | Lubricants containing amine salts of n-substituted pyrrolidone carboxylic acids | |
US2316083A (en) | Lubricant | |
US3294684A (en) | Lubricant compositions containing detergency additives | |
US3002924A (en) | Lubricant additive and composition containing same | |
US3113106A (en) | Rust inhibited lubricants | |
US2812319A (en) | Lubricating oil additives |