US3082169A - Adducts of alkarylborates with trialkylphosphites or alkyl sulfoxide - Google Patents
Adducts of alkarylborates with trialkylphosphites or alkyl sulfoxide Download PDFInfo
- Publication number
- US3082169A US3082169A US57913A US5791360A US3082169A US 3082169 A US3082169 A US 3082169A US 57913 A US57913 A US 57913A US 5791360 A US5791360 A US 5791360A US 3082169 A US3082169 A US 3082169A
- Authority
- US
- United States
- Prior art keywords
- tri
- borate
- phosphite
- adducts
- lubricating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 125000005360 alkyl sulfoxide group Chemical group 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims description 24
- 150000003462 sulfoxides Chemical class 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 4
- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 claims description 3
- -1 borate ester Chemical class 0.000 description 20
- 239000000314 lubricant Substances 0.000 description 19
- 239000010687 lubricating oil Substances 0.000 description 14
- 239000002199 base oil Substances 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 12
- SGMVEWJRXZMRSN-UHFFFAOYSA-N tris(2-nonylphenyl) borate Chemical compound CCCCCCCCCC1=CC=CC=C1OB(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC SGMVEWJRXZMRSN-UHFFFAOYSA-N 0.000 description 12
- 239000000654 additive Substances 0.000 description 10
- 230000001050 lubricating effect Effects 0.000 description 10
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 7
- 235000006708 antioxidants Nutrition 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 229940067597 azelate Drugs 0.000 description 3
- 150000001642 boronic acid derivatives Chemical class 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- ONKUXPIBXRRIDU-UHFFFAOYSA-N Diethyl decanedioate Chemical compound CCOC(=O)CCCCCCCCC(=O)OCC ONKUXPIBXRRIDU-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000003463 sulfur Chemical class 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- LOWMYOWHQMKBTM-UHFFFAOYSA-N 1-butylsulfinylbutane Chemical compound CCCCS(=O)CCCC LOWMYOWHQMKBTM-UHFFFAOYSA-N 0.000 description 1
- DLEXINLCPPEMMI-UHFFFAOYSA-N 1-hexylsulfinylhexane Chemical compound CCCCCCS(=O)CCCCCC DLEXINLCPPEMMI-UHFFFAOYSA-N 0.000 description 1
- VYXNJCCBPKNMBN-UHFFFAOYSA-N 1-nonylsulfinylnonane Chemical compound CCCCCCCCCS(=O)CCCCCCCCC VYXNJCCBPKNMBN-UHFFFAOYSA-N 0.000 description 1
- VVNDEUQQZUVMNA-UHFFFAOYSA-N 2,6-bis(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC(C(C)(C)CC(C)(C)C)=C1O VVNDEUQQZUVMNA-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WFJXYIUAMJAURQ-UHFFFAOYSA-N 2-propan-2-ylsulfinylpropane Chemical compound CC(C)S(=O)C(C)C WFJXYIUAMJAURQ-UHFFFAOYSA-N 0.000 description 1
- PNTYWMCFKKJDAA-UHFFFAOYSA-N 4-methyl-2,6-di(propan-2-yl)phenol Chemical compound CC(C)C1=CC(C)=CC(C(C)C)=C1O PNTYWMCFKKJDAA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000012988 Dithioester Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- HYQSRPWWFPRCPW-UHFFFAOYSA-N [2-methyl-2-(6-methylheptanoyloxymethyl)butyl] octanoate Chemical compound CCCCCCCC(=O)OCC(C)(CC)COC(=O)CCCCC(C)C HYQSRPWWFPRCPW-UHFFFAOYSA-N 0.000 description 1
- AOZDHFFNBZAHJF-UHFFFAOYSA-N [3-hexanoyloxy-2,2-bis(hexanoyloxymethyl)propyl] hexanoate Chemical compound CCCCCC(=O)OCC(COC(=O)CCCCC)(COC(=O)CCCCC)COC(=O)CCCCC AOZDHFFNBZAHJF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- XWJJFJIOTQSSAR-UHFFFAOYSA-N cyclohexylsulfinylcyclohexane Chemical compound C1CCCCC1S(=O)C1CCCCC1 XWJJFJIOTQSSAR-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- JTJNOHFRNUDPDF-UHFFFAOYSA-N didodecyl nonanedioate Chemical compound CCCCCCCCCCCCOC(=O)CCCCCCCC(=O)OCCCCCCCCCCCC JTJNOHFRNUDPDF-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UAKYREKCWXBHCW-UHFFFAOYSA-N dipentan-2-yl decanedioate Chemical compound CCCC(C)OC(=O)CCCCCCCCC(=O)OC(C)CCC UAKYREKCWXBHCW-UHFFFAOYSA-N 0.000 description 1
- 125000005022 dithioester group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DYFCREIBBROJRS-UHFFFAOYSA-N octyl 6-octoxy-6-sulfanylidenehexanoate Chemical compound C(CCCCC(=O)OCCCCCCCC)(=S)OCCCCCCCC DYFCREIBBROJRS-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- KMTUBAIXCBHPIZ-UHFFFAOYSA-N pentane-1,5-dithiol Chemical compound SCCCCCS KMTUBAIXCBHPIZ-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- BOOITXALNJLNMB-UHFFFAOYSA-N tricyclohexyl borate Chemical compound C1CCCCC1OB(OC1CCCCC1)OC1CCCCC1 BOOITXALNJLNMB-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- KDQYHGMMZKMQAA-UHFFFAOYSA-N trihexyl borate Chemical compound CCCCCCOB(OCCCCCC)OCCCCCC KDQYHGMMZKMQAA-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- AZLXEMARTGQBEN-UHFFFAOYSA-N trinonyl borate Chemical compound CCCCCCCCCOB(OCCCCCCCCC)OCCCCCCCCC AZLXEMARTGQBEN-UHFFFAOYSA-N 0.000 description 1
- QUTZUATVZPXUJR-UHFFFAOYSA-N trinonyl phosphite Chemical compound CCCCCCCCCOP(OCCCCCCCCC)OCCCCCCCCC QUTZUATVZPXUJR-UHFFFAOYSA-N 0.000 description 1
- DTBRTYHFHGNZFX-UHFFFAOYSA-N trioctyl borate Chemical compound CCCCCCCCOB(OCCCCCCCC)OCCCCCCCC DTBRTYHFHGNZFX-UHFFFAOYSA-N 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 0.000 description 1
- WAXLMVCEFHKADZ-UHFFFAOYSA-N tris-decyl borate Chemical compound CCCCCCCCCCOB(OCCCCCCCCCC)OCCCCCCCCCC WAXLMVCEFHKADZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous 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
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
-
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- 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
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
-
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/066—Arylene diamines
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- 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
- C10M2227/061—Esters derived from boron
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- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
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- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
Definitions
- This invention relates to a novel composition of matter and to an improved lubricant containing saidmoyel composition as an additive and exhibit-ing. ;de sii3ablythigh extreme pressure properties. More particglgrly, this invention relates-to hydrocarbon and synthetio base lubricating oils containing an adduct of a borate ester and an alkyl phosphite or an alkyl sulfoxide.
- novel compositions of matter are prepared by reacting a borate ester with alkyl phosphitesor alkyl sulfoxides thereby forming adducts ofsaid materials.
- An improved lubricating composition having increased load-carrying properties is obtained by the inclusion of from 0.1 to 5.0 weight percent, preferably 1 to 3 weight percent, of the novel adduct compounds of the presentinvention in lubricating oils.
- preferred additives are adduets of tri-(nonylphenyl) borate and tri-Z-ethylhexyl phosphiteor dimethyl sulfoxide.
- the method of preparing the adduct additive of the present invention is by slowly adding, with agitation the donor molecule, that is, the phosphite or sultoxide to the borate.
- the reactions for the preparation are as follows:
- R may be the same or different hydrocarbyl radicals preferablyalkyl, aryl, alkaryl and aralkyl radicals and R is a monovalent hydrocarbyl radical containing from 1 to 24 carbon atoms and preferably from 1 to carbon l atoms.
- Examples of the various alkyl phosphites that are reactedwith the borate esters to form the adducts of the present invention are tri-Z-ethylhexylphosphite, tri-methyl phosphite, tri-ethyl phosphite,trbZ-methylhexyl phosphite,
- tri-tri-cyclohexy-l phosphi-te tri-isopropyl phosphite, tri-2-iso- .propylhexyl phosphite,. tri-2-ethylcyclohexyl phosphite, tri-2-methylcyclohexyl phosphite, tri-Z-isopropyl-cyclohexyl phosphite, tri-nonyl-phosphite and trinonylphenyl phosphite.
- the lubricating oils of this invention include mineral oils and synthetic lubricating oils.
- the mineral oils found to be useful for this invention include oils having a vis oosity in the range required for lubricating fluids and in particular hydrocarbon mineral oils which include, paraflin base, naphthene base, mixed paraflin-naphthene base and mineral oils of the residual or distillate type.
- the hydrocanbon lubricating base generally has been subjected to solvent refining to improve its oxidation and thermal solvent dewaxing to remove waxy components and to improve the pour properties of the oil.
- hydrocarbon lubricating oils having an SUS viscosity at F. of between 50 to 700 are used in the formulation of the improved lubricants of this invention.
- the mineral lubricating oils to which the additive adducts of this invention are added usually contain other additives designed to impart desirable properties thereto.
- viscosity index improves such as the polymethacrylates having a molecular weight ranging from 500 to 25,000 are usually included therein.
- the V1 'improver normally used is a polymethacrylate having the following recurring structural unit:
- R is an aliphatic radical ranging from 4 to 18 carbon atoms and n is an integer of more than 1.
- esters which constitute the synthetic lubricant composition of this invention are broadly described as esters of hydrocarbyl carboxylic acids. They are high molecular weight materials of lubricating oil characteristics derived from alcohols which are usually aliphatic alcohols containing 1 or more hydroxyl radicals and monocarboxylic acids which are usually aliphatic carboxylic acids containing 1 or more carboxylic acid radicals.
- Widely used synthetic ester lubricants areali-phatic diesters of aliphatic dicarboxylic acids containing 6-42 carbon atoms. From the standpoint of cost and availability, the preferred dibasic acids are adipic acid, sebacic acid and azelaic acid.
- the aliphatic alcohols used to form the diesters usually contain at least 4 carbon atoms and up to 20 or more carbon atoms. C to C alcohols are most commonly used.
- Ether alcohols such as Cellosolve and Car-bitol may also be used in the formation of the aliphatic diesters of organic dicarboxylic acids used as .the lubricating base in the compositions of this invention. Alcohols containing 2 or more hydroxyl radiwls and no hydrogen substituted on the beta carbon atom such as trimethylol propane and pentaerythritol have proven particularly effective in formulating stable high temperature ester lubricants.
- alkyl esters of aliphatic carboxylic acids are the following: di-isooctyl azelate, di-Z-ethylhexyl seb. acate, di-Z-ethylhexyl azelate, di-Z-ethylhexyl adipate, dilauryl azelate, di-sec-amyl sebacate, di-Z-ethylhexyl alkenyl-succinate, di-2-ethoxyethyl sebacate, di-2-(2'-methoxy.- ethoxy) ethyl sebacate, di-2-(2'-ethylbutoxy) ethyl sebacate, di-Z-butoxyethyl azelate, di-2-(2'-butoxyethoxy) ethyl alkenyl-succinate, pentaerythritol tetracaproate and trimethylol
- polyester lubricants formed by a reaction of an aliphatic dicarboxylic acid, a dihydroxy compound and a monofunctional compound, which is either an aliphatic monohydroxy alcohol or an aliphatic monocar-boxylic acid, in specified mol ratios are also employed as the synthetic lubricating base in the compositions of this invention; polyesters of this type are described in US. 2,628,974 on Polyester Synthetic Lubricants, which issued to R. T. Sanderson on February 17, 1953.
- l'olyesters formed by reaction of a mixture containing specified amounts of 2-ethyl-1,B-hexanedtol, sebacic acid, and Z-cthylhexanol and by reaction of a mixture containing adipic acid, diethylene glycol and 2- ethylhexanoic acid illustrate this class of synthetic polyester lubricating bases.
- esters are also used in the formulation of the lubricating composttions of this invention.
- Dithioesters are exemplified by di-Z-ethylhexyl thiosebacate, di-n-octyl thioadipate and the dilaurate of 1,5-pentanedithiol;
- sulfur analogs of polyesters are exemplified by the reaction product of adiphic acid, tltioglycol and Z-ethylhexyl mercaptan.
- Alkyl-substituted phenols are usually incorporated tn the lubricants of the invention as anti-oxidants.
- the preferred and most commonly used alkyl phenol antioxidants is 2,6-di-tertiary octylphenol; 2,6-di-tertiary amyl 4 methylphcnol; and 2,6-di-isopropyl-4-methylphenol. Hindered phenols of this type are employed in concentrations between 0.1 and 1.0 weight percent.
- hindered phenol type anti-oxidants are the most widely used anti-oxidants in the lubricant compositions of the invention
- aryl-substituted amine anti-oxidants such as pltenylnaphthylamine, phenylene diamine, and diphenylamine are also used in lubricants in conjunction with the extreme pressure additive of the invention.
- the amine anti-oxidants are employed in the same concentrations as the hindered phenol anti-oxidant.
- Organic silicones are normally incorporated in the lubricants of the invention to impart thereto anti-foam properties.
- the silicones are usually of the dialkyl or mixed alkyl-aryl silicone type. Dimethyl silicone is normally employed as the anti-foam agent.
- the silicone is incorporated in the lubricant by means of a kerosene concentrate containing 5 to weight percent silicone.
- a very satisfactory anti-foam agent is a kerosene concentrate 10 weight percent dimethyl silicone.
- the kerosene concentrate is employed in an amount sufficient to provide a silicone polymer concentration of from 50 to 250 parts per million based on the total lubricant composition.
- the I.A.E. Gear Test is one of the requirements of British Specification D.E.R.D. 2487, Lubricating Oil, Aircraft Turbine Engine.”
- the I.A.E. Gear Test is also designed to evaluate the scutl-limited load-carrying ability of aircraft gear lubricants.
- Tri-2-ethylhexyl phosphite 75 Dimethyl sulfoxide 60 N. B.--No test data obtained on dimethyl sulfoxlde alone in base 011 because of its insolubility.
- solvent dewaxed and has an SUS viscosity of 100 at 100 F.
- Base oil A gave an I.A.E. Gear Test value of 18.
- Table 1 demonstrates the improvement in toudarrying ability of the base oil when the additives o the present invention are included therein, the LAB.
- Gear Test gave a value of from 60 to 75 for all the samples tested that contained the adduct additives of tri alkaryl borate and alkyl phosphite or sulfoxide of the present invention, whereas the base oil containing the non-adducted phosphite gave a reading of 25 and the non-adducted sulfoxide was insoluble in the hydrocarbon oil. Even though the base oil plus the borate alone gave a favorable reading of 68, it will be seen from the following table that the.
- hydrolytic instability of the borate precludes its use as a lubricant oil additive.
- the GM. oxidation procedure is as follows:
- the Saybolt Universal viscosity at 210 F. is determined on the original sample.
- the lubricant remaining, after removing the samples for the Insoluble Material Test," should be allowed to viscosity at 210 F. is determined upon the decanted portion of the sample.
- Base oil B is a parafiin based distillate which has been furfural refined. lightly acid treated, clay contacted and solvent dewaxed and hasan SUS viscosity of 325 to 350 at 100 F. v
- An adduct composition consisting of an alkaryl borate ester and a reactant selected from the group consisting of tri-(Z-ethylhexyl) phosphite and an alkyl sulfoxide.
- An adduct composition consisting of tri-(nonylphenyl)borate and a reactant selected from the group consisting of tri-(Z-ethylhexyl) phosphite and dimethyl sulfoxide.
- An adduct composition consisting of equal molar amounts of tri(nonylphenyl) borate and dimethyl sulfoxide.
- a lubricating composition containing a major portion of a lubricating oil and an adduct consisting of equal molar amounts of tri(nonylphenyl) borate and'dimethyl sulfoxide.
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Description
3,082,169 ADDUCTS F ALKARYLBORATES WITH TRIAL- KYLPHOSPHITES' 0R ALKYL SULFOXIDE Edward L. Kay, Akron, Ohio, and Edwin C. Knowles,
Ponghlreepsie, N.Y., assignors to Texaco Inc, New
York, N.Y., a corporation of Delaware No Drawing. Filed Sept. 23, 1960, Ser. No. 57,913
9 Claims. (Cl. 252-463) This invention relates to a novel composition of matter and to an improved lubricant containing saidmoyel composition as an additive and exhibit-ing. ;de sii3ablythigh extreme pressure properties. More particglgrly, this invention relates-to hydrocarbon and synthetio base lubricating oils containing an adduct of a borate ester and an alkyl phosphite or an alkyl sulfoxide.
There is an ever increasing need for the improvement of the extreme pressure properties of lubricating oils with ful in the formulation of jet engine lubricants.
in accordance with the present invention novel compositions of matter are prepared by reacting a borate ester with alkyl phosphitesor alkyl sulfoxides thereby forming adducts ofsaid materials. An improved lubricating composition having increased load-carrying properties is obtained by the inclusion of from 0.1 to 5.0 weight percent, preferably 1 to 3 weight percent, of the novel adduct compounds of the presentinvention in lubricating oils. The
preferred additives are adduets of tri-(nonylphenyl) borate and tri-Z-ethylhexyl phosphiteor dimethyl sulfoxide.
The method of preparing the adduct additive of the present invention is by slowly adding, with agitation the donor molecule, that is, the phosphite or sultoxide to the borate. The reactions for the preparation are as follows:
. wherein R may be the same or different hydrocarbyl radicals preferablyalkyl, aryl, alkaryl and aralkyl radicals and R is a monovalent hydrocarbyl radical containing from 1 to 24 carbon atoms and preferably from 1 to carbon l atoms.
Examples of the various borate esters used to form the adducts of thepresent invention are: trihexyl borate,
trioctyl borate, trinonyl borate, tridecyl borate, tridodecyl flborate, tricyclohexyl borate, trihexylphenyl bot-ate, trioctylphenyl borate, trinonylphenylborate, dip-chlorophenyl-monononylphenyb borate, tri-(m,p)-cresyl borate and tridodecylphenyl borat'e. r
Examples of the various alkyl phosphites that are reactedwith the borate esters to form the adducts of the present invention are tri-Z-ethylhexylphosphite, tri-methyl phosphite, tri-ethyl phosphite,trbZ-methylhexyl phosphite,
-tri-cyclohexy-l phosphi-te, tri-isopropyl phosphite, tri-2-iso- .propylhexyl phosphite,. tri-2-ethylcyclohexyl phosphite, tri-2-methylcyclohexyl phosphite, tri-Z-isopropyl-cyclohexyl phosphite, tri-nonyl-phosphite and trinonylphenyl phosphite.
Examples of the various alkyl sulfoxides that are reacted with the borate esters to form the adducts of the present invention-are: dimethyl sultoxide, diethyl sulfbxide, diisopropyl sulfoxide, di-butylsulfoxide, diamyl 70 sulfoxide, dihexyl sulfoxide, dicyclohexyl sulfoxide, di-
j U i d tates Patent 0 Patented Mar. 19, "1963 nonyl sulfoxide, dinonylphenyl sulfoxide and didodecyl stability and viscosity-temperature properties as well as.
sul-foxide.
The lubricating oils of this invention include mineral oils and synthetic lubricating oils. The mineral oils found to be useful for this invention include oils having a vis oosity in the range required for lubricating fluids and in particular hydrocarbon mineral oils which include, paraflin base, naphthene base, mixed paraflin-naphthene base and mineral oils of the residual or distillate type. The hydrocanbon lubricating base generally has been subjected to solvent refining to improve its oxidation and thermal solvent dewaxing to remove waxy components and to improve the pour properties of the oil. Broadly speaking, hydrocarbon lubricating oils having an SUS viscosity at F. of between 50 to 700 are used in the formulation of the improved lubricants of this invention.
The mineral lubricating oils to which the additive adducts of this invention are added usually contain other additives designed to impart desirable properties thereto. For example, viscosity index improves such as the polymethacrylates having a molecular weight ranging from 500 to 25,000 are usually included therein. The V1 'improver normally used is a polymethacrylate having the following recurring structural unit:
wherein R is an aliphatic radical ranging from 4 to 18 carbon atoms and n is an integer of more than 1.
The esters which constitute the synthetic lubricant composition of this invention are broadly described as esters of hydrocarbyl carboxylic acids. They are high molecular weight materials of lubricating oil characteristics derived from alcohols which are usually aliphatic alcohols containing 1 or more hydroxyl radicals and monocarboxylic acids which are usually aliphatic carboxylic acids containing 1 or more carboxylic acid radicals.
Widely used synthetic ester lubricants areali-phatic diesters of aliphatic dicarboxylic acids containing 6-42 carbon atoms. From the standpoint of cost and availability, the preferred dibasic acids are adipic acid, sebacic acid and azelaic acid. The aliphatic alcohols used to form the diesters usually contain at least 4 carbon atoms and up to 20 or more carbon atoms. C to C alcohols are most commonly used. Ether alcohols such as Cellosolve and Car-bitol may also be used in the formation of the aliphatic diesters of organic dicarboxylic acids used as .the lubricating base in the compositions of this invention. Alcohols containing 2 or more hydroxyl radiwls and no hydrogen substituted on the beta carbon atom such as trimethylol propane and pentaerythritol have proven particularly effective in formulating stable high temperature ester lubricants.
Examples of alkyl esters of aliphatic carboxylic acids are the following: di-isooctyl azelate, di-Z-ethylhexyl seb. acate, di-Z-ethylhexyl azelate, di-Z-ethylhexyl adipate, dilauryl azelate, di-sec-amyl sebacate, di-Z-ethylhexyl alkenyl-succinate, di-2-ethoxyethyl sebacate, di-2-(2'-methoxy.- ethoxy) ethyl sebacate, di-2-(2'-ethylbutoxy) ethyl sebacate, di-Z-butoxyethyl azelate, di-2-(2'-butoxyethoxy) ethyl alkenyl-succinate, pentaerythritol tetracaproate and trimethylol propane tri-isooctanoate. I
In addition to such esters, polyester lubricants formed by a reaction of an aliphatic dicarboxylic acid, a dihydroxy compound and a monofunctional compound, which is either an aliphatic monohydroxy alcohol or an aliphatic monocar-boxylic acid, in specified mol ratios are also employed as the synthetic lubricating base in the compositions of this invention; polyesters of this type are described in US. 2,628,974 on Polyester Synthetic Lubricants, which issued to R. T. Sanderson on February 17, 1953. l'olyesters formed by reaction of a mixture containing specified amounts of 2-ethyl-1,B-hexanedtol, sebacic acid, and Z-cthylhexanol and by reaction of a mixture containing adipic acid, diethylene glycol and 2- ethylhexanoic acid illustrate this class of synthetic polyester lubricating bases.
The sulfur analogs of the above-described esters are also used in the formulation of the lubricating composttions of this invention. Dithioesters are exemplified by di-Z-ethylhexyl thiosebacate, di-n-octyl thioadipate and the dilaurate of 1,5-pentanedithiol; sulfur analogs of polyesters are exemplified by the reaction product of adiphic acid, tltioglycol and Z-ethylhexyl mercaptan.
Alkyl-substituted phenols are usually incorporated tn the lubricants of the invention as anti-oxidants. The preferred and most commonly used alkyl phenol antioxidants is 2,6-di-tertiary octylphenol; 2,6-di-tertiary amyl 4 methylphcnol; and 2,6-di-isopropyl-4-methylphenol. Hindered phenols of this type are employed in concentrations between 0.1 and 1.0 weight percent.
Although hindered phenol type anti-oxidants are the most widely used anti-oxidants in the lubricant compositions of the invention, aryl-substituted amine anti-oxidants such as pltenylnaphthylamine, phenylene diamine, and diphenylamine are also used in lubricants in conjunction with the extreme pressure additive of the invention. The amine anti-oxidants are employed in the same concentrations as the hindered phenol anti-oxidant.
Organic silicones are normally incorporated in the lubricants of the invention to impart thereto anti-foam properties. The silicones are usually of the dialkyl or mixed alkyl-aryl silicone type. Dimethyl silicone is normally employed as the anti-foam agent. The silicone is incorporated in the lubricant by means of a kerosene concentrate containing 5 to weight percent silicone. A very satisfactory anti-foam agent is a kerosene concentrate 10 weight percent dimethyl silicone. The kerosene concentrate is employed in an amount sufficient to provide a silicone polymer concentration of from 50 to 250 parts per million based on the total lubricant composition.
To demonstrate the excellent improvement in the loadcarrying ability of lubricating oils containing the additive complex of the present invention, the compositions were subjected to the I.A.E. Gear Test. The I.A.E. Gear Test is one of the requirements of British Specification D.E.R.D. 2487, Lubricating Oil, Aircraft Turbine Engine." The I.A.E. Gear Test is also designed to evaluate the scutl-limited load-carrying ability of aircraft gear lubricants.
The results of the I.A.E. Gear Test on lubricating oil compositions of the present invention are set forth in the following table:
I TABLE I I.A.E. Gear Test Oil: Tooth Load, lbs. Base oil A 18 Base oil A plus 1.25 wt. percent tri-(nonylphenyl) borate 68 Base oil A plus 1.25 wt. percent tri-Z-ethylhexyl phosphite Base Oil A plus 2.0 wt. percent tri-(nonylphenyl) borate adduct of:
Tri-2-ethylhexyl phosphite 75 Dimethyl sulfoxide 60 N. B.--No test data obtained on dimethyl sulfoxlde alone in base 011 because of its insolubility.
solvent dewaxed and has an SUS viscosity of 100 at 100 F.
Base oil A gave an I.A.E. Gear Test value of 18. Table 1 demonstrates the improvement in toudarrying ability of the base oil when the additives o the present invention are included therein, the LAB. Gear Test gave a value of from 60 to 75 for all the samples tested that contained the adduct additives of tri alkaryl borate and alkyl phosphite or sulfoxide of the present invention, whereas the base oil containing the non-adducted phosphite gave a reading of 25 and the non-adducted sulfoxide was insoluble in the hydrocarbon oil. Even though the base oil plus the borate alone gave a favorable reading of 68, it will be seen from the following table that the.
hydrolytic instability of the borate precludes its use as a lubricant oil additive.
To demonstrate the hydrolytic stability of the adducts of the present invention 5 milliliters of water were added to 25 milliliters of the compounds as shown in Table 11 below. The samples were allowed to stand for one hour at ambient temperature. The amount of precipitate present, (boric acid) in the sample was then estimated.
TABLE II Hydrolylic Stability Compound: Amount precipitate Tri-(nonylphenyl) borate Heavy Tri-(nonylphenyl) borate tri-2-ethylhexyl phosphite adduct Trace Tri-(nonylphenyl) borate dimethyl sulfoxide adduct Slight The above demonstrates the hydrolytic instability of the tri-(nonylphenyl) borate as compared to the relatively stable adducts of the present invention.
To demonstrate the oxidation stability of the adducts of the present invention the lubricating oils containing these adducts were subjected to the G.M.. Oxidation Test," the results of which are shown below in Table III.
The GM. oxidation procedure is as follows:
The Saybolt Universal viscosity at 210 F. is determined on the original sample.
Two hundred grams (14).! gram) of the original sample are weighed into a tared 400 ml. beaker; the beaker with its contents are placed on the turntable in the oven, which is maintained at 325 F. (12 F.). The temperature of the oven is read from an ASTM loss on heat thermometer placed in one of the samples on the shelf. The thermometer is observed through the glass window, without opening the door. Rotation of the shelf is maintained at all times, even during temperature observation. The turntable is rotated at a speed of 5 to 6 rpm. After hours, the beaker is removed from the oven, allowed to cool and reweighed. After the measurement of the evaporation loss, stir the lubricant thoroughly in order to distribute any precipitate uniformly throughout the oil. Weigh out approximately 10 grams of the lubricant into an Erlenmeyer fiask of 125 ml. capacity, noting the weight to 0.1 gram. The lubricant remaining after removing the samples for this test is retained for the viscosity test. By means of a graduated cylinder, add 90 ml. of precipitation naphtha, stopper the flask, shake thoroughly and allow to stand for one hour at a temperature of 25 C. At the end of the one hour period filter the mixture through a Gooch crucible that has been previously dried and weighed. Wash the precipitate with a small amount of precipitation naphtha. Allow the suction to continue for five minutes to dry the crucible. Place the crucible in a drying oven at C. for one hour cool in a desiccator and weigh.
The lubricant remaining, after removing the samples for the Insoluble Material Test," should be allowed to viscosity at 210 F. is determined upon the decanted portion of the sample.
TABLE III G. M. Oxidation Test 100 F. Neut. Amount Oil Kin. Vis. No.
Inc., Inc, Sludge percent Base Oil 13 ll 0.4 trace. Base Oil I3 plus 1.25 wt. percent tri- 23 0.6 trace. (nonylphcnyl)bornte.
Base Oil B plus 2.0 wt. percent tri- (nonylphenyl) bornlc utlduct oi:
'Iri-2-ethylhoxyl phosphite 6 0v 2 slight. Dilnethyl sulioxiile I 28 0. 6 slight.
Base oil B is a parafiin based distillate which has been furfural refined. lightly acid treated, clay contacted and solvent dewaxed and hasan SUS viscosity of 325 to 350 at 100 F. v
The oxidation data shown in Table III above indicates the superiority of the adduct of tri-(nonylphenyl) borate with tri-Z-ethylhexyl phosphite. Although the adduct of tri(nonylphenyl) borate and dimethyl sulfoxide gave data comparable to that of the borate alone, it must be remembered from Table II that the borate alone is hydrolytically unstable and therefore not feasible as a lube oil additive.
We claim:
1. An adduct composition consisting of an alkaryl borate ester and a reactant selected from the group consisting of tri-(Z-ethylhexyl) phosphite and an alkyl sulfoxide.
2. An adduct composition consisting of tri-(nonylphenyl)borate and a reactant selected from the group consisting of tri-(Z-ethylhexyl) phosphite and dimethyl sulfoxide.
3. An aduct composition consisting of equal molar,
amounts of tri(nonylphenyl) borate and Iri-(Z-ethylhexyl) phosphite.
4. An adduct composition consisting of equal molar amounts of tri(nonylphenyl) borate and dimethyl sulfoxide.
5. A lubricating composition containing a major portion of a lubricating oil and an adduct consisting of an alkaryl boratc ester and a reactant selected from the group 8. A lubricating composition containing a major por-v tion of a lubricating oil and an adduct consisting of equal molar amounts of tri-(nonylphen yl) borate and tri-Z- (ethylhexyl) phosphite.
9. A lubricating compositioncontaining a major portion of a lubricating oil and an adduct consisting of equal molar amounts of tri(nonylphenyl) borate and'dimethyl sulfoxide.
References Cited" in the file of this patent UNITED STATES PATENTS 2,160,881 Loane et al. June 6, 1939 2,160,917 Shoemaker et al. June 6, 1939 2,648,696 Whetstone Aug. 11, 1953 2,816,128 Allen Dec. 10, 1957 2,956,869
DeGray Oct. 18, 1960
Claims (1)
1. AN ADDUCT COMPOSITION CONSISTING OF AN ALKARYL BORATE ESTER AND A REACTANT SELECTED FROM THE GROUP CONSISTING OF TRI-(2-ETHYLHEXYL) PHOSPHITE AND AN ALKYL SULFOXIDE.
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US57913A US3082169A (en) | 1960-09-23 | 1960-09-23 | Adducts of alkarylborates with trialkylphosphites or alkyl sulfoxide |
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US57913A US3082169A (en) | 1960-09-23 | 1960-09-23 | Adducts of alkarylborates with trialkylphosphites or alkyl sulfoxide |
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2160917A (en) * | 1937-06-10 | 1939-06-06 | Standard Oil Co | Lubricant |
US2160881A (en) * | 1937-06-10 | 1939-06-06 | Standard Oil Co | Lubricant |
US2648696A (en) * | 1951-06-19 | 1953-08-11 | Shell Dev | Mixed acid anhydrides and process for production of same |
US2816128A (en) * | 1956-07-27 | 1957-12-10 | Fmc Corp | Phosphate esters of oximes |
US2956869A (en) * | 1958-04-21 | 1960-10-18 | Standard Oil Co | Motor fuel composition effective for minimizing the formation of carburetor deposits |
-
1960
- 1960-09-23 US US57913A patent/US3082169A/en not_active Expired - Lifetime
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2160917A (en) * | 1937-06-10 | 1939-06-06 | Standard Oil Co | Lubricant |
US2160881A (en) * | 1937-06-10 | 1939-06-06 | Standard Oil Co | Lubricant |
US2648696A (en) * | 1951-06-19 | 1953-08-11 | Shell Dev | Mixed acid anhydrides and process for production of same |
US2816128A (en) * | 1956-07-27 | 1957-12-10 | Fmc Corp | Phosphate esters of oximes |
US2956869A (en) * | 1958-04-21 | 1960-10-18 | Standard Oil Co | Motor fuel composition effective for minimizing the formation of carburetor deposits |
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