US3185644A - Lubricating compositions containing amine salts of boron-containing compounds - Google Patents
Lubricating compositions containing amine salts of boron-containing compounds Download PDFInfo
- Publication number
- US3185644A US3185644A US83173A US8317361A US3185644A US 3185644 A US3185644 A US 3185644A US 83173 A US83173 A US 83173A US 8317361 A US8317361 A US 8317361A US 3185644 A US3185644 A US 3185644A
- Authority
- US
- United States
- Prior art keywords
- lubricating
- boron
- tri
- amine salts
- carbon atoms
- 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
- -1 amine salts Chemical class 0.000 title claims description 48
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical class [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims description 5
- 229910052796 boron Inorganic materials 0.000 title claims description 5
- 239000000203 mixture Substances 0.000 title description 15
- 230000001050 lubricating effect Effects 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 title description 5
- 239000010687 lubricating oil Substances 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 239000000314 lubricant Substances 0.000 description 15
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 235000006708 antioxidants Nutrition 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 239000002199 base oil Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000002518 antifoaming agent Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 150000001638 boron Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 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
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229940067597 azelate Drugs 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
- 238000009472 formulation Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000010688 mineral lubricating oil Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 229940116351 sebacate Drugs 0.000 description 2
- 229920005573 silicon-containing polymer Polymers 0.000 description 2
- 150000003463 sulfur Chemical class 0.000 description 2
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 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
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical compound CC(N)O UJPKMTDFFUTLGM-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
- HYVGFUIWHXLVNV-UHFFFAOYSA-N 2-(n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=CC=C1 HYVGFUIWHXLVNV-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- UCJMHYXRQZYNNL-UHFFFAOYSA-N 2-Ethyl-1-hexanethiol Chemical compound CCCCC(CC)CS UCJMHYXRQZYNNL-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SOASHAVJCWKTKL-UHFFFAOYSA-N 4-methyl-2,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C)=CC(C(C)(C)CC)=C1O SOASHAVJCWKTKL-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
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-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
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 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
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- ZDWGXBPVPXVXMQ-UHFFFAOYSA-N bis(2-ethylhexyl) nonanedioate Chemical compound CCCCC(CC)COC(=O)CCCCCCCC(=O)OCC(CC)CCCC ZDWGXBPVPXVXMQ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 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
- 150000005690 diesters Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000005022 dithioester group Chemical group 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
- 238000011156 evaluation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000000743 hydrocarbylene group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 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
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 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
- 239000002244 precipitate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007670 refining 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
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-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
- C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
-
- 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic 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
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated 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
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
- C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/11—Complex polyesters
- C10M2209/111—Complex polyesters having dicarboxylic acid centres
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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
- 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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- 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
- 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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- 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
- 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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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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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
- 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
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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
- 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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- 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
- C10M2229/02—Unspecified siloxanes; Silicones
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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
- 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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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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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
- 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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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen bonds
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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
- 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
Definitions
- novel amine salts of the present invention are formed by the reaction of a hydroxy substituted amine and a tri-hydrocarbyl borate and are useful as load carrying additives for mineral and synthetic base lubricating oils.
- the present invention is concerned with these novel salts and with their use as lubricating additives.
- the amine salts of tetra-covalent boron acids of the present invention are known as intra-molecular type salts and are represented by the following general formula:
- Ris a monovalent hydrocarbyl radical containing one or more carbon atoms to about 30 carbon atoms
- R is a divalent hydrocarbylene radical containing 1 to carbon atoms
- R" and R' are hydrogen or monovalent hydrocarbyl radicals containing -1 to 24 carbon .atoms.
- the acid amine salt is present in the lubricating oil in a concentration suflicient to lend load carrying properties to the lubricating oil.
- the acid 'arnine saltconcentration is usually between 0.05 and 5.0 weight percent.
- hydrocanbyl when used herein denotes a monovalent hydrocarbon radical and the term hydrocarby-lene when used herein denotes a divalent hydrocarbon radical.
- compositions of the present invennon are prepared by the reaction of a hydroxy substituted amine with a tri-alkyl or -aryl borate to form the intra-molecular substituted aminesalts of the tetra-covalent boron acid.
- hydroxy substituted amines employed in the formation of the novel amine salt of th intra-molecular tetra-covalent boron acids are represented by the formula:
- R is a divalent hydrocarbylene radical containing 1 .to 1 0 and preferably 2 to 6' carbon atoms and R and R are hydrogen or a monovalent hydrocarbyl radical containing 1 to 24 and preferably 1 to 8 carbon atoms.
- R and R are hydrogen or a monovalent hydrocarbyl radical containing 1 to 24 and preferably 1 to 8 carbon atoms.
- effective hydroxy substituted amines are N- phenyl, N-ethyl aminoethan-ol N,N-diethylaminoethanol,
- the intra-molecular tetra-covalent boronacids employed in the formation of the present invention are transitory compounds and as such do not exist in the isolated state. They do, however, form st-able salts.
- the acids are formed by reaction of a tri-alkyl, or tri-aryl borate with a hydroxy substituted amine which immediately, as the brackets in the equation below indicate, is neutralized by the amine portion thereof to form the salt which may be illustrated by the following general equation:
- the amine salts of the present invention are illustrated by the following: N,N-diethylaminoethylate bore-trimethylate, N-phenyl N ethylaminoethylate 'boro-tri-npropylate N,N-diethylaminoethylate 'boro-tri-n-propylate, octyl aminoethylate bono-tri-n-propylate and t-C -C aminoethylate boro-tri-n-propylate.
- the lubricating oils of this invention include hydrocarbon lubricating oils and synthetic lubricating oils.
- the hydrocarbon oils found to be useful for this invention include oils having'a viscosity in the range required for lubricating fluids and'in particular hydrocarbon mineral oils which include paraflin base, naphthene base, mixed paraffin-naphthene base and mineral oils of the residual or distillate type.
- the hydrocarbon lubricating base generally has been subjected to solvent refining to improve its oxidation and thermal stability and viscosity-temperature properties as well as solvent dewaxing to. remove esters of hydrocarbyl carboxylic acids.
- hydrocarbon lubricating oils having an SUS viscosity at 100 F. of between 50 to 2500 are used in the formulation of the improved lubricants of this invention.
- the mineral lubricating oils to which the amine salts of this invention are added usually contain other additives designed to impart desirable properties thereto.
- viscosity index improvers 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:
- hydrocarbon lubricating oils of this invention may also contain other useful additives such as metal sulfonates to afford additional detergent-dispersant properties, metal dialkyl dithiophosphates to afford additional corrosion and oxidation resistance, anti-foam agents such as silicone polymers in the amount of about 5 to 200 parts per million, etc.
- esters which constituted the synthetic lubricant composition of this invention are broadly described as 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 are aliphatic diesters of aliphatic dicarboxylic acids containing 6 to 12 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. (I -C alcohols are most commonly used.
- Ether alcohols such as Cellosolve and Carbitolmay 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 radicals and no hydrogen substituted on the beta carbon atom such as triethylol 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 sebacate, di-2-ethylhexyl azelate, di-Z-ethylhexyl adipate, dilauryl azelate, di-2-sec-amyl sebacate, di-Z-ethylhexyl alkenyl succinate, di-2-ethoxyethyl sebacate, di-2-(2'- methoxyethoxy) ethyl sebacate, di2(2'-ethylbutoxy) ethyl sebacate, di-Z-butoxyethyl azelate, di-2-(2butoxyethoxy)ethyl alkenyl-succinate, pentaerythritol tetracaproate and trimethylol propane tri-iso-octanoate
- 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 monocarboxylic 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 U.S. 2,628,974 on Polyester Synthetic Lubricants, which issued to R. T. Sanderson on February 17, 1953.
- Polyesters formed by reaction of a mixture containing specified amounts of 2-ethyl1,3-hexanediol, sebacic acid, and Z-ethylhexanol 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 compositions of this invention.
- Dithioesters are exemplified by di- Z-ethylhexyl thiosebacate, di-n-octyl thioadipate and the di-laurate of 1,5-pentanedithiol; sulfur analogs of polyesters are exemplified by the reaction product of adipic acid, thioglycol and 2-ethylhexyl mercaptan.
- Alkyl-substituted phenols are usually incorporated in the lubricants of the invention as anti-oxidants.
- the preferred and most commonly used alkyl phenol anti-oxidants is 2,6-di-tertiary octylphenol; 2,6-di-tertiary amyl-4- methylphenol; 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 phenylnaphthylamine, 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 incor-- porated in the lubricant by means of a kerosene concen trate containing 5 to 15 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 to 250 parts per million based on the total lubricant composition.
- the I.A.E. Gear Test is one of the requirements of the British Specification D.E.R.D. 2487, Lubricating Oil, Aircraft Turbine Engine, Synthetic Type.
- the I.A.E. Gear Test is also designed to evaluate the scuff limited, load carrying ability of aircraft gear bydrocarbon lubricants.
- Table l I.A.E. GEAR TEST Oil Tooth load, lbs. Base Oil B 20 Base Oil B plus 0.7 wt. percent beta-diethylarninoethanolate boro-tri-n-propylate Base Oil B plus 1.0 wt. percent t-(C -C aminoethanolate boro-tri-n-propylate 105 Base Oil B consisted of a paraffin base crude which has been furfural refined, lightly acid treated, clay contacted and solvent dewaxed and has an SUS viscosity at F. of 150. Table I demonstrates the improvement in the load carrying ability of the base oil when the additives of the present invention are included therein.
- the amine salt of the intra-molecular tetra-covalent boron all-ls a was) (R0 B OR'N+HRR" wherein R is a monovalent hydrocarbyl radical containing one carbon atom to about 30 carbon atoms, R is a divalent hydrocarbylene radical containing 1 to 10 carbon atoms and R" and R' are selected from the group consisting of hydrogen and a monovalent hydrocarbyl radical containing 1 to 24 carbon atoms.
- a lubricating oil as described in claim 2 containing 0.5 to 5.0 weight percent of an amine salt having the formula:
- a lubricating oil as described in claim 2 containing 0.5 .to 5.0 weight percent of an amine salt having the formula:
- R is an alkyl group containing 11 to 14 carbon atoms.
- a lubricating oil composition comprising a mineral lubricating oil and 0.05 to 5 .0 Weight percent of an amine salt of a tetra-covalent boron acid having the general formula:
- R is a monovalent hydrocarbyl radical containing 1 to about 30 carbon atoms
- R is a divalent hydrocarbylene radical containing 1 to 10 carbon atoms
- R" and R are selected from the group consisting of hydrogen and a monovalent hydrocarbyl radical containing 1 to 24 carbon atoms.
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Description
United States Patent 3,185,644 LUBRICATING COMPOSITIONS CONTAHNING AMINE SALTS 0F BORON-CONTAINING COMPOUNDS Edwin C. Knowles, Poughkeepsie, N.Y., and Edward L. Kay, Akron, Ohio, assignors to Texaco Inc, New York,
N.Y., a corporation of Delaware No Drawing. Filed Jan. 17, 1961, Ser. No. 83,173
6 Claims. (Cl. 252-336) V and thermally stable in both storage and use. The novel amine salts of the present invention are formed by the reaction of a hydroxy substituted amine and a tri-hydrocarbyl borate and are useful as load carrying additives for mineral and synthetic base lubricating oils.
The present invention is concerned with these novel salts and with their use as lubricating additives. The amine salts of tetra-covalent boron acids of the present invention are known as intra-molecular type salts and are represented by the following general formula:
wherein Risa monovalent hydrocarbyl radical containing one or more carbon atoms to about 30 carbon atoms, R is a divalent hydrocarbylene radical containing 1 to carbon atoms and R" and R' are hydrogen or monovalent hydrocarbyl radicals containing -1 to 24 carbon .atoms. The acid amine salt is present in the lubricating oil in a concentration suflicient to lend load carrying properties to the lubricating oil. The acid 'arnine saltconcentration is usually between 0.05 and 5.0 weight percent.
The term hydrocanbyl when used herein denotes a monovalent hydrocarbon radical and the term hydrocarby-lene when used herein denotes a divalent hydrocarbon radical. a The compositions of the present invennon are prepared by the reaction of a hydroxy substituted amine with a tri-alkyl or -aryl borate to form the intra-molecular substituted aminesalts of the tetra-covalent boron acid.
The hydroxy substituted amines employed in the formation of the novel amine salt of th intra-molecular tetra-covalent boron acids are represented by the formula:
/RII 1E[OR"N RI/I wherein R is a divalent hydrocarbylene radical containing 1 .to 1 0 and preferably 2 to 6' carbon atoms and R and R are hydrogen or a monovalent hydrocarbyl radical containing 1 to 24 and preferably 1 to 8 carbon atoms. Examples of effective hydroxy substituted amines are N- phenyl, N-ethyl aminoethan-ol N,N-diethylaminoethanol,
tC C aminoethanol, octyl aminoisopropanol. octyl aminobutanol and o-aminophenol. V
The intra-molecular tetra-covalent boronacids employed in the formation of the present invention are transitory compounds and as such do not exist in the isolated state. They do, however, form st-able salts. The acids are formed by reaction of a tri-alkyl, or tri-aryl borate with a hydroxy substituted amine which immediately, as the brackets in the equation below indicate, is neutralized by the amine portion thereof to form the salt which may be illustrated by the following general equation:
wherein the values for R, R, R" and R are the same as previously indicated.
The amine salts of the present invention are illustrated by the following: N,N-diethylaminoethylate bore-trimethylate, N-phenyl N ethylaminoethylate 'boro-tri-npropylate N,N-diethylaminoethylate 'boro-tri-n-propylate, octyl aminoethylate bono-tri-n-propylate and t-C -C aminoethylate boro-tri-n-propylate.
The preparation of the specific novel acid amine salts of the tetra-covalent boron acids of the present invention are illustrated in the following examples,
EXAMPLE 1 Preparation of N,N-diethylaminoethylate borotrimethylate 234 grams, 2. 0 mols, N,N-diethylaminoethanol were added to 207 grams, 2.0 mols, tri-met'hyl borate, the pot temperature rose from 27 C. to about 30 C. The reaction product was a clear Water-white liquid.
EXAMPLE 2 Preparation of N-phenyl-N-ethylaminoethylate boro-tri-npropylate 165 grams, 1.0 mol, N-phenyl-N-ethyl-ethanol amine were added to 188 grams, 1.0 mol of tri-n-pnopyl borate, no exothermic reaction took place. The reaction mixture was refluxed for one hour and the reaction product was a clear light amber liquid.
EXAMPLE 3 Preparation of N,N-diethylaminoethy late boro-zri-n- .p p a 117 grams, 1.0 mol, N,N-diethylaminoethano1 were added to 188 grams, 1.0 mol, tri-n-propyl borate, as the aminoethanol was addeda white precipitate formed which dissolved upon further addition of the N,N-diet-hylaminoethanol. The pot temperature rose from 30 to 34 C.
EXAMPLE 4 v Preparation of t-'(C C )amin0ethylate boro-tripropylate grams (0.5 mol) MG -C aminoethanol was added slowly to 86 grams (0.46 mol) of tri-n-propyl borate. The temperature rose from 27 C. to about 30 C, over a fifteen minute addition period. The reaction product was a clear water-White liquid.
The lubricating oils of this invention include hydrocarbon lubricating oils and synthetic lubricating oils. The hydrocarbon oils found to be useful for this invention include oils having'a viscosity in the range required for lubricating fluids and'in particular hydrocarbon mineral oils which include paraflin base, naphthene base, mixed paraffin-naphthene base and mineral oils of the residual or distillate type. The hydrocarbon lubricating base generally has been subjected to solvent refining to improve its oxidation and thermal stability and viscosity-temperature properties as well as solvent dewaxing to. remove esters of hydrocarbyl carboxylic acids.
the oil. Broadly speaking, hydrocarbon lubricating oils having an SUS viscosity at 100 F. of between 50 to 2500 are used in the formulation of the improved lubricants of this invention.
The mineral lubricating oils to which the amine salts of this invention are added usually contain other additives designed to impart desirable properties thereto. For example, viscosity index improvers 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:
[deni OOOR 11 wherein R is an aliphatic radical ranging from butyl to stearyl and n is an integer of more than 1.
The use of various metal base organic type additives has been found effective and are generally incorporated in the lubricating oils of this invention, particularly those oils used in high speed, spark ignition and diesel engines to reduce ring sticking, minimize lacquer formation and carbon deposits.
The hydrocarbon lubricating oils of this invention may also contain other useful additives such as metal sulfonates to afford additional detergent-dispersant properties, metal dialkyl dithiophosphates to afford additional corrosion and oxidation resistance, anti-foam agents such as silicone polymers in the amount of about 5 to 200 parts per million, etc.
The esters which constituted the synthetic lubricant composition of this invention are broadly described as 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 are aliphatic diesters of aliphatic dicarboxylic acids containing 6 to 12 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. (I -C alcohols are most commonly used. Ether alcohols such as Cellosolve and Carbitolmay 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 radicals and no hydrogen substituted on the beta carbon atom such as triethylol 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 sebacate, di-2-ethylhexyl azelate, di-Z-ethylhexyl adipate, dilauryl azelate, di-2-sec-amyl sebacate, di-Z-ethylhexyl alkenyl succinate, di-2-ethoxyethyl sebacate, di-2-(2'- methoxyethoxy) ethyl sebacate, di2(2'-ethylbutoxy) ethyl sebacate, di-Z-butoxyethyl azelate, di-2-(2butoxyethoxy)ethyl alkenyl-succinate, pentaerythritol tetracaproate and trimethylol propane tri-iso-octanoate.
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 monocarboxylic 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 U.S. 2,628,974 on Polyester Synthetic Lubricants, which issued to R. T. Sanderson on February 17, 1953. Polyesters formed by reaction of a mixture containing specified amounts of 2-ethyl1,3-hexanediol, sebacic acid, and Z-ethylhexanol 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 compositions of this invention. Dithioesters are exemplified by di- Z-ethylhexyl thiosebacate, di-n-octyl thioadipate and the di-laurate of 1,5-pentanedithiol; sulfur analogs of polyesters are exemplified by the reaction product of adipic acid, thioglycol and 2-ethylhexyl mercaptan.
Alkyl-substituted phenols are usually incorporated in the lubricants of the invention as anti-oxidants. The preferred and most commonly used alkyl phenol anti-oxidants is 2,6-di-tertiary octylphenol; 2,6-di-tertiary amyl-4- methylphenol; 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 phenylnaphthylamine, 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. I
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 incor-- porated in the lubricant by means of a kerosene concen trate containing 5 to 15 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 to 250 parts per million based on the total lubricant composition.
To demonstrate the excellent improvement in the load carrying ability of lubricating oil containing the amine salts of the present invention, high speed gear scuff test was used. This test is called the I.A.E. Gear Test and is intended for the evaluation of the load carrying ability or the scuff limited load carrying ability of those lubricants used in reduction and accessory drives of turbo-jet and turbo-prop engines. The I.A.E. Gear Test is one of the requirements of the British Specification D.E.R.D. 2487, Lubricating Oil, Aircraft Turbine Engine, Synthetic Type. The I.A.E. Gear Test is also designed to evaluate the scuff limited, load carrying ability of aircraft gear bydrocarbon lubricants.
The results of the LAB. Gear Test on lubricating oil compositions of the present invention are set forth in the following table:
Table l I.A.E. GEAR TEST Oil: Tooth load, lbs. Base Oil B 20 Base Oil B plus 0.7 wt. percent beta-diethylarninoethanolate boro-tri-n-propylate Base Oil B plus 1.0 wt. percent t-(C -C aminoethanolate boro-tri-n-propylate 105 Base Oil B consisted of a paraffin base crude which has been furfural refined, lightly acid treated, clay contacted and solvent dewaxed and has an SUS viscosity at F. of 150. Table I demonstrates the improvement in the load carrying ability of the base oil when the additives of the present invention are included therein.
As is known in the art many organo borate compounds do not always perform as satisfactory additives for lubri cants, fuel and the like because of their hydrolytic instability and it is to this end that the salts of the present invention demonstrate at least one of their advantages. The amine salt of the intra-molecular tetra-covalent boron all-ls a was) (R0 B OR'N+HRR" wherein R is a monovalent hydrocarbyl radical containing one carbon atom to about 30 carbon atoms, R is a divalent hydrocarbylene radical containing 1 to 10 carbon atoms and R" and R' are selected from the group consisting of hydrogen and a monovalent hydrocarbyl radical containing 1 to 24 carbon atoms.
2. A lubricating oil as described in claim 2 containing 0.5 to 5.0 weight percent of an amine salt having the formula:
(C2H5 2N+HCH2CH2OB (OCH3 3 3. A lubricating oil as described in claim 2 containing a 0.5 to 5.0 weight percent of an amine salt having the formula:
4. A lubricating oil as described in claim 2 containing 0.5 .to 5.0 weight percent of an amine salt having the formula:
(CZHS)2N+H CH2CHZO B -(OC3HT)3 5. A lubricating oil as described in claim 2 containing 6 0.5 to 5.0 weight percent of an ammonium salt having the formula:
wherein R is an alkyl group containing 11 to 14 carbon atoms.
6. A lubricating oil composition comprising a mineral lubricating oil and 0.05 to 5 .0 Weight percent of an amine salt of a tetra-covalent boron acid having the general formula:
wherein R is a monovalent hydrocarbyl radical containing 1 to about 30 carbon atoms, R is a divalent hydrocarbylene radical containing 1 to 10 carbon atoms and R" and R are selected from the group consisting of hydrogen and a monovalent hydrocarbyl radical containing 1 to 24 carbon atoms.
References Cited by the Examiner UNITED STATES PATENTS 2,312,208 2/43 Clayton et al 25233.6 2,582,191 1/52 Curtis 260462 2,629,732 2/53 Schechter 260 -462 2,795,547 6/57 Harle et a1. 252-496 2,795,548 6/57 Thomas et al. 25249.6 2,957,840 10/60 Groszos et a1. 260-462 X DANIEL E. WYMAN, Primary Examiner.
JULIUS GREENWALD, Examiner.
Claims (1)
1. A LUBRICATING OIL CONTAINING AN AMINE SALT OF A TETRACOVALENT BORON ACID IN AN AMOUNT SUFFICIENT TO IMPROVE THE LOAD CARRYING PROPERTIES THEREOF, SAID AMINE SALT HAVING THE FOLLOWING GENERAL FORMULA:
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83173A US3185644A (en) | 1961-01-17 | 1961-01-17 | Lubricating compositions containing amine salts of boron-containing compounds |
| US400875A US3321506A (en) | 1961-01-17 | 1964-10-01 | Borate amine salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83173A US3185644A (en) | 1961-01-17 | 1961-01-17 | Lubricating compositions containing amine salts of boron-containing compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3185644A true US3185644A (en) | 1965-05-25 |
Family
ID=22176644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US83173A Expired - Lifetime US3185644A (en) | 1961-01-17 | 1961-01-17 | Lubricating compositions containing amine salts of boron-containing compounds |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3185644A (en) |
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3321506A (en) * | 1961-01-17 | 1967-05-23 | Texaco Inc | Borate amine salt |
| US3853818A (en) * | 1973-01-22 | 1974-12-10 | Air Prod & Chem | Aminoborate esters as polyurethane catalysts |
| US3969236A (en) * | 1974-03-13 | 1976-07-13 | Waldstein David A | Compositions containing monoalkanolamide borates |
| US4155739A (en) * | 1977-10-17 | 1979-05-22 | Texaco Trinidad, Inc. | Boron-containing spray oil composition for foliar application |
| US4382006A (en) * | 1979-11-06 | 1983-05-03 | Mobil Oil Corporation | Friction reduction additives and compositions thereof |
| US4400284A (en) * | 1980-06-12 | 1983-08-23 | Union Oil Company Of California | Boron derivatives as lubricant additives |
| JPS58176299A (en) * | 1982-04-12 | 1983-10-15 | Kyodo Yushi Kk | Hot rolling oil for steel materials |
| US4511516A (en) * | 1980-06-12 | 1985-04-16 | Union Oil Company Of California | Boron containing heterocyclic compounds |
| US4557843A (en) * | 1981-11-09 | 1985-12-10 | Union Oil Company Of California | Boron-containing heterocyclic compounds and lubricating compositions containing the same |
| US4595514A (en) * | 1983-08-23 | 1986-06-17 | Union Oil Company Of California | Boron-containing heterocyclic compound and lubricating compositions containing same |
| US4623474A (en) * | 1981-12-10 | 1986-11-18 | Union Oil Company Of California | Oxidation and corrosion inhibitors for boron-containing lubricants |
| US4627930A (en) * | 1980-06-12 | 1986-12-09 | Union Oil Company Of California | Boron-containing heterocyclic compounds and lubricating oil containing same |
| US4629579A (en) * | 1980-06-12 | 1986-12-16 | Union Oil Company Of California | Boron derivatives |
| US4629580A (en) * | 1980-06-12 | 1986-12-16 | Union Oil Company Of California | Boron-containing heterocyclic compounds and lubricating oil containing same |
| US4657686A (en) * | 1980-06-12 | 1987-04-14 | Union Oil Company Of California | Lubricating compositions |
| US4686056A (en) * | 1980-06-12 | 1987-08-11 | Union Oil Company Of California | Metal-boron derivatives as lubricant additives |
| US4724099A (en) * | 1980-06-12 | 1988-02-09 | Union Oil Company Of California | Lubricating compositions |
| US4801729A (en) * | 1980-06-12 | 1989-01-31 | Union Oil Company Of California | Lubricating compositions |
| US4892670A (en) * | 1985-01-29 | 1990-01-09 | Union Oil Company Of California | Lubricating compositions |
| US20060106243A1 (en) * | 2004-10-21 | 2006-05-18 | R. T. Vanderbilt Company, Inc. | Hydroxyalkyldithiocarbamate esters |
| JP2012193129A (en) * | 2011-03-15 | 2012-10-11 | Idemitsu Kosan Co Ltd | Boronated amino alcohol compound, additive for lubricating oil, and lubricating oil composition |
| EP3249029A1 (en) | 2016-05-23 | 2017-11-29 | Infineum International Limited | Highly borated dispersant concentrates for lubricating oil compositions and methods for forming same |
| US10336963B2 (en) | 2015-02-26 | 2019-07-02 | The Lubrizol Corporation | Aromatic tetrahedral borate compounds for lubricating compositions |
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|---|---|---|---|---|
| US2312208A (en) * | 1941-04-12 | 1943-02-23 | Standard Oil Co California | Compounded hydrocarbon oil |
| US2582191A (en) * | 1946-09-30 | 1952-01-08 | Curtis David | Amino salts of boric acid-aliphatic polyhydroxy carboxylic acid condensation product |
| US2629732A (en) * | 1951-05-10 | 1953-02-24 | Callery Chemical Co | Ammonia-methyl borate compound |
| US2795548A (en) * | 1954-06-29 | 1957-06-11 | California Research Corp | Lubricant compositions |
| US2795547A (en) * | 1954-06-29 | 1957-06-11 | California Research Corp | Lubricating oil compositions |
| US2957840A (en) * | 1957-10-28 | 1960-10-25 | American Cyanamid Co | Composition comprising an acrylonitrile polymer and tri-n-propanolamine borate |
-
1961
- 1961-01-17 US US83173A patent/US3185644A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2312208A (en) * | 1941-04-12 | 1943-02-23 | Standard Oil Co California | Compounded hydrocarbon oil |
| US2582191A (en) * | 1946-09-30 | 1952-01-08 | Curtis David | Amino salts of boric acid-aliphatic polyhydroxy carboxylic acid condensation product |
| US2629732A (en) * | 1951-05-10 | 1953-02-24 | Callery Chemical Co | Ammonia-methyl borate compound |
| US2795548A (en) * | 1954-06-29 | 1957-06-11 | California Research Corp | Lubricant compositions |
| US2795547A (en) * | 1954-06-29 | 1957-06-11 | California Research Corp | Lubricating oil compositions |
| US2957840A (en) * | 1957-10-28 | 1960-10-25 | American Cyanamid Co | Composition comprising an acrylonitrile polymer and tri-n-propanolamine borate |
Cited By (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3321506A (en) * | 1961-01-17 | 1967-05-23 | Texaco Inc | Borate amine salt |
| US3853818A (en) * | 1973-01-22 | 1974-12-10 | Air Prod & Chem | Aminoborate esters as polyurethane catalysts |
| US3969236A (en) * | 1974-03-13 | 1976-07-13 | Waldstein David A | Compositions containing monoalkanolamide borates |
| US4022713A (en) * | 1974-03-13 | 1977-05-10 | Waldstein David A | Compositions containing monoalkanolamide borates |
| US4155739A (en) * | 1977-10-17 | 1979-05-22 | Texaco Trinidad, Inc. | Boron-containing spray oil composition for foliar application |
| US4382006A (en) * | 1979-11-06 | 1983-05-03 | Mobil Oil Corporation | Friction reduction additives and compositions thereof |
| US4511516A (en) * | 1980-06-12 | 1985-04-16 | Union Oil Company Of California | Boron containing heterocyclic compounds |
| US4400284A (en) * | 1980-06-12 | 1983-08-23 | Union Oil Company Of California | Boron derivatives as lubricant additives |
| US4686056A (en) * | 1980-06-12 | 1987-08-11 | Union Oil Company Of California | Metal-boron derivatives as lubricant additives |
| US4801729A (en) * | 1980-06-12 | 1989-01-31 | Union Oil Company Of California | Lubricating compositions |
| US4724099A (en) * | 1980-06-12 | 1988-02-09 | Union Oil Company Of California | Lubricating compositions |
| US4627930A (en) * | 1980-06-12 | 1986-12-09 | Union Oil Company Of California | Boron-containing heterocyclic compounds and lubricating oil containing same |
| US4629579A (en) * | 1980-06-12 | 1986-12-16 | Union Oil Company Of California | Boron derivatives |
| US4629580A (en) * | 1980-06-12 | 1986-12-16 | Union Oil Company Of California | Boron-containing heterocyclic compounds and lubricating oil containing same |
| US4657686A (en) * | 1980-06-12 | 1987-04-14 | Union Oil Company Of California | Lubricating compositions |
| US4557843A (en) * | 1981-11-09 | 1985-12-10 | Union Oil Company Of California | Boron-containing heterocyclic compounds and lubricating compositions containing the same |
| US4623474A (en) * | 1981-12-10 | 1986-11-18 | Union Oil Company Of California | Oxidation and corrosion inhibitors for boron-containing lubricants |
| JPS58176299A (en) * | 1982-04-12 | 1983-10-15 | Kyodo Yushi Kk | Hot rolling oil for steel materials |
| JPS6147199B2 (en) * | 1982-04-12 | 1986-10-17 | Kyodo Yushi Kk | |
| US4595514A (en) * | 1983-08-23 | 1986-06-17 | Union Oil Company Of California | Boron-containing heterocyclic compound and lubricating compositions containing same |
| US4892670A (en) * | 1985-01-29 | 1990-01-09 | Union Oil Company Of California | Lubricating compositions |
| US20060106243A1 (en) * | 2004-10-21 | 2006-05-18 | R. T. Vanderbilt Company, Inc. | Hydroxyalkyldithiocarbamate esters |
| US20060105922A1 (en) * | 2004-10-21 | 2006-05-18 | R. T. Vanderbilt Company, Inc. | Hydroxyalkyldithiocarbamate borate esters |
| US7544644B2 (en) | 2004-10-21 | 2009-06-09 | R.T. Vanderbilt, Inc. | Hydroxyalkyldithiocarbamate borate esters |
| US7589226B2 (en) | 2004-10-21 | 2009-09-15 | R.T. Vanderbilt Company, Inc. | Hydroxyalkyldithiocarbamate esters |
| JP2012193129A (en) * | 2011-03-15 | 2012-10-11 | Idemitsu Kosan Co Ltd | Boronated amino alcohol compound, additive for lubricating oil, and lubricating oil composition |
| US10336963B2 (en) | 2015-02-26 | 2019-07-02 | The Lubrizol Corporation | Aromatic tetrahedral borate compounds for lubricating compositions |
| EP3249029A1 (en) | 2016-05-23 | 2017-11-29 | Infineum International Limited | Highly borated dispersant concentrates for lubricating oil compositions and methods for forming same |
| US10487286B2 (en) | 2016-05-23 | 2019-11-26 | Infineum International Ltd. | Highly borated dispersant concentrates for lubricating oil compositions and methods for forming same |
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