US2866755A - Ester-base lubricant containing non-corrosive ep agent - Google Patents
Ester-base lubricant containing non-corrosive ep agent Download PDFInfo
- Publication number
- US2866755A US2866755A US512304A US51230455A US2866755A US 2866755 A US2866755 A US 2866755A US 512304 A US512304 A US 512304A US 51230455 A US51230455 A US 51230455A US 2866755 A US2866755 A US 2866755A
- Authority
- US
- United States
- Prior art keywords
- ester
- phosphate
- chlorophenyl
- base
- percent
- 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
- 239000000314 lubricant Substances 0.000 title claims description 40
- 239000003795 chemical substances by application Substances 0.000 title description 9
- 230000009972 noncorrosive effect Effects 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 40
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 claims description 6
- 239000010687 lubricating oil Substances 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 description 20
- -1 aryl phosphates Chemical class 0.000 description 17
- 238000005260 corrosion Methods 0.000 description 15
- QGJHPPKJOSJFIV-UHFFFAOYSA-N bis(2-chlorophenyl) phenyl phosphate Chemical compound ClC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)Cl)OC1=CC=CC=C1 QGJHPPKJOSJFIV-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 239000002199 base oil Substances 0.000 description 11
- 230000007797 corrosion Effects 0.000 description 11
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 10
- 230000003647 oxidation Effects 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- 229950000688 phenothiazine Drugs 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 229910019142 PO4 Inorganic materials 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 230000001050 lubricating effect Effects 0.000 description 9
- 235000021317 phosphate Nutrition 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 238000005461 lubrication Methods 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 229940067597 azelate Drugs 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XXRLNDANLSBJHO-UHFFFAOYSA-N tris(3,3,3-trichloropropyl) phosphate Chemical compound ClC(Cl)(Cl)CCOP(=O)(OCCC(Cl)(Cl)Cl)OCCC(Cl)(Cl)Cl XXRLNDANLSBJHO-UHFFFAOYSA-N 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ONKUXPIBXRRIDU-UHFFFAOYSA-N Diethyl decanedioate Chemical compound CCOC(=O)CCCCCCCCC(=O)OCC ONKUXPIBXRRIDU-UHFFFAOYSA-N 0.000 description 2
- 239000005069 Extreme pressure additive Substances 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- CJFLBOQMPJCWLR-UHFFFAOYSA-N bis(6-methylheptyl) hexanedioate Chemical compound CC(C)CCCCCOC(=O)CCCCC(=O)OCCCCCC(C)C CJFLBOQMPJCWLR-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000005826 halohydrocarbons Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 229940116351 sebacate Drugs 0.000 description 2
- 150000003463 sulfur Chemical class 0.000 description 2
- DFQHFXCKNSCDFW-UHFFFAOYSA-N tris(4-chlorophenyl) phosphate Chemical compound C1=CC(Cl)=CC=C1OP(=O)(OC=1C=CC(Cl)=CC=1)OC1=CC=C(Cl)C=C1 DFQHFXCKNSCDFW-UHFFFAOYSA-N 0.000 description 2
- XBGIYLMKMCTDEB-UHFFFAOYSA-N (2-chloro-3,4-diphenylphenyl) dihydrogen phosphate Chemical compound C=1C=CC=CC=1C1=C(Cl)C(OP(O)(=O)O)=CC=C1C1=CC=CC=C1 XBGIYLMKMCTDEB-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
- KLDZYURQCUYZBL-UHFFFAOYSA-N 2-[3-[(2-hydroxyphenyl)methylideneamino]propyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCN=CC1=CC=CC=C1O KLDZYURQCUYZBL-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- LJKDOMVGKKPJBH-UHFFFAOYSA-N 2-ethylhexyl dihydrogen phosphate Chemical compound CCCCC(CC)COP(O)(O)=O LJKDOMVGKKPJBH-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
- STECJAGHUSJQJN-USLFZFAMSA-N LSM-4015 Chemical compound C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-USLFZFAMSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- DEMJYWYZJFNNNB-UHFFFAOYSA-N OP(O)(O)=O.OP(O)(O)=O.OP(O)(O)=O Chemical compound OP(O)(O)=O.OP(O)(O)=O.OP(O)(O)=O DEMJYWYZJFNNNB-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 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
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 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
- 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
- 244000309464 bull Species 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 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
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XWVQUJDBOICHGH-UHFFFAOYSA-N dioctyl nonanedioate Chemical group CCCCCCCCOC(=O)CCCCCCCC(=O)OCCCCCCCC XWVQUJDBOICHGH-UHFFFAOYSA-N 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical class OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- QVTWBMUAJHVAIJ-UHFFFAOYSA-N hexane-1,4-diol Chemical compound CCC(O)CCCO QVTWBMUAJHVAIJ-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- DYEBQBWYGSPVPH-UHFFFAOYSA-N n-(6-benzamidohexyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NCCCCCCNC(=O)C1=CC=CC=C1 DYEBQBWYGSPVPH-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 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
- 125000000913 palmityl 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])[H] 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- KMTUBAIXCBHPIZ-UHFFFAOYSA-N pentane-1,5-dithiol Chemical compound SCCCCCS KMTUBAIXCBHPIZ-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 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
- 239000000126 substance Substances 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- LFRFOEVCFVCHEV-UHFFFAOYSA-N tris(2-chlorophenyl) phosphate Chemical compound ClC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)Cl)OC1=CC=CC=C1Cl LFRFOEVCFVCHEV-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- C—CHEMISTRY; METALLURGY
- 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
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/104—Aromatic fractions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/106—Naphthenic fractions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
- C10M2207/302—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 monocarboxylic acids, dicarboxylic acids and dihydroxy compounds 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
- C10M2207/30—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
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- 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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- 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
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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- 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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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
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- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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- 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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- 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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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
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- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2221/043—Polyoxyalkylene ethers with a thioether group
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- 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
- C10M2223/041—Triaryl phosphates
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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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- 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
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
Definitions
- This invention relates to a lubricating composition which is particularly designed for lubrication of turbines used in aircraft, particularly in turbo-prop and turbojet planes. More particularly, this invention discloses a lubricating composition containing an EP and antiwear'additive which does not adversely affect the oxidation and corrosion properties of the lubricating composition.
- Mineral oil base lubricants are not satisfactory for lubrication of turbines used in jet engines which operate over a wide temperature range and usually under severe operating conditions.
- Specially formulated lubricants which have thermal stability, oxidation stability, good EP and anti-Wear properties and a high viscosity index are required for lubrication of turbo-jet and turboprop engines.
- the requirements for a lubricating oil for turbo-prop and turbo-jet engines are set forth in MIL-L-7808B. Up to the present time, only ester-base lubricants have met these requirements.
- the lubricant composition of this invention comprises a diester or a polyester as the major component and di(o-chlorophenyl) phenyl phosphate in an amount sufficient to impart EP and anti-wear properties to said lubricant composition.
- the di(o-chlorophenyl) phenyl phosphate usually constitutes 0.5 to 5 weight percent of the lubricant composition and materially improves the EP and anti-wear properties of the ester-base lubricant without adversely alfecting its oxidation and corrosion properties.
- phosphate esters particularly aryl phosphates and halo-substituted hydrocarbon phosphates
- Tricresyl phosphate, tris-tri-chloropropyl phosphate and tri(p-chlorophenyl) phosphate are known to possess EP properties.
- di(o-chlorophenyl) phenyl phosphate is unique in its action in imparting the desired EP and anti-wear properties to an ester-base lubricant without adversely aifecting its oxidation and corrosion properties.
- Di(o-chlorophenyl) phenyl phosphate has the follow- 7 ing structural formula:
- this compound has a Neut. No. less than 5.0 and preferably less than 2.0 in order to formulate lubricant compositions of the desired oxidation and corrosion properties.
- Serial No. 512,305 filed of even date in the names of Raymond B. Tierney and Robert H. Krug, a novel method of treating di(o-chlorophenyl) phenyl phosphate to yield a product of low Neut. No. is dis closed.
- the method of the copending application involves contact of the di(o-chlorophenyl) phenyl phosphate under anhydrous conditions with anhydrous alkali metal carbonate at a temperature less than F.
- the lubricant composition of this invention contains the di(o-chlorophenyl) phenyl phosphate in an amount sufficient to improve its EP and anti-wear properties.
- the desired improvement in EP and anti-Wear properties is effected by use of between 0.2 and 5 weight percent of di(o-chlorophenyl) phenyl phosphate.
- the usual concentration of the EP additive of this invention is between 1.0 and 3.0 percent.
- the most commonly used ester base is an aliphatic diester of an organic dicarboxylic acid.
- the dicarboxylic acid component is usually an aliphatic dicarboxylic acid containing 6 to 12 carbon atoms but glutaric acid esters and succinic acid esters may also be used. 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 may contain 20 C to C alcohols are most commonly used. Ether alcohols such as Cellosolve and carbitol 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.
- dialkyl esters of aliphatic dicarboxylic acids which are the preferred reagents for use in the lubricant compositions of the invention, are as follows: di-Z-ethylhexyl sebacate, di-2-ethylhexyl azelate, di-Z-ethylhexyl adipate, dilauryl azelate, di-sec-amyl sebacate, di-Z-ethylhexyl alkenylsuccinate, di-2-ethoxyethyl sebacate, di-Z-(Zmethoxyethoxy) ethyl sebacate, di-2-(2ethylbutoxy) ethyl sebacate, di-Z-butoxyethyl azelate, di-2-(2butoxyethoxy) ethyl alkenylsuccinate, etc.
- polyester lubricants formed by a reaction of an aliphatic dicarboxylic acid, a glycol 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-ethyl-1,3-hexanediol, sebacic acid and 2-ethylhexanol and by reaction of a mixture containing adipic acid, diethylene glycol and Z-ethylhexanoic acid illustrate this class ofsynthetic polyester lubricating bases.
- Polyesters formed by reaction of a monocarboxylic acid and a glycol may also be used as the ester component.
- the acid component is usually an aliphatic acid containing at least 6 carbon atoms.
- component is advantageously a straight glycol such as 1,6-hexanediol, but ether glycols, such as tetraethylene glycol, may also be used.
- diesters of glycols are the following: di-n-decanoate of 1,4-butanediol, di-2-ethylhexanoate of 1,6-hexanedio1, dilaurate of 1,4-hexanediol, dioctanoate of 1,5-pe'ntanediol, dilaurate of tetraethylene glycol, dilaurate of triethylene glycol, dioctoate of pentaethylene glycol.
- the glycol 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 dilaurate of 1,5-pentanedithiol; sulfur analogs of polyesters areexernplified by the reaction product of adipic acid, thioglycol and 2-ethy1hexyl mercaptan.
- the finished lubricant composition of this invention normally contains other well known additives which act as V. I. improvers and anti-oxidants.
- phenothiazine which acts as an anti-oxidant and a methacrylate polymer, which acts as a V. I. irnprover, are usually includedin the finished lubricants and are often necessary in order to meet the rigid requirements of MIL-L-7808B.
- Phenothiazine which has the formula is a particularly eflective anti-oxidant and anti-corrosive agent. Phenothiazine inhibits corrosion by preventing oxidation of the components of the lubricating composition to acidic bodies which are inherently corrosive in nature. Phenothiazine is usually present in a concentration of 0.1 to 1.5 weight percent-of the lubricant composition.
- Methacrylate polymers are well known V. I. improvers and pour point depressors. Polyester base lubricants, althoughthey, .perse, possess excellent V. I. and pour, usually require the presence of small concentrations of methacrylate polymers to meet the rigid requirements of MIL-L-7808B. These methacrylate polymers are usually copolymers of two or more esters of methacrylic acid and usually have'a molecular weight between 10,000 and 20,000. The methacrylateesters have the following general formula:
- Copolymers which find particular use as V. I. improvers and pour point depressants are the following: a copolymer wherein Rin the above formula comprises20% lauryl, 40% octyl and 40% cetyl; a copolymer wherein R in the above formula is 50% stearyl and 50% lauryl; a copolymer wherein R in the above formula comprises 50% lauryl and'50% octyl.
- Methacrylate polymers are usually sold in the form of aconcentrate comprising approximatcly50% polymer and50%'carrier oil.
- an ester-type carrier oil rather than the usual mineral base lubricatingoil.
- the use of a methacrylate ester in an ester-type carrier oil has proven particularly effective in having two nitrogen atoms attached directly to different carbon atoms ofthe same open chain, are also sometimes incorporated in the finished lubricant.
- Compounds of this type which generally constitute'0.05 to0.6 weight percent of the, composition actas metal. deactivators as disclosed in theDowning et al., No. 2,282,513.
- a preferred compound of this class is disalicylal propylenediamine which is also known as disalicylidene-1,2-diaminopropane.
- This compound is sold undcr the trade name DMD by E. I. Du Pont de Nemours and Company and as Tenarnene 60 by Tennessee Eastman.
- Examples of other compounds of this type are the following:
- Avalueabove 35 in this test is necessary in order to mark acompound of interest as an EP and anti-wear agent for polyester base lubricants.
- Table I there are shown the results obtained by'incorporation of various phosphate and halohydrocarbon phosphate esters in a base oil comprising approximately 96.5 percent di-isooctyl adipate and 0.5 percent phenothiazine.
- Example I A blend was prepared having the following composition:
- Di-isooctyl azelate 95.3 Copolymer of 50% lauryl methacrylate and 50% stearyl methacrylate in a di-Z-ethylhexyl sebacate base oil (50% concentrate) 2.0 .Di-(o-chlorophenyl) phenyl phosphate 2.0 Phenothiazine 0.5 Disalicylidene 1,2-diaminopropane 0.2
- Phenothiazine do 0.5
- Table III indicate the superior turbine lubricants which are formulated using the extreme pressure additive of this invention.
- the compositions of Examples I, II and III meet the rigid requirements of the MIL-L-7808B specification from the standpoints of extreme pressure and wear properties and of oxidation and corrosion resistance.
- a lubricant composition according to claim 4 con- 9.
- a lubricant composition.accorciingto claim ;.4 in which the major component ds a dioctyl adipate ester having lubricating characteristics, 1 to 3 weight percent di(o-chlorophenyl) phenyl phosphate, 0.1 to 1.5 percent phenothiazine, 1.5 to 8 weight percent methacrylate polymer, and 0.05 to 0.6 weight percent disalicylidene, 1,2-diaminopropane.
- omposition consisting essentiallyiof a dialiphatic ester of an organic dicarboxylic 'acidfsaid
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Description
V 2,865,755 Patented Dec. 30, 1958 dice ESTER-BASE LUBRICANT CONTAINING NON-CORROSIVE EP AGENT Raymond B. Tierney, Beacon, and Robert H. Krug, Cornwall, N. Y., assignors to The Texas Company, New York, N. Y., a corporation of Delaware No Drawing. Application May 31, 1955 Serial No. 512,304
9 Claims. (Cl. 252-475) This invention relates to a lubricating composition which is particularly designed for lubrication of turbines used in aircraft, particularly in turbo-prop and turbojet planes. More particularly, this invention discloses a lubricating composition containing an EP and antiwear'additive which does not adversely affect the oxidation and corrosion properties of the lubricating composition.
Mineral oil base lubricants are not satisfactory for lubrication of turbines used in jet engines which operate over a wide temperature range and usually under severe operating conditions. Specially formulated lubricants which have thermal stability, oxidation stability, good EP and anti-Wear properties and a high viscosity index are required for lubrication of turbo-jet and turboprop engines. The requirements for a lubricating oil for turbo-prop and turbo-jet engines are set forth in MIL-L-7808B. Up to the present time, only ester-base lubricants have met these requirements.
The lubricant composition of this invention comprises a diester or a polyester as the major component and di(o-chlorophenyl) phenyl phosphate in an amount sufficient to impart EP and anti-wear properties to said lubricant composition. The di(o-chlorophenyl) phenyl phosphate usually constitutes 0.5 to 5 weight percent of the lubricant composition and materially improves the EP and anti-wear properties of the ester-base lubricant without adversely alfecting its oxidation and corrosion properties.
It is well known in the art that phosphate esters, particularly aryl phosphates and halo-substituted hydrocarbon phosphates, are EP agents. Tricresyl phosphate, tris-tri-chloropropyl phosphate and tri(p-chlorophenyl) phosphate are known to possess EP properties. Of all the aryl and halo-hydrocarbon substituted phosphates tested, di(o-chlorophenyl) phenyl phosphate is unique in its action in imparting the desired EP and anti-wear properties to an ester-base lubricant without adversely aifecting its oxidation and corrosion properties. Other hydrocarbon phosphates and halo hydrocarbon substituted phosphates, even though thty are closely related to di(o-chlorophenyl) phenyl phosphate in chemical constitution, were either ineffective in imparting the desired EP and anti-wear properties or seriously degraded the oxidation and corrosion properties of the ester-base lubricants. The unique action of this compound in a particular environment of an ester-base lubricant is entirely unexpected since there is no analogous action in mineral oil base lubricants.
Di(o-chlorophenyl) phenyl phosphate has the follow- 7 ing structural formula:
. or more carbon atoms.
It is recommended that this compound have a Neut. No. less than 5.0 and preferably less than 2.0 in order to formulate lubricant compositions of the desired oxidation and corrosion properties. In a copending application Serial No. 512,305, filed of even date in the names of Raymond B. Tierney and Robert H. Krug, a novel method of treating di(o-chlorophenyl) phenyl phosphate to yield a product of low Neut. No. is dis closed. The method of the copending application involves contact of the di(o-chlorophenyl) phenyl phosphate under anhydrous conditions with anhydrous alkali metal carbonate at a temperature less than F. The lubricant composition of this invention contains the di(o-chlorophenyl) phenyl phosphate in an amount sufficient to improve its EP and anti-wear properties. The desired improvement in EP and anti-Wear properties is effected by use of between 0.2 and 5 weight percent of di(o-chlorophenyl) phenyl phosphate. The usual concentration of the EP additive of this invention is between 1.0 and 3.0 percent.
The most commonly used ester base is an aliphatic diester of an organic dicarboxylic acid. The dicarboxylic acid component is usually an aliphatic dicarboxylic acid containing 6 to 12 carbon atoms but glutaric acid esters and succinic acid esters may also be used. 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 may contain 20 C to C alcohols are most commonly used. Ether alcohols such as Cellosolve and carbitol 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.
Specific examples of the dialkyl esters of aliphatic dicarboxylic acids, which are the preferred reagents for use in the lubricant compositions of the invention, are as follows: di-Z-ethylhexyl sebacate, di-2-ethylhexyl azelate, di-Z-ethylhexyl adipate, dilauryl azelate, di-sec-amyl sebacate, di-Z-ethylhexyl alkenylsuccinate, di-2-ethoxyethyl sebacate, di-Z-(Zmethoxyethoxy) ethyl sebacate, di-2-(2ethylbutoxy) ethyl sebacate, di-Z-butoxyethyl azelate, di-2-(2butoxyethoxy) ethyl alkenylsuccinate, etc.
In addition to the aliphatic dicarboxylic acid esters described above, polyester lubricants formed by a reaction of an aliphatic dicarboxylic acid, a glycol 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-ethyl-1,3-hexanediol, sebacic acid and 2-ethylhexanol and by reaction of a mixture containing adipic acid, diethylene glycol and Z-ethylhexanoic acid illustrate this class ofsynthetic polyester lubricating bases.
Polyesters formed by reaction of a monocarboxylic acid and a glycol may also be used as the ester component. The acid component is usually an aliphatic acid containing at least 6 carbon atoms. component is advantageously a straight glycol such as 1,6-hexanediol, but ether glycols, such as tetraethylene glycol, may also be used.
Specific examples of the diesters of glycols are the following: di-n-decanoate of 1,4-butanediol, di-2-ethylhexanoate of 1,6-hexanedio1, dilaurate of 1,4-hexanediol, dioctanoate of 1,5-pe'ntanediol, dilaurate of tetraethylene glycol, dilaurate of triethylene glycol, dioctoate of pentaethylene glycol.
The glycol 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 dilaurate of 1,5-pentanedithiol; sulfur analogs of polyesters areexernplified by the reaction product of adipic acid, thioglycol and 2-ethy1hexyl mercaptan.
The finished lubricant composition of this invention normally contains other well known additives which act as V. I. improvers and anti-oxidants. For example, phenothiazine, which acts as an anti-oxidant and a methacrylate polymer, which acts as a V. I. irnprover, are usually includedin the finished lubricants and are often necessary in order to meet the rigid requirements of MIL-L-7808B. Phenothiazine, which has the formula is a particularly eflective anti-oxidant and anti-corrosive agent. Phenothiazine inhibits corrosion by preventing oxidation of the components of the lubricating composition to acidic bodies which are inherently corrosive in nature. Phenothiazine is usually present in a concentration of 0.1 to 1.5 weight percent-of the lubricant composition.
Methacrylate polymers are well known V. I. improvers and pour point depressors. Polyester base lubricants, althoughthey, .perse, possess excellent V. I. and pour, usually require the presence of small concentrations of methacrylate polymers to meet the rigid requirements of MIL-L-7808B. These methacrylate polymers are usually copolymers of two or more esters of methacrylic acid and usually have'a molecular weight between 10,000 and 20,000. The methacrylateesters have the following general formula:
CH; [-CH:.-] 0 R whereinR is an aliphatic radical. Copolymers which find particular use as V. I. improvers and pour point depressants are the following: a copolymer wherein Rin the above formula comprises20% lauryl, 40% octyl and 40% cetyl; a copolymer wherein R in the above formula is 50% stearyl and 50% lauryl; a copolymer wherein R in the above formula comprises 50% lauryl and'50% octyl.
Methacrylate polymers are usually sold in the form of aconcentrate comprising approximatcly50% polymer and50%'carrier oil. Forthe lubricant compositions of this invention, ithas beenfound advisable to use an ester-type carrier oil rather than the usual mineral base lubricatingoil. The use of a methacrylate ester in an ester-type carrier oil has proven particularly effective in having two nitrogen atoms attached directly to different carbon atoms ofthe same open chain, are also sometimes incorporated in the finished lubricant. Compounds of this typewhich generally constitute'0.05 to0.6 weight percent of the, composition actas metal. deactivators as disclosed in theDowning et al., No. 2,282,513. A preferred compound of this class, which is commercially available, is disalicylal propylenediamine which is also known as disalicylidene-1,2-diaminopropane. This compound is sold undcr the trade name DMD by E. I. Du Pont de Nemours and Company and as Tenarnene 60 by Tennessee Eastman. Examples of other compounds of this type are the following:
Di-(2-hydroxy-3-methoxybenzal) ethylenediamine Di-(Z-hydroxybenzal) ethylenediamine Di-(Z-hydroxybenzal) decamethylenediamine Di-(Z-hydroxybenzal) triethylenetetramine Di-(Z-hydroxybenzal) hexamethylenediamine DMZ-hydroxybenzal) 1:3 propylenediamine Dibenzal ethylenediamine Dibenzal hexamethylenediamine Dibenzal diethylenetriamine Dibenzal triethylenetetramine Disalicylal ethylenediamine The four-ball mean Hertz load test is used as a test for screening EP and anti-wear agents. Avalueabove 35 in this test is necessary in order to mark acompound of interest as an EP and anti-wear agent for polyester base lubricants. In Table I there are shown the results obtained by'incorporation of various phosphate and halohydrocarbon phosphate esters in a base oil comprising approximately 96.5 percent di-isooctyl adipate and 0.5 percent phenothiazine.
TABLE I Four bull menu Hertz load test,,kg.
Base nil Base oil+3% tricresyl phosphate 32 Base oil+3% tri(p-chlorophenyl) phosphate 25 Base .oi1+3% diphenyl-o-chlorophenyl phosphate." 29 Base oil+3% di-(fi-chloroethyl) 2-ethylhexyl phosphate 35 Base oi1+3% tris(trichloropropyl) phosphate 38 Base oil+3% bis(o'chlorophenyl) phenyl .phosphate 40 .thefformation of tri(o-chlorophenyl) phosphate. The superiority of di(o-chlorophenyl) phenylphosphate over all the EP and anti-wear agents tested is also significant.
In Table II there are shown the results of subjecting the ester lubricants containing the three EP agents which passed the screening test in Table I in the oxidationcorrosion test of MILL-7808B. The base oil was the same used in Table .1, namely comprising 96.5 percent di-isooctyl adipate, 0.5 percent phenothiazine; 3% EP agent was used in each test.
TABLE II Di (o-chlor- Di (fi-ehlor- Tris-(tri- Oxidation-Corrosion MIL-L- Ophenyl) oethyl)2- chloro- Test (347 F./72 Hr.) 7808B phenyl ethylhexyl propyl) Spec. phosphate phosphate phosphate mg./sq. 0111.:
Cu i0. 4 0.0 .2. 0 5. 5 i0. 2 .0. 0 +0. 2 +0. 1 1:0.2 0:0 -4;0 -11.2 i0. 2 0.-0 +0. 2 +0.1 i0. 2 0.0 +1.2 +0. 6
The data in the above table clearly indicate that di(fichloroethyl) Z-ethylhexyl phosphate and tris(trichloropropyl) phosphate degrade the oxidation-corrsion properties of an ester-base lubricant to a serious degree. In contrast, di(o-chlorophenyl) phenyl phosphate completely meets the rigid requirements of the oXidatiori-corrosion test of MIL-L-7808B, demonstrating thatit alone of all the phosphate and halo-phosphate esters tested provides a high level of EP and anti-wear properties without de- 6 Example IV V A blend was prepared having the following composition:
Percent by weight grading the oxidation and corrosion properties of ester- 5 Di-Z-ethylhexyl sebacate 79.5 type lubricants designed for lubrication of turbo-prop Polymer of butyl methacrylate in di-Z-ethylhexyl and turbo-jet engines. sebacate (40% concentrate) 18.0 The formulation of finished lubricants containing the Di(o-chlorophenyl) phenyl phosphate 2.0 HP additive of this invention is illustrated in the follow- Pheflolhlallne ing examples. The properties of this blend are shown in Table IV.
TABLE HI Examples MILL-7808B limits I II III Flash 000 "F 350 min. 41 Kin. Vis., est, at: 405 0 460 210:1 3.0 (min.) 4.60 4.70 7. 63 F l'totl ltll 5 2522 122 max Viscosity stability (3 hr. at 65 F.), percent =l=3 (max.) +1. 9 +0. 4 0.3 Pour Point, F 76 (main) 75 --75 75 Foam Test, Seq. 1, 2, 3 ml 100-25-100 max. -0-0 10-10-20 0-20-0 Panel Coking Test, 600 F./8 Hrs., mg 100 (max.) 23 37 49 Evaporation, 400 F/fik Hrs, percent 50 (max) 12.1 12.9 8.3 22. 7 18.0 "15 Rubber Swelling, per n 12-35 21 8 22. 7 18.0 .6 1 .2 Corrosion, 450 F/50 Hr. mgJsq. in.: 22 8 S3858! Emax.) 0. 1g 0. 7 0.0 80D Load Corrosion, 325 F./1 Hr., MgJsq. in 6 1113 3. 0. 2 2 Corrosion and Oxidation stability, 347 F./72 Hrs, wt.
change, mg./sq. cm.:
on =e0.4 0. 4 0. 0 0. 0 Al :l:0.2 0. 0 0. 0 0. 0 M 5:02.. 0. 0 0. 0 0. 0 85 88 -2 0. Vis. Inc., 100 F., percent 5 to +15 +1. 6 0. 91 2. 8 Total Acid N 0. In 2.0 (max) 0. 9 0. 95 0. 3
Example I A blend was prepared having the following composition:
Percent by weight Di-isooctyl azelate 95.3 Copolymer of 50% lauryl methacrylate and 50% stearyl methacrylate in a di-Z-ethylhexyl sebacate base oil (50% concentrate) 2.0 .Di-(o-chlorophenyl) phenyl phosphate 2.0 Phenothiazine 0.5 Disalicylidene 1,2-diaminopropane 0.2
The properties of this product are shown in Table III.
- Example II A blend was prepared having the following composition:
Percent by weight Di-isooctyl azelate 95.5 Copolymer of 50% lauryl methacrylate and 50% stearyl methacrylate in a di-Z-ethylhexyl sebacate base oil (50% concentrate) 2.0 Di(o-chlorophenyl) phenyl phosphate 2.0 Phenothiazine I 0.5
The properties of this blend are shown in Table III.
Example III Di(o-chlorophenyl) phenyl phosphate ....do.... 2.0
Phenothiazine do 0.5
Kerosine concentrate of 10 weight percent dimethyl silicone p p. m-.. 150
The properties of this blend are shown in Table III.
The data in Table III indicate the superior turbine lubricants which are formulated using the extreme pressure additive of this invention. The compositions of Examples I, II and III, meet the rigid requirements of the MIL-L-7808B specification from the standpoints of extreme pressure and wear properties and of oxidation and corrosion resistance.
In Table IV there is shown the properties of the high viscosity composition of Example 4, which was formulated to meet the requirements of a British specification for jet engine lubricants wherein the viscosity requirements are substantially higher than they are in the U. S. military specification.
TABLE IV Example 4 Kim Vis. at: Compositions Pour point -.-75. Flash 430.
Vis. stab., 65 F Foam test, Sq. l, 2, 3 30; 30; 30. Panel coking test, 600 F./8 hr., mg 29.
Evap., 400 F./6 /2 hr., percent 10.3.
H rubber swell, percent Corr. 450 F./ 50 hr., mg./sq. in.:
Ag 0.3. SOD Pb corr Oxidation-corrosion test,
Cu +0.0 stain.
Al 0.0 stain.
Mg 0.1 stain.
Fe 0.0 stain.
Ag 0.0 stain. Vis. inc., percent 1.8.
Neut. no. inc 0.68,
The high viscosity product,who'se properties are shown in Tablc'r'ly, meutslthe extreme pressnre; :weacandmxirlai tion-corrosion requirements of MIL-L-7808B. It is noteworthy *that 'di(b-chlorophenyl) phenyl phosphate is effective as an EP and anti-wear agentdn a wide varietyof ester base lubricants. L k
Obviously, many modifications"andwvariation of the invention, as hereinbefore -set forth; may bc ma'cle without departing from the spirit and scop e thereof and there-m hon atoms."
phenyl phosphate.
4. A lubricant composition'consi'stin'g essentially'of an aliphatic di-carboXylic"'acid ester of lubricating oil characteristics, 0.2 to 5 weight percent di(o-chlorophenyl) of an aliphatic 20 3. A lubricant composition according-{to claim -1 con-' taining. 0.2 to 5 weight pcrcent'tofxdi(ochlorophenyl) phenyl phosphate, an oxidationinhibiting amount of-- phenothiazineand a methacrylate polymer in 'aV. I. im-.-
proving amount.
5. A lubricant composition according to claim 4 con- 9. A lubricant c taining between "1.0 to 3.0' weighbpercent :di(o-chloro-i: phenyl phenyl-phosphatep 0.15 10 1.5. percent 1phenothia-w zinc; and 1.5 to 8 weight percent imethacrylate:polymer;i
6. A ..lubricant rcomposition according' 'ito :claim 54 in which'themajorucomponentwis a diOctyIEsebacater 7 A :lubricant composition according .to claim 4 in which the major component is a dioctylazelate.
8. A lubricant composition.accorciingto claim ;.4 in which the major component ds a=dioctyl adipate ester having lubricating characteristics, 1 to 3 weight percent di(o-chlorophenyl) phenyl phosphate, 0.1 to 1.5 percent phenothiazine, 1.5 to 8 weight percent methacrylate polymer, and 0.05 to 0.6 weight percent disalicylidene, 1,2-diaminopropane.
keferenc esfffiteil fiii the file of this patent znosgss 1.- 1935 2,282,513 1942 2529,190 1950 2,542,604 1951 OTHER REFERENCES fsymposiumidn.Syiithetic Lubricants, A. S. T. M. Tech. Pub No.; 77 1947), page 23.
Davey} The Mechanism of Action of E. P. Agents,
Scientific Lubricationpseptember 1949, pages 7-14.
omposition consisting essentiallyiof a dialiphatic ester of an organic dicarboxylic 'acidfsaid
Claims (1)
1. A LUBRICANT COMPOSITION OF MATTER CONSISTING ESSENTIALLY OF AN ALIPHATIC CARBOXYLIC ACID ESTER OF LUBRICATING OIL CHARACTERISTICS AND DI(O-CHLOROPHENYL) PHENYL PHOSPHATE IN AN AMOUNT SUFFICIENT TO IMPART EP AND ANTI-WEAR PROPERTIES TO SAID COMPOSITION.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US512304A US2866755A (en) | 1955-05-31 | 1955-05-31 | Ester-base lubricant containing non-corrosive ep agent |
| GB15535/56A GB813484A (en) | 1955-05-31 | 1956-05-18 | A lubricant composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US512304A US2866755A (en) | 1955-05-31 | 1955-05-31 | Ester-base lubricant containing non-corrosive ep agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2866755A true US2866755A (en) | 1958-12-30 |
Family
ID=24038546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US512304A Expired - Lifetime US2866755A (en) | 1955-05-31 | 1955-05-31 | Ester-base lubricant containing non-corrosive ep agent |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2866755A (en) |
| GB (1) | GB813484A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3048542A (en) * | 1959-01-30 | 1962-08-07 | Texaco Inc | Lubricating compositions |
| US3074889A (en) * | 1958-05-23 | 1963-01-22 | Labofina Sa | Uninflammable hydraulic fluids |
| US3251821A (en) * | 1961-06-01 | 1966-05-17 | Ethyl Corp | Residual oil obtained from reacting 3, 5-hydrocarbon-4-hydroxy-1-tertiaryamino methyl benzenes and sulfur |
| EP0384724A1 (en) * | 1989-02-22 | 1990-08-29 | Nippon Oil Co. Ltd. | A method for lubricating refrigerating machines |
| US5196130A (en) * | 1991-12-09 | 1993-03-23 | The United States Of America As Represented By The Secretary Of The Air Force | Lubricity additive for high-temperature gas turbine engine oils |
| US5279752A (en) * | 1989-02-22 | 1994-01-18 | Nippon Oil Co., Ltd. | Composition for lubricating oil |
| US6218344B1 (en) * | 2000-01-21 | 2001-04-17 | The United States Of America As Represented By The Secretary Of The Air Force | Antiwear additives for spacecraft lubricants |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2006756A (en) * | 1932-04-04 | 1935-07-02 | Rubber Service Lab Co | Liquid fuel composition |
| US2282513A (en) * | 1939-05-19 | 1942-05-12 | Du Pont | Stabilization of viscous petroleum oils |
| US2529190A (en) * | 1948-04-07 | 1950-11-07 | Gulf Research Development Co | Lubricating metal surfaces during cold working |
| US2542604A (en) * | 1948-12-01 | 1951-02-20 | Standard Oil Dev Co | Extreme pressure lubricant and extreme pressure agents therefor |
-
1955
- 1955-05-31 US US512304A patent/US2866755A/en not_active Expired - Lifetime
-
1956
- 1956-05-18 GB GB15535/56A patent/GB813484A/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2006756A (en) * | 1932-04-04 | 1935-07-02 | Rubber Service Lab Co | Liquid fuel composition |
| US2282513A (en) * | 1939-05-19 | 1942-05-12 | Du Pont | Stabilization of viscous petroleum oils |
| US2529190A (en) * | 1948-04-07 | 1950-11-07 | Gulf Research Development Co | Lubricating metal surfaces during cold working |
| US2542604A (en) * | 1948-12-01 | 1951-02-20 | Standard Oil Dev Co | Extreme pressure lubricant and extreme pressure agents therefor |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3074889A (en) * | 1958-05-23 | 1963-01-22 | Labofina Sa | Uninflammable hydraulic fluids |
| US3048542A (en) * | 1959-01-30 | 1962-08-07 | Texaco Inc | Lubricating compositions |
| US3251821A (en) * | 1961-06-01 | 1966-05-17 | Ethyl Corp | Residual oil obtained from reacting 3, 5-hydrocarbon-4-hydroxy-1-tertiaryamino methyl benzenes and sulfur |
| EP0384724A1 (en) * | 1989-02-22 | 1990-08-29 | Nippon Oil Co. Ltd. | A method for lubricating refrigerating machines |
| US5279752A (en) * | 1989-02-22 | 1994-01-18 | Nippon Oil Co., Ltd. | Composition for lubricating oil |
| US5196130A (en) * | 1991-12-09 | 1993-03-23 | The United States Of America As Represented By The Secretary Of The Air Force | Lubricity additive for high-temperature gas turbine engine oils |
| US6218344B1 (en) * | 2000-01-21 | 2001-04-17 | The United States Of America As Represented By The Secretary Of The Air Force | Antiwear additives for spacecraft lubricants |
Also Published As
| Publication number | Publication date |
|---|---|
| GB813484A (en) | 1959-05-21 |
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