US2788326A - Extreme pressure lubricant - Google Patents
Extreme pressure lubricant Download PDFInfo
- Publication number
- US2788326A US2788326A US202826A US20282650A US2788326A US 2788326 A US2788326 A US 2788326A US 202826 A US202826 A US 202826A US 20282650 A US20282650 A US 20282650A US 2788326 A US2788326 A US 2788326A
- Authority
- US
- United States
- Prior art keywords
- acid
- oil
- acids
- compounds
- extreme pressure
- 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 description 17
- 239000000203 mixture Substances 0.000 claims description 36
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 13
- 239000011975 tartaric acid Substances 0.000 claims description 13
- 235000002906 tartaric acid Nutrition 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 7
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 claims description 6
- 230000001050 lubricating effect Effects 0.000 claims description 6
- 239000001593 sorbitan monooleate Substances 0.000 claims description 6
- 235000011069 sorbitan monooleate Nutrition 0.000 claims description 6
- 229940035049 sorbitan monooleate Drugs 0.000 claims description 6
- 239000010688 mineral lubricating oil Substances 0.000 claims description 4
- 229920001214 Polysorbate 60 Polymers 0.000 claims 1
- 239000002253 acid Substances 0.000 description 31
- 150000002148 esters Chemical class 0.000 description 28
- -1 hydroxyl radicals Chemical class 0.000 description 26
- 150000007513 acids Chemical class 0.000 description 19
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical class OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 239000002480 mineral oil Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 235000010446 mineral oil Nutrition 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 6
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 6
- 229920000053 polysorbate 80 Polymers 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- 239000011575 calcium Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 4
- 239000004310 lactic acid Substances 0.000 description 4
- 235000014655 lactic acid Nutrition 0.000 description 4
- 229920005573 silicon-containing polymer Polymers 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- QQVGEJLUEOSDBB-KTKRTIGZSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(CO)(CO)CO QQVGEJLUEOSDBB-KTKRTIGZSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000011133 lead Substances 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 238000005461 lubrication Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Chemical class C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- HWXBTNAVRSUOJR-UHFFFAOYSA-N alpha-hydroxyglutaric acid Natural products OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 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
- 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 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000010685 fatty oil Substances 0.000 description 2
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 125000001421 myristyl 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])[H] 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 150000003017 phosphorus Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- WZUNUACWCJJERC-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CC)(CO)CO WZUNUACWCJJERC-UHFFFAOYSA-N 0.000 description 1
- WALBTDFSFTVXII-UHFFFAOYSA-N 2,3,4,5,6-pentamethylphenol Chemical compound CC1=C(C)C(C)=C(O)C(C)=C1C WALBTDFSFTVXII-UHFFFAOYSA-N 0.000 description 1
- RSZXXBTXZJGELH-UHFFFAOYSA-N 2,3,4-tri(propan-2-yl)naphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=C(C(C)C)C(S(O)(=O)=O)=C21 RSZXXBTXZJGELH-UHFFFAOYSA-N 0.000 description 1
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 1
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 1
- DRRDTKUTHYHEKE-UHFFFAOYSA-N 2,4-dimethyl-6-octylphenol Chemical compound CCCCCCCCC1=CC(C)=CC(C)=C1O DRRDTKUTHYHEKE-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical class OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WGTDLPBPQKAPMN-MDZDMXLPSA-N 2-[2-[(e)-heptadec-8-enyl]-4,5-dihydroimidazol-1-yl]ethanol Chemical compound CCCCCCCC\C=C\CCCCCCCC1=NCCN1CCO WGTDLPBPQKAPMN-MDZDMXLPSA-N 0.000 description 1
- WCWCBLDWXBFHHT-UHFFFAOYSA-N 2-amino-3-benzylphenol Chemical class NC1=C(O)C=CC=C1CC1=CC=CC=C1 WCWCBLDWXBFHHT-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- AHZRNZSJQJDAQP-UHFFFAOYSA-N 2-cyanooctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(C#N)C(O)=O AHZRNZSJQJDAQP-UHFFFAOYSA-N 0.000 description 1
- OTTXIFWBPRRYOG-UHFFFAOYSA-N 2-hydroxyadipic acid Chemical compound OC(=O)C(O)CCCC(O)=O OTTXIFWBPRRYOG-UHFFFAOYSA-N 0.000 description 1
- MKJHXLKVZNDNDB-UHFFFAOYSA-N 2-phenyloctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C1=CC=CC=C1 MKJHXLKVZNDNDB-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- REIDAMBAPLIATC-UHFFFAOYSA-N 4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
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- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
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- 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
- 239000010959 steel Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical group SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
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- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000005329 tetralinyl group Chemical class C1(CCCC2=CC=CC=C12)* 0.000 description 1
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- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Chemical class OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Chemical class 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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- C10M2203/06—Well-defined aromatic compounds
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- C10M2205/026—Butene
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- C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
- C10N2060/04—Oxidation, e.g. ozonisation
Definitions
- This invention relates to lubricants particularly suit- .able for lubrication under extreme operating conditions,
- improved extreme pressure lubricants can be obtained by introducing into a base lubricant a heat polymerizable polyfunctional organic compound containing a plurality of hydroxyl groups, including alcoholic and carboxylic hydroxyl groups, the oxygen content of the initial material not exceeding around about 2 /2 grams, per gram of carbon, said heat polymerizable compound being substantially unreactive with contacting metal surfaces being lubricated and substantially insoluble alone in the base lubricants to which it is added for imparting extreme pressure properties, thus forming a heterogeneous lubricating composition.
- certain agents which will be hereinafter fully identified, are admixed with the heterogeneous lubricant of this invention, the function of said agents being to suspend or maintain in the base fluid, as well as to activate, the extreme pressure properties of said heat polymerizable compound without making it reactive with contacting surfaces.
- the extreme pressure agents of this invention are oil-insoluble heat polymerizable polyfunctional organic compounds containing a plural- 2,788,326 Patented Apr. 9, T957 ity of hydroxyl groups (or oxy groups such as keto groups capable of forming enols), preferably at least one carboxylic hydroxyl and one alcoholic hydroxyl radical (attached to carbon atoms) in the molecule, the oxygen content of the initial material not exceeding about 2 /2 grams per gram of carbon, said compounds being capable of forming highly viscous fusible polymolecular films between the rubbing surfaces.
- Representative and illustrative specific compounds which are embraced within the scope of this invention are tartaric acid, hydroxy malonic acid, citric acid, hydroxy glutaric acid, hydroxy adipic acid, malic acid, tartronic acid, oxalacet'ic acid, citraconic acid, mesaconic acid, aconitic acid, maleic acid, fumaric acid, itaconic acid, citraconic anhydride, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, sebacic acid, 'azelaic acid, 'suberic acid, laevulinic acid, pyruvic acid, acetoacetic acid, glyoxy'lic acid, hydroxy-butyric acid, glycollic acid, lactic acid, homoterephthalic acid or other polymerizable aromatic polyacids having a melting point below about 230 and mixtures of said acids.
- Any of these acids can be modified by esterification with a polyhydric alcohol to such a degree so as not to oil-solubilize said acids or interfere with the polymerization of the resulting oilinsoluble products under operating extreme pressure lubricating conditions so as to prevent formation of viscous fusible polymolecular film formation between contacting surfaces being lubricated.
- the polyhydric alcohols which are preferred are: ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol and the like.
- Mixtures of the free acids and condensed esters of said acids can be used such as mixtures of tartaric acid and a condensed ester of tartaric acid with propylene glycol mixtures of citric acid and a condensed ester of citric acid with propylene glycol; mixture of lactic acid and an ester of tartaric acid with propylene glycol; mixtures of maleic acid and an ester of tartaric acid with ethylene glycol.
- the free acid be present in predominant amount, preferably from to of the mixture of the heat polymerizable compounds mentioned.
- Other compounds which can be used are carbohydrates such as sugars and derivatives thereof, :e. g.
- the pentoses and hexoses (ribose, arabinose, glucose, fructose, galactose, mannose, etc.)., amino-sugars, starch, degenerated cellulose, degenerated ethylcellulose; hexitols sorbitol, mannitol), glucarnine, salicylal glucamine and the like.
- the compounds can be pre-polymerized and then added to the base lubricant or the polymerization process can be, and preferably is, allowed to take place in situ, thus acting as a continuous supply of polymolecular film-forming materials between contacting metal surfaces, whereby preventing their wear.
- solubilizing agents for the extreme pressure additives of this invention are selected from oil-soluble materials which are less strongly adsorbed on metal surfaces than the extreme pressure agents and are preferably amphipathic non-ionic in nature, or mixtures of amphipathic non-ionic and ionic solubilizers can be used in which the non-ionic solubilizers are present 'in predominant proportion, preferably from 75% to 90% of the solubilizing mixture.
- Non-ionic solubilizers are alcohols, e. g. lauryl alcohol, oleyl alcohol, 4atertiary butyl .cyclohexanol, phosphatides, organic oxides, preferably the mono ethers .of polyalkylene glycol such as undecanoxy polyethoxy ethanol, esters, of which the oil-soluble partial respectively, on the other.
- esters of polyhydric alcohols are preferred, said esters having at least one free hydroxyl radical.
- a predominantly hydrocarbon portion containing a number of carbon atoms sufficient to give the molecule a'totalminimum carbon content of about :12 and preferably about 15 to 46 carbon atoms.
- This hydrocarbon portion is attached to the alcoholic portion of the molecule through an ester linkage which may be formed between the hydroxyl or an acid radical (if there is one), of the poly,- hydric alcohol on the one hand, and an acid or alcohol,
- hydroxyl radicals and ester linkages of the'ester alcohol be as close together as possible, at least two hydroxyl radicals being separated from each other by not more than three directly connected atoms, and preferably being attached to vicinal carbon atoms. It is advantageous if the several polar groups are attached to directly connected carbon atoms.
- ester alcohols may be derivatives of glycerine, erythritol, pentaerythritol, mannitol, s'orbitol, sorbitan, tartaric acid, etc.
- the acid (or alcohol, as the case may be) forming the ester with the polyhydric alcohol should have at least about 10, and preferably between about l and 40 carbon atoms, in the form of an aliphatic or cycloaliphatic radical.
- Suitable radicals comprise, for example, capryl, decyl, undecyl, undecylenyl, lauryl, (dodecyl), tridecyl, myristyl (tetradecyl), myristolenyl, pentadecyl palmityl' (hexadecyl), palmitolenyl, oleyl, elaidyl, erucyl, stearyl, abietyl, etc.
- Radicals such as are contained in the acids obtained from resin or tall oil as well as naphthenic (i.e'. cycloaliphatic) acids having the requisite number ofcarbon atoms are also applicable.
- the acid which may form the ester with the polyhydric alcohol is preferably a carboxylic acid, although sulfonic, alkyl sulfuric, phosphoric alkyl phosphoric, etc., acids are also useful.
- Specific monoesters are: glycerol monooleate, glycerol monostearate; sorbitan monooleate; sorbitan monostearate, glycerol monoricinoleate, glycerol mononaphthenate, mannitan monolaurate, mannitan monooleate, pentaerythritol monooleate, pentaerythritol monostearate, pentaerythritol monocaprylate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, polyethylene glycol monoand di-ricinoleate, glycerol monoester of soya bean fatty acids, etc.
- Ionic solubilizers The use of ionic solubilizers in combination with the above non-ionic solubilizers is optional.
- the ionic solubilizers which are useful are the cation active and anion active compounds such as the nitrogen base compounds, e. g. amines, heterocyclic amines, e. g. glyoxalidine or imidazoline ring compound, e. g. l-hydroxy-ethyl- 2-heptadecenyl glyoxalidine, dimethylmono stearlamine, quaternary ammonium compounds; e. g.
- the weakly basic amines being weakly-ionic surface aetlve agents, may serve in part the purpose of non-ionic agents. Therefore, they may be used to replace part of the strictly non-ionic agents.
- Preferred ionic-active agents are the glyoxalidines and soaps thereof or the oil-soluble organic sulfonates, obtained from petroleum sulfonic acids, such as the mahogany acids or oil-insoluble green acids produced in the manufacture of medicinal oils or refine- I ment of lubricating oils by treatment with fuming sulfuric .acid, oleum, chlorosulfonic acid, sulfur trioxide, etc.; or
- the sulfo compounds may be derived from various aliphatic, alicyclic or aromatic compounds, such as alkylated benzenes, diphenyl, xylenes, diphenylmethanes, tetralines,
- naphthalenes e.g., naphthalenes, anthracenes, phenanthrenes, alkyl phenolic compounds, alkylated halo aromatic compounds, e. g.
- amines diphenyl sulfides, phenyl naphthyl amines; alkylated pyridines, quinolines, isoquinolines, pyrroles, pyrrolidines, piperidine, thiophenes, thiophanes, etc.; or of various sulfonic acids of carboxylic. acid esters or amides; acids of the sulfuric: acid ester type such as turkey red oil, sulfated fish oils, sulfate acidsor mono ester of sulfuric acid obtained by treatment with strong sulfuric acid various olefines or alcohols such as the long chain olefines obtained in the vapor phase cracking of wax at about 550 C.
- acid ester type such as turkey red oil, sulfated fish oils, sulfate acidsor mono ester of sulfuric acid obtained by treatment with strong sulfuric acid various olefines or alcohols such as the long chain olefines obtained in the vapor phase cracking of wax at about 550
- Theabove compounds may contain substituent groups such as halogen, hydroxy, hydrosulfide, ether, amino, imino, sulfide, carboxyl, ester, etc.
- any of the above-referred-to acids may be neutralized with alkali, alkaline earth metal basic compounds, ammonia, or organic nitrogen bases, to form salts thereof.
- Preferred are the sodium, potassium, calcium, barium, magnesium, ammonium andamine salts of the following specific sulfo acids: benzene sulfonic acid, toluene sulfonic acid, tri-isopropyl naphthalene sulfonic acid, polyamyl naphthalene sulfonic acid, diwax benzene sulfonic acid, oil-soluble petroleum sulfonic acid derived from various petroleum fractions, such as gas oil, kerosene, turbine oil, heavy oil, lubricating oil, petrolatum and mixtures thereof.
- sodium lauryl sulfate, sodium oleyl sulfate, ammonium lauryl sulfate and other alkali salts of'sulfated alcohols having from about 8 to 20 carbon atoms in the molecule may be used.
- the salts of the sulfo acids may be replaced in part With salts of lauric, palmitic, stean'c, oleic, linoleic, ricinoleic acids, oxidized paraffin acids, tall. oil acids, rosin acids, abietic acid, wool fat acids, naphthenic acid, alkylated benzoic and naphthoic acids, aromatic fatty acids such as phenylacetic to phenylstearic acid, terpenic acid and the like.
- the following salts can be used: Cu, Mg, Ca, Sr, Ba, Zn, Cd, Al, Sn, Pb, Cr, Mn, Fe, Ni, Co etc., and/or organic bases, e. g. fnitrogen .bases as primary, secondary and tertiary amines and quaternary ammonium bases of from 10 to 30 carbon thiophosphoric, arsonic and antimony acids; phosphonic and arsonic acids and the like.
- Additional detergents are the alkaline earth phosphate diesters, including the thiophosphate, diesters; the alkaline earth diphenolates, specifically the calcium and barium salts of diphenol mono and poly sulfides.
- Base oils to which agents of this invention are added may be selected from a variety of natural oils such 'as paraflinic, naphthenic, and mixed base mineral oils hav ing a viscosity rangesuch as from at F., SUS, to up to 250 SUS at 210 F.
- synthetic oils may be used such as polymerized olefins, alkylated. arm
- polyalkyl silicone polymers e. g; liquid dirnethyl siliconepolymer, other silicone polymers, HzS-adducts of unsaturated ethers and thioethers, e. g. HzS adduct of dialkyl ether, di(2 ethyl hexyl) sebacate.
- Mixtures of natural and synthetic oils can be used.
- minor amounts of a fixed oil such as castor oil, lard oil and the like, may be admixed with a hydrocarbon oil and/ or synthetic oil.
- compositions of this invention can be represented by:
- Amount (percent y w Broad Range Preferred Range Extreme Pressure Agent(s):
- Oil-insoluble heat-polymerizable polyacidic organic compound e. g. tartaric acid, lactic acid, ester of propylene glycol-tartartic acid and mixtures thereof
- il-soluble non-ionic or mixture of nonionic with ionic solubilizers e. g. Sorbitan monooleate, polyoxyethylene sorbitan monooleate, sodium petroleum sulfonate,
- Natural oil e. g. mineral oil and/or fixed oils and derivatives thereof and/or synthetic lubricants Balance Preferred compositions of this invention are illustrated by the following examples:
- Composition A Comments 1 Composition D Percent Tartaric acid 1.9 Gluconic acid 0.1 Sorbitan monooleate 4 Polyoxyethylene sorbitan monooleate 2 Mineral oil Balance Composition E Percent Tartaric acid 2 Glycerol monooleate a 4 Polyoxyethylene glycerol monooleate i 2 Mineral oil (SAE 90) a Balance Composition F Percent Condensed di-ester of tartaric acid and propylene glycol 2 Pentaerythritrol monooleate 4 Polyoxyethylene pentaerythritrol monooleate 2 Mineral oil (SAE 90) Balance Composition G Percent Succinic acid 1.33 Sorbitan monooleate 4 Polyoxyethylene Sorbitan monooleate 2 Ca petroleum sulfonate (oil soluble) 1 Mineral oil Balance Composition H Percent Condensed ester of tartaric acid and propylene glycol (15%) l-hydroxy-ethyl-2-heptadecenyl glyoxalidinc 0.
- the E. P. additives are present in amounts varying from 0.1 to 5%.
- solubilizers are present in amounts sufiicient to solubillze said E. P. agents and are present in amounts varying from two to four times that of the E. P. agent.
- compositions of this invention can be combined with other additives in lubricants, such as blooming agents, pour point depressants or viscosity improvers, antifoaming agents e. g. dimethyl silicone polymer and the like.
- Antioxidants comprise several types, for example, alkyl phenols such as 2,4,6-trimethyl phenol, pentamethyl phenol, 2,4 dimethyl 6 -tertiary-butyl phenol, 2,4 dimethyl 6 octyl phenol, 2,6 ditertiary-butyl 4 methyl phenol, 2,4,6-tri-tertiary-butyl phenol and the like; amino phenols as benzyl amino phenols; amines such as dibutylphenylene diamine, diphenyl amine, phenyl-beta-naphthylamine, phenyl-alpha-naphthylamine, dinaphthyl amine.
- alkyl phenols such as 2,4,6-trimethyl phenol, pentamethyl phenol, 2,4 dimethyl 6 -tertiary-butyl phenol, 2,4 dimethyl 6 octyl phenol, 2,6 ditertiary-butyl 4
- Corrosion inhibitors or anti-rusting compounds may also be present, such as dicarboxylic acids of 16 and more carbon atoms; organic compounds containing acidic radical in close proximity to a nitrile, nitro or nitroso group (e. g. alpha cyano stearic acid).
- Wear reducing agents which may be used comprise: esters of phosphorus acids such as triaryl, alkyl hydroxy aryl, or aralkyl phosphates, thiophosphates or phosphites and the like; neutral aromatic sulfur compounds of relatively high boiling temperatures such as diaryl sulfides, diaryl disulfides, alkyl aryl disulfides, e. g.
- sulfurized long chain olefins such as may be obtained by dehydrogenation or cracking of wax
- chlorinated hydrocarbons such as chlorinated paraflin aromatic hydrocarbons, terpenes, mineral lubricating oil, etc.; or chlorinated esters of fatty acids containing the chlorine in position other than alpha position.
- Additional ingredients may comprise oil-soluble urea or thiourea derivatives, e. g. urethanes, allophanates, carbazides, carbazones, etc.; polyisobutylene polymers,
- unsaturated polymerized esters of fatty acids and monohydric alcohols and other high molecular weight oil-soluble compounds unsaturated polymerized esters of fatty acids and monohydric alcohols and other high molecular weight oil-soluble compounds.
- the amount of additive used may vary from 0.01 to 2% or higher.
- a lubricating composition comprising a major amount of a mineral lubricating oil having incorporated therein from about a fraction of 1% to 10% of tartaric acid and from 2 to 20% of a mixture of sorbitan monooleate and polyoxyethylene sorbitan monooleate, each of said additives of said mixture being present in substantial amounts.
- a lubricating composition consisting essentially of:
Description
United States Fatent O Berkeley, Calif., assignors to Shell Development Company, Emeryville, Califl, a corporation of Delaware No Drawing. Application December 26, 1950, Serial No. 202,826
2 Claims. (Cl. 252-56) This invention relates to lubricants particularly suit- .able for lubrication under extreme operating conditions,
such as under extreme pressure, high speed and high temperature conditions.
It is well known that the high pressure occurring in certain types of gears and bearings may cause a film of lubricant to rupture with consequent damage to the machinery. It has been shown that base lubricants such as mineral oil and/ or synthetic oil can be improved with regard to their protective effect particularly on rubbing surfaces by the addition of certain substances, so that excessive wear, scuffing and seizure, which normally follow a breakin the film of lubricant, can be prevented even under the most unfavorable pressure and speed conditions. Lubricants possessing this highly desirable property are called extreme pressure lubricants.
It is known that certain elements or compounds of elements of the type of chlorine, sulfur, phosphorus and lead are capable of imparting extreme pressure properties to lubricants, which may be lubricating oils and greases, when blended therewith. Among the compounds heretofore used are notably the lead soaps, phosphoric acid esters, free or loosely bound sulfur, and certain chlorinated organic compounds. ,A principal objection to extreme pressure compounds of this class is that they are highly reactive with contacting surfaces causing etching, corrosion and discoloration of said surfaces.
Another objection to reactive extreme pressure agents is that they alter the original chemical nature of the contacting surface and this, under certain conditions, is undesirable. Additionally because of the activity of agents of the type under discussion they deplete rapidly resulting in, at the very best, only a temporary solution to extreme pressure lubrication.
It has now been discovered that improved extreme pressure lubricants can be obtained by introducing into a base lubricant a heat polymerizable polyfunctional organic compound containing a plurality of hydroxyl groups, including alcoholic and carboxylic hydroxyl groups, the oxygen content of the initial material not exceeding around about 2 /2 grams, per gram of carbon, said heat polymerizable compound being substantially unreactive with contacting metal surfaces being lubricated and substantially insoluble alone in the base lubricants to which it is added for imparting extreme pressure properties, thus forming a heterogeneous lubricating composition. In order to maintain the heat polymerizable compound .(suspensoid) in dispersion in the base lubricant, certain agents, which will be hereinafter fully identified, are admixed with the heterogeneous lubricant of this invention, the function of said agents being to suspend or maintain in the base fluid, as well as to activate, the extreme pressure properties of said heat polymerizable compound without making it reactive with contacting surfaces.
THE EXTREME PRESSURE AGENTS As broadly stated above, the extreme pressure agents of this invention are oil-insoluble heat polymerizable polyfunctional organic compounds containing a plural- 2,788,326 Patented Apr. 9, T957 ity of hydroxyl groups (or oxy groups such as keto groups capable of forming enols), preferably at least one carboxylic hydroxyl and one alcoholic hydroxyl radical (attached to carbon atoms) in the molecule, the oxygen content of the initial material not exceeding about 2 /2 grams per gram of carbon, said compounds being capable of forming highly viscous fusible polymolecular films between the rubbing surfaces. Representative and illustrative specific compounds which are embraced within the scope of this invention are tartaric acid, hydroxy malonic acid, citric acid, hydroxy glutaric acid, hydroxy adipic acid, malic acid, tartronic acid, oxalacet'ic acid, citraconic acid, mesaconic acid, aconitic acid, maleic acid, fumaric acid, itaconic acid, citraconic anhydride, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, sebacic acid, 'azelaic acid, 'suberic acid, laevulinic acid, pyruvic acid, acetoacetic acid, glyoxy'lic acid, hydroxy-butyric acid, glycollic acid, lactic acid, homoterephthalic acid or other polymerizable aromatic polyacids having a melting point below about 230 and mixtures of said acids. Any of these acids can be modified by esterification with a polyhydric alcohol to such a degree so as not to oil-solubilize said acids or interfere with the polymerization of the resulting oilinsoluble products under operating extreme pressure lubricating conditions so as to prevent formation of viscous fusible polymolecular film formation between contacting surfaces being lubricated. The polyhydric alcohols which are preferred are: ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol and the like. Mixtures of the free acids and condensed esters of said acids can be used such as mixtures of tartaric acid and a condensed ester of tartaric acid with propylene glycol mixtures of citric acid and a condensed ester of citric acid with propylene glycol; mixture of lactic acid and an ester of tartaric acid with propylene glycol; mixtures of maleic acid and an ester of tartaric acid with ethylene glycol. Where mixtures of the free acid and condensable esters are used, it is preferred that the free acid be present in predominant amount, preferably from to of the mixture of the heat polymerizable compounds mentioned. Other compounds which can be used are carbohydrates such as sugars and derivatives thereof, :e. g. the pentoses and hexoses (ribose, arabinose, glucose, fructose, galactose, mannose, etc.)., amino-sugars, starch, degenerated cellulose, degenerated ethylcellulose; hexitols sorbitol, mannitol), glucarnine, salicylal glucamine and the like. The compounds can be pre-polymerized and then added to the base lubricant or the polymerization process can be, and preferably is, allowed to take place in situ, thus acting as a continuous supply of polymolecular film-forming materials between contacting metal surfaces, whereby preventing their wear.
SOLUBILIZING AGENTS The solubilizing agents for the extreme pressure additives of this invention are selected from oil-soluble materials which are less strongly adsorbed on metal surfaces than the extreme pressure agents and are preferably amphipathic non-ionic in nature, or mixtures of amphipathic non-ionic and ionic solubilizers can be used in which the non-ionic solubilizers are present 'in predominant proportion, preferably from 75% to 90% of the solubilizing mixture.
A. Non-ionic solubilizers The non-ionic solubilizers of this invention are alcohols, e. g. lauryl alcohol, oleyl alcohol, 4atertiary butyl .cyclohexanol, phosphatides, organic oxides, preferably the mono ethers .of polyalkylene glycol such as undecanoxy polyethoxy ethanol, esters, of which the oil-soluble partial respectively, on the other.
esters of polyhydric alcohols are preferred, said esters having at least one free hydroxyl radical. Tothis alcoholic portion of the molecule there is attached a predominantly hydrocarbon portion containing a number of carbon atoms, sufficient to give the molecule a'totalminimum carbon content of about :12 and preferably about 15 to 46 carbon atoms. This hydrocarbon portion is attached to the alcoholic portion of the molecule through an ester linkage which may be formed between the hydroxyl or an acid radical (if there is one), of the poly,- hydric alcohol on the one hand, and an acid or alcohol,
It is desirablethat the hydroxyl radicals and ester linkages of the'ester alcohol be as close together as possible, at least two hydroxyl radicals being separated from each other by not more than three directly connected atoms, and preferably being attached to vicinal carbon atoms. It is advantageous if the several polar groups are attached to directly connected carbon atoms. A
It will be seen that the ester alcohols may be derivatives of glycerine, erythritol, pentaerythritol, mannitol, s'orbitol, sorbitan, tartaric acid, etc. The acid (or alcohol, as the case may be) forming the ester with the polyhydric alcohol should have at least about 10, and preferably between about l and 40 carbon atoms, in the form of an aliphatic or cycloaliphatic radical.
Suitable radicals comprise, for example, capryl, decyl, undecyl, undecylenyl, lauryl, (dodecyl), tridecyl, myristyl (tetradecyl), myristolenyl, pentadecyl palmityl' (hexadecyl), palmitolenyl, oleyl, elaidyl, erucyl, stearyl, abietyl, etc. Radicals such as are contained in the acids obtained from resin or tall oil as well as naphthenic (i.e'. cycloaliphatic) acids having the requisite number ofcarbon atoms are also applicable.
The acid which may form the ester with the polyhydric alcohol is preferably a carboxylic acid, although sulfonic, alkyl sulfuric, phosphoric alkyl phosphoric, etc., acids are also useful. Specific monoesters are: glycerol monooleate, glycerol monostearate; sorbitan monooleate; sorbitan monostearate, glycerol monoricinoleate, glycerol mononaphthenate, mannitan monolaurate, mannitan monooleate, pentaerythritol monooleate, pentaerythritol monostearate, pentaerythritol monocaprylate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, polyethylene glycol monoand di-ricinoleate, glycerol monoester of soya bean fatty acids, etc.
B. Ionic solubilizers The use of ionic solubilizers in combination with the above non-ionic solubilizers is optional. Among the ionic solubilizers which are useful are the cation active and anion active compounds such as the nitrogen base compounds, e. g. amines, heterocyclic amines, e. g. glyoxalidine or imidazoline ring compound, e. g. l-hydroxy-ethyl- 2-heptadecenyl glyoxalidine, dimethylmono stearlamine, quaternary ammonium compounds; e. g. trimethyl benzyl ammonium chloride, sulfate, phosphate, dirnethyl distearly ammonium chloride and the like; soaps such as the amine and alkali metal, alkaline earth metal soap of fatty acids (Na, K or Ca oleate) or heavy metal soaps as well as oil-soluble sulfonates and sulfates or l-hydroxyethyl-Z hepta decenyl glyoxalidine soap of lactic acid. The weakly basic amines, being weakly-ionic surface aetlve agents, may serve in part the purpose of non-ionic agents. Therefore, they may be used to replace part of the strictly non-ionic agents. Preferred ionic-active agents are the glyoxalidines and soaps thereof or the oil-soluble organic sulfonates, obtained from petroleum sulfonic acids, such as the mahogany acids or oil-insoluble green acids produced in the manufacture of medicinal oils or refine- I ment of lubricating oils by treatment with fuming sulfuric .acid, oleum, chlorosulfonic acid, sulfur trioxide, etc.; or
the sulfo compounds may be derived from various aliphatic, alicyclic or aromatic compounds, such as alkylated benzenes, diphenyl, xylenes, diphenylmethanes, tetralines,
naphthalenes, anthracenes, phenanthrenes, alkyl phenolic compounds, alkylated halo aromatic compounds, e. g.
amines, diphenyl sulfides, phenyl naphthyl amines; alkylated pyridines, quinolines, isoquinolines, pyrroles, pyrrolidines, piperidine, thiophenes, thiophanes, etc.; or of various sulfonic acids of carboxylic. acid esters or amides; acids of the sulfuric: acid ester type such as turkey red oil, sulfated fish oils, sulfate acidsor mono ester of sulfuric acid obtained by treatment with strong sulfuric acid various olefines or alcohols such as the long chain olefines obtained in the vapor phase cracking of wax at about 550 C. polymers obtained by'polyme'rization of normally gaseous olefines with inorganic polyoxy acids or Friedel-Crafts catalysts; fatty ornaphthenic alcohols obtained in the catalytic reduction of fatty or naphthenic acids; alcohols obtained'by condensation of ketones or aldehydes followed by hydrogenation;- oralkyl aromatic mono esters of sulfuric acid, etc. Theabove compounds may contain substituent groups such as halogen, hydroxy, hydrosulfide, ether, amino, imino, sulfide, carboxyl, ester, etc. I
Any of the above-referred-to acids may be neutralized with alkali, alkaline earth metal basic compounds, ammonia, or organic nitrogen bases, to form salts thereof. Preferred are the sodium, potassium, calcium, barium, magnesium, ammonium andamine salts of the following specific sulfo acids: benzene sulfonic acid, toluene sulfonic acid, tri-isopropyl naphthalene sulfonic acid, polyamyl naphthalene sulfonic acid, diwax benzene sulfonic acid, oil-soluble petroleum sulfonic acid derived from various petroleum fractions, such as gas oil, kerosene, turbine oil, heavy oil, lubricating oil, petrolatum and mixtures thereof. In addition, sodium lauryl sulfate, sodium oleyl sulfate, ammonium lauryl sulfate and other alkali salts of'sulfated alcohols having from about 8 to 20 carbon atoms in the molecule may be used.
The salts of the sulfo acids may be replaced in part With salts of lauric, palmitic, stean'c, oleic, linoleic, ricinoleic acids, oxidized paraffin acids, tall. oil acids, rosin acids, abietic acid, wool fat acids, naphthenic acid, alkylated benzoic and naphthoic acids, aromatic fatty acids such as phenylacetic to phenylstearic acid, terpenic acid and the like. Also, the following salts can be used: Cu, Mg, Ca, Sr, Ba, Zn, Cd, Al, Sn, Pb, Cr, Mn, Fe, Ni, Co etc., and/or organic bases, e. g. fnitrogen .bases as primary, secondary and tertiary amines and quaternary ammonium bases of from 10 to 30 carbon thiophosphoric, arsonic and antimony acids; phosphonic and arsonic acids and the like.
Additional detergents are the alkaline earth phosphate diesters, including the thiophosphate, diesters; the alkaline earth diphenolates, specifically the calcium and barium salts of diphenol mono and poly sulfides.
BASE LUBRICANT.
Base oils to which agents of this invention are added may be selected from a variety of natural oils such 'as paraflinic, naphthenic, and mixed base mineral oils hav ing a viscosity rangesuch as from at F., SUS, to up to 250 SUS at 210 F. In addition, synthetic oils may be used such as polymerized olefins, alkylated. arm
matics; polyalkyl silicone polymers, e. g; liquid dirnethyl siliconepolymer, other silicone polymers, HzS-adducts of unsaturated ethers and thioethers, e. g. HzS adduct of dialkyl ether, di(2 ethyl hexyl) sebacate. Mixtures of natural and synthetic oils can be used. Under certain conditions of lubrication, minor amounts of a fixed oil such as castor oil, lard oil and the like, may be admixed with a hydrocarbon oil and/ or synthetic oil.
The general formulation of compositions of this invention can be represented by:
Amount (percent y w Broad Range Preferred Range Extreme Pressure Agent(s):
Oil-insoluble heat-polymerizable polyacidic organic compound e. g. tartaric acid, lactic acid, ester of propylene glycol-tartartic acid and mixtures thereof Solubilizer(s):
il-soluble non-ionic or mixture of nonionic with ionic solubilizers e. g. Sorbitan monooleate, polyoxyethylene sorbitan monooleate, sodium petroleum sulfonate,
etc Optional Additives:
Detergents, antioxidants, corrosion inhibir, etc
0.01 to 1D 0.001 to 5 Base.
Natural oil, e. g. mineral oil and/or fixed oils and derivatives thereof and/or synthetic lubricants Balance Preferred compositions of this invention are illustrated by the following examples:
Composition A Comments 1 Composition D Percent Tartaric acid 1.9 Gluconic acid 0.1 Sorbitan monooleate 4 Polyoxyethylene sorbitan monooleate 2 Mineral oil Balance Composition E Percent Tartaric acid 2 Glycerol monooleate a 4 Polyoxyethylene glycerol monooleate i 2 Mineral oil (SAE 90) a Balance Composition F Percent Condensed di-ester of tartaric acid and propylene glycol 2 Pentaerythritrol monooleate 4 Polyoxyethylene pentaerythritrol monooleate 2 Mineral oil (SAE 90) Balance Composition G Percent Succinic acid 1.33 Sorbitan monooleate 4 Polyoxyethylene Sorbitan monooleate 2 Ca petroleum sulfonate (oil soluble) 1 Mineral oil Balance Composition H Percent Condensed ester of tartaric acid and propylene glycol (15%) l-hydroxy-ethyl-2-heptadecenyl glyoxalidinc 0.02 Pentaerythritol monooleate 2 Mineral oil Balance Composition J Percent Mixture of condensed ester of ethylene glycol tartarate+10% glycerol 1-hydroxyethyl-2-heptadecenyl glyoxalidine lactate- 0.19 Pentaerythritol monooleate 2 Mineral oil Balance The following table illustrates additional compositions of this invention:
Composition l-hydroxy-ethyl 2-heptadecyl glyoxalidlne l-hyiroxy-ethyl 2-heptadecyl glyoxalldine lacta e Base:
Mineral lubricating oil Mineral lubricating oilalkyl naphthalene Polymerlzed olefin 1 The E. P. additives are present in amounts varying from 0.1 to 5%.
The solubilizers are present in amounts sufiicient to solubillze said E. P. agents and are present in amounts varying from two to four times that of the E. P. agent.
Speed: 3000 R. P. M. Test duration: mins. running at each load Specimen: involute spur gear (SAE 3312 steel) Compositions of this invention can be combined with other additives in lubricants, such as blooming agents, pour point depressants or viscosity improvers, antifoaming agents e. g. dimethyl silicone polymer and the like.
Antioxidants comprise several types, for example, alkyl phenols such as 2,4,6-trimethyl phenol, pentamethyl phenol, 2,4 dimethyl 6 -tertiary-butyl phenol, 2,4 dimethyl 6 octyl phenol, 2,6 ditertiary-butyl 4 methyl phenol, 2,4,6-tri-tertiary-butyl phenol and the like; amino phenols as benzyl amino phenols; amines such as dibutylphenylene diamine, diphenyl amine, phenyl-beta-naphthylamine, phenyl-alpha-naphthylamine, dinaphthyl amine.
Corrosion inhibitors or anti-rusting compounds may also be present, such as dicarboxylic acids of 16 and more carbon atoms; organic compounds containing acidic radical in close proximity to a nitrile, nitro or nitroso group (e. g. alpha cyano stearic acid).
Wear reducing agents which may be used comprise: esters of phosphorus acids such as triaryl, alkyl hydroxy aryl, or aralkyl phosphates, thiophosphates or phosphites and the like; neutral aromatic sulfur compounds of relatively high boiling temperatures such as diaryl sulfides, diaryl disulfides, alkyl aryl disulfides, e. g. diphenyl sulfide, diphen-ol sulfide, dicresol sulfide, dixylenol sulfide, methyl butyl diphenol sulfide, dibenzyl sulfide, corresponding diand tri-sulfides, and the like; sulfurized fatty oils or esters of fatty acids and monohydric alcohols, e. g. sperm oil, jojoba oil, etc.; in which the sulfur is strongly bonded; sulfurized long chain olefins such as may be obtained by dehydrogenation or cracking of wax; sulfurized phosphorized fatty oils or acids, phosphorus acid esters having sulfurized organic radicals, such as esters of phosphoric or phosphorus acids with sulfurized hydroxy fatty acids; chlorinated hydrocarbons, such as chlorinated paraflin aromatic hydrocarbons, terpenes, mineral lubricating oil, etc.; or chlorinated esters of fatty acids containing the chlorine in position other than alpha position.
Additional ingredients may comprise oil-soluble urea or thiourea derivatives, e. g. urethanes, allophanates, carbazides, carbazones, etc.; polyisobutylene polymers,
unsaturated polymerized esters of fatty acids and monohydric alcohols and other high molecular weight oil-soluble compounds.
Depending upon the additive used and conditions under which it is used, the amount of additive used may vary from 0.01 to 2% or higher.
It is to be understood that while the features of the invention have been described and illustrated in connec tion with certain specific examples, the invention, how,- ever, is not to be limited thereto or otherwise restricted, except by the prior art and the broad scope of the disclosed invention. a
The invention claimed is:
' 1'. A lubricating composition comprising a major amount of a mineral lubricating oil having incorporated therein from about a fraction of 1% to 10% of tartaric acid and from 2 to 20% of a mixture of sorbitan monooleate and polyoxyethylene sorbitan monooleate, each of said additives of said mixture being present in substantial amounts. 7 A
2. A lubricating composition consisting essentially of:
. Weight percent Tartaric a id Sorbitan mono l at 4 Polyoxyethylene sorbitan monooleate 2 Mineral oil Balance References Cited in the file of this patent UNITED STATES PATENTS 2,134,736 'Reuter Nov. 1, 1938 2,158,096 Werntz May 16, 1939 2,204,601 Kavanagh June 18, 1940 2,368,602 Weiss Jan. 30, 1945 2,370,299 Farrington Feb. 27, 1945 2,414,293 Farrington et al. .a Jan. 14, 1947 2,470,537 Waugh May 17, 1949 2,479,424 Sproule et al. Aug. 16, 1949 FOREIGN PATENTS 104,699 Australia Jan. 27, 1938 106,383 Australia Jan. 11,
OTHER REFERENCES Atlas Surface Active Agents; Atlas Powder Co., 1948, pp. 37, 38.
Claims (1)
1. A LUBRICATING COMPOSITION COMPRISING A MAJOR AMOUNT OF A MINERAL LUBRICATING OIL HAVING INCORPORATED THEREIN FROM ABOUT A FRACTION OF 1% TO 10% OF TARTARIC ACID AND FROM 2 TO 20% OF A MIXTURE OF SORBITAN MONOOLEATE AND POLYOXYETHYLENE SORBITAN MONOLEATE, EACH OF SAID ADDITIVES OF SAID MIXTURES BEING PRESENT IN SUBSTANTIAL AMOUNTS.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US202826A US2788326A (en) | 1950-12-26 | 1950-12-26 | Extreme pressure lubricant |
DEN4864A DE884990C (en) | 1950-12-26 | 1951-12-23 | lubricant |
FR1047117D FR1047117A (en) | 1950-12-26 | 1951-12-26 | Lubricating composition |
GB30227/51A GB721285A (en) | 1950-12-26 | 1951-12-27 | Lubricating composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US202826A US2788326A (en) | 1950-12-26 | 1950-12-26 | Extreme pressure lubricant |
Publications (1)
Publication Number | Publication Date |
---|---|
US2788326A true US2788326A (en) | 1957-04-09 |
Family
ID=22751415
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US202826A Expired - Lifetime US2788326A (en) | 1950-12-26 | 1950-12-26 | Extreme pressure lubricant |
Country Status (4)
Country | Link |
---|---|
US (1) | US2788326A (en) |
DE (1) | DE884990C (en) |
FR (1) | FR1047117A (en) |
GB (1) | GB721285A (en) |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2938871A (en) * | 1956-12-24 | 1960-05-31 | Exxon Research Engineering Co | Aviation gas turbine lubricants |
US2960469A (en) * | 1956-04-19 | 1960-11-15 | Sinclair Refining Co | Load carrying lubricant |
US2971915A (en) * | 1957-02-11 | 1961-02-14 | Shell Oil Co | Lubricating oil compositions |
US2971910A (en) * | 1957-12-16 | 1961-02-14 | Shell Oil Co | Lubricating compositions |
US2998387A (en) * | 1957-05-03 | 1961-08-29 | Sinclair Refining Co | Synthetic lubricating oil compositions |
US3029204A (en) * | 1959-05-12 | 1962-04-10 | Exxon Research Engineering Co | Acidic partial esters as lubricating oil additives |
US3047493A (en) * | 1958-05-26 | 1962-07-31 | Gulf Research Development Co | Drilling process and water base drilling muds |
US3048542A (en) * | 1959-01-30 | 1962-08-07 | Texaco Inc | Lubricating compositions |
US3090753A (en) * | 1960-08-02 | 1963-05-21 | Exxon Research Engineering Co | Ester oil compositions containing acid anhydride |
US3102098A (en) * | 1959-05-01 | 1963-08-27 | Exxon Research Engineering Co | Lubricating compositions comprising esters of tricarboxy acids |
US3223636A (en) * | 1961-05-23 | 1965-12-14 | Exxon Research Engineering Co | Lead corrosion inhibitor |
US3251774A (en) * | 1962-03-05 | 1966-05-17 | Standard Oil Co | Lubricant grease |
US3280027A (en) * | 1961-04-10 | 1966-10-18 | Gen Electric | Lubricants and lubricated structures |
US3436348A (en) * | 1966-10-20 | 1969-04-01 | Sinclair Research Inc | Ester base lubricating oil containing a stabilizing mixture of alkali metal organic compound and an aromatic amine |
US4175046A (en) * | 1978-09-20 | 1979-11-20 | Mobil Oil Corporation | Synthetic lubricant |
US4304678A (en) * | 1978-09-11 | 1981-12-08 | Mobil Oil Corporation | Lubricant composition for reduction of fuel consumption in internal combustion engines |
US4390438A (en) * | 1981-10-16 | 1983-06-28 | Nalco Chemical Company | Dibasic acids to reduce coefficient of friction in rolling oils |
US4957651A (en) * | 1988-01-15 | 1990-09-18 | The Lubrizol Corporation | Mixtures of partial fatty acid esters of polyhydric alcohols and sulfurized compositions, and use as lubricant additives |
EP0466297A1 (en) * | 1990-07-09 | 1992-01-15 | Texaco Development Corporation | Use of a particular ester |
US5244591A (en) * | 1992-03-23 | 1993-09-14 | Chevron Research And Technology Company | Lubricating oil compositions for internal combustion engines having silver bearing parts |
WO2006061436A1 (en) * | 2004-12-10 | 2006-06-15 | Shell Internationale Research Maatschappij B.V. | Lubricating oil composition |
WO2010093519A1 (en) * | 2009-02-16 | 2010-08-19 | Chemtura Corporation | Fatty sorbitan ester based friction modifiers |
US9296969B2 (en) | 2009-02-16 | 2016-03-29 | Chemtura Corporation | Fatty sorbitan ester based friction modifiers |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1001792B (en) * | 1953-05-12 | 1957-01-31 | Bataafsche Petroleum | High pressure lubricant |
US4715973A (en) * | 1985-03-15 | 1987-12-29 | Shell Oil Company | Lubricating oil compositions |
EP0302149B1 (en) * | 1987-08-03 | 1992-01-02 | Exxon Research And Engineering Company | Lubricant oil composition with improved friction reducing properties |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2134736A (en) * | 1935-04-19 | 1938-11-01 | Atlantic Refining Co | Lubricant |
US2158096A (en) * | 1936-04-24 | 1939-05-16 | Du Pont | Lubricant |
US2204601A (en) * | 1937-02-23 | 1940-06-18 | Standard Oil Co | Compounded lubricant |
US2368602A (en) * | 1943-02-09 | 1945-01-30 | Shell Dev | Anticorrosive |
US2370299A (en) * | 1941-02-26 | 1945-02-27 | Standard Oil Co California | Compounded lubricant |
US2414293A (en) * | 1939-08-07 | 1947-01-14 | California Research Corp | Treatment of frictional surfaces to facilitate wearing-in |
US2470537A (en) * | 1947-06-26 | 1949-05-17 | Tide Water Associated Oil Comp | Mineral oil compositions |
US2479424A (en) * | 1947-12-03 | 1949-08-16 | Standard Oil Dev Co | Rust inhibiting lubricants |
-
1950
- 1950-12-26 US US202826A patent/US2788326A/en not_active Expired - Lifetime
-
1951
- 1951-12-23 DE DEN4864A patent/DE884990C/en not_active Expired
- 1951-12-26 FR FR1047117D patent/FR1047117A/en not_active Expired
- 1951-12-27 GB GB30227/51A patent/GB721285A/en not_active Expired
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2134736A (en) * | 1935-04-19 | 1938-11-01 | Atlantic Refining Co | Lubricant |
US2158096A (en) * | 1936-04-24 | 1939-05-16 | Du Pont | Lubricant |
US2204601A (en) * | 1937-02-23 | 1940-06-18 | Standard Oil Co | Compounded lubricant |
US2414293A (en) * | 1939-08-07 | 1947-01-14 | California Research Corp | Treatment of frictional surfaces to facilitate wearing-in |
US2370299A (en) * | 1941-02-26 | 1945-02-27 | Standard Oil Co California | Compounded lubricant |
US2368602A (en) * | 1943-02-09 | 1945-01-30 | Shell Dev | Anticorrosive |
US2470537A (en) * | 1947-06-26 | 1949-05-17 | Tide Water Associated Oil Comp | Mineral oil compositions |
US2479424A (en) * | 1947-12-03 | 1949-08-16 | Standard Oil Dev Co | Rust inhibiting lubricants |
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2960469A (en) * | 1956-04-19 | 1960-11-15 | Sinclair Refining Co | Load carrying lubricant |
US2938871A (en) * | 1956-12-24 | 1960-05-31 | Exxon Research Engineering Co | Aviation gas turbine lubricants |
US2971915A (en) * | 1957-02-11 | 1961-02-14 | Shell Oil Co | Lubricating oil compositions |
US2998387A (en) * | 1957-05-03 | 1961-08-29 | Sinclair Refining Co | Synthetic lubricating oil compositions |
US2971910A (en) * | 1957-12-16 | 1961-02-14 | Shell Oil Co | Lubricating compositions |
US3047493A (en) * | 1958-05-26 | 1962-07-31 | Gulf Research Development Co | Drilling process and water base drilling muds |
US3048542A (en) * | 1959-01-30 | 1962-08-07 | Texaco Inc | Lubricating compositions |
US3102098A (en) * | 1959-05-01 | 1963-08-27 | Exxon Research Engineering Co | Lubricating compositions comprising esters of tricarboxy acids |
US3029204A (en) * | 1959-05-12 | 1962-04-10 | Exxon Research Engineering Co | Acidic partial esters as lubricating oil additives |
US3090753A (en) * | 1960-08-02 | 1963-05-21 | Exxon Research Engineering Co | Ester oil compositions containing acid anhydride |
US3280027A (en) * | 1961-04-10 | 1966-10-18 | Gen Electric | Lubricants and lubricated structures |
US3223636A (en) * | 1961-05-23 | 1965-12-14 | Exxon Research Engineering Co | Lead corrosion inhibitor |
US3251774A (en) * | 1962-03-05 | 1966-05-17 | Standard Oil Co | Lubricant grease |
US3436348A (en) * | 1966-10-20 | 1969-04-01 | Sinclair Research Inc | Ester base lubricating oil containing a stabilizing mixture of alkali metal organic compound and an aromatic amine |
US4304678A (en) * | 1978-09-11 | 1981-12-08 | Mobil Oil Corporation | Lubricant composition for reduction of fuel consumption in internal combustion engines |
US4175046A (en) * | 1978-09-20 | 1979-11-20 | Mobil Oil Corporation | Synthetic lubricant |
US4390438A (en) * | 1981-10-16 | 1983-06-28 | Nalco Chemical Company | Dibasic acids to reduce coefficient of friction in rolling oils |
US4957651A (en) * | 1988-01-15 | 1990-09-18 | The Lubrizol Corporation | Mixtures of partial fatty acid esters of polyhydric alcohols and sulfurized compositions, and use as lubricant additives |
EP0466297A1 (en) * | 1990-07-09 | 1992-01-15 | Texaco Development Corporation | Use of a particular ester |
US5244591A (en) * | 1992-03-23 | 1993-09-14 | Chevron Research And Technology Company | Lubricating oil compositions for internal combustion engines having silver bearing parts |
WO2006061436A1 (en) * | 2004-12-10 | 2006-06-15 | Shell Internationale Research Maatschappij B.V. | Lubricating oil composition |
US20060189489A1 (en) * | 2004-12-10 | 2006-08-24 | Takashi Fujitsu | Lubricating oil composition |
US7550415B2 (en) | 2004-12-10 | 2009-06-23 | Shell Oil Company | Lubricating oil composition |
WO2010093519A1 (en) * | 2009-02-16 | 2010-08-19 | Chemtura Corporation | Fatty sorbitan ester based friction modifiers |
US9296969B2 (en) | 2009-02-16 | 2016-03-29 | Chemtura Corporation | Fatty sorbitan ester based friction modifiers |
Also Published As
Publication number | Publication date |
---|---|
FR1047117A (en) | 1953-12-11 |
DE884990C (en) | 1953-07-30 |
GB721285A (en) | 1955-01-05 |
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