US2795550A - Lubricating oil compositions - Google Patents
Lubricating oil compositions Download PDFInfo
- Publication number
- US2795550A US2795550A US440262A US44026254A US2795550A US 2795550 A US2795550 A US 2795550A US 440262 A US440262 A US 440262A US 44026254 A US44026254 A US 44026254A US 2795550 A US2795550 A US 2795550A
- Authority
- US
- United States
- Prior art keywords
- acid
- lubricating oil
- oil
- oils
- compositions
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 49
- 239000010687 lubricating oil Substances 0.000 title description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 19
- 239000010688 mineral lubricating oil Substances 0.000 claims description 19
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 16
- 238000002485 combustion reaction Methods 0.000 claims description 12
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000003208 petroleum Substances 0.000 claims description 10
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- 239000000314 lubricant Substances 0.000 claims description 8
- 235000006408 oxalic acid Nutrition 0.000 claims description 7
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 239000003921 oil Substances 0.000 description 36
- 239000002738 chelating agent Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 230000003647 oxidation Effects 0.000 description 13
- 238000007254 oxidation reaction Methods 0.000 description 13
- 230000007797 corrosion Effects 0.000 description 12
- 238000005260 corrosion Methods 0.000 description 12
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical class [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 10
- 150000002739 metals Chemical class 0.000 description 10
- 229910052750 molybdenum Inorganic materials 0.000 description 10
- 239000011733 molybdenum Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000956 alloy Substances 0.000 description 8
- 229910045601 alloy Inorganic materials 0.000 description 8
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 229910052791 calcium Inorganic materials 0.000 description 7
- 239000011575 calcium Substances 0.000 description 7
- 229960004275 glycolic acid Drugs 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 6
- -1 mercapto alcohols Chemical class 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
- WIKSRXFQIZQFEH-UHFFFAOYSA-N [Cu].[Pb] Chemical compound [Cu].[Pb] WIKSRXFQIZQFEH-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000001050 lubricating effect Effects 0.000 description 4
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 230000009972 noncorrosive effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 230000002411 adverse Effects 0.000 description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- GHPVDCPCKSNJDR-UHFFFAOYSA-N 2-hydroxydecanoic acid Chemical compound CCCCCCCCC(O)C(O)=O GHPVDCPCKSNJDR-UHFFFAOYSA-N 0.000 description 2
- VMKYTRPNOVFCGZ-UHFFFAOYSA-N 2-sulfanylphenol Chemical class OC1=CC=CC=C1S VMKYTRPNOVFCGZ-UHFFFAOYSA-N 0.000 description 2
- OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000005012 alkyl thioether group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000003435 aroyl group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 150000004832 aryl thioethers Chemical class 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000004662 dithiols Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000003441 thioacyl group Chemical group 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- JRNVQLOKVMWBFR-UHFFFAOYSA-N 1,2-benzenedithiol Chemical class SC1=CC=CC=C1S JRNVQLOKVMWBFR-UHFFFAOYSA-N 0.000 description 1
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-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
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- AEUVIXACNOXTBX-UHFFFAOYSA-N 1-sulfanylpropan-1-ol Chemical compound CCC(O)S AEUVIXACNOXTBX-UHFFFAOYSA-N 0.000 description 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 1
- OORRCVPWRPVJEK-UHFFFAOYSA-N 2-oxidanylethanoic acid Chemical compound OCC(O)=O.OCC(O)=O OORRCVPWRPVJEK-UHFFFAOYSA-N 0.000 description 1
- POMQYTSPMKEQNB-UHFFFAOYSA-N 3-hydroxyoctadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)CC(O)=O POMQYTSPMKEQNB-UHFFFAOYSA-N 0.000 description 1
- CXMBJBCPGQIVET-UHFFFAOYSA-N 3-sulfanylbenzene-1,2-diol Chemical compound OC1=CC=CC(S)=C1O CXMBJBCPGQIVET-UHFFFAOYSA-N 0.000 description 1
- RQPNXPWEGVCPCX-UHFFFAOYSA-N 3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O RQPNXPWEGVCPCX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229910002065 alloy metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000005365 aminothiol group Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 210000000078 claw Anatomy 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- DZQISOJKASMITI-UHFFFAOYSA-N decyl-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound CCCCCCCCCCP(O)(O)=O DZQISOJKASMITI-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229940100539 dibutyl adipate Drugs 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- JTJNOHFRNUDPDF-UHFFFAOYSA-N didodecyl nonanedioate Chemical compound CCCCCCCCCCCCOC(=O)CCCCCCCC(=O)OCCCCCCCCCCCC JTJNOHFRNUDPDF-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 239000010733 inhibited oil Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000010721 machine oil Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
- HOOANQZZUGPTRH-UHFFFAOYSA-N molybdenum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Mo+3].[Mo+3] HOOANQZZUGPTRH-UHFFFAOYSA-N 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- MAGSSGQAJNNDLU-UHFFFAOYSA-N s-phenylthiohydroxylamine Chemical class NSC1=CC=CC=C1 MAGSSGQAJNNDLU-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000010723 turbine oil 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
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
- C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic Table compounds without a metal-carbon linkage
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/027—Neutral salts thereof
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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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
- C10M2209/086—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 polycarboxylic, e.g. maleic acid
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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
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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
- C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three 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
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
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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
- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbasedsulfonic acid salts
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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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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/02—Esters of silicic acids
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- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/066—Organic compounds derived from inorganic acids or metal salts derived from Mo or W
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- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/09—Complexes with metals
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- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
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- C10M2229/04—Siloxanes with specific structure
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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- C10M2229/04—Siloxanes with specific structure
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- C10M2229/04—Siloxanes with specific structure
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- C10M2229/04—Siloxanes with specific structure
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- C10M2229/04—Siloxanes with specific structure
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- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Definitions
- Lubricating oils generally have a tendency to deteriorate due to oxidation and form decomposition products which are corrosive to metals. Since lubricating oils in use today almost invariably come into contact with metal surfaces, the problem of overcoming oxidation and corrosion is considered to be one of major importance. Opcrating conditions encountered in modern internal combustion engines in which these oils are commonly employed involve increased temperatures, higher speeds and reduced clearances which tend to promote decomposition and the formation of corrosive products. Furthermore, these engines generally employ alloy metal bearings which, besides their possible catalytic effect on the decomposition of the hydrocarbon type mineral lubricating oils, are easily corroded and this, in turn, has seriously accentuated the oxidation and corrosion problems in-rnineral lubrieating oils.
- Inhibitors have been added to lubricating oils to improve their resistance to decomposition and avoid corrosivity.
- Mineral lubricating oils for internal combustion engines due to the severity of their service, have also been compounded with additional agents such as wear inhibitors, sludge inhibitors and detergents to loosen and suspend products of decomposition and counteract their effect.
- wear inhibitors such as wear inhibitors, sludge inhibitors and detergents to loosen and suspend products of decomposition and counteract their effect.
- many of these agents may adversely affect the efiiciency of the oxidation and corrosion inhibitors and it is a problem to find inhibitors which will function in combination with them.
- some of the most effective oxidation and corrosion inhibitors contain active sulfur and are, therefore, extremely corrosive to silver and similar metals which are subject to attack by active sulfur.
- a more particular object of the invention is to provide lubricating oil compositions which are noncorrosive to silver and similar metals.
- Anothermore particular object is the provision of mineral lubricating oil compositions in which the tendency to corrode alloy bearings of internal combustion engines has been inhibited.
- a further and somewhat related object is to provide compounded mineral lubricating oil compositions having improved anticorrosion properties without adversely affect-ing the stabilizing, deterging and lubricating qualities of'the' hydrocarbon oil composition.
- Another and still more particular object of the invention is the provision of mineral lubricating oil compositions which are noncorrosive to silver metal-containing bearings of the type employed in railroad diesel engines.
- compositions comprising an oil of lubricating viscosity and a complex of a metal compound selected from the group consisting of acids, oxides and salts of molybdenum with a metal chelating agent having two functional groups, not more than one of which is a hydroxyl radical, in vicinal or beta position to one another on the carbon skeleton of a hydrocarbon linkage have greatly enhanced anticorrosion properties. It has also been found that, in particular, compositions comprising a compounded mineral lubricating oil for internal combustion engines which is normally corrosive to alloy bearings and such chelates are substantially noncorrosive.
- the metal chelating agent referred to above is the accepted terminology for a definite and well-known class of chemical compounds. Such compounds have been heretofore described in many published texts including the recent book entitled Chemistry of the Metal Cbelate Compounds by Martel] and Calvin which was published by Prentice-Hall, Inc. of New York in 1952.
- the more suitable compounds of this class are members of the group consisting of dithiols, diamines, mercapto alcohols, amino alcohols.
- amino thiols dicarboxylic acids, hydroxycarboxylic acids, mercoptocarboxylic acids, aminocarboxylic acids, beta-diketones, betaketo carboxylic acid esters, dimercapto benzenes, mercaptohydroxy benzenes, diamino benzenes, aminohydroxy benzenes, aminomercapto benzenes, hydroxycarboxy benzenes, aminocarboxy benzenes, and mcrcaptocarboxy ben- Zenes having the two functional groups in vicinal or beta position to one another on the carbon skeleton.
- the complexes of the lubricating oil compositions according to this invention are prepared by the reaction of a mixture of the acid, oxide or salt of the metal and chelating agent.
- the mixtures are ordinarily heated to accelerate the reaction.
- two of the functional groups of a single hydroxycarboxylic acid, dithiol, dicarboxylic acid, etc. react with the acid to form what is commonly termed a metal chelate compound.
- These compounds are characterized by a "claw" type of structure in which one or more rings of similar or unlike structure due to the use of mixed chelating agents are formed including the molybdenum.
- the preferred chelates of the above type are oil-soluble and the chelating agents are usually selected so as to impart oil solubility to the complex or chelate.
- Chelating agents containing from 2 to 18 carbon atoms are usually suitable since the less oil-soluble chelates may be used in combination with dispersants such as alkaline earth metal petroleum sulfonatesor oil-solubilizing agents such as glycols and other polyhydric alcohols as-well as ethers thereof.
- dispersants such as alkaline earth metal petroleum sulfonatesor oil-solubilizing agents such as glycols and other polyhydric alcohols as-well as ethers thereof.
- Those containing from 6 to 10 carbon atoms in the carbon skeleton are preferred since they impart an optimum degree of oil solubility to the chelate or complex.
- Suitable chelating agents within the above-described class include vicinaland beta-dithiols such as ethylene mercaptan and 1,3-propanedithiol; vicinaland beta-mercapto alcohols such as beta-mercaptoethanol, 3 mercapto-l-propanol; vicinaland beta-diamines such as ethylenediamine and propylenediamine; vicinaland beta-amino alcohols such as ethanolamine and 3-amino-l-propanol; vicinaland beta-aminothiols such as thioethanolamine and 3-amine-l-mercaptopropane; vicinaland beta-dicarboxylic acids such as oxalic acid and malonic acid; vicinaland beta-hydroxy carboxylic acids such as glycolic acid and beta-hydroxybutyric acid; vicinaland beta-mercapto carboxylic acids such as thioglycolic acid and beta-mercaptobutyric acid; vicinal
- the foregoing compounds are characterized by normal or branched carbon skeletons. in various positions along the carbon skeleton, aromatic and substituted aromatic rings; hydroxy, alkoxy, and aryloxy radicals; sulfhydryl, alkylthioether, arylthioether, alkylthioester, and arylthioester groups; acyl, aroyl, thioacyl and thioaroyl radicals; amino, alkylamine, arylamino, acylamido and aroylamido radicals; and nitro, halogen and sulfato groups.
- preferred chelating agents of the aforementioned type for present purposes are those having an aliphatic hydrocarbon group between the two functional groups.
- chelating agents include various carbocyclic or aromatic chelating agents including vicinal-dimercaptoaromatic compounds such as thiocatechol; vicinal-mercaptohydroxy aromatic compounds such as monothiocatechol or mercaptohydroxy benzene; vicinaldiaminoaromatic compounds such as o-phenylenediamine; vicinal-aminohydroxyaromatic compounds such as o-aminophenol; vicinal-aminomercaptoaromatic compounds such as o-aminothiophenol; vicinal-hydroxycarboxyaromatic compounds such as salicylic acid; vicinalaminocarboxyaromatic compounds such as o-aminobenzoic acid; vicinal-mercaptocarboxyaromatic compounds such as omercaptobenzoic acid; etc.
- vicinal-dimercaptoaromatic compounds such as thiocatechol
- vicinal-mercaptohydroxy aromatic compounds such as monothiocatechol or mer
- the aforementioned carbocyclic or aromatic chelating agents may have various ring substituents including aromatic and substituted aromatic rings; hydroxy, alkoxy, and aryloxy radicals; sulfhydryl, alkylthioether, arylthioether, alkylthioester, and arylthioester groups; acyl, aroyl, thioacyl and thioaroyl radicals; amino, alkylamino, arylamino, acylamido, and aroylamido radicals; and nitro, halogen and sulfate groups.
- aromatic chelating agents having the two functional groups on a benzene ring or an alkyl benzene containing from 2 to 18 carbon atoms in the alkyl group are preferred since the chelates of the above-described metals prepared with them possess the most satisfactory oil-solubility characteristics.
- the chelating agents most preferred out of the above-described classes are the aliphatic and carbocyclic vicinaland beta-dicarboxylic and hydroxycarboxylic acids of from 2 to 18 and preferably 2 to 10 aliphatic carbon atoms.
- Illustrative chelating agents of this particular group are alpha-hydroxyacetic acid (glycolic acid), alpha-hydroxydecanoic acid, betahydroxystearic acid, salicylic acid, cetylsalicylic acid, 2- hydroxy-cyclohcxanoic acid, tetrahydrophthalic acid, tartaric acid, citric acid, lactic acid, glutaric acid, oxalic acid, malonic acid, phthalic acid, etc.
- These chelating agents give complexes of the previously described types which are superior corrosion and/or oxidation inhibitors in the lubricating oil compositions of the invention.
- Suitable acids include molybdic acid or molybdic hydroxide and molybdic anhydride as illustrative examples.
- Oxides of molybdenum which form complexes with the chelating agents adapted for use in the lubricating oil compositions of the invention are illustrated by compounds such as molybdenum sesquioxide, etc.
- Suitable salts are the inorganic salts such as ammonium paramolybdate, ammonium molybdate, molybdanyl chloride, etc.
- amine salts of the acid complexes of molybdenum and chelating agents referred to above may also be employed advantageously in the lubricating oil compositions of the invention.
- These amine salts are conveniently prepared by heating a mixture of the acid complex with an organic amine such as trimethylamine, triethanolamine, laurylamine, phenyl-alpha-naphthylamine, phenylene diamines, aminophenol, pyridine, and morpholine.
- Esters of the acid complexes such as the monobutyl esters and monopentaerythritol esters are also suitable.
- Such substituted complexes are generally characterized by enhanced oil solubility which may be desirable in the compounding of certain mineral lubricating oil compositions.
- the complex of molybdenum described above is present in the compositions of the invention in an amount at least suflicient to inhibit corrosion or oxidation.
- Small amounts usually from about 0.01 to about 5.0 percent by weight based on the oil, are etfective.
- Proportions ranging from about 0.05 to about 1.0 percent are preferred in most lubricating oil compositions. Concentrates containing larger proportions, up to 50 percent, either in solution or suspension, are particularly suitable in compounding operations.
- oils of lubricating viscosity are suitable base oils for the compositions of the invention. They include hydrocarbon or mineral lubricating oils of naphthenic, paratfinic, and mixed naphthenic and paraflinic types. They may be refined by any of the conventional methods such as solvent refining and acid refining. Synthetic hydrocarbon oils of the alkylene polymer type or those derived from coal and shale may also be employed. Alkylene oxide polymers and their derivatives such as the propylene oxide polymers and their ethyl esters and acetyl derivatives in which the terminal hydroxyl groups have been modified are also suitable.
- Synthetic oils of the dicarboxylic acid ester type including dibutyl adipate, di-2-ethylhexyl sebacate, di-nhexyl fumaric polymer, dilauryl azelate, and the like may be used.
- Alkyl benzene types of synthetic oils such as tetradecyl benzene, etc. are also included.
- Liquid esters of acids of phosphorus including tricresyl phosphate, diethyl esters of decane phosphonic acid, and the like may also be employed.
- polysiloxane oils of the type of polyalkyl, polyaryl, polyalkoxy and polyaryloxy siloxanes such as polymethyl siloxane, polymethylphenyl siloxane and polymethoxyphenoxy siloxane and silicate ester oils such as tetraalkyl and tetraaryl silicates of the tetra-Z-ethylhexyl silicate and tetra-p-tert.-butylphenyl silicate types.
- the complexes are employed in combination with compounded mineral lubricating oils of the internal combustion engine type which are normally corrosive to alloy bearings.
- compounded mineral lubricating oils of the internal combustion engine type which are normally corrosive to alloy bearings.
- straight oils of lubricating viscosity at major proportion of the lubricating oil normally corrosive to metals and/or subject to oxidation and a small amount, sufficient to inhibit said corrosion and/or oxidation, of the complex provides a remarkably improved composition.
- These compounded oils customarily contain detergents such as the oil-soluble petroleum sulfonates and stabilizers such as the metal alkyl phenates.
- EXAMPLE 2 A slurry of 50 parts of ammonium paramolybdate and 60 parts of a 70% aqueous solution of glycolic acid in 100 parts of toluene is heated with stirring at reflux tem perature and the azeotropic water is separated and removed. A deep blue-green color appears after about 15 minutes. The reaction is complete after about 45 minutes. 500 parts of a basic calcium petroleum sulfonate concentrate in neutral mineral lubricating oil analyzing 4.35% calcium is added and the mixture is stirred and heated at 380 F. under 50 mm. Hg pressure for 30 minutes to remove the last traces of water. The product consisting of neutral mineral oil, glycolic acid molybdate and calcium petroleum sulfonate is filtered and used as a concentrate. Analysis of the concentrate shows about 2.3% molybdenum.
- the effectiveness of the lubricating oil compositions of the invention is demonstrated by the copper-lead strip corrosion test.
- a polished copper-lead strip is weighed and immersed in 300 cubic centimeters of test oil in a 100-milliliter lipless Berezelius breaker.
- the test oil is maintained at 340 F. under a pressure of one atmosphere of air and stirred with a mechanical stirrer at 1000 R. P. M.
- a synthetic naphthenate catalyst is added, unless otherwise specified, to provide the following catalytic metals:
- the test is continued 20 hours.
- the copper-lead strip is then removed, rubbed vigorously with a soft cloth and weighed to determine the net weight loss.
- test oils include various types of mineral lubricating oil compositions as reference oils.
- compounded oil (A) consists of a solvent refined SAE 40 mineral lubricating oil base having a viscosity index of 60 and containing 40 millimoles per kilogram of neutral calcium petroleum sulfonate.
- compounded oil (B) consists of the same base oil but contains 20 millimoles per kilogram of basic calcium petroluem sulfonate. Th test results are shown in the following table. The concentrations of complex employed are given in millimoles of molybdenum per kilogram of oil or percent by weight of the composition.
- compositions in accordance with this invention containing the same mineral lubricating oil base and a complex of the previously described type give as little as 1.9 milligrams for the same period. This shows that the compositions of the present invention are effectively inhibited against oxidation and/or corrosion characteristics due to the oxidative deterioration of the oil.
- compositions of the invention have been primarily described as crankcase lubricants for internal combustion engines, they are also useful as turbine oils, hydraulic fluids, instrument oils, constituent oils in grease manufacture, ice-machine oils, and the like.
- a lubricant composition consisting essentially of a mineral lubricating oil for internal combustion engines containing minor amounts of alkaline earth metal petroleum sulfonate and alkaline earth metal alkyl phenate, which is normally corrosive to alloy bearings, and from 0.01 to about 5.0 percent by weight based on the oil of a member of the group consisting of glycolic acid molybdate and oxalic acid molybdate.
- a lubricant composition consisting essentially of mineral lubricating oil for internal combustion engines containing minor amounts of alkaline earth metal petroleum sulfonate and alkaline earth metal alkyl phenate which is normally corrosive to alloy bearings and from about 0.01 to about 5.0 percent by weight based on the oil of glycolic acid molybdate.
- a lubricant composition consisting essentially of mineral lubricating oil for internal combustion engines containing minor amounts of alkaline earth metal petroleum sulfonate and alkaline earth metal alkyl phenate which is normally corrosive to alloy bearings and from about 0.01 to about 5.0 percent by weight based on the oil of oxalic acid molybdate.
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Description
'provide lubricating oil compositions United States Patent O 2,795,550 LUBRICATING OIL COMPOSITIONS Oliver L."Harle, Berkeley, John R. Thomas, Albany, and Andrew D. Abbott, Ross, Calif., assignors to California 'Research Corporation, San Francisco, Calif., is corporation of Delaware No Drawing. Application June 29, 1954, Serial No. 440,262 3 Claims. (Cl. 252-495) This invention relates to novel lubricant compositions. More particularly, the invention is concerned with novel lubricating oil compositions having improved oxidation and corrosion inhibiting properties.
Lubricating oils generally have a tendency to deteriorate due to oxidation and form decomposition products which are corrosive to metals. Since lubricating oils in use today almost invariably come into contact with metal surfaces, the problem of overcoming oxidation and corrosion is considered to be one of major importance. Opcrating conditions encountered in modern internal combustion engines in which these oils are commonly employed involve increased temperatures, higher speeds and reduced clearances which tend to promote decomposition and the formation of corrosive products. Furthermore, these engines generally employ alloy metal bearings which, besides their possible catalytic effect on the decomposition of the hydrocarbon type mineral lubricating oils, are easily corroded and this, in turn, has seriously accentuated the oxidation and corrosion problems in-rnineral lubrieating oils.
Inhibitors have been added to lubricating oils to improve their resistance to decomposition and avoid corrosivity. Mineral lubricating oils for internal combustion engines, due to the severity of their service, have also been compounded with additional agents such as wear inhibitors, sludge inhibitors and detergents to loosen and suspend products of decomposition and counteract their effect. Unfortunately, many of these agents may adversely affect the efiiciency of the oxidation and corrosion inhibitors and it is a problem to find inhibitors which will function in combination with them. Furthermore, some of the most effective oxidation and corrosion inhibitors contain active sulfur and are, therefore, extremely corrosive to silver and similar metals which are subject to attack by active sulfur. These types of metals, although once not so widely used in contact with lubricating oils and therefore considered to constitute only a minor prob- 1 lem, are being increasingly employed today. Particularly in certainimporta'nt classes of internal combustion engines as, for example, marine and railroad diesel engines, silver metal-containing bearings are more and more com- "mon and the problem of providing proper lubrication for them is one of major importance.
It is, therefore, a general object of this invention to having improved antioxidant and anticorrosion properties.
A more particular object of the invention is to provide lubricating oil compositions which are noncorrosive to silver and similar metals.
Anothermore particular object is the provision of mineral lubricating oil compositions in which the tendency to corrode alloy bearings of internal combustion engines has been inhibited.
A further and somewhat related object is to provide compounded mineral lubricating oil compositions having improved anticorrosion properties without adversely affect-ing the stabilizing, deterging and lubricating qualities of'the' hydrocarbon oil composition.
Another and still more particular object of the invention is the provision of mineral lubricating oil compositions which are noncorrosive to silver metal-containing bearings of the type employed in railroad diesel engines.
Patented June 11, 1957 "ice Additional objects of the invention will become apparent from the description and claims which follow.
in the accomplishment of the above objects, it has been found that compositions comprising an oil of lubricating viscosity and a complex of a metal compound selected from the group consisting of acids, oxides and salts of molybdenum with a metal chelating agent having two functional groups, not more than one of which is a hydroxyl radical, in vicinal or beta position to one another on the carbon skeleton of a hydrocarbon linkage have greatly enhanced anticorrosion properties. It has also been found that, in particular, compositions comprising a compounded mineral lubricating oil for internal combustion engines which is normally corrosive to alloy bearings and such chelates are substantially noncorrosive.
The metal chelating agent referred to above is the accepted terminology for a definite and well-known class of chemical compounds. Such compounds have been heretofore described in many published texts including the recent book entitled Chemistry of the Metal Cbelate Compounds by Martel] and Calvin which was published by Prentice-Hall, Inc. of New York in 1952. For present purposes the more suitable compounds of this class are members of the group consisting of dithiols, diamines, mercapto alcohols, amino alcohols. amino thiols, dicarboxylic acids, hydroxycarboxylic acids, mercoptocarboxylic acids, aminocarboxylic acids, beta-diketones, betaketo carboxylic acid esters, dimercapto benzenes, mercaptohydroxy benzenes, diamino benzenes, aminohydroxy benzenes, aminomercapto benzenes, hydroxycarboxy benzenes, aminocarboxy benzenes, and mcrcaptocarboxy ben- Zenes having the two functional groups in vicinal or beta position to one another on the carbon skeleton.
The normal tendency of oils to become oxidized and corrosive is definitely inhibited in the improved compositions of the invention. Metal surfaces in general are not corroded by contact with these compositions and internal combustion engine alloy bearings, in particular, are re markably benefited. Bearings of silver and similar metals which, as stated above are increasingly important due to their presently expanded use in marine and railroad diesel engines, are not corroded by these compositions whereas conventional oxidation inhibited oils have severely pitted and corroded such bearings. The advantages of these improvements are obtained in the compositions of this invention without loss of stability or detergency in the composition.
The complexes of the lubricating oil compositions according to this invention are prepared by the reaction of a mixture of the acid, oxide or salt of the metal and chelating agent. The mixtures are ordinarily heated to accelerate the reaction. Although the nature of the reactionis not definitely known, it is believed that two of the functional groups of a single hydroxycarboxylic acid, dithiol, dicarboxylic acid, etc. react with the acid to form what is commonly termed a metal chelate compound. These compounds are characterized by a "claw" type of structure in which one or more rings of similar or unlike structure due to the use of mixed chelating agents are formed including the molybdenum.
The preferred chelates of the above type are oil-soluble and the chelating agents are usually selected so as to impart oil solubility to the complex or chelate. Chelating agents containing from 2 to 18 carbon atoms are usually suitable since the less oil-soluble chelates may be used in combination with dispersants such as alkaline earth metal petroleum sulfonatesor oil-solubilizing agents such as glycols and other polyhydric alcohols as-well as ethers thereof. Those containing from 6 to 10 carbon atoms in the carbon skeleton are preferred since they impart an optimum degree of oil solubility to the chelate or complex.
Examples of suitable chelating agents within the above-described class include vicinaland beta-dithiols such as ethylene mercaptan and 1,3-propanedithiol; vicinaland beta-mercapto alcohols such as beta-mercaptoethanol, 3 mercapto-l-propanol; vicinaland beta-diamines such as ethylenediamine and propylenediamine; vicinaland beta-amino alcohols such as ethanolamine and 3-amino-l-propanol; vicinaland beta-aminothiols such as thioethanolamine and 3-amine-l-mercaptopropane; vicinaland beta-dicarboxylic acids such as oxalic acid and malonic acid; vicinaland beta-hydroxy carboxylic acids such as glycolic acid and beta-hydroxybutyric acid; vicinaland beta-mercapto carboxylic acids such as thioglycolic acid and beta-mercaptobutyric acid; vicinaland beta-amino carboxylic acids such as glycine and beta-aminobutyric acid; beta-diketones such as acetylacetone and benzoylacetone; beta-ketocarboxylic acid esters such as ethyl acetoacetate; etc. The foregoing compounds are characterized by normal or branched carbon skeletons. in various positions along the carbon skeleton, aromatic and substituted aromatic rings; hydroxy, alkoxy, and aryloxy radicals; sulfhydryl, alkylthioether, arylthioether, alkylthioester, and arylthioester groups; acyl, aroyl, thioacyl and thioaroyl radicals; amino, alkylamine, arylamino, acylamido and aroylamido radicals; and nitro, halogen and sulfato groups. However, preferred chelating agents of the aforementioned type for present purposes are those having an aliphatic hydrocarbon group between the two functional groups.
Also suitable as chelating agents are various carbocyclic or aromatic chelating agents including vicinal-dimercaptoaromatic compounds such as thiocatechol; vicinal-mercaptohydroxy aromatic compounds such as monothiocatechol or mercaptohydroxy benzene; vicinaldiaminoaromatic compounds such as o-phenylenediamine; vicinal-aminohydroxyaromatic compounds such as o-aminophenol; vicinal-aminomercaptoaromatic compounds such as o-aminothiophenol; vicinal-hydroxycarboxyaromatic compounds such as salicylic acid; vicinalaminocarboxyaromatic compounds such as o-aminobenzoic acid; vicinal-mercaptocarboxyaromatic compounds such as omercaptobenzoic acid; etc. The aforementioned carbocyclic or aromatic chelating agents may have various ring substituents including aromatic and substituted aromatic rings; hydroxy, alkoxy, and aryloxy radicals; sulfhydryl, alkylthioether, arylthioether, alkylthioester, and arylthioester groups; acyl, aroyl, thioacyl and thioaroyl radicals; amino, alkylamino, arylamino, acylamido, and aroylamido radicals; and nitro, halogen and sulfate groups. For present purposes those aromatic chelating agents having the two functional groups on a benzene ring or an alkyl benzene containing from 2 to 18 carbon atoms in the alkyl group are preferred since the chelates of the above-described metals prepared with them possess the most satisfactory oil-solubility characteristics.
For present purposes the chelating agents most preferred out of the above-described classes are the aliphatic and carbocyclic vicinaland beta-dicarboxylic and hydroxycarboxylic acids of from 2 to 18 and preferably 2 to 10 aliphatic carbon atoms. Illustrative chelating agents of this particular group are alpha-hydroxyacetic acid (glycolic acid), alpha-hydroxydecanoic acid, betahydroxystearic acid, salicylic acid, cetylsalicylic acid, 2- hydroxy-cyclohcxanoic acid, tetrahydrophthalic acid, tartaric acid, citric acid, lactic acid, glutaric acid, oxalic acid, malonic acid, phthalic acid, etc. These chelating agents give complexes of the previously described types which are superior corrosion and/or oxidation inhibitors in the lubricating oil compositions of the invention.
Although it is convenient for the sake of illustration in the above description of the invention to refer to the reaction of an acid of molybdenum with the various chelating agents or mixtures thereof to form the com- They may have substituted plexes for the lubricating oil compositions, other compounds of molybdenum such as the oxides and salts mentioned above may also be employed to provide similar chelates. Suitable acids include molybdic acid or molybdic hydroxide and molybdic anhydride as illustrative examples. Oxides of molybdenum which form complexes with the chelating agents adapted for use in the lubricating oil compositions of the invention are illustrated by compounds such as molybdenum sesquioxide, etc. Suitable salts are the inorganic salts such as ammonium paramolybdate, ammonium molybdate, molybdanyl chloride, etc.
Various amine salts of the acid complexes of molybdenum and chelating agents referred to above may also be employed advantageously in the lubricating oil compositions of the invention. These amine salts are conveniently prepared by heating a mixture of the acid complex with an organic amine such as trimethylamine, triethanolamine, laurylamine, phenyl-alpha-naphthylamine, phenylene diamines, aminophenol, pyridine, and morpholine. Esters of the acid complexes such as the monobutyl esters and monopentaerythritol esters are also suitable. Such substituted complexes are generally characterized by enhanced oil solubility which may be desirable in the compounding of certain mineral lubricating oil compositions.
The complex of molybdenum described above is present in the compositions of the invention in an amount at least suflicient to inhibit corrosion or oxidation. Small amounts, usually from about 0.01 to about 5.0 percent by weight based on the oil, are etfective. Proportions ranging from about 0.05 to about 1.0 percent are preferred in most lubricating oil compositions. Concentrates containing larger proportions, up to 50 percent, either in solution or suspension, are particularly suitable in compounding operations.
Any of the well-known types of oils of lubricating viscosity are suitable base oils for the compositions of the invention. They include hydrocarbon or mineral lubricating oils of naphthenic, paratfinic, and mixed naphthenic and paraflinic types. They may be refined by any of the conventional methods such as solvent refining and acid refining. Synthetic hydrocarbon oils of the alkylene polymer type or those derived from coal and shale may also be employed. Alkylene oxide polymers and their derivatives such as the propylene oxide polymers and their ethyl esters and acetyl derivatives in which the terminal hydroxyl groups have been modified are also suitable. Synthetic oils of the dicarboxylic acid ester type including dibutyl adipate, di-2-ethylhexyl sebacate, di-nhexyl fumaric polymer, dilauryl azelate, and the like may be used. Alkyl benzene types of synthetic oils such as tetradecyl benzene, etc. are also included. Liquid esters of acids of phosphorus including tricresyl phosphate, diethyl esters of decane phosphonic acid, and the like may also be employed. Also suitable are the polysiloxane oils of the type of polyalkyl, polyaryl, polyalkoxy and polyaryloxy siloxanes such as polymethyl siloxane, polymethylphenyl siloxane and polymethoxyphenoxy siloxane and silicate ester oils such as tetraalkyl and tetraaryl silicates of the tetra-Z-ethylhexyl silicate and tetra-p-tert.-butylphenyl silicate types.
In a preferred embodiment of the invention, as mentioned above, the complexes are employed in combination with compounded mineral lubricating oils of the internal combustion engine type which are normally corrosive to alloy bearings. In such an embodiment, as in the case of the other, straight oils of lubricating viscosity, at major proportion of the lubricating oil normally corrosive to metals and/or subject to oxidation and a small amount, sufficient to inhibit said corrosion and/or oxidation, of the complex provides a remarkably improved composition. These compounded oils customarily contain detergents such as the oil-soluble petroleum sulfonates and stabilizers such as the metal alkyl phenates. Other EXAMPLE 1 To a solution prepared from 36 grams (0.25 mole) of molybdenum trioxide and 150 milliliters of concentrated ammonium hydroxide (28% ammonia) in a 2-liter, 3- necked flask is added 200 milliliters of toluene and 63 grams (0.50 mole) of oxalic acid dihydrate. The mixture is refluxed with continuous water separation. A deep blue color appears after about 15 minutes. After complete removal of the water, the mixture is heated for one hour at 250 F. The toluene is then removed by distillation and 300 grams of ethylene glycol is added. After stirring for one-half hour at 250 F., 500 grams of basic calcium petroleum sulfonate in neutral mineral lubricating oil analyzing 4.35% calcium is added and the ethylene glycol removed by distillation at 385 F. under 50 mm. Hg pressure. The resulting solution of oxalic acid molybdate is used as a concentrate in blending test oils. By analysis, the per cent molybdenum is 3.25.
EXAMPLE 2 A slurry of 50 parts of ammonium paramolybdate and 60 parts of a 70% aqueous solution of glycolic acid in 100 parts of toluene is heated with stirring at reflux tem perature and the azeotropic water is separated and removed. A deep blue-green color appears after about 15 minutes. The reaction is complete after about 45 minutes. 500 parts of a basic calcium petroleum sulfonate concentrate in neutral mineral lubricating oil analyzing 4.35% calcium is added and the mixture is stirred and heated at 380 F. under 50 mm. Hg pressure for 30 minutes to remove the last traces of water. The product consisting of neutral mineral oil, glycolic acid molybdate and calcium petroleum sulfonate is filtered and used as a concentrate. Analysis of the concentrate shows about 2.3% molybdenum.
The effectiveness of the lubricating oil compositions of the invention is demonstrated by the copper-lead strip corrosion test. In this test a polished copper-lead strip is weighed and immersed in 300 cubic centimeters of test oil in a 100-milliliter lipless Berezelius breaker. The test oil is maintained at 340 F. under a pressure of one atmosphere of air and stirred with a mechanical stirrer at 1000 R. P. M. After two hours a synthetic naphthenate catalyst is added, unless otherwise specified, to provide the following catalytic metals:
Percent by weight Iron 0.008 Lead 0.004 Copper 0.002 Manganese 0.005 Chromium 0.004
The test is continued 20 hours. The copper-lead strip is then removed, rubbed vigorously with a soft cloth and weighed to determine the net weight loss.
The test oils include various types of mineral lubricating oil compositions as reference oils. compounded oil (A) consists of a solvent refined SAE 40 mineral lubricating oil base having a viscosity index of 60 and containing 40 millimoles per kilogram of neutral calcium petroleum sulfonate. compounded oil (B) consists of the same base oil but contains 20 millimoles per kilogram of basic calcium petroluem sulfonate. Th test results are shown in the following table. The concentrations of complex employed are given in millimoles of molybdenum per kilogram of oil or percent by weight of the composition.
Table I COPPERLEAD STRIP CORROSION TEST Copper- Oil Lead Strip Weight Loss e -J Reference oil (A) 225.0 20 mMJkg. glycolic acid molybdate in reference oil (A)... 1.0 20 mM./kg. oxalic acid molybdate in reference oil (A) 10. 7 Reference oil (B) 219. 0 10 mMJkg. glycolic acid molybdate in reference oil (B). 3. B
As shown by the above test data, the reference mineral lubricating oil compositions alone give copper-lead strip weight losses due to corrosion of as high as 225 milligrams in the 20hour period. By way of distinction, compositions in accordance with this invention containing the same mineral lubricating oil base and a complex of the previously described type give as little as 1.9 milligrams for the same period. This shows that the compositions of the present invention are effectively inhibited against oxidation and/or corrosion characteristics due to the oxidative deterioration of the oil.
The nature of the improved lubricating oil compositions of the invention and their effectiveness should be readily apparent from the many illustrations given above. Oxidation and corrosivity in the compositions are definitely inhibited to a very substantial degree. Particularly corrodible metals such as engine alloy bearings of copper, lead, and the like, as well as bearings of silver, are not adversely affected. This is indeed remarkable since the problem of devising lubricant compositions uniformly noncorrosive to both types of bearing metals has long confronted workers in the art. The advantages of these improvements are obtained without loss of other desirable properties of the lubricant compositions.
Although the compositions of the invention have been primarily described as crankcase lubricants for internal combustion engines, they are also useful as turbine oils, hydraulic fluids, instrument oils, constituent oils in grease manufacture, ice-machine oils, and the like.
We claim:
1. A lubricant composition consisting essentially of a mineral lubricating oil for internal combustion engines containing minor amounts of alkaline earth metal petroleum sulfonate and alkaline earth metal alkyl phenate, which is normally corrosive to alloy bearings, and from 0.01 to about 5.0 percent by weight based on the oil of a member of the group consisting of glycolic acid molybdate and oxalic acid molybdate.
2. A lubricant composition consisting essentially of mineral lubricating oil for internal combustion engines containing minor amounts of alkaline earth metal petroleum sulfonate and alkaline earth metal alkyl phenate which is normally corrosive to alloy bearings and from about 0.01 to about 5.0 percent by weight based on the oil of glycolic acid molybdate.
3. A lubricant composition consisting essentially of mineral lubricating oil for internal combustion engines containing minor amounts of alkaline earth metal petroleum sulfonate and alkaline earth metal alkyl phenate which is normally corrosive to alloy bearings and from about 0.01 to about 5.0 percent by weight based on the oil of oxalic acid molybdate.
References Cited in the file of this patent UNITED STATES PATENTS 2,144,654 Guthmann Ian. 24, 1939 2,161,184 McKone et al. June 6, 1939 2,305,627 Lincoln et al. Dec. 22, 1942 2,465,296 Swiss Mar. 22, 1949
Claims (1)
1. A LUBRICANT COMPOSITION CONSISTING ESSENTIALLY OF A MINERAL LUBRICATING OIL FOR INTERNAL COMBUSTION ENGINES CONTAINING A MINOR AMOUNTS OF ALKALINE EARTH METAL PETROLEUM SULFONATE AND ALKALINE EARHT METAL ALKYL PHENSATE, WHICH IS NORMALLY CORROSIVE TO ALLOY BEARINGS, AND FROM 0.01 TO ABOUT 5.0 PERCENT BY WEIGHT BASED ON THE OIL OF A MEMBER OF THE GROUP CONSISTING OF GLYCOLIC ACID MOLYBDATE AND OXALIC ACID MOLYBDATE.
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Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
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US3121059A (en) * | 1960-12-05 | 1964-02-11 | Standard Oil Co | Compositions of matter having anti-rust properties |
US3223625A (en) * | 1963-11-12 | 1965-12-14 | Exxon Research Engineering Co | Colloidal molybdenum complexes and their preparation |
US3231497A (en) * | 1963-04-30 | 1966-01-25 | Monsanto Res Corp | Polyphenyl ether blends |
US3282838A (en) * | 1960-05-10 | 1966-11-01 | Texaco Inc | Petroleum liquids containing amine salts of molybdic acid |
US3290245A (en) * | 1959-06-05 | 1966-12-06 | Castrol Ltd | Lubricating compositions containing amine tungstates |
US3314887A (en) * | 1964-01-02 | 1967-04-18 | Monsanto Co | Functional fluid compositions |
US3541014A (en) * | 1967-07-12 | 1970-11-17 | Lubrizol Corp | Molybdenum-containing lubricant compositions |
US4235770A (en) * | 1979-06-18 | 1980-11-25 | The B. F. Goodrich Company | Ammelinium beta-octamolybdate and composition containing same |
US4247451A (en) * | 1979-06-18 | 1981-01-27 | The B. F. Goodrich Company | Dicyclohexylammonium alpha-octamolybdate and composition containing same |
US4248767A (en) * | 1979-06-18 | 1981-02-03 | The B. F. Goodrich Company | Dodecylammonium alpha-octamolybdate and composition containing same |
USRE30642E (en) * | 1980-01-23 | 1981-06-09 | Halcon Research & Development Corp. | Process for preparing molybdenum acid salts |
US4746507A (en) * | 1985-04-02 | 1988-05-24 | Salutar, Inc. | EDHPA based contrast agents for MR imaging, apparatus and methods |
US5017712A (en) * | 1984-03-09 | 1991-05-21 | Arco Chemical Technology, Inc. | Production of hydrocarbon-soluble salts of molybdenum for epoxidation of olefins |
US5403502A (en) * | 1984-08-08 | 1995-04-04 | Phillips Petroleum Company | Lubricating additive comprising a molybdenum (VI) hydroxymercaptide |
US20040214731A1 (en) * | 2003-04-22 | 2004-10-28 | R.T. Vanderbilt Company, Inc. | Organoammonium tungstate and molybate compounds, and process for preparing such compounds |
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US2144654A (en) * | 1936-09-14 | 1939-01-24 | Leo Corp | Method of increasing solubility of metal salts of beta carboxy compounds in motor fuels |
US2161184A (en) * | 1935-10-18 | 1939-06-06 | Leo Corp | Motor lubricating oil |
US2305627A (en) * | 1939-05-24 | 1942-12-22 | Lubri Zol Dev Corp | Lubricating oil |
US2465296A (en) * | 1944-09-20 | 1949-03-22 | Westinghouse Electric Corp | Metal chelate stabilized organic silicon compositions and products thereof |
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Publication number | Priority date | Publication date | Assignee | Title |
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US2161184A (en) * | 1935-10-18 | 1939-06-06 | Leo Corp | Motor lubricating oil |
US2144654A (en) * | 1936-09-14 | 1939-01-24 | Leo Corp | Method of increasing solubility of metal salts of beta carboxy compounds in motor fuels |
US2305627A (en) * | 1939-05-24 | 1942-12-22 | Lubri Zol Dev Corp | Lubricating oil |
US2465296A (en) * | 1944-09-20 | 1949-03-22 | Westinghouse Electric Corp | Metal chelate stabilized organic silicon compositions and products thereof |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3290245A (en) * | 1959-06-05 | 1966-12-06 | Castrol Ltd | Lubricating compositions containing amine tungstates |
US3282838A (en) * | 1960-05-10 | 1966-11-01 | Texaco Inc | Petroleum liquids containing amine salts of molybdic acid |
US3121059A (en) * | 1960-12-05 | 1964-02-11 | Standard Oil Co | Compositions of matter having anti-rust properties |
US3231497A (en) * | 1963-04-30 | 1966-01-25 | Monsanto Res Corp | Polyphenyl ether blends |
US3223625A (en) * | 1963-11-12 | 1965-12-14 | Exxon Research Engineering Co | Colloidal molybdenum complexes and their preparation |
US3314887A (en) * | 1964-01-02 | 1967-04-18 | Monsanto Co | Functional fluid compositions |
US3541014A (en) * | 1967-07-12 | 1970-11-17 | Lubrizol Corp | Molybdenum-containing lubricant compositions |
US4235770A (en) * | 1979-06-18 | 1980-11-25 | The B. F. Goodrich Company | Ammelinium beta-octamolybdate and composition containing same |
US4247451A (en) * | 1979-06-18 | 1981-01-27 | The B. F. Goodrich Company | Dicyclohexylammonium alpha-octamolybdate and composition containing same |
US4248767A (en) * | 1979-06-18 | 1981-02-03 | The B. F. Goodrich Company | Dodecylammonium alpha-octamolybdate and composition containing same |
USRE30642E (en) * | 1980-01-23 | 1981-06-09 | Halcon Research & Development Corp. | Process for preparing molybdenum acid salts |
US5017712A (en) * | 1984-03-09 | 1991-05-21 | Arco Chemical Technology, Inc. | Production of hydrocarbon-soluble salts of molybdenum for epoxidation of olefins |
US5403502A (en) * | 1984-08-08 | 1995-04-04 | Phillips Petroleum Company | Lubricating additive comprising a molybdenum (VI) hydroxymercaptide |
US4746507A (en) * | 1985-04-02 | 1988-05-24 | Salutar, Inc. | EDHPA based contrast agents for MR imaging, apparatus and methods |
US20040214731A1 (en) * | 2003-04-22 | 2004-10-28 | R.T. Vanderbilt Company, Inc. | Organoammonium tungstate and molybate compounds, and process for preparing such compounds |
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