US2882228A - Metal working lubricants - Google Patents
Metal working lubricants Download PDFInfo
- Publication number
- US2882228A US2882228A US516784A US51678455A US2882228A US 2882228 A US2882228 A US 2882228A US 516784 A US516784 A US 516784A US 51678455 A US51678455 A US 51678455A US 2882228 A US2882228 A US 2882228A
- Authority
- US
- United States
- Prior art keywords
- acid
- carbon atoms
- acids
- amine
- alcohols
- 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 7
- 238000005555 metalworking Methods 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 40
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
- 239000000194 fatty acid Substances 0.000 claims description 12
- 229930195729 fatty acid Natural products 0.000 claims description 12
- 150000005846 sugar alcohols Polymers 0.000 claims description 10
- 239000010687 lubricating oil Substances 0.000 claims description 9
- 239000010688 mineral lubricating oil Substances 0.000 claims description 6
- 150000003510 tertiary aliphatic amines Chemical class 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- MOFCYHDQWIZKMY-UHFFFAOYSA-N chloromethylphosphonic acid Chemical compound OP(O)(=O)CCl MOFCYHDQWIZKMY-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 description 45
- -1 amine salt Chemical class 0.000 description 40
- 150000002148 esters Chemical class 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 239000003921 oil Substances 0.000 description 16
- NWEPJDPAVFDLBY-UHFFFAOYSA-N trichloromethylphosphonic acid Chemical compound OP(O)(=O)C(Cl)(Cl)Cl NWEPJDPAVFDLBY-UHFFFAOYSA-N 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 150000003973 alkyl amines Chemical class 0.000 description 11
- 150000004665 fatty acids Chemical class 0.000 description 11
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 10
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 10
- 239000002480 mineral oil Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 235000010446 mineral oil Nutrition 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- OPQWPLYRDAASTK-UHFFFAOYSA-N (2,3,4-trichlorophenyl)phosphonic acid Chemical class OP(O)(=O)C1=CC=C(Cl)C(Cl)=C1Cl OPQWPLYRDAASTK-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 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 5
- 239000000654 additive Substances 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- 239000004386 Erythritol Substances 0.000 description 4
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229930195725 Mannitol Natural products 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- TTZKGYULRVDFJJ-GIVMLJSASA-N [(2r)-2-[(2s,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-[(z)-octadec-9-enoyl]oxyethyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1O TTZKGYULRVDFJJ-GIVMLJSASA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 4
- 235000019414 erythritol Nutrition 0.000 description 4
- 229940009714 erythritol Drugs 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 229960005150 glycerol Drugs 0.000 description 4
- 230000001050 lubricating effect Effects 0.000 description 4
- 239000000594 mannitol Substances 0.000 description 4
- 235000010355 mannitol Nutrition 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- 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 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 235000019388 lanolin Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- JNYAEWCLZODPBN-KVTDHHQDSA-N (2r,3r,4r)-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-KVTDHHQDSA-N 0.000 description 2
- OPWCSZKCSWVMCL-ARJAWSKDSA-N (z)-19-methylicos-9-en-1-amine Chemical compound CC(C)CCCCCCCC\C=C/CCCCCCCCN OPWCSZKCSWVMCL-ARJAWSKDSA-N 0.000 description 2
- OIJAYOZHXTXUBD-TXDFQOQUSA-N (z)-octadec-9-enoic acid;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.CCCCCCCC\C=C/CCCCCCCC(O)=O OIJAYOZHXTXUBD-TXDFQOQUSA-N 0.000 description 2
- CCUBUDCJHCKPCI-UHFFFAOYSA-N 1,1-dichloroethylphosphonic acid Chemical compound CC(Cl)(Cl)P(O)(O)=O CCUBUDCJHCKPCI-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004166 Lanolin Substances 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- LWZFANDGMFTDAV-JOCBIADPSA-N [(2r)-2-[(2r,3r,4r)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@@H](O)[C@H]1O LWZFANDGMFTDAV-JOCBIADPSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical class ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- JYTMDBGMUIAIQH-UHFFFAOYSA-N hexadecyl oleate Natural products CCCCCCCCCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC JYTMDBGMUIAIQH-UHFFFAOYSA-N 0.000 description 2
- LSCOMKYDDYQNTJ-UHFFFAOYSA-N hydroxy-sulfanyl-sulfanylidene-(trichloromethyl)-$l^{5}-phosphane Chemical class OP(S)(=S)C(Cl)(Cl)Cl LSCOMKYDDYQNTJ-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229940039717 lanolin Drugs 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 2
- UOIWOHLIGKIYFE-UHFFFAOYSA-N n-methylpentan-1-amine Chemical compound CCCCCNC UOIWOHLIGKIYFE-UHFFFAOYSA-N 0.000 description 2
- 235000021313 oleic acid Nutrition 0.000 description 2
- JYTMDBGMUIAIQH-ZPHPHTNESA-N palmityl oleate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC JYTMDBGMUIAIQH-ZPHPHTNESA-N 0.000 description 2
- SSZBUIDZHHWXNJ-UHFFFAOYSA-N palmityl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC SSZBUIDZHHWXNJ-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 229920005573 silicon-containing polymer Polymers 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- QELWBSUUOJGQHR-KHPPLWFESA-N (z)-nonadec-9-en-1-amine Chemical compound CCCCCCCCC\C=C/CCCCCCCCN QELWBSUUOJGQHR-KHPPLWFESA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-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
- GIKNHHRFLCDOEU-UHFFFAOYSA-N 4-(2-aminopropyl)phenol Chemical compound CC(N)CC1=CC=C(O)C=C1 GIKNHHRFLCDOEU-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-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
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 101100061188 Drosophila melanogaster dila gene Proteins 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 208000007976 Ketosis Diseases 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 240000000038 Ziziphus mauritiana Species 0.000 description 1
- 235000006545 Ziziphus mauritiana Nutrition 0.000 description 1
- WERKSKAQRVDLDW-ANOHMWSOSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO WERKSKAQRVDLDW-ANOHMWSOSA-N 0.000 description 1
- 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 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001323 aldoses Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- DVRQHPGPSJMVRD-UHFFFAOYSA-N butoxy(trichloromethyl)phosphinic acid Chemical compound CCCCOP(O)(=O)C(Cl)(Cl)Cl DVRQHPGPSJMVRD-UHFFFAOYSA-N 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- VBAQNPAGWPVJGD-UHFFFAOYSA-N dihydroxy-selanylidene-(trichloromethyl)-lambda5-phosphane Chemical compound ClC(P(O)(O)=[Se])(Cl)Cl VBAQNPAGWPVJGD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000000694 effects Effects 0.000 description 1
- 229910001651 emery Inorganic materials 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ORTRWBYBJVGVQC-UHFFFAOYSA-N hexadecane-1-thiol Chemical group CCCCCCCCCCCCCCCCS ORTRWBYBJVGVQC-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229940119170 jojoba wax Drugs 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 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 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- SDQCOADWEMMSGK-UHFFFAOYSA-N n-ethyloctan-1-amine Chemical compound CCCCCCCCNCC SDQCOADWEMMSGK-UHFFFAOYSA-N 0.000 description 1
- NQYKSVOHDVVDOR-UHFFFAOYSA-N n-hexadecylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCC NQYKSVOHDVVDOR-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- GEKDEMKPCKTKEC-UHFFFAOYSA-N tetradecane-1-thiol Chemical group CCCCCCCCCCCCCCS GEKDEMKPCKTKEC-UHFFFAOYSA-N 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical class CCCCCCCCCCCCCN ABVVEAHYODGCLZ-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
- XJAAVVLEUZQVNJ-UHFFFAOYSA-N trifluoromethylphosphonic acid Chemical class OP(O)(=O)C(F)(F)F XJAAVVLEUZQVNJ-UHFFFAOYSA-N 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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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Definitions
- This invention relates to improved lubricating compositions and more particularly to lubricating oil compositions which are stable, non' c'orrosive non-staining and possess extreme pressure and anti-wear properties.
- organic phosphonic and phosphinic acids having the above general formulaeanbe prepared by a -n' irnber of suitable. methods such as reportedby Arbuzov-t l. Gen. Ghent. (U'.S;S.R. 898-900, 1934 Coover; (Organic Qhmical Bulletin, Vol.23, No; 4;. 19551 Kosolapofis 60 Organic Phosphorus Qompounds (Wiley and Sons);
- dgcyl 2 ethylhexylamine (1-isobtitylfB-methYlbtityI) 6,3, thyleyclojliei ylamine, di(l-isobu'tyl 3 f methylbutyh timing; N-n dodecyldiethylenetriamine, .N-nrtetradecyldi- Ifi-heaadecyl jtriethylene .te'trarnine, j heptyl t rirnethylene d n' ,N-'
- One group of useful esters comprises those derived tram simple water-soluble alkanepolyols of from 2 to 6 "carbon atoms such as ethylene glycol, propylene glycol,
- Esters derived frornthe sugar snarl-'01s include glucose monooleate, glucose monoricino'leat'e, 'serbsse Tmonostearate, fructose monooleate and the like.
- minor amounts of secondary additives can be used in -coniunction with the two primary additives in compositions-of this invent-ion.
- additives are the sulfurized and/or .su'lfoh'alogena't'ed fattylm'aterials such as animal, vegetable and marine fats and oils and derivatives thereof. Materials of this type canj be prepared by the methods described in US. Patents 2,322,859, 2,454,034, 2,459,717, 2,467,137,, 2,614,078, 2,644,825 and 2,7 01,237.
- waxes such as chlorinated p'araffin wax, 'tihlofl ated tal-' low, etc., of these "materials preferred are the fsulfurized sperm oil, lanolin, rapeseed oils, oleic acid chlorinated paraffin wax and cetyl oleate as well as mixtures thereof.
- a lubricating oil composition comprising a major amount of a mineral lubricating oil containing from about 0.1% to about 10% each of a long chain highly branched primary tertiary aliphatic amine of at least8 carbon atoms salt of a chloromethanephosphonic acid, and a partial ester of a polyhydric alcohol having froin 2 to 6 carbon atoms and a C -C fatty acid.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL208213D NL208213A (is") | 1955-06-20 | ||
| BE548812D BE548812A (is") | 1955-06-20 | ||
| NL102996D NL102996C (is") | 1955-06-20 | ||
| US516784A US2882228A (en) | 1955-06-20 | 1955-06-20 | Metal working lubricants |
| FR1154532D FR1154532A (fr) | 1955-06-20 | 1956-06-18 | Compositions d'huile lubrifiante |
| GB18809/56A GB798635A (en) | 1955-06-20 | 1956-06-18 | Lubricating oil compositions |
| DEN12365A DE1015169B (de) | 1955-06-20 | 1956-06-18 | Schmieroel |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US516784A US2882228A (en) | 1955-06-20 | 1955-06-20 | Metal working lubricants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2882228A true US2882228A (en) | 1959-04-14 |
Family
ID=24057075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US516784A Expired - Lifetime US2882228A (en) | 1955-06-20 | 1955-06-20 | Metal working lubricants |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2882228A (is") |
| BE (1) | BE548812A (is") |
| DE (1) | DE1015169B (is") |
| FR (1) | FR1154532A (is") |
| GB (1) | GB798635A (is") |
| NL (2) | NL208213A (is") |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3112267A (en) * | 1960-06-15 | 1963-11-26 | Shell Oil Co | Lubricating compositions |
| US3143506A (en) * | 1960-06-20 | 1964-08-04 | Texaco Inc | Lubricants containing amine salts |
| US3185728A (en) * | 1960-06-20 | 1965-05-25 | Texaco Inc | Ethylene diamine salts of thiophosphonic acids |
| US3243452A (en) * | 1962-06-28 | 1966-03-29 | Olin Mathieson | Bis (hydroxydiarylphosphine) decaboranes |
| US3380928A (en) * | 1958-09-22 | 1968-04-30 | Shell Oil Co | Lubricating oil composition |
| US3499923A (en) * | 1965-09-07 | 1970-03-10 | Universal Oil Prod Co | Polychloroalkylphosphonic acid salts |
| US3635823A (en) * | 1966-11-04 | 1972-01-18 | Universal Oil Prod Co | Synergistic composition and use thereof |
| US3793199A (en) * | 1970-06-08 | 1974-02-19 | Texaco Inc | Friction reducing agent for lubricants |
| US3984599A (en) * | 1973-10-30 | 1976-10-05 | Exxon Research And Engineering Company | Lubricant coating compositions for use in metal drawing operations |
| US4252660A (en) * | 1979-11-23 | 1981-02-24 | Mobil Oil Corporation | Reaction products of organophosphorus halides with inorganic thiocyanates as load-carrying additives in lubricating oil compositions |
| WO1986005508A1 (en) * | 1985-03-15 | 1986-09-25 | The Lubrizol Corporation | Hydrogen sulfide stabilized oil-soluble sulfurized organic compositions |
| US5092908A (en) * | 1990-06-28 | 1992-03-03 | Exxon Research And Engineering Company | Composition for improving cold flow properties of middle distillates (OP-3571) |
| EP0712924A1 (en) * | 1994-11-15 | 1996-05-22 | The Lubrizol Corporation | Lubricants and fluids containing thiocarbamates and phosphonates |
| US5866520A (en) * | 1996-01-31 | 1999-02-02 | Chevron Chemical Company | Lubricant composition suitable for direct fuel injected, crankcase-scavenged two-stroke cycle engines |
| WO2003020855A1 (en) * | 2001-09-05 | 2003-03-13 | United Soybean Board | Soybean oil based metalworking fluids |
| US20040248744A1 (en) * | 2001-08-14 | 2004-12-09 | King James P. | Soy-based methyl ester high performance metal working fluids |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1463092A (en) * | 1921-07-07 | 1923-07-24 | Technical Res Works Ltd | Lubricant and process of preparing same |
| US2249800A (en) * | 1936-04-24 | 1941-07-22 | Du Pont | Hydraulic fluid |
| US2479424A (en) * | 1947-12-03 | 1949-08-16 | Standard Oil Dev Co | Rust inhibiting lubricants |
| US2515115A (en) * | 1947-10-29 | 1950-07-11 | Standard Oil Dev Co | Nonfoaming compositions |
| US2683691A (en) * | 1951-08-18 | 1954-07-13 | Shell Dev | Extreme pressure lubricants |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA471213A (en) * | 1951-01-30 | F. Schiermeier Knapel | Corrosion inhibiting compositions | |
| US2531801A (en) * | 1946-06-21 | 1950-11-28 | Monsanto Chemicals | Lubricating oil composition |
| US2587545A (en) * | 1949-04-14 | 1952-02-26 | Standard Oil Dev Co | Rust-preventing lubricant |
| GB709903A (en) * | 1950-04-06 | 1954-06-02 | Standard Oil Dev Co | Lubricating oil composition |
-
0
- NL NL102996D patent/NL102996C/xx active
- BE BE548812D patent/BE548812A/xx unknown
- NL NL208213D patent/NL208213A/xx unknown
-
1955
- 1955-06-20 US US516784A patent/US2882228A/en not_active Expired - Lifetime
-
1956
- 1956-06-18 FR FR1154532D patent/FR1154532A/fr not_active Expired
- 1956-06-18 GB GB18809/56A patent/GB798635A/en not_active Expired
- 1956-06-18 DE DEN12365A patent/DE1015169B/de active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1463092A (en) * | 1921-07-07 | 1923-07-24 | Technical Res Works Ltd | Lubricant and process of preparing same |
| US2249800A (en) * | 1936-04-24 | 1941-07-22 | Du Pont | Hydraulic fluid |
| US2515115A (en) * | 1947-10-29 | 1950-07-11 | Standard Oil Dev Co | Nonfoaming compositions |
| US2479424A (en) * | 1947-12-03 | 1949-08-16 | Standard Oil Dev Co | Rust inhibiting lubricants |
| US2683691A (en) * | 1951-08-18 | 1954-07-13 | Shell Dev | Extreme pressure lubricants |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3380928A (en) * | 1958-09-22 | 1968-04-30 | Shell Oil Co | Lubricating oil composition |
| US3112267A (en) * | 1960-06-15 | 1963-11-26 | Shell Oil Co | Lubricating compositions |
| DE1160967B (de) * | 1960-06-15 | 1964-01-09 | Shell Int Research | Schmiermittel |
| US3160657A (en) * | 1960-06-15 | 1964-12-08 | Shell Oil Co | Alkali metal-amine salt of halohydrocarbylphosphonic acid |
| US3143506A (en) * | 1960-06-20 | 1964-08-04 | Texaco Inc | Lubricants containing amine salts |
| US3185728A (en) * | 1960-06-20 | 1965-05-25 | Texaco Inc | Ethylene diamine salts of thiophosphonic acids |
| US3243452A (en) * | 1962-06-28 | 1966-03-29 | Olin Mathieson | Bis (hydroxydiarylphosphine) decaboranes |
| US3499923A (en) * | 1965-09-07 | 1970-03-10 | Universal Oil Prod Co | Polychloroalkylphosphonic acid salts |
| US3635823A (en) * | 1966-11-04 | 1972-01-18 | Universal Oil Prod Co | Synergistic composition and use thereof |
| US3793199A (en) * | 1970-06-08 | 1974-02-19 | Texaco Inc | Friction reducing agent for lubricants |
| US3984599A (en) * | 1973-10-30 | 1976-10-05 | Exxon Research And Engineering Company | Lubricant coating compositions for use in metal drawing operations |
| US4252660A (en) * | 1979-11-23 | 1981-02-24 | Mobil Oil Corporation | Reaction products of organophosphorus halides with inorganic thiocyanates as load-carrying additives in lubricating oil compositions |
| WO1986005508A1 (en) * | 1985-03-15 | 1986-09-25 | The Lubrizol Corporation | Hydrogen sulfide stabilized oil-soluble sulfurized organic compositions |
| US5092908A (en) * | 1990-06-28 | 1992-03-03 | Exxon Research And Engineering Company | Composition for improving cold flow properties of middle distillates (OP-3571) |
| EP0712924A1 (en) * | 1994-11-15 | 1996-05-22 | The Lubrizol Corporation | Lubricants and fluids containing thiocarbamates and phosphonates |
| US5866520A (en) * | 1996-01-31 | 1999-02-02 | Chevron Chemical Company | Lubricant composition suitable for direct fuel injected, crankcase-scavenged two-stroke cycle engines |
| US20040248744A1 (en) * | 2001-08-14 | 2004-12-09 | King James P. | Soy-based methyl ester high performance metal working fluids |
| US7683016B2 (en) | 2001-08-14 | 2010-03-23 | United Soybean Board | Soy-based methyl ester high performance metal working fluids |
| WO2003020855A1 (en) * | 2001-09-05 | 2003-03-13 | United Soybean Board | Soybean oil based metalworking fluids |
| US7439212B2 (en) | 2001-09-05 | 2008-10-21 | United Soybean Board | Soybean oil based metalworking fluids |
Also Published As
| Publication number | Publication date |
|---|---|
| NL208213A (is") | |
| GB798635A (en) | 1958-07-23 |
| NL102996C (is") | |
| BE548812A (is") | |
| DE1015169B (de) | 1957-09-05 |
| FR1154532A (fr) | 1958-04-11 |
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