CA2637401A1 - Use of esters comprising branched alkyl groups as lubricants - Google Patents
Use of esters comprising branched alkyl groups as lubricants Download PDFInfo
- Publication number
- CA2637401A1 CA2637401A1 CA002637401A CA2637401A CA2637401A1 CA 2637401 A1 CA2637401 A1 CA 2637401A1 CA 002637401 A CA002637401 A CA 002637401A CA 2637401 A CA2637401 A CA 2637401A CA 2637401 A1 CA2637401 A1 CA 2637401A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- branched alkyl
- esters
- alkyl groups
- group
- 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.)
- Abandoned
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 80
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 58
- 239000000314 lubricant Substances 0.000 title claims abstract description 42
- 230000003647 oxidation Effects 0.000 claims abstract description 32
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 32
- 239000003566 sealing material Substances 0.000 claims abstract description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 22
- 238000012360 testing method Methods 0.000 claims abstract description 21
- 150000001298 alcohols Chemical class 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 15
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 14
- 150000002763 monocarboxylic acids Chemical class 0.000 claims abstract description 11
- -1 aliphatic dicarboxylic acids Chemical class 0.000 claims abstract description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 239000012530 fluid Substances 0.000 claims description 31
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 12
- 239000002480 mineral oil Substances 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 11
- 239000002994 raw material Substances 0.000 claims description 11
- 238000013112 stability test Methods 0.000 claims description 10
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 8
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 8
- 239000003921 oil Substances 0.000 claims description 8
- 150000002825 nitriles Chemical class 0.000 claims description 7
- 239000010723 turbine oil Substances 0.000 claims description 7
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 claims description 6
- 229920000459 Nitrile rubber Polymers 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 6
- MHPUGCYGQWGLJL-UHFFFAOYSA-N dimethyl pentanoic acid Natural products CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 claims description 6
- 230000001050 lubricating effect Effects 0.000 claims description 6
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 6
- XULHFMYCBKQGEE-UHFFFAOYSA-N 2-hexyl-1-Decanol Chemical compound CCCCCCCCC(CO)CCCCCC XULHFMYCBKQGEE-UHFFFAOYSA-N 0.000 claims description 5
- 230000005540 biological transmission Effects 0.000 claims description 5
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 4
- XMVBHZBLHNOQON-UHFFFAOYSA-N 2-butyl-1-octanol Chemical compound CCCCCCC(CO)CCCC XMVBHZBLHNOQON-UHFFFAOYSA-N 0.000 claims description 4
- YEGNTQBFSQBGJT-UHFFFAOYSA-N 2-heptylundecan-1-ol Chemical compound CCCCCCCCCC(CO)CCCCCCC YEGNTQBFSQBGJT-UHFFFAOYSA-N 0.000 claims description 4
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- 244000043261 Hevea brasiliensis Species 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 235000021314 Palmitic acid Nutrition 0.000 claims description 4
- 235000021355 Stearic acid Nutrition 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 4
- 229920001971 elastomer Polymers 0.000 claims description 4
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 claims description 4
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- 239000010687 lubricating oil Substances 0.000 claims description 4
- 239000003607 modifier Substances 0.000 claims description 4
- 229920003052 natural elastomer Polymers 0.000 claims description 4
- 229920001194 natural rubber Polymers 0.000 claims description 4
- ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 0.000 claims description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 4
- MWMPEAHGUXCSMY-UHFFFAOYSA-N pentacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC(O)=O MWMPEAHGUXCSMY-UHFFFAOYSA-N 0.000 claims description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- 239000005060 rubber Substances 0.000 claims description 4
- 239000008117 stearic acid Substances 0.000 claims description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 4
- VHOCUJPBKOZGJD-UHFFFAOYSA-N triacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O VHOCUJPBKOZGJD-UHFFFAOYSA-N 0.000 claims description 4
- XEZVDURJDFGERA-UHFFFAOYSA-N tricosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCC(O)=O XEZVDURJDFGERA-UHFFFAOYSA-N 0.000 claims description 4
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 claims description 4
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
- ZONJATNKKGGVSU-UHFFFAOYSA-N 14-methylpentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCC(O)=O ZONJATNKKGGVSU-UHFFFAOYSA-N 0.000 claims description 3
- CAYHVMBQBLYQMT-UHFFFAOYSA-N 2-decyltetradecan-1-ol Chemical compound CCCCCCCCCCCCC(CO)CCCCCCCCCC CAYHVMBQBLYQMT-UHFFFAOYSA-N 0.000 claims description 3
- PDBKSKNFOPOYTP-UHFFFAOYSA-N 2-nonyltridecan-1-ol Chemical compound CCCCCCCCCCCC(CO)CCCCCCCCC PDBKSKNFOPOYTP-UHFFFAOYSA-N 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 229920005549 butyl rubber Polymers 0.000 claims description 3
- 239000010725 compressor oil Substances 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 239000010705 motor oil Substances 0.000 claims description 3
- 229920002857 polybutadiene Polymers 0.000 claims description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- DEMBLPGWNXUBIQ-UHFFFAOYSA-N 2-dodecylhexadecan-1-ol Chemical compound CCCCCCCCCCCCCCC(CO)CCCCCCCCCCCC DEMBLPGWNXUBIQ-UHFFFAOYSA-N 0.000 claims description 2
- JQJGGMZIMBGQQY-UHFFFAOYSA-N 2-hexadecylicosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCC(CO)CCCCCCCCCCCCCCCC JQJGGMZIMBGQQY-UHFFFAOYSA-N 0.000 claims description 2
- JPTRUQGKLMQGMD-UHFFFAOYSA-N 2-pentadecylnonadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCC(CO)CCCCCCCCCCCCCCC JPTRUQGKLMQGMD-UHFFFAOYSA-N 0.000 claims description 2
- DHMRGSATSWRQFT-UHFFFAOYSA-N 2-pentylnonan-1-ol Chemical compound CCCCCCCC(CO)CCCCC DHMRGSATSWRQFT-UHFFFAOYSA-N 0.000 claims description 2
- RTXVDAJGIYOHFY-UHFFFAOYSA-N 2-tetradecyloctadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCC(CO)CCCCCCCCCCCCCC RTXVDAJGIYOHFY-UHFFFAOYSA-N 0.000 claims description 2
- XYVXFHBIYUGIFM-UHFFFAOYSA-N 2-tridecylheptadecan-1-ol Chemical compound CCCCCCCCCCCCCCCC(CO)CCCCCCCCCCCCC XYVXFHBIYUGIFM-UHFFFAOYSA-N 0.000 claims description 2
- CYSSSYKSBHKJQE-UHFFFAOYSA-N 2-undecylpentadecan-1-ol Chemical compound CCCCCCCCCCCCCC(CO)CCCCCCCCCCC CYSSSYKSBHKJQE-UHFFFAOYSA-N 0.000 claims description 2
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 claims description 2
- HMMSZUQCCUWXRA-UHFFFAOYSA-N 4,4-dimethyl valeric acid Chemical compound CC(C)(C)CCC(O)=O HMMSZUQCCUWXRA-UHFFFAOYSA-N 0.000 claims description 2
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims description 2
- VBHRLSQLJDHSCO-UHFFFAOYSA-N 5,5-dimethylhexanoic acid Chemical compound CC(C)(C)CCCC(O)=O VBHRLSQLJDHSCO-UHFFFAOYSA-N 0.000 claims description 2
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 claims description 2
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 claims description 2
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 claims description 2
- AAOISIQFPPAFQO-UHFFFAOYSA-N 7:0(6Me,6Me) Chemical compound CC(C)(C)CCCCC(O)=O AAOISIQFPPAFQO-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- 235000021357 Behenic acid Nutrition 0.000 claims description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005639 Lauric acid Substances 0.000 claims description 2
- 235000021353 Lignoceric acid Nutrition 0.000 claims description 2
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 claims description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 2
- 239000005643 Pelargonic acid Substances 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004809 Teflon Substances 0.000 claims description 2
- 229920006362 Teflon® Polymers 0.000 claims description 2
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- 229940116226 behenic acid Drugs 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- DGXRZJSPDXZJFG-UHFFFAOYSA-N docosanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCCCCCC(O)=O DGXRZJSPDXZJFG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 claims description 2
- QQHJDPROMQRDLA-UHFFFAOYSA-N hexadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC(O)=O QQHJDPROMQRDLA-UHFFFAOYSA-N 0.000 claims description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims description 2
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 claims description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 claims description 2
- FIPPFBHCBUDBRR-UHFFFAOYSA-N n-Heneikosylalkohol Natural products CCCCCCCCCCCCCCCCCCCCCO FIPPFBHCBUDBRR-UHFFFAOYSA-N 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 229960002446 octanoic acid Drugs 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 2
- 229920001084 poly(chloroprene) Polymers 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- YLQLIQIAXYRMDL-UHFFFAOYSA-N propylheptyl alcohol Chemical compound CCCCCC(CO)CCC YLQLIQIAXYRMDL-UHFFFAOYSA-N 0.000 claims description 2
- 230000035939 shock Effects 0.000 claims description 2
- 229920002545 silicone oil Polymers 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 claims description 2
- 229940005605 valeric acid Drugs 0.000 claims description 2
- 239000000047 product Substances 0.000 description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 238000012065 two one-sided test Methods 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000009970 fire resistant effect Effects 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000003911 water pollution Methods 0.000 description 2
- LOIMOHMWAXGSLR-UHFFFAOYSA-N 2-hexyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCC LOIMOHMWAXGSLR-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000483002 Euproctis similis Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/36—Esters of polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/34—Esters of monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/68—Esters
- C10M129/70—Esters of monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/68—Esters
- C10M129/72—Esters of polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
- C10M2207/2815—Esters of (cyclo)aliphatic monocarboxylic acids used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
- C10M2207/2825—Esters of (cyclo)aliphatic oolycarboxylic acids used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/065—Saturated Compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/071—Branched chain compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/36—Seal compatibility, e.g. with rubber
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/64—Environmental friendly compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/135—Steam engines or turbines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/30—Refrigerators lubricants or compressors lubricants
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Lubricants (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006001768A DE102006001768A1 (de) | 2006-01-12 | 2006-01-12 | Verwendung von Estern mit verzweigten Alkylgruppen als Schmiermittel |
| DE102006001768.4 | 2006-01-12 | ||
| PCT/EP2007/000034 WO2007082639A1 (de) | 2006-01-12 | 2007-01-04 | Verwendung von estern mit verzweigten alkylgruppen als schmiermittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2637401A1 true CA2637401A1 (en) | 2007-07-26 |
Family
ID=37963769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002637401A Abandoned CA2637401A1 (en) | 2006-01-12 | 2007-01-04 | Use of esters comprising branched alkyl groups as lubricants |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US20100261628A1 (enExample) |
| EP (1) | EP1973999A1 (enExample) |
| JP (1) | JP5412116B2 (enExample) |
| CA (1) | CA2637401A1 (enExample) |
| DE (1) | DE102006001768A1 (enExample) |
| WO (1) | WO2007082639A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011034829A1 (en) | 2009-09-16 | 2011-03-24 | The Lubrizol Corporation | Lubricating composition containing an ester |
| WO2014184068A1 (en) | 2013-05-14 | 2014-11-20 | Basf Se | Lubricating oil composition with enhanced energy efficiency |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1889640A1 (de) | 2006-08-18 | 2008-02-20 | Cognis IP Management GmbH | Kosmetische Zusammensetzungen enthaltend Ester auf Basis von 2-Butyl-1-octanol |
| JP5334421B2 (ja) * | 2008-02-07 | 2013-11-06 | コスモ石油ルブリカンツ株式会社 | 潤滑油用エステル基油及び潤滑油 |
| JP5334425B2 (ja) * | 2008-02-26 | 2013-11-06 | コスモ石油ルブリカンツ株式会社 | 軸受油組成物 |
| JP5334432B2 (ja) * | 2008-03-17 | 2013-11-06 | コスモ石油ルブリカンツ株式会社 | グリース組成物 |
| GB0807372D0 (en) * | 2008-04-23 | 2008-05-28 | Croda Int Plc | Engine lubricants |
| EP2192105A1 (de) * | 2008-11-25 | 2010-06-02 | Dako Ag | Schmiermittel und Verfahren zu dessen Herstellung |
| CH703629A8 (de) | 2010-08-25 | 2012-04-30 | Panolin Ag | Esteröle. |
| DE102011006557A1 (de) * | 2011-03-31 | 2012-10-04 | Evonik Oxeno Gmbh | Gemisch von Bersteinsäureestern |
| US8980808B2 (en) | 2011-08-03 | 2015-03-17 | Cognis Ip Management Gmbh | Lubricant compositions with improved oxidation stability and service life |
| ES2707624T3 (es) * | 2012-07-06 | 2019-04-04 | Basf Se | El uso de ésteres de ácidos carboxílicos como lubricantes |
| KR102273229B1 (ko) | 2013-09-16 | 2021-07-05 | 바스프 에스이 | 폴리에스테르 및 윤활제에서의 폴리에스테르의 용도 |
| EP3074491B1 (en) * | 2013-11-28 | 2021-01-13 | Basf Se | Composition for low temperature |
| CA2935261C (en) * | 2014-01-13 | 2022-01-11 | Novamont S.P.A. | Polymer compositions containing aliphatic esters as plasticisers |
| EP2937408B1 (en) * | 2014-04-22 | 2017-01-04 | Basf Se | Lubricant composition comprising an ester of a C17 alcohol mixture |
| CA2918575A1 (en) * | 2014-05-15 | 2015-11-19 | Chevron U.S.A. Inc. | Monoester-based lubricants and methods of making same |
| FR3027915B1 (fr) * | 2014-10-29 | 2018-02-16 | Oleon Nv | Compositions lubrifiantes comportant un alternatif a l'adipate de di-isotridecyle |
| CN107532099A (zh) * | 2015-04-28 | 2018-01-02 | Ｋｙｂ株式会社 | 油压减震器用工作油和油压减震器 |
| JP2016210843A (ja) * | 2015-04-30 | 2016-12-15 | 協同油脂株式会社 | 流体動圧軸受用潤滑油及び該潤滑油を備えたスピンドルモータ |
| EP3178907A1 (en) * | 2015-12-09 | 2017-06-14 | Basf Se | The use of isostearic acid esters as lubricants |
| DE102015122273A1 (de) * | 2015-12-18 | 2017-06-22 | Minebea Co., Ltd. | Verfahren zur Herstellung eines Basisfluids für Schmiermittelzusammensetzungen zur Verwendung in fluiddynamischen Lagersystemen |
| US10077409B2 (en) | 2015-12-28 | 2018-09-18 | Exxonmobil Research And Engineering Company | Low viscosity low volatility lubricating oil base stocks and methods of use thereof |
| US10316265B2 (en) | 2015-12-28 | 2019-06-11 | Exxonmobil Research And Engineering Company | Low viscosity low volatility lubricating oil base stocks and methods of use thereof |
| US10233403B2 (en) | 2016-11-03 | 2019-03-19 | EXXONMOBiL RESEARCH AND ENGiNEERENG COMPANY | High viscosity index monomethyl ester lubricating oil base stocks and methods of making and use thereof |
| US9976099B2 (en) | 2015-12-28 | 2018-05-22 | Exxonmobil Research And Engineering Company | Low viscosity low volatility lubricating oil base stocks and methods of use thereof |
| CN109415294A (zh) * | 2016-04-07 | 2019-03-01 | 伊诺莱克斯投资公司 | 用于个人护理应用的衍生自1-甲基庚基醇的二酯 |
| SG11201908484PA (en) * | 2017-03-28 | 2019-10-30 | Exxonmobil Chemical Patents Inc | Cold cranking simulator viscosity reducing base stocks and lubricating oil formulations containing the same |
| US10808196B2 (en) * | 2017-03-28 | 2020-10-20 | Exxonmobil Chemical Patents Inc. | Cold cranking simulator viscosity reducing base stocks and lubricating oil formulations containing the same |
| US20190062668A1 (en) * | 2017-08-25 | 2019-02-28 | Exxonmobil Research And Engineering Company | Ashless engine lubricants for high temperature applications |
| US10711216B2 (en) * | 2017-09-29 | 2020-07-14 | Exxonmobil Chemical Patents Inc. | Ester compounds, lubricating oil compositions containing same and processes for making same |
| WO2019067061A1 (en) * | 2017-09-29 | 2019-04-04 | Exxonmobil Chemical Patents Inc. | ESTER COMPOUNDS, LUBRICATING OIL COMPOSITIONS CONTAINING SAME AND METHODS OF MAKING THE SAME |
| US12221404B2 (en) | 2020-06-05 | 2025-02-11 | SCION Holdings LLC | Composition comprising branched aldehydes |
| US20210380510A1 (en) | 2020-06-05 | 2021-12-09 | SCION Holdings LLC | Branched Compounds |
| US20230159422A1 (en) | 2020-06-05 | 2023-05-25 | SCION Holdings LLC | Alcohols Production |
| US12674112B2 (en) * | 2020-07-22 | 2026-07-07 | Idemitsu Kosan Co., Ltd. | Lubricating oil composition |
| US12145904B2 (en) | 2020-12-17 | 2024-11-19 | SCION Holdings LLC | Branched products |
| WO2023074698A1 (ja) * | 2021-10-25 | 2023-05-04 | ミネベアミツミ株式会社 | 流体動圧軸受油、スピンドルモータおよびディスク駆動装置 |
| CN118234965A (zh) | 2021-10-25 | 2024-06-21 | 美蓓亚三美株式会社 | 滚动轴承、枢轴组件轴承以及盘片驱动装置 |
| WO2023074701A1 (ja) | 2021-10-25 | 2023-05-04 | ミネベアミツミ株式会社 | グリース組成物、ピボットアッシー軸受および該軸受を備えた軸受装置 |
| JP2024051414A (ja) * | 2022-09-30 | 2024-04-11 | 新日本理化株式会社 | 潤滑油基油、グリース基油、およびグリース組成物 |
| WO2026018551A1 (ja) * | 2024-07-19 | 2026-01-22 | Ａｓｔｅｍｏ株式会社 | 油圧機器および油圧機器用作動流体 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2757139A (en) * | 1953-11-30 | 1956-07-31 | Exxon Research Engineering Co | Synthetic lubricating composition |
| DE1269118B (de) * | 1964-07-30 | 1968-05-30 | Technochemie G M B H Verfahren | Verfahren zur Verbesserung der Eigenschaften von Hochleistungsschmierstoffe dienenden Diester-Schmieroelen |
| DE1594388A1 (de) * | 1964-08-27 | 1970-04-09 | Deutsche Erdoel Ag | Schmier- und Industrieoele |
| DE1594634B2 (de) * | 1965-04-20 | 1973-12-06 | Technochemie Gmbh -Verfahrenstechnik, 6901 Dossenheim | Schmiermittel |
| DE2302918C2 (de) | 1973-01-22 | 1982-04-08 | Henkel KGaA, 4000 Düsseldorf | Neue Esteröle, sowie deren Verwendung in Schmiermitteln und Hydraulikflüssigkeiten |
| DE3929069A1 (de) * | 1989-09-01 | 1991-03-07 | Henkel Kgaa | Neues basisoel fuer die schmierstoffindustrie |
| US5652201A (en) * | 1991-05-29 | 1997-07-29 | Ethyl Petroleum Additives Inc. | Lubricating oil compositions and concentrates and the use thereof |
| DE4202034A1 (de) * | 1992-01-25 | 1993-07-29 | Rwe Dea Ag | Hydraulikfluessigkeiten |
| DE4214653A1 (de) * | 1992-05-02 | 1993-11-04 | Henkel Kgaa | Motorengrundoele mit verbesserter dichtungsvertraeglichkeit |
| DE4313948A1 (de) * | 1993-04-28 | 1994-11-03 | Henkel Kgaa | Hydrauliköle mit verbesserter Dichtungsverträglichkeit |
| US5488121A (en) * | 1994-10-31 | 1996-01-30 | Siltech Inc. | Di-guerbet esters |
| AU706477B2 (en) * | 1994-11-14 | 1999-06-17 | Croda International Plc | Lubricant |
| JP2002020774A (ja) * | 2000-07-06 | 2002-01-23 | Japan Energy Corp | ディーゼルエンジン用潤滑油組成物 |
| DE10220754A1 (de) * | 2002-05-08 | 2003-11-27 | Sasol Germany Gmbh | 2,4-Dialkylverzweigte Aldehyde und aus diesen herstellbare Derivate |
| DE102004034202A1 (de) * | 2004-07-14 | 2005-11-10 | Sasol Germany Gmbh | Dicarbonsäure-Estermischungen und deren Verwendung |
| US7380305B2 (en) * | 2005-03-14 | 2008-06-03 | Rite-Hite Holding Corporation | Loading dock system with biodegradable fluid |
-
2006
- 2006-01-12 DE DE102006001768A patent/DE102006001768A1/de not_active Withdrawn
-
2007
- 2007-01-04 JP JP2008549812A patent/JP5412116B2/ja not_active Expired - Fee Related
- 2007-01-04 EP EP07700179A patent/EP1973999A1/de not_active Withdrawn
- 2007-01-04 WO PCT/EP2007/000034 patent/WO2007082639A1/de not_active Ceased
- 2007-01-04 US US12/160,464 patent/US20100261628A1/en not_active Abandoned
- 2007-01-04 CA CA002637401A patent/CA2637401A1/en not_active Abandoned
-
2013
- 2013-01-24 US US13/749,084 patent/US8921289B2/en active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011034829A1 (en) | 2009-09-16 | 2011-03-24 | The Lubrizol Corporation | Lubricating composition containing an ester |
| WO2014184068A1 (en) | 2013-05-14 | 2014-11-20 | Basf Se | Lubricating oil composition with enhanced energy efficiency |
| US9708561B2 (en) | 2013-05-14 | 2017-07-18 | Basf Se | Lubricating oil composition with enhanced energy efficiency |
Also Published As
| Publication number | Publication date |
|---|---|
| US8921289B2 (en) | 2014-12-30 |
| DE102006001768A1 (de) | 2007-07-19 |
| US20100261628A1 (en) | 2010-10-14 |
| JP2009523182A (ja) | 2009-06-18 |
| JP5412116B2 (ja) | 2014-02-12 |
| WO2007082639A1 (de) | 2007-07-26 |
| US20130137614A1 (en) | 2013-05-30 |
| EP1973999A1 (de) | 2008-10-01 |
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