CA2655040A1 - Lubricant compounds containing complex esters - Google Patents
Lubricant compounds containing complex esters Download PDFInfo
- Publication number
- CA2655040A1 CA2655040A1 CA002655040A CA2655040A CA2655040A1 CA 2655040 A1 CA2655040 A1 CA 2655040A1 CA 002655040 A CA002655040 A CA 002655040A CA 2655040 A CA2655040 A CA 2655040A CA 2655040 A1 CA2655040 A1 CA 2655040A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- oils
- lubricant composition
- oil
- polyols
- 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
- 239000000314 lubricant Substances 0.000 title claims abstract description 70
- 150000002148 esters Chemical class 0.000 title claims abstract description 58
- 150000001875 compounds Chemical class 0.000 title abstract description 5
- 239000003921 oil Substances 0.000 claims abstract description 49
- 230000005540 biological transmission Effects 0.000 claims abstract description 19
- 229920005862 polyol Polymers 0.000 claims abstract description 17
- 150000003077 polyols Chemical class 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 239000002199 base oil Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 60
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 17
- 239000000654 additive Substances 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 15
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 13
- 239000010705 motor oil Substances 0.000 claims description 12
- 239000002562 thickening agent Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 8
- 239000012530 fluid Substances 0.000 claims description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 6
- 229920006112 polar polymer Polymers 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 239000010725 compressor oil Substances 0.000 claims description 5
- 239000010723 turbine oil Substances 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 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
- 125000001931 aliphatic group Chemical group 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
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 4
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 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
- 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
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003963 antioxidant agent Substances 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
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 claims description 2
- 238000005260 corrosion Methods 0.000 claims description 2
- 239000003599 detergent Substances 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
- QQHJDPROMQRDLA-UHFFFAOYSA-N hexadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC(O)=O QQHJDPROMQRDLA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 230000001050 lubricating effect Effects 0.000 claims description 2
- 239000003607 modifier Substances 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 230000035939 shock Effects 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
- 239000004711 α-olefin Substances 0.000 claims 3
- 239000002253 acid Substances 0.000 abstract description 13
- 150000007513 acids Chemical class 0.000 abstract description 8
- 239000002480 mineral oil Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 238000009472 formulation Methods 0.000 description 10
- 229920000459 Nitrile rubber Polymers 0.000 description 8
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 6
- 229920002367 Polyisobutene Polymers 0.000 description 6
- -1 monopentaerythitol Chemical compound 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- YKGYQYOQRGPFTO-UHFFFAOYSA-N bis(8-methylnonyl) hexanedioate Chemical compound CC(C)CCCCCCCOC(=O)CCCCC(=O)OCCCCCCCC(C)C YKGYQYOQRGPFTO-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- MHPUGCYGQWGLJL-UHFFFAOYSA-N dimethyl pentanoic acid Natural products CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 description 3
- 229920006168 hydrated nitrile rubber Polymers 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- ALKCLFLTXBBMMP-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl hexanoate Chemical compound CCCCCC(=O)OC(C)(C=C)CCC=C(C)C ALKCLFLTXBBMMP-UHFFFAOYSA-N 0.000 description 2
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 2
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- SIOLDWZBFABPJU-UHFFFAOYSA-N isotridecanoic acid Chemical compound CC(C)CCCCCCCCCC(O)=O SIOLDWZBFABPJU-UHFFFAOYSA-N 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- MWMPEAHGUXCSMY-UHFFFAOYSA-N pentacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC(O)=O MWMPEAHGUXCSMY-UHFFFAOYSA-N 0.000 description 2
- 229940059574 pentaerithrityl Drugs 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 2
- XEZVDURJDFGERA-UHFFFAOYSA-N tricosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCC(O)=O XEZVDURJDFGERA-UHFFFAOYSA-N 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- CFOQKXQWGLAKSK-KTKRTIGZSA-N (13Z)-docosen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCO CFOQKXQWGLAKSK-KTKRTIGZSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- CUXYLFPMQMFGPL-WPOADVJFSA-N (9Z,11E,13E)-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C/CCCCCCCC(O)=O CUXYLFPMQMFGPL-WPOADVJFSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- IKYKEVDKGZYRMQ-PDBXOOCHSA-N (9Z,12Z,15Z)-octadecatrien-1-ol Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCCO IKYKEVDKGZYRMQ-PDBXOOCHSA-N 0.000 description 1
- DJYWKXYRGAMLRE-QXMHVHEDSA-N (z)-icos-9-en-1-ol Chemical compound CCCCCCCCCC\C=C/CCCCCCCCO DJYWKXYRGAMLRE-QXMHVHEDSA-N 0.000 description 1
- TVPWKOCQOFBNML-SEYXRHQNSA-N (z)-octadec-6-en-1-ol Chemical compound CCCCCCCCCCC\C=C/CCCCCO TVPWKOCQOFBNML-SEYXRHQNSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- CFOQKXQWGLAKSK-UHFFFAOYSA-N 13-docosen-1-ol Natural products CCCCCCCCC=CCCCCCCCCCCCCO CFOQKXQWGLAKSK-UHFFFAOYSA-N 0.000 description 1
- ZONJATNKKGGVSU-UHFFFAOYSA-N 14-methylpentadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCC(O)=O ZONJATNKKGGVSU-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
- CWTQBXKJKDAOSQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;octanoic acid Chemical compound CCC(CO)(CO)CO.CCCCCCCC(O)=O CWTQBXKJKDAOSQ-UHFFFAOYSA-N 0.000 description 1
- VNAWKNVDKFZFSU-UHFFFAOYSA-N 2-ethyl-2-methylpropane-1,3-diol Chemical compound CCC(C)(CO)CO VNAWKNVDKFZFSU-UHFFFAOYSA-N 0.000 description 1
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 1
- VSWVHHCWUCZFBB-UHFFFAOYSA-N 3-propylhexanoic acid Chemical compound CCCC(CCC)CC(O)=O VSWVHHCWUCZFBB-UHFFFAOYSA-N 0.000 description 1
- HMMSZUQCCUWXRA-UHFFFAOYSA-N 4,4-dimethyl valeric acid Chemical compound CC(C)(C)CCC(O)=O HMMSZUQCCUWXRA-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- VBHRLSQLJDHSCO-UHFFFAOYSA-N 5,5-dimethylhexanoic acid Chemical compound CC(C)(C)CCCC(O)=O VBHRLSQLJDHSCO-UHFFFAOYSA-N 0.000 description 1
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- AAOISIQFPPAFQO-UHFFFAOYSA-N 7:0(6Me,6Me) Chemical compound CC(C)(C)CCCCC(O)=O AAOISIQFPPAFQO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 240000005369 Alstonia scholaris Species 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000021353 Lignoceric acid Nutrition 0.000 description 1
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/048—Mixtures of base-materials and additives the additives being a mixture of compounds of unknown or incompletely defined constitution, non-macromolecular and macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
- C10M111/02—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a non-macromolecular organic compound
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- C—CHEMISTRY; METALLURGY
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- 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
- C10M129/78—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids, hydroxy carboxylic 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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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- 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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
- C10M2207/301—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids 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
- 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
- C10M2209/084—Acrylate; Methacrylate
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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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- 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
- C10N2020/02—Viscosity; Viscosity index
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- 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
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- 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
- C10N2030/02—Pour-point; Viscosity index
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- 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
- C10N2030/68—Shear stability
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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- 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
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- 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
- C10N2040/12—Gas-turbines
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- 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
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- 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
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- 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
- C10N2040/252—Diesel engines
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/26—Two-strokes or two-cycle engines
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/30—Refrigerators lubricants or compressors lubricants
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- 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)
Abstract
Proposed are lubricant compounds with a good shear stability defined by the loss of the kinematic viscosity at 100 °C, containing base oil and a synthetic complex ester, the complex ester having a kinematic viscosity at 40°C of greater than 400 and up to 50,000 mm2/s and being obtained by conversion of a) polyols and monocarbonic acids and dicarbonic acids, or of b) polyols and mono-alcohols and dicarbonic acids, or of c) polyols and mono-alcohols and monocarbonic acids and dicarbonic acids. In addition the use of the said lubricant compounds containing the complex esters as oils for vehicle transmission, axles, industrial drives, compressors, turbines or engines is proposed.
Description
Lubricant compounds containing complex esters Field of the invention The invention is in the field of lubricants. It relates to lubricant compositions comprising complex esters of elevated viscosity, and to the use of these lubricant compositions as, for example, transmission oil, industrial oil or motor oil.
State of the art The commercially available lubricant compositions or else lubricants are produced from a multitude of different natural or synthetic components. To improve the required properties, according to the field of use, additions and/or further additives are added. The base oils often consist of mineral oils, highly refined mineral oils, alkylated mineral oils, poly-a-olefins (PAOs), polyalkylene glycols, phosphate esters, silicone oils, diesters and esters of polyhydric alcohols. Especially mineral oils of the Solvent Neutral class and mineral oils of the XHVI, VHVI, group II and group III classes are used.
The different lubricants, such as motor oil, turbine oil, hydraulic fluid, transmission oil, compressor oil and the like, must satisfy extremely high criteria such as high viscosity index, good lubricant performance, high oxidation sensitivity, good thermal stability or comparable properties.
High-performance lubricant oil formulations which are used as transmission, industrial or motor oils are especially oils with a high performance profile with regard to shear stability, low-temperature viscosity, long life, evaporation loss, fuel efficiency, seal compatibility and wear protection. Such oils are currently being formulated preferentially with PAO
State of the art The commercially available lubricant compositions or else lubricants are produced from a multitude of different natural or synthetic components. To improve the required properties, according to the field of use, additions and/or further additives are added. The base oils often consist of mineral oils, highly refined mineral oils, alkylated mineral oils, poly-a-olefins (PAOs), polyalkylene glycols, phosphate esters, silicone oils, diesters and esters of polyhydric alcohols. Especially mineral oils of the Solvent Neutral class and mineral oils of the XHVI, VHVI, group II and group III classes are used.
The different lubricants, such as motor oil, turbine oil, hydraulic fluid, transmission oil, compressor oil and the like, must satisfy extremely high criteria such as high viscosity index, good lubricant performance, high oxidation sensitivity, good thermal stability or comparable properties.
High-performance lubricant oil formulations which are used as transmission, industrial or motor oils are especially oils with a high performance profile with regard to shear stability, low-temperature viscosity, long life, evaporation loss, fuel efficiency, seal compatibility and wear protection. Such oils are currently being formulated preferentially with PAO
(especially PAO 6) or group II or Group III mineral oils as carrier fluids, and with specific polymers (polyisobutylenes = PIBs, olefin copolymers = ethylene/
propylene copolymers = OCPs, polyalkyl methacrylates =
PMAs) as thickeners or viscosity index improvers in addition to the customary additive components. Together with PAOs, low-viscosity esters, for example DIDA
(diisodecyl adipate), DITA (diisotridecyl adipate) or TMTC (trimethylolpropane caprylate), are typically also being used especially as solubilizers for polar additive types and for optimizing seal compatibilities.
Disadvantages in the case of use of the PAOs or of the polymers are generally the high costs and the low shear stability, and also the low-temperature viscosity of the lubricants in the case of use of polymers.
Ester-based lubricant oils are known per se and have already been used for some time (see Ullmanns Encyklopadie der technischen Chemie, 3rd Edition, volume 15, 1964, p. 285-294). Common esters are reaction products of dicarboxylic acids with alcohols, for example 2-ethylhexanol, or reaction products of polyols, for example trimethylolpropane, and fatty acids, for example oleic acid or a mixture of n-octanoic acid and n-decanoic acid. When, for example, dicarboxylic acids are used as well as monocarboxylic acids and polyols in the ester preparation, the dicarboxylic acid has crosslinking action, which leads to an increase in molecular weights of the ester and ultimately to higher viscosities and improved thickening actions in lubricant formulations. Such esters are typically referred to as complex esters.
Low-temperature viscosities of the formulations produced with esters and hence improved handling at low temperatures have been described especially for esters with branched alkyl chains.
The industrial requirements on lubricant oils are reflected in the common specifications according to classes, for example multiregion oils which satisfy .
propylene copolymers = OCPs, polyalkyl methacrylates =
PMAs) as thickeners or viscosity index improvers in addition to the customary additive components. Together with PAOs, low-viscosity esters, for example DIDA
(diisodecyl adipate), DITA (diisotridecyl adipate) or TMTC (trimethylolpropane caprylate), are typically also being used especially as solubilizers for polar additive types and for optimizing seal compatibilities.
Disadvantages in the case of use of the PAOs or of the polymers are generally the high costs and the low shear stability, and also the low-temperature viscosity of the lubricants in the case of use of polymers.
Ester-based lubricant oils are known per se and have already been used for some time (see Ullmanns Encyklopadie der technischen Chemie, 3rd Edition, volume 15, 1964, p. 285-294). Common esters are reaction products of dicarboxylic acids with alcohols, for example 2-ethylhexanol, or reaction products of polyols, for example trimethylolpropane, and fatty acids, for example oleic acid or a mixture of n-octanoic acid and n-decanoic acid. When, for example, dicarboxylic acids are used as well as monocarboxylic acids and polyols in the ester preparation, the dicarboxylic acid has crosslinking action, which leads to an increase in molecular weights of the ester and ultimately to higher viscosities and improved thickening actions in lubricant formulations. Such esters are typically referred to as complex esters.
Low-temperature viscosities of the formulations produced with esters and hence improved handling at low temperatures have been described especially for esters with branched alkyl chains.
The industrial requirements on lubricant oils are reflected in the common specifications according to classes, for example multiregion oils which satisfy .
viscosity classes SAE 75-W90 for transmision oils, or O-W20 or O-W30 for motor oils, can be used virtually in all seasons.
There is still a particular demand for additions of polymeric or oligomeric nature which, used as additives, contribute to the satisfaction of requirements for very shear-stable lubricant compositions which can be used within wide ranges.
These additives should additionally at least not worsen the viscosity index. Some viscosity index improvers are known which, however, do not exhibit good shear stability, as shown, for example, in US 4,156,673. EP
488432 (=US5070131) discloses polymers with good shear stability, which are prepared from poly(polyalkenyl) couplings.
DE 3544061 (=US4822508) describes high-shear stability transmision oils which comprise viscosity index-improving additives based on esters of acrylic acid and/or methacrylic acid.
US 5,451,630 describes olefin copolymers (OCPs) which have good shear stability. It is additionally stated that the good shear stability decreases with the size of the molecule and hence with an elevated viscosity.
This decomposition of the polymers as a result of elevated shear forces leads to a reduction in the viscosity in the lubricant.
An optimal viscosity index improver exhibits a minor contribution to the viscosity of the lubricant at low temperatures, and a major contribution at operating temperatures. Moreover, a high stability should also be present under elevated shear forces.
It was thus an object of the invention to increase the shear stability of the lubricant composition and to achieve a good low-temperature viscosity. Both are generally worsened by polymeric or oligmeric additions, for example thickeners, viscosity index improvers or polymeric dispersants.
EP 1281701 discloses synthetic lubricants prepared from polyneopentylpolyol and a mixture of linear and branched acids, wherein the ester has a viscosity of from 68 to 400 mm2/s at 40 C. These have been developed for use in cooling compressor fluids.
EP 938536 discloses lubricants which comprise synthetic esters which are obtained by reacting polyols with mixtures of monocarboxylic acids and optionally polybasic acids, and which have an elevated thermal and oxidative stability. The viscosity of the esters at 100 C is not more than approx. 80 mm2/s. No statements regarding the shear stability were made.
It was firstly an object of the invention to provide high-shear stability lubricant compositions comprising novel thickener systems, which at least do not worsen the viscosity index and are usable within wide ranges.
Low-temperature viscosities and/or shear stabilities should be improved in comparison to customary thickeners or VI improvers corresponding to the state of the art, and the compatibility of the thickener system with the remaining components of the lubricant formulations, especially at relatively low temperatures, should remain guaranteed. It was a further object of the invention either to reduce or to eliminate the content of common polymeric and/or oligomeric thickeners or VI improvers (e.g. OCPs, PIBs, polyalkyl methacrylates) in the lubricant compositions, and to replace expensive carrier components such as PAOs with group II or III oils. For lubricant oils which are already formulated with group II or group III
oils, in contrast, a replacement of these group II and III oils with cheaper group I oils was desirable. In industry, the reduction or elimination of customary polymers should give rise to advantages with regard to shear stability and low-temperature viscosity.
There is a particular problem when the lubricants, as well as elevated oxidation stability and low-temperature viscosity, must have improved compatibility with respect to seal materials. The known lubricants based on linear esters with good oxidation stability are saturated in nature, but lead to the softening of the customary seal materials. Conversely, unsaturated ester types which originate, for example, from oleic acid have better behavior toward seal materials but have significantly reduced oxidation stabilities.
Particular problems occur with respect to seal materials such as NBR (nitrile butyl rubber) and hydrogenated variants thereof (HNBR).
There is still a need for improved lubricants with high biodegradability. A further object of the present invention consisted in providing lubricants which, as well as the properties mentioned, have a good compatibility with respect to seal materials.
At the same time, the other properties, especially the lubricity and rheological properties of the lubricant, must not be adversely affected.
It has been found that particular high-viscosity esters solve the problems outlined above in an outstanding manner.
Description of the invention The invention provides a lubricant composition having a good shear stability determined by the loss of kinematic viscosity at 100 C, comprising base oil and a synthetic complex ester, said complex ester having a kinematic viscosity at 40 C of greater than 400 and up to 50 000 mmz/s and being obtained by reaction of:
a) polyols and monocarboxylic acids and dicarboxylic acids or of b) polyols and monoalcohols and dicarboxylic acids or of c) polyols and monoalcohols and monocarboxylic acids and dicarboxylic acids.
For the complex esters mentioned, it has been found that the shear stability of the lubricant composition comprising these esters achieves very good results and decreases the viscosity only slightly. Furthermore, it has been possible to reduce the content of polymers.
The loss of kinematic viscosity was determined at 1000C
i) for transmission oils, axle oils and clutch oils for automatic and manual transmission to CEC L-45-T-93 (20 hours) and is less than 8%, preferably less than 5o and especially preferably less than 4%;
ii) for hydraulic fluids, for industrial transmission oils with stationary uses, for oils for lubricating wind turbines, for gas turbine oils, for compressor oils and shock absorber fluids, determined to CEC L-45-T-93 (20 hours), and is less than 15%, and preferably less than 8%;
iii) for two-stroke and four-stroke engine oils and for diesel and gasoline motor oils, determined after shear to ASTM D 3945 (30 cycles), and is less than 15%, preferably less than 10o and especially preferably less than 7%.
In the context of the invention, shear is considered to be permanent shear. Since the viscosity of the base oil decreases as a result of shear only to a very insignificantly minor degree, if at all, the determination of the loss of viscosity after shear is meaningful as a parameter for the complex esters.
Moreover, it has surprisingly been found that oil temperatures in transmission or axle applications are lower when lubricants are formulated with the high-viscosity complex esters. This has been found by means of the industry standard ARKL test (VW PV 1454).
There is still a particular demand for additions of polymeric or oligomeric nature which, used as additives, contribute to the satisfaction of requirements for very shear-stable lubricant compositions which can be used within wide ranges.
These additives should additionally at least not worsen the viscosity index. Some viscosity index improvers are known which, however, do not exhibit good shear stability, as shown, for example, in US 4,156,673. EP
488432 (=US5070131) discloses polymers with good shear stability, which are prepared from poly(polyalkenyl) couplings.
DE 3544061 (=US4822508) describes high-shear stability transmision oils which comprise viscosity index-improving additives based on esters of acrylic acid and/or methacrylic acid.
US 5,451,630 describes olefin copolymers (OCPs) which have good shear stability. It is additionally stated that the good shear stability decreases with the size of the molecule and hence with an elevated viscosity.
This decomposition of the polymers as a result of elevated shear forces leads to a reduction in the viscosity in the lubricant.
An optimal viscosity index improver exhibits a minor contribution to the viscosity of the lubricant at low temperatures, and a major contribution at operating temperatures. Moreover, a high stability should also be present under elevated shear forces.
It was thus an object of the invention to increase the shear stability of the lubricant composition and to achieve a good low-temperature viscosity. Both are generally worsened by polymeric or oligmeric additions, for example thickeners, viscosity index improvers or polymeric dispersants.
EP 1281701 discloses synthetic lubricants prepared from polyneopentylpolyol and a mixture of linear and branched acids, wherein the ester has a viscosity of from 68 to 400 mm2/s at 40 C. These have been developed for use in cooling compressor fluids.
EP 938536 discloses lubricants which comprise synthetic esters which are obtained by reacting polyols with mixtures of monocarboxylic acids and optionally polybasic acids, and which have an elevated thermal and oxidative stability. The viscosity of the esters at 100 C is not more than approx. 80 mm2/s. No statements regarding the shear stability were made.
It was firstly an object of the invention to provide high-shear stability lubricant compositions comprising novel thickener systems, which at least do not worsen the viscosity index and are usable within wide ranges.
Low-temperature viscosities and/or shear stabilities should be improved in comparison to customary thickeners or VI improvers corresponding to the state of the art, and the compatibility of the thickener system with the remaining components of the lubricant formulations, especially at relatively low temperatures, should remain guaranteed. It was a further object of the invention either to reduce or to eliminate the content of common polymeric and/or oligomeric thickeners or VI improvers (e.g. OCPs, PIBs, polyalkyl methacrylates) in the lubricant compositions, and to replace expensive carrier components such as PAOs with group II or III oils. For lubricant oils which are already formulated with group II or group III
oils, in contrast, a replacement of these group II and III oils with cheaper group I oils was desirable. In industry, the reduction or elimination of customary polymers should give rise to advantages with regard to shear stability and low-temperature viscosity.
There is a particular problem when the lubricants, as well as elevated oxidation stability and low-temperature viscosity, must have improved compatibility with respect to seal materials. The known lubricants based on linear esters with good oxidation stability are saturated in nature, but lead to the softening of the customary seal materials. Conversely, unsaturated ester types which originate, for example, from oleic acid have better behavior toward seal materials but have significantly reduced oxidation stabilities.
Particular problems occur with respect to seal materials such as NBR (nitrile butyl rubber) and hydrogenated variants thereof (HNBR).
There is still a need for improved lubricants with high biodegradability. A further object of the present invention consisted in providing lubricants which, as well as the properties mentioned, have a good compatibility with respect to seal materials.
At the same time, the other properties, especially the lubricity and rheological properties of the lubricant, must not be adversely affected.
It has been found that particular high-viscosity esters solve the problems outlined above in an outstanding manner.
Description of the invention The invention provides a lubricant composition having a good shear stability determined by the loss of kinematic viscosity at 100 C, comprising base oil and a synthetic complex ester, said complex ester having a kinematic viscosity at 40 C of greater than 400 and up to 50 000 mmz/s and being obtained by reaction of:
a) polyols and monocarboxylic acids and dicarboxylic acids or of b) polyols and monoalcohols and dicarboxylic acids or of c) polyols and monoalcohols and monocarboxylic acids and dicarboxylic acids.
For the complex esters mentioned, it has been found that the shear stability of the lubricant composition comprising these esters achieves very good results and decreases the viscosity only slightly. Furthermore, it has been possible to reduce the content of polymers.
The loss of kinematic viscosity was determined at 1000C
i) for transmission oils, axle oils and clutch oils for automatic and manual transmission to CEC L-45-T-93 (20 hours) and is less than 8%, preferably less than 5o and especially preferably less than 4%;
ii) for hydraulic fluids, for industrial transmission oils with stationary uses, for oils for lubricating wind turbines, for gas turbine oils, for compressor oils and shock absorber fluids, determined to CEC L-45-T-93 (20 hours), and is less than 15%, and preferably less than 8%;
iii) for two-stroke and four-stroke engine oils and for diesel and gasoline motor oils, determined after shear to ASTM D 3945 (30 cycles), and is less than 15%, preferably less than 10o and especially preferably less than 7%.
In the context of the invention, shear is considered to be permanent shear. Since the viscosity of the base oil decreases as a result of shear only to a very insignificantly minor degree, if at all, the determination of the loss of viscosity after shear is meaningful as a parameter for the complex esters.
Moreover, it has surprisingly been found that oil temperatures in transmission or axle applications are lower when lubricants are formulated with the high-viscosity complex esters. This has been found by means of the industry standard ARKL test (VW PV 1454).
In addition, it has been found that the further utilization of low concentrations of a polar polymer, for example of an alkyl fumarate-a-olefin, of a polyalkyl methacrylate or of an alkyl methacrylate-a-olefin system, in a lubricant composition comprising the relatively high-viscosity ester in many cases acts as a solubilizer for the ester, and can lower low-temperature viscosities of the lubricant composition in a synergistic manner.
It has additionally been found that expensive, high-viscosity PAO types, for example PAO 60 or PAO 100, or customary thickeners such as OCP or PIB, which have been added to the lubricants as thickeners, can alternatively be formulated with the complex esters to be present in accordance with the invention and lead to comparably good or improved properties. Preference is given to the simultaneous addition of polar polymers as a further component, for example those mentioned above.
The kinematic viscosity of the complex ester for use is preferably from 800 to 25 000 mm2/s, especially from 1200 to 10 000 mm2/s, more preferably from 1300 to 5000 mm2/s and most preferably from 1500 to 3000 mmz/s.
It has been found that, surprisingly, the use of these esters leads to very low losses in the kinematic viscosity of the lubricant composition after permanent shear. This property makes possible use in lubricants which are exposed to high shear stress.
Preference is given in accordance with the invention to lubricant compositions comprising the complex ester in a concentration of from 3 to 90% by weight based on the total amount of lubricant composition. Especially preferred is a concentration of 7-50% by weight and more preferably of 10-34 s by weight.
In a further preferred embodiment, the lubricant compositions are characterized in that the monocarboxylic acids used in the reaction according to a) are branched monocarboxylic acids or mixtures of linear and branched monocarboxylic acids, each of which has a carbon number of from 5 to 40 carbon atoms, where the content of branched monoacid is preferably greater than 90 mol% based on the total content of the acid mixture. The monocarboxylic acids preferably have from 8 to 30 carbon atoms and especially from 10 to 18 carbon atoms. In particular, the monocarboxylic acids are selected from the group formed by the following branched acids: 2,2-dimethylpropanoic acid, neoheptanoic acid, neooctanoic acid, neononanoic acid, isohexanoic acid, neodecanoic acid, 2-ethylhexanoic acid, 3-propylhexanoic acid, 3,5,5-trimethylhexanoic acid, isoheptanoic acid, isooctanoic acid, isononanoic acid, isostearic acid, isopalmitic acid, Guerbet acid C32, Guerbet acid C34 or Guerbet acid C36, and isodecanoic acid. The linear acids are preferably selected from the group formed by valeric acid, caproic acid, heptanoic acid, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, nonadecanoic acid, arachic acid, behenic acid, lignoceric acid, myristic acid, cerotic acid, mellissic acid, tricosanoic acid and pentacosanoic acid, 2-ethylhexanoic acid, isotridecanoic acid, myristic acid, palmitoleic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, elaeostearic acid, gadoleic acid and erucic acid, and the technical-grade mixtures thereof. Preferred branched monocarboxylic acids are isononanoic acid, isostearic acid and 2-ethylhexanoic acid.
Preference is given to lubricant compositions which comprise complex esters which are obtained by reacting polyols with dicarboxylic acids and branched monocarboxylic acids. These preferred esters formed from polyols, dicarboxylic acids and branched monocarboxylic acids preferably have a viscosity from 1300 to 5000 mm2/s and most preferably from 1500 to 3000 mm2/s .
In the context of the invention, the base oil present in the lubricant composition is understood to mean an oil which is selected from the group formed by mineral oils, highly refined mineral oils, alkylated mineral oils, poly-a-olefins, polyalkylene glycols, phosphate esters, silicone oils, diesters and esters of polyhydric alcohols, and also mineral oils of the Solvent Neutral class and mineral oils of the XHVI, VHVI, group II and group III and GTL basestock (gas-to-liquid base oil) classes. The poly-a-olefins may preferably be formed from C6 to C18-a-olefins and mixtures thereof. Especially preferred are poly-a-decenes.
According to the invention, the polyols are branched or linear alcohols of the general formula (I) R1(OH)n in which R' is an aliphatic or cycloaliphatic group having from 2 to 20 carbon atoms and n is at least 2. The polyols are preferably selected from the group formed by neopentyl glycol, 2,2-dimethylolbutane, trimethylolethane, trimethylolpropane, trimethylol-butane, monopentaerythitol, dipentaerythritol, tripentaerythritol, ethylene glycol, propylene glycol, polyalkylene glycol, 1,4-butanediol, 1,3-propanediol and glycerol. Especially preferred are trimethylolpropane, monopentaerythritol and dipentaerythritol.
In further preferred embodiments, the lubricant compositions are characterized in that, in the reaction according to b), the monoalcohols used are branched or linear alcohols of the general formula (II)(R2OH) in which R2 is an aliphatic or cycloaliphatic group having from 2 to 24 carbon atoms and bears 0 and/or 1, 2 or 3 double bonds. The monoalcohols are preferably selected from the group formed by caproic alcohol, capryl alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol, and technical-grade mixtures thereof.
The dicarboxylic acids used in accordance with the invention to prepare the complex esters are preferably oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, brassylic acid, thapsic acid and phellogenic acid. The anhydrides of the dicarboxylic acids are also suitable in accordance with the invention for the reaction. Especially preferred are azelaic acid or sebacic acid, and anhydrides thereof.
The conversion to the reaction products of the complex esters proceeds in syntheses known per se for preparing esters. The preparation of the esters can also be carried out in accordance with the invention by known processes such that free carboxyl groups and/or free hydroxyl groups are present in a controlled manner, and these products with free carboxyl and/or free hydroxyl groups are used in the lubricant composition. According to the invention, the free carboxyl groups present may be reacted further with amines to give amides, and the resulting compounds may be present in the lubricant composition as complex esters in the context of the invention.
In further preferred embodiments, the inventive lubricant compositions comprise, as a further component, a polar polymer in a concentration of from 0.5 to 30% by weight based on the total amount of lubricant composition. Preference is given to a concentration of from 1 to 18% by weight and more preferably from 2 to 12% by weight.
The polar polymers for use in accordance with the invention are preferably selected from the group formed by alkyl fumarate-a-olefin copolymer, alkyl maleate-a-olefin copolymer, polyalkyl methacrylate, propylene oxide polymer, ethylene oxide-propylene oxide copolymer and alkyl methacrylate-a-olefin copolymer.
In addition to good shear stability, the complex esters for use in accordance with the invention exhibit a high compatibility toward seal materials which typically find use. The test for compatibility toward seal materials can be carried out, for example, according to the standard test ASTM D 471, for example over 168 h at 100 C. According to this test, the complex esters for use in accordance with the invention exhibit, for the seal materials, a volume increase of not more than 20%, preferably not more than 10%, a hardness loss of less than 15%, preferably less than 100, and a decrease in the elongation at break of less than 50%, preferably less than 30%.
Stability problems of seal materials with respect to lubricant compositions based on esters occur particularly in the case of use of nitrile rubber or acrylonitrile-butadiene rubber or hydrogenated variants thereof. Typically, these seal materials are softened by esters as lubricants, which is manifested by an increase in volume. This softening leads to reduced hardness and reduced breaking strength or elongation at break.
In a preferred embodiment of the invention, the complex esters for use are compatible toward seal materials which are selected from the group formed by NR (natural rubber), NBR (nitrile-butadiene rubber), HNBR
It has additionally been found that expensive, high-viscosity PAO types, for example PAO 60 or PAO 100, or customary thickeners such as OCP or PIB, which have been added to the lubricants as thickeners, can alternatively be formulated with the complex esters to be present in accordance with the invention and lead to comparably good or improved properties. Preference is given to the simultaneous addition of polar polymers as a further component, for example those mentioned above.
The kinematic viscosity of the complex ester for use is preferably from 800 to 25 000 mm2/s, especially from 1200 to 10 000 mm2/s, more preferably from 1300 to 5000 mm2/s and most preferably from 1500 to 3000 mmz/s.
It has been found that, surprisingly, the use of these esters leads to very low losses in the kinematic viscosity of the lubricant composition after permanent shear. This property makes possible use in lubricants which are exposed to high shear stress.
Preference is given in accordance with the invention to lubricant compositions comprising the complex ester in a concentration of from 3 to 90% by weight based on the total amount of lubricant composition. Especially preferred is a concentration of 7-50% by weight and more preferably of 10-34 s by weight.
In a further preferred embodiment, the lubricant compositions are characterized in that the monocarboxylic acids used in the reaction according to a) are branched monocarboxylic acids or mixtures of linear and branched monocarboxylic acids, each of which has a carbon number of from 5 to 40 carbon atoms, where the content of branched monoacid is preferably greater than 90 mol% based on the total content of the acid mixture. The monocarboxylic acids preferably have from 8 to 30 carbon atoms and especially from 10 to 18 carbon atoms. In particular, the monocarboxylic acids are selected from the group formed by the following branched acids: 2,2-dimethylpropanoic acid, neoheptanoic acid, neooctanoic acid, neononanoic acid, isohexanoic acid, neodecanoic acid, 2-ethylhexanoic acid, 3-propylhexanoic acid, 3,5,5-trimethylhexanoic acid, isoheptanoic acid, isooctanoic acid, isononanoic acid, isostearic acid, isopalmitic acid, Guerbet acid C32, Guerbet acid C34 or Guerbet acid C36, and isodecanoic acid. The linear acids are preferably selected from the group formed by valeric acid, caproic acid, heptanoic acid, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, nonadecanoic acid, arachic acid, behenic acid, lignoceric acid, myristic acid, cerotic acid, mellissic acid, tricosanoic acid and pentacosanoic acid, 2-ethylhexanoic acid, isotridecanoic acid, myristic acid, palmitoleic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, elaeostearic acid, gadoleic acid and erucic acid, and the technical-grade mixtures thereof. Preferred branched monocarboxylic acids are isononanoic acid, isostearic acid and 2-ethylhexanoic acid.
Preference is given to lubricant compositions which comprise complex esters which are obtained by reacting polyols with dicarboxylic acids and branched monocarboxylic acids. These preferred esters formed from polyols, dicarboxylic acids and branched monocarboxylic acids preferably have a viscosity from 1300 to 5000 mm2/s and most preferably from 1500 to 3000 mm2/s .
In the context of the invention, the base oil present in the lubricant composition is understood to mean an oil which is selected from the group formed by mineral oils, highly refined mineral oils, alkylated mineral oils, poly-a-olefins, polyalkylene glycols, phosphate esters, silicone oils, diesters and esters of polyhydric alcohols, and also mineral oils of the Solvent Neutral class and mineral oils of the XHVI, VHVI, group II and group III and GTL basestock (gas-to-liquid base oil) classes. The poly-a-olefins may preferably be formed from C6 to C18-a-olefins and mixtures thereof. Especially preferred are poly-a-decenes.
According to the invention, the polyols are branched or linear alcohols of the general formula (I) R1(OH)n in which R' is an aliphatic or cycloaliphatic group having from 2 to 20 carbon atoms and n is at least 2. The polyols are preferably selected from the group formed by neopentyl glycol, 2,2-dimethylolbutane, trimethylolethane, trimethylolpropane, trimethylol-butane, monopentaerythitol, dipentaerythritol, tripentaerythritol, ethylene glycol, propylene glycol, polyalkylene glycol, 1,4-butanediol, 1,3-propanediol and glycerol. Especially preferred are trimethylolpropane, monopentaerythritol and dipentaerythritol.
In further preferred embodiments, the lubricant compositions are characterized in that, in the reaction according to b), the monoalcohols used are branched or linear alcohols of the general formula (II)(R2OH) in which R2 is an aliphatic or cycloaliphatic group having from 2 to 24 carbon atoms and bears 0 and/or 1, 2 or 3 double bonds. The monoalcohols are preferably selected from the group formed by caproic alcohol, capryl alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol, and technical-grade mixtures thereof.
The dicarboxylic acids used in accordance with the invention to prepare the complex esters are preferably oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, brassylic acid, thapsic acid and phellogenic acid. The anhydrides of the dicarboxylic acids are also suitable in accordance with the invention for the reaction. Especially preferred are azelaic acid or sebacic acid, and anhydrides thereof.
The conversion to the reaction products of the complex esters proceeds in syntheses known per se for preparing esters. The preparation of the esters can also be carried out in accordance with the invention by known processes such that free carboxyl groups and/or free hydroxyl groups are present in a controlled manner, and these products with free carboxyl and/or free hydroxyl groups are used in the lubricant composition. According to the invention, the free carboxyl groups present may be reacted further with amines to give amides, and the resulting compounds may be present in the lubricant composition as complex esters in the context of the invention.
In further preferred embodiments, the inventive lubricant compositions comprise, as a further component, a polar polymer in a concentration of from 0.5 to 30% by weight based on the total amount of lubricant composition. Preference is given to a concentration of from 1 to 18% by weight and more preferably from 2 to 12% by weight.
The polar polymers for use in accordance with the invention are preferably selected from the group formed by alkyl fumarate-a-olefin copolymer, alkyl maleate-a-olefin copolymer, polyalkyl methacrylate, propylene oxide polymer, ethylene oxide-propylene oxide copolymer and alkyl methacrylate-a-olefin copolymer.
In addition to good shear stability, the complex esters for use in accordance with the invention exhibit a high compatibility toward seal materials which typically find use. The test for compatibility toward seal materials can be carried out, for example, according to the standard test ASTM D 471, for example over 168 h at 100 C. According to this test, the complex esters for use in accordance with the invention exhibit, for the seal materials, a volume increase of not more than 20%, preferably not more than 10%, a hardness loss of less than 15%, preferably less than 100, and a decrease in the elongation at break of less than 50%, preferably less than 30%.
Stability problems of seal materials with respect to lubricant compositions based on esters occur particularly in the case of use of nitrile rubber or acrylonitrile-butadiene rubber or hydrogenated variants thereof. Typically, these seal materials are softened by esters as lubricants, which is manifested by an increase in volume. This softening leads to reduced hardness and reduced breaking strength or elongation at break.
In a preferred embodiment of the invention, the complex esters for use are compatible toward seal materials which are selected from the group formed by NR (natural rubber), NBR (nitrile-butadiene rubber), HNBR
(hydrogenated nitrile butyl rubber), FPM (fluorine rubber), ACM (acrylate rubber), PTFE (Teflon), PU
(polyurethane), silicone, polyacrylate and neoprene, more preferably toward NBR, HNBR and ACM.
In a preferred embodiment of the inventive use, the stability of the seal materials toward esters with branched alkyl groups is determined by the ASTM D 471 test mentioned, and the criteria specified are met.
The complex esters for use in accordance with the invention exhibit, in addition to the properties already mentioned, also good oxidation stability and thermal stability. This has been determined to DIN EN
ISO 4263-3.
In the context of the invention, the terms "lubricant composition", "lubricant", "lubricant oil" and "formulation" are used synonymously.
In addition to the further components mentioned, the inventive lubricant composition may comprise further additives which are selected from the group formed by polymer thickeners, viscosity index improvers, antioxidants, corrosion inhibitors, detergents, dispersants, demulsifiers, defoamers, dyes, wear protection additives, EP (extreme pressure) and AW
(antiwear) additives and friction modifiers.
The invention further provides for the use of the inventive lubricant composition, especially in the preferred embodiments, as a vehicle transmission oil, axle oil, industrial transmission oil, compressor oil, turbine oil or motor oil. Particular preference is given to use as a vehicle transmission oil, axle oil, clutch oil or industrial transmission oil.
(polyurethane), silicone, polyacrylate and neoprene, more preferably toward NBR, HNBR and ACM.
In a preferred embodiment of the inventive use, the stability of the seal materials toward esters with branched alkyl groups is determined by the ASTM D 471 test mentioned, and the criteria specified are met.
The complex esters for use in accordance with the invention exhibit, in addition to the properties already mentioned, also good oxidation stability and thermal stability. This has been determined to DIN EN
ISO 4263-3.
In the context of the invention, the terms "lubricant composition", "lubricant", "lubricant oil" and "formulation" are used synonymously.
In addition to the further components mentioned, the inventive lubricant composition may comprise further additives which are selected from the group formed by polymer thickeners, viscosity index improvers, antioxidants, corrosion inhibitors, detergents, dispersants, demulsifiers, defoamers, dyes, wear protection additives, EP (extreme pressure) and AW
(antiwear) additives and friction modifiers.
The invention further provides for the use of the inventive lubricant composition, especially in the preferred embodiments, as a vehicle transmission oil, axle oil, industrial transmission oil, compressor oil, turbine oil or motor oil. Particular preference is given to use as a vehicle transmission oil, axle oil, clutch oil or industrial transmission oil.
Examples Examples 1-10 (El-E10):
Comparison of different lubricant compositions Table 1 shows a compilation of example and comparative example formulations.
It is found clearly that, based on the high-viscosity esters HVE I or HVE II, transmission oils of SAE class 75W-90 were formulable with good low-temperature properties (low dynamic viscosities, all <300,000 mPa.s; measured at -400C). What is noticeable is the improved shear stability of the example formulations (apart from E5 and E6, which are aimed exclusively at one inventive effect of improving low-temperature properties and the possibility of utilizing group III mineral oils instead of PAO 6) as compared with the comparative example (CE1) . The effect is all the clearer when it is considered that- CE1 has been formulated with PIB and OCP systems which are classified as particularly shear-stable. It is noticeable that the utilization of high-viscosity esters makes available formulations with good low-temperature viscosities likewise by means of PAO 8 or a group III mineral oil instead of by means of PAO 6 (see E4, E5, E6). It is found that the utilization of particular polymers in relatively low concentrations has synergistic effects on an improvement of low-temperature viscosities (see E2 in comparison with E3, E2 in comparison with E7, E2 in comparison with El0 and E5 in comparison with E6) . This was shown by means of alkyl methacrylate polymers (see E5 and E6), alkyl methacrylate-a-olefin copolymers (see E3), alkyl maleate-a-olefin copolymers (see E7) and by means of alkyl fumarate-a-olefin copolymers (see E10). In the case of utilization of alkyl methacrylate polymers, the shear stability of the formulations was found to be worse (see E5 and E6), which was attributable to the shear of the alkyl methacrylate polymer. It is likewise apparent that formulations based on HVE II bring advantages in the mean end of test temperature in the ARKL test (VW PV 1454) (see CE1 in comparison to E8 and E9) . This test reflects operating oil temperatures in transmission and axle applications and is all the more positive the lower the temperatures observed are. It was likewise apparent that friction values had decreased, as had wear as a result of utilization of the inventive oils. This was shown by means of the industry standard SRV test (see CE1 in comparison to E2).
All methods used and the exact names of the feedstocks used are explained in table 1.
~
o-O
O
n O
N
\ o w o m U) o m o ~~ ~ o o v~ \ w\ o ID
= ' u"E ro"'E
M N ,O \p E4 W m 1d O
U2 N d m m~ n ~
A. A. b b b 01 H p M p p M f11 N Ul O UI
=~ w . . . ,o "'. \ N \ oo rtf mH
d' H N m cN I r ~ ~
~
~
~4 o\o o\o o\o d^
~--~ ~ O O O O M ~1 ~ Vl O Ul ~ . = . O ID \ = N O ' H
W
0 Ln o M ' \p E ~ E m qro w ri M ~ ~ E o E m E
~ ' o\o I ~ ~ ~ N Pj N y O (n U
M O N\ Ifl \ O . p u) 10 W d, m . = " = co (b m ID Lf) Ln N w ~ r~-1 E m E '- M
ul 1D o ~ ~ oo ro~ M ~ N o co \o W ~ o . = r 0 "E - E m ro ~n r b Ln r-~ 10 10 010 N o o Ln M 0~ O o ~ fA r Ul O Ul U o0 ~ w . . N ~ = \ ~ rv N N GO f, Ln N I ~ .
0 M m E ~ H
o\o A. \
O o A. lfl p d ~ 0\ O ri O \p In ~ U1 pO 0' ifl O
~ . . . O ^~ \ . \ =
W r o o = to E E N H %D N
W ~r ~ M õNi .-a E o E (N E T ~ .
~I
w =o A. A. M lp H O O U) N o Ul U o\
M b ~\ .\ o = o C' b N N E O~i ~ v1 ~ f'1 rW
G
X t O
o w N N m O ~~ N o do = tIl O
. "E p Lj W N o p a ~ ~
Ln ~ M r1 N 'i E ~-I E M
ID
rI
W H o 0 0 0 ^~ to 0 U o 0 0 0 o N~ `~. ~ o N o m o ro ~ w E n m N M rl H c' E N E E [~ ~
~ H ry I"/-~~cw~. o\^ o\ o\^ o\
G(~' ~ O O O O O v VI ~ U1 O Ul = . . . o b \ . \ p ' ~ I~ ri X [s]
U N o = e'"E E b o in N,-Mi N .=~i N ul ,-~ =
(\ OJ Ln H <
r+ ''~ E ,y E ,y E
O
I~I =rI q N I~ H ~ H iJ H = . Ul 1"I J-~ S-1 J-, RS G' ~~ G' ~ N H~ f11 H
H fp z' U H u r~
aJ ,o m H H O
H H N r N ~ b v -~ .~ > -.~ [n 0 j ~
O E ~~ ~+ x x a ~
OD
O
rn O
O
r CN
a w H
U
U
o M
~
U
m rl r~
r o E E E
~ o ao m ~ ro r r M
H 0 r-i o o Ln F E E
m M ~ O O M
~ M O N 1D
~ O N N O
rl O U~w-.~i> E E Oi~ -r \ '~ i~ oo r.~ O .i ~ E 7 a.~
r E'1 N ~ 'd C1 +-i ~ r O"X ~ b p, F, q E m d, > E-~ ro a~ N
O ~i ~ '1 a E U E O N O
N H u' d' mua~~ E u A w Z al u~ b4 a' H w~ x ~ rtf ~ a~i O"'~ Q 4 .~i ~ Nx ~~ N 3 3 a] > s a i - 17 - PAO 4: Nexbase 2004 from Neste Oil Corp.
PAO 6: Nexbase 2006 from Neste Oil Corp.
PAO 8: Nexbase 2008 from Neste Oil Corp.
HVE I: commercially available high-viscosity ester with a kinematic viscosity measured at 40 C of 445 mmz/s (e.g. Synative ES 3237 from Cognis) HVE II: high-viscosity ester with a kinematic viscosity measured at 40 C of 2000 mm2/s; determined by known methods by reacting pentaerythritol, isostearic acid and sebacic acid DIDA: diisodecyl adipate, e.g. Synative ES DIDA from Cognis Deutschland Gmbh & Co. KG
Group III mineral oil: Nexbase 3043 from Neste Oil Corp.
Alkyl methacrylate-a-olefin copolymer I: Viscobase 11-574 from RohMax Alkyl methacrylate I: Viscoplex 0-101 from RohMax Alkyl maleate-a-olefin copolymer I: Gear-Lube 7930 Alkyl fumarate-a-olefin copolymer I: Gear-Lube 7960 Additive package I: Anglamol 6004 J from Lubrizol PIB I: Lubrizol 8406 from Lubrizol OCP I: Lubrizol 8407 from Lubrizol *SRV test conditions:
- SRV1 instrument from Optimol Instruments Pruftechnik GmbH
- Load increased to 200 N within 22 minutes, 300 N for a further 5 minutes, 600 N for the remaining 43 minutes; test time: 70 minutes - Temperature: 100 C
- Sliding path of the sphere: 1.00 mm - Frequency: 50 Hz - Material pair: 10 mm diameter sphere on cylinder with lapped surface Several motor oils were produced with esters according to the present invention (E13 - E15) and their properties were tested. For comparison, the test results for comparable prior art motor oils (Ell and E12) are listed as well. The results can be found in table 2 below:
Composition E11 E12 E13 E14 E15 PAO 4 20 47 20 41.5 47 PAO 6 44.2 11.1 44.5 9.8 26 HVE II 3.5 19 15 Group III mineral 20 20 20 17.7 oil Alkyl 3.5 9.9 methacrylate-a-olefin copolymer I
Alkyl 0.3 methacrylate I
Additive package 12 12 12 12 12 I
Results kinem. visc. 10.77/ 10.59/
100 C (DIN 51562) 7.18 10.61 6.93 10.48 9.50 kinem. visc. 40 C
(DIN 51562) 38.82 61.79 38.71 62.40 59.40 dyn.visc. -35 C 5800 26100 8500 (DIN 51398) Viscosity index 150 166 140 160 142 Shear stability:
loss of kinemat. 36.81 3.0%
visc. at 100 C
(DIN 51562; CEC
L-45-T-93)
Comparison of different lubricant compositions Table 1 shows a compilation of example and comparative example formulations.
It is found clearly that, based on the high-viscosity esters HVE I or HVE II, transmission oils of SAE class 75W-90 were formulable with good low-temperature properties (low dynamic viscosities, all <300,000 mPa.s; measured at -400C). What is noticeable is the improved shear stability of the example formulations (apart from E5 and E6, which are aimed exclusively at one inventive effect of improving low-temperature properties and the possibility of utilizing group III mineral oils instead of PAO 6) as compared with the comparative example (CE1) . The effect is all the clearer when it is considered that- CE1 has been formulated with PIB and OCP systems which are classified as particularly shear-stable. It is noticeable that the utilization of high-viscosity esters makes available formulations with good low-temperature viscosities likewise by means of PAO 8 or a group III mineral oil instead of by means of PAO 6 (see E4, E5, E6). It is found that the utilization of particular polymers in relatively low concentrations has synergistic effects on an improvement of low-temperature viscosities (see E2 in comparison with E3, E2 in comparison with E7, E2 in comparison with El0 and E5 in comparison with E6) . This was shown by means of alkyl methacrylate polymers (see E5 and E6), alkyl methacrylate-a-olefin copolymers (see E3), alkyl maleate-a-olefin copolymers (see E7) and by means of alkyl fumarate-a-olefin copolymers (see E10). In the case of utilization of alkyl methacrylate polymers, the shear stability of the formulations was found to be worse (see E5 and E6), which was attributable to the shear of the alkyl methacrylate polymer. It is likewise apparent that formulations based on HVE II bring advantages in the mean end of test temperature in the ARKL test (VW PV 1454) (see CE1 in comparison to E8 and E9) . This test reflects operating oil temperatures in transmission and axle applications and is all the more positive the lower the temperatures observed are. It was likewise apparent that friction values had decreased, as had wear as a result of utilization of the inventive oils. This was shown by means of the industry standard SRV test (see CE1 in comparison to E2).
All methods used and the exact names of the feedstocks used are explained in table 1.
~
o-O
O
n O
N
\ o w o m U) o m o ~~ ~ o o v~ \ w\ o ID
= ' u"E ro"'E
M N ,O \p E4 W m 1d O
U2 N d m m~ n ~
A. A. b b b 01 H p M p p M f11 N Ul O UI
=~ w . . . ,o "'. \ N \ oo rtf mH
d' H N m cN I r ~ ~
~
~
~4 o\o o\o o\o d^
~--~ ~ O O O O M ~1 ~ Vl O Ul ~ . = . O ID \ = N O ' H
W
0 Ln o M ' \p E ~ E m qro w ri M ~ ~ E o E m E
~ ' o\o I ~ ~ ~ N Pj N y O (n U
M O N\ Ifl \ O . p u) 10 W d, m . = " = co (b m ID Lf) Ln N w ~ r~-1 E m E '- M
ul 1D o ~ ~ oo ro~ M ~ N o co \o W ~ o . = r 0 "E - E m ro ~n r b Ln r-~ 10 10 010 N o o Ln M 0~ O o ~ fA r Ul O Ul U o0 ~ w . . N ~ = \ ~ rv N N GO f, Ln N I ~ .
0 M m E ~ H
o\o A. \
O o A. lfl p d ~ 0\ O ri O \p In ~ U1 pO 0' ifl O
~ . . . O ^~ \ . \ =
W r o o = to E E N H %D N
W ~r ~ M õNi .-a E o E (N E T ~ .
~I
w =o A. A. M lp H O O U) N o Ul U o\
M b ~\ .\ o = o C' b N N E O~i ~ v1 ~ f'1 rW
G
X t O
o w N N m O ~~ N o do = tIl O
. "E p Lj W N o p a ~ ~
Ln ~ M r1 N 'i E ~-I E M
ID
rI
W H o 0 0 0 ^~ to 0 U o 0 0 0 o N~ `~. ~ o N o m o ro ~ w E n m N M rl H c' E N E E [~ ~
~ H ry I"/-~~cw~. o\^ o\ o\^ o\
G(~' ~ O O O O O v VI ~ U1 O Ul = . . . o b \ . \ p ' ~ I~ ri X [s]
U N o = e'"E E b o in N,-Mi N .=~i N ul ,-~ =
(\ OJ Ln H <
r+ ''~ E ,y E ,y E
O
I~I =rI q N I~ H ~ H iJ H = . Ul 1"I J-~ S-1 J-, RS G' ~~ G' ~ N H~ f11 H
H fp z' U H u r~
aJ ,o m H H O
H H N r N ~ b v -~ .~ > -.~ [n 0 j ~
O E ~~ ~+ x x a ~
OD
O
rn O
O
r CN
a w H
U
U
o M
~
U
m rl r~
r o E E E
~ o ao m ~ ro r r M
H 0 r-i o o Ln F E E
m M ~ O O M
~ M O N 1D
~ O N N O
rl O U~w-.~i> E E Oi~ -r \ '~ i~ oo r.~ O .i ~ E 7 a.~
r E'1 N ~ 'd C1 +-i ~ r O"X ~ b p, F, q E m d, > E-~ ro a~ N
O ~i ~ '1 a E U E O N O
N H u' d' mua~~ E u A w Z al u~ b4 a' H w~ x ~ rtf ~ a~i O"'~ Q 4 .~i ~ Nx ~~ N 3 3 a] > s a i - 17 - PAO 4: Nexbase 2004 from Neste Oil Corp.
PAO 6: Nexbase 2006 from Neste Oil Corp.
PAO 8: Nexbase 2008 from Neste Oil Corp.
HVE I: commercially available high-viscosity ester with a kinematic viscosity measured at 40 C of 445 mmz/s (e.g. Synative ES 3237 from Cognis) HVE II: high-viscosity ester with a kinematic viscosity measured at 40 C of 2000 mm2/s; determined by known methods by reacting pentaerythritol, isostearic acid and sebacic acid DIDA: diisodecyl adipate, e.g. Synative ES DIDA from Cognis Deutschland Gmbh & Co. KG
Group III mineral oil: Nexbase 3043 from Neste Oil Corp.
Alkyl methacrylate-a-olefin copolymer I: Viscobase 11-574 from RohMax Alkyl methacrylate I: Viscoplex 0-101 from RohMax Alkyl maleate-a-olefin copolymer I: Gear-Lube 7930 Alkyl fumarate-a-olefin copolymer I: Gear-Lube 7960 Additive package I: Anglamol 6004 J from Lubrizol PIB I: Lubrizol 8406 from Lubrizol OCP I: Lubrizol 8407 from Lubrizol *SRV test conditions:
- SRV1 instrument from Optimol Instruments Pruftechnik GmbH
- Load increased to 200 N within 22 minutes, 300 N for a further 5 minutes, 600 N for the remaining 43 minutes; test time: 70 minutes - Temperature: 100 C
- Sliding path of the sphere: 1.00 mm - Frequency: 50 Hz - Material pair: 10 mm diameter sphere on cylinder with lapped surface Several motor oils were produced with esters according to the present invention (E13 - E15) and their properties were tested. For comparison, the test results for comparable prior art motor oils (Ell and E12) are listed as well. The results can be found in table 2 below:
Composition E11 E12 E13 E14 E15 PAO 4 20 47 20 41.5 47 PAO 6 44.2 11.1 44.5 9.8 26 HVE II 3.5 19 15 Group III mineral 20 20 20 17.7 oil Alkyl 3.5 9.9 methacrylate-a-olefin copolymer I
Alkyl 0.3 methacrylate I
Additive package 12 12 12 12 12 I
Results kinem. visc. 10.77/ 10.59/
100 C (DIN 51562) 7.18 10.61 6.93 10.48 9.50 kinem. visc. 40 C
(DIN 51562) 38.82 61.79 38.71 62.40 59.40 dyn.visc. -35 C 5800 26100 8500 (DIN 51398) Viscosity index 150 166 140 160 142 Shear stability:
loss of kinemat. 36.81 3.0%
visc. at 100 C
(DIN 51562; CEC
L-45-T-93)
Claims (11)
1. A lubricant composition having a good shear stability determined by the loss of kinematic viscosity at 100°C, comprising base oil and a synthetic complex ester, said complex ester having a kinematic viscosity at 40°C of greater than 400 and up to 50 000 mm2/s and being obtained by reaction of:
a) polyols and monocarboxylic acids and dicarboxylic acids or of b) polyols and monoalcohols and dicarboxylic acids or of c) polyols and monoalcohols and monocarboxylic acids and dicarboxylic acids.
a) polyols and monocarboxylic acids and dicarboxylic acids or of b) polyols and monoalcohols and dicarboxylic acids or of c) polyols and monoalcohols and monocarboxylic acids and dicarboxylic acids.
2. The lubricant composition as claimed in claim 1, characterized in that the loss of kinematic viscosity at 100°C
i) for transmission oils, axle oils and clutch oils for automatic and manual transmission, determined to CEC L-45-T-93 (20 hours), is less than 8%, ii) for hydraulic fluids, for industrial transmission oils with stationary uses, for oils for lubricating wind turbines, for gas turbine oils, for compressor oils and shock absorber fluids, determined to CEC L-45-T-93 (20 hours), is less than 15%, iii) for two-stroke and four-stroke engine oils and for diesel and gasoline motor oils, determined to ASTM D 3945 (30 cycles), is less than 15%.
i) for transmission oils, axle oils and clutch oils for automatic and manual transmission, determined to CEC L-45-T-93 (20 hours), is less than 8%, ii) for hydraulic fluids, for industrial transmission oils with stationary uses, for oils for lubricating wind turbines, for gas turbine oils, for compressor oils and shock absorber fluids, determined to CEC L-45-T-93 (20 hours), is less than 15%, iii) for two-stroke and four-stroke engine oils and for diesel and gasoline motor oils, determined to ASTM D 3945 (30 cycles), is less than 15%.
3. The lubricant composition as claimed in claim 1 or 2, characterized in that the complex ester is present in a concentration of from 3 to 90% by weight based on the total amount of lubricant composition.
4. The lubricant composition as claimed in any one of claims 1 to 3, characterized in that the monocarboxylic acids used in the reaction according to a) in claim 1 are branched monocarboxylic acids or mixtures of linear and branched monocarboxylic acids, each of which has a carbon number of from 5 to 40 carbon atoms.
5. The lubricant composition as claimed in any one of claims 1 to 4, characterized in that the polyols are branched or linear alcohols of the general formula (I) R1 (OH) n in which R1 is an aliphatic or cycloaliphatic group having from 2 to 20 carbon atoms and n is at least 2.
6. The lubricant composition as claimed in any one of claims 1 to 5, characterized in that the monoalcohols are branched or linear alcohols of the general formula (II) (R2OH) in which R2 is an aliphatic or cycloaliphatic group having from 2 to 20 carbon atoms.
7. The lubricant composition as claimed in claims 1 to 6, characterized in that dicarboxylic acids are selected from the group formed by oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, brassylic acid, thapsic acid and phellogenic acid.
8. The lubricant composition as claimed in any one of claims 1 to 7, characterized in that, as a further component, a polar polymer is present in a concentration of from 0.5 to 30% by weight (especially 1-18 and more preferably from 2 to 12) based on the total amount of lubricant composition.
9. The lubricant composition as claimed in any one of claims 1 to 8, characterized in that the polar polymer is selected from the group formed by polyalkyl methacrylate, alkyl fumarate-alpha-olefin copolymer, alkyl maleate-alpha-olefin copolymer, propylene oxide polymer, ethylene oxide-propylene oxide copolymer and alkyl methacrylate-alpha-olefin copolymer.
10. The lubricant composition as claimed in any one of claims 1 to 9, characterized in that further additives may be present, said additives being selected from the group formed by polymer thickeners, viscosity index improvers, antioxidants, corrosion inhibitors, detergents, dispersants, demulsifiers, defoamers, dyes, wear protection additives, EP (extreme pressure) and AW
(antiwear) additives and friction modifiers.
(antiwear) additives and friction modifiers.
11. The use of lubricant compositions as claimed in claims 1 to 10 as vehicle transmission oil, axle oil, industrial transmission oil, compressor oil, turbine oil or motor oil.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE102006027602.7 | 2006-06-13 | ||
DE102006027602A DE102006027602A1 (en) | 2006-06-13 | 2006-06-13 | Lubricant compositions containing complex esters |
PCT/EP2007/004908 WO2007144079A2 (en) | 2006-06-13 | 2007-06-02 | Lubricant compounds containing complex esters |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2655040A1 true CA2655040A1 (en) | 2007-12-21 |
Family
ID=38658472
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002655040A Abandoned CA2655040A1 (en) | 2006-06-13 | 2007-06-02 | Lubricant compounds containing complex esters |
Country Status (12)
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US (1) | US20090186787A1 (en) |
EP (1) | EP2027234B1 (en) |
JP (1) | JP2009540070A (en) |
KR (1) | KR20090016703A (en) |
CN (1) | CN101466817B (en) |
AU (1) | AU2007260340B2 (en) |
BR (1) | BRPI0713592A2 (en) |
CA (1) | CA2655040A1 (en) |
DE (1) | DE102006027602A1 (en) |
HK (1) | HK1129235A1 (en) |
MX (1) | MX2008014259A (en) |
WO (1) | WO2007144079A2 (en) |
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WO2010063099A1 (en) * | 2008-12-01 | 2010-06-10 | Keith Donald Norman Klayh | Oil lubricant for use in air tools or air motors |
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2006
- 2006-06-13 DE DE102006027602A patent/DE102006027602A1/en not_active Withdrawn
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2007
- 2007-06-02 CN CN2007800220457A patent/CN101466817B/en not_active Expired - Fee Related
- 2007-06-02 JP JP2009514660A patent/JP2009540070A/en active Pending
- 2007-06-02 WO PCT/EP2007/004908 patent/WO2007144079A2/en active Application Filing
- 2007-06-02 BR BRPI0713592-0A patent/BRPI0713592A2/en not_active Application Discontinuation
- 2007-06-02 US US12/305,576 patent/US20090186787A1/en not_active Abandoned
- 2007-06-02 MX MX2008014259A patent/MX2008014259A/en active IP Right Grant
- 2007-06-02 CA CA002655040A patent/CA2655040A1/en not_active Abandoned
- 2007-06-02 EP EP07725786.3A patent/EP2027234B1/en active Active
- 2007-06-02 KR KR1020087030319A patent/KR20090016703A/en not_active Application Discontinuation
- 2007-06-02 AU AU2007260340A patent/AU2007260340B2/en not_active Ceased
-
2009
- 2009-09-29 HK HK09108999.5A patent/HK1129235A1/en not_active IP Right Cessation
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2010063099A1 (en) * | 2008-12-01 | 2010-06-10 | Keith Donald Norman Klayh | Oil lubricant for use in air tools or air motors |
US8800678B2 (en) | 2008-12-01 | 2014-08-12 | Keith Donald Norman Klayh | Oil lubricant |
AU2009322020B2 (en) * | 2008-12-01 | 2015-07-23 | Pneuma-Tool Canada Inc. | Oil lubricant for use in air tools or air motors |
Also Published As
Publication number | Publication date |
---|---|
AU2007260340A1 (en) | 2007-12-21 |
HK1129235A1 (en) | 2009-11-20 |
JP2009540070A (en) | 2009-11-19 |
BRPI0713592A2 (en) | 2012-11-06 |
MX2008014259A (en) | 2008-11-26 |
WO2007144079A2 (en) | 2007-12-21 |
EP2027234A2 (en) | 2009-02-25 |
AU2007260340B2 (en) | 2011-12-15 |
EP2027234B1 (en) | 2018-01-31 |
DE102006027602A1 (en) | 2007-12-20 |
CN101466817B (en) | 2013-06-12 |
CN101466817A (en) | 2009-06-24 |
WO2007144079A3 (en) | 2008-02-28 |
US20090186787A1 (en) | 2009-07-23 |
KR20090016703A (en) | 2009-02-17 |
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