JP2017515949A - 潤滑油 - Google Patents
潤滑油 Download PDFInfo
- Publication number
- JP2017515949A JP2017515949A JP2016567592A JP2016567592A JP2017515949A JP 2017515949 A JP2017515949 A JP 2017515949A JP 2016567592 A JP2016567592 A JP 2016567592A JP 2016567592 A JP2016567592 A JP 2016567592A JP 2017515949 A JP2017515949 A JP 2017515949A
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- JP
- Japan
- Prior art keywords
- acid
- lubricant composition
- amide
- branched
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000314 lubricant Substances 0.000 title claims abstract description 105
- 239000000203 mixture Substances 0.000 claims abstract description 118
- 239000000654 additive Substances 0.000 claims abstract description 79
- 150000001408 amides Chemical class 0.000 claims abstract description 70
- 230000000996 additive effect Effects 0.000 claims abstract description 50
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 13
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims abstract description 12
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 11
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 10
- 239000002199 base oil Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 8
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 8
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 5
- 239000002253 acid Substances 0.000 abstract description 37
- 150000003335 secondary amines Chemical class 0.000 abstract description 12
- 239000000539 dimer Substances 0.000 abstract description 11
- 150000007513 acids Chemical class 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- 239000012530 fluid Substances 0.000 description 36
- 239000000463 material Substances 0.000 description 32
- -1 polyol esters Chemical class 0.000 description 32
- 239000012208 gear oil Substances 0.000 description 31
- 239000010705 motor oil Substances 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 238000005555 metalworking Methods 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 18
- 239000002270 dispersing agent Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 15
- 239000003963 antioxidant agent Substances 0.000 description 14
- 235000014113 dietary fatty acids Nutrition 0.000 description 14
- 229930195729 fatty acid Natural products 0.000 description 14
- 239000000194 fatty acid Substances 0.000 description 14
- 150000002430 hydrocarbons Chemical group 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 13
- 150000004665 fatty acids Chemical class 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 10
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 10
- 239000002480 mineral oil Substances 0.000 description 10
- 230000001590 oxidative effect Effects 0.000 description 9
- KRAHLZAGPKKBSW-UHFFFAOYSA-N tetrasodium;dioxidophosphanyl phosphite Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])OP([O-])[O-] KRAHLZAGPKKBSW-UHFFFAOYSA-N 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 229920013639 polyalphaolefin Polymers 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 7
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 7
- 239000002518 antifoaming agent Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000004450 alkenylene group Chemical group 0.000 description 6
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000010721 machine oil Substances 0.000 description 5
- 150000002763 monocarboxylic acids Chemical class 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 239000005639 Lauric acid Substances 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 239000007866 anti-wear additive Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 229940043279 diisopropylamine Drugs 0.000 description 4
- 238000006471 dimerization reaction Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000010722 industrial gear oil Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 235000021313 oleic acid Nutrition 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 229920000193 polymethacrylate Polymers 0.000 description 4
- PDEDQSAFHNADLV-UHFFFAOYSA-M potassium;disodium;dinitrate;nitrite Chemical compound [Na+].[Na+].[K+].[O-]N=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PDEDQSAFHNADLV-UHFFFAOYSA-M 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 238000007655 standard test method Methods 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 3
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000000356 contaminant Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
- 239000010720 hydraulic oil Substances 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 3
- 229960004488 linolenic acid Drugs 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 229960002446 octanoic acid Drugs 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 238000005057 refrigeration Methods 0.000 description 3
- 229920005573 silicon-containing polymer Polymers 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- SZAQZZKNQILGPU-UHFFFAOYSA-N 2-[1-(2-hydroxy-3,5-dimethylphenyl)-2-methylpropyl]-4,6-dimethylphenol Chemical compound C=1C(C)=CC(C)=C(O)C=1C(C(C)C)C1=CC(C)=CC(C)=C1O SZAQZZKNQILGPU-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- 239000005069 Extreme pressure additive Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- 101150092791 PAO4 gene Proteins 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
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- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
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- 235000012343 cottonseed oil Nutrition 0.000 description 2
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 239000012990 dithiocarbamate Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 238000005553 drilling Methods 0.000 description 2
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- 125000000524 functional group Chemical group 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- YYVJAABUJYRQJO-UHFFFAOYSA-N isomyristic acid Chemical compound CC(C)CCCCCCCCCCC(O)=O YYVJAABUJYRQJO-UHFFFAOYSA-N 0.000 description 2
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 230000000704 physical effect Effects 0.000 description 2
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- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
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- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- GSOYMOAPJZYXTB-UHFFFAOYSA-N 2,6-ditert-butyl-4-(3,5-ditert-butyl-4-hydroxyphenyl)phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 GSOYMOAPJZYXTB-UHFFFAOYSA-N 0.000 description 1
- QHPKIUDQDCWRKO-UHFFFAOYSA-N 2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 QHPKIUDQDCWRKO-UHFFFAOYSA-N 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
-
- 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
- C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
- C10M105/68—Amides; Imides
-
- 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/16—Amides; Imides
-
- 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/16—Amides; Imides
- C10M133/18—Amides; Imides of carbonic or haloformic 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
- C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
- C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
-
- 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
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/024—Well-defined aliphatic compounds unsaturated
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
本出願は、2014年5月15日出願の米国仮特許出願第61/993520号の優先権を主張し、この出願の全ての開示は、参照することにより、全ての目的についてその全体が本明細書に組み込まれる。
a)分枝状の第2級アミン及びカルボン酸の反応生成物であるアミドと、
b)少なくとも1種の添加剤と
を含む潤滑剤組成物が提供される。
a)分枝状の第2級アミン及びカルボン酸の反応生成物であるアミドと、
b)少なくとも1種の添加剤と
を含む潤滑剤組成物を使用することを含む、潤滑剤組成物の添加剤の溶解性又は洗浄性を向上させる方法が提供される。
a)分枝状の第2級アミン及びカルボン酸の反応生成物であるアミドと、
b)少なくとも1種の添加剤と
を含む潤滑剤組成物を使用することを含む、潤滑剤組成物の添加剤の溶解性を向上させる方法が提供される。
R1及びR2が、C3〜C18の直鎖状又は分枝状の、飽和又は不飽和の炭化水素基からなる群より独立して選択され、
R3が、C3〜C50の直鎖状又は分枝状の、飽和又は不飽和の炭化水素基からなる群より選択され、
R4が、C1〜C50の直鎖状又は分枝状の、飽和又は不飽和のヒドロカルビレン基からなる群より選択され、
nが0又は1であり、
少なくともR1及びR2の1つが分枝状である。
例1
水凝縮器に接続したディーンスターク装置に備え付けた1リットルの丸底フラスコに、イソステアリン酸(284g、1モル)と、(ジ−2−エチルヘキシル)アミン(295g、1.05モル)と、ジ亜リン酸ナトリウム(3g、0.028モル)とを入れた。反応混合物を40分間かけて室温から240℃まで熱した。水がその反応から生成されて、その水をディーンスタークにおいて回収/分離した。有機物をディーンスタークからフラスコへ還流した。反応は、酸価が1.0未満になるまで240℃で行った。真空は1時間で250−200mmHgで徐々に適用して、次いで、その後に、塩基価が2未満になるまで35mmHg/240℃で余分な(ジ−2−エチルヘキシル)アミンを剥離した。反応混合物を110℃で冷却して、完全な真空下で濾紙を通じて濾過して、透明液、ストローカラーとして生成物を得た。その試料に以下の結果を生成したQC分析を行った。
水凝縮器に接続したディーンスターク装置に備え付けた1リットルの丸底フラスコに、2−エチルヘキサン酸(184g、1.2モル)と、(ジ−2−エチルヘキシル)アミン(281g、1モル)と、ジ亜リン酸ナトリウム(3g、0.028モル)とを入れた。反応混合物を40分間かけて室温から240℃まで熱した。水がその反応から生成されて、その水をディーンスタークにおいて回収/分離した。有機物をディーンスタークからフラスコへ還流した。反応は、酸価が1.0未満になるまで240℃で行った。真空は1時間で250−200mmHgで徐々に適用して、次いで、その後に、AVが1未満になるまで35mmHg/240℃で余分な2−エチルヘキサン酸を剥離した。反応混合物を110℃で冷却して、完全な真空下で濾紙を通じて濾過して、液体アミドとして生成物を得た。その試料に以下の結果を生成したQC分析を行った。
水凝縮器に接続したディーンスターク装置に備え付けた1リットルの丸底フラスコに、アジピン酸(146g、1.0モル)と、(ジ−2−エチルヘキシル)アミン(600g、2.1モル)と、ジ亜リン酸ナトリウム(3g、0.028モル)とを入れた。反応混合物を40分間かけて室温から240℃まで熱した。水がその反応から生成されて、その水をディーンスタークにおいて回収/分離した。有機物をディーンスタークからフラスコへ還流した。反応は、酸価が1.0未満になるまで240℃で行った。真空は1時間で250−200mmHgで徐々に適用して、次いで、その後に、塩基価が0.5満になるまで35mmHg/240℃で余分なジ−(2−エチルヘキシル)アミンを剥離した。反応混合物を110℃で冷却して、完全な真空下で濾紙を通じて濾過して、液体アミドとして生成物を得た。その試料に以下の結果を生成したQC分析を行った。
水凝縮器に接続したディーンスターク装置に備え付けた1リットルの丸底フラスコに、3,5,5’−トリメチルヘキサン酸(284g、1.9モル)と、(ジ−2−エチルヘキシル)アミン(295g、1.05モル)と、ジ亜リン酸ナトリウム(3g、0.028モル)とを入れた。反応混合物を40分間かけて室温から240℃まで熱した。水がその反応から生成されて、その水をディーンスタークにおいて回収/分離した。有機物をディーンスタークからフラスコへ還流した。反応は、酸価が1.0未満になるまで240℃で行った。真空は1時間で250−200mmHgで徐々に適用して、次いで、その後に、塩基価が2未満になるまで35mmHg/240℃で余分なジ−(2−エチルヘキシル)アミンを剥離した。反応混合物を110℃で冷却して、完全な真空下で濾紙を通じて濾過して、液体アミドとして生成物を得た。その試料に以下の結果を生成したQC分析を行った。
水凝縮器に接続したディーンスターク装置に備え付けた1リットルの丸底フラスコに、C8〜10脂肪酸(P&Gにより供給されるC−810L)(200g、1.31モル)と、(ジ−2−エチルヘキシル)アミン(281g、1モル)と、ジ亜リン酸ナトリウム(3g、0.028モル)とを入れた。反応混合物を40分間かけて室温から240℃まで熱した。水がその反応から生成されて、その水をディーンスタークにおいて回収/分離した。有機物をディーンスタークからフラスコへ還流した。反応は、酸価が1.0未満になるまで240℃で行った。真空は1時間で250−200mmHgで徐々に適用して、次いで、その後に、AVが0.5未満になるまで35mmHg/240℃で余分な酸を剥離した。反応混合物を110℃で冷却して、完全な真空下で濾紙を通じて濾過して、液体アミドとして生成物を得た。
水凝縮器に接続したディーンスターク装置に備え付けた1リットルの丸底フラスコに、ラウリル酸(210g、1.05モル)と、(ジ−2−エチルヘキシル)アミン(337g、1.20モル)と、ジ亜リン酸ナトリウム(3g、0.028モル)とを入れた。反応混合物を40分間かけて室温から240℃まで熱した。水がその反応から生成されて、その水をディーンスタークにおいて回収/分離した。有機物をディーンスタークからフラスコへ還流した。反応は、酸価が1.0未満になるまで240℃で行った。真空は1時間で250−200mmHgで徐々に適用して、次いで、その後に、塩基価が2未満になるまで35mmHg/240℃で余分なジ−(2−エチルヘキシル)アミンを剥離した。反応混合物を110℃で冷却して、完全な真空下で濾紙を通じて濾過して、液体アミドとして生成物を得た。
水凝縮器に接続したディーンスターク装置に備え付けた1リットルの丸底フラスコに、事前に溶融したヤシ脂肪酸(約50wt%でC12/ラウリル酸と、約18wt%でC14/ミリスチン酸とを含む主要脂肪酸成分を含む250g)と、ジ−(2−エチルヘキシル)アミン(358g)と、ジ亜リン酸ナトリウム(3g)とを入れた。反応混合物を2時間かけて室温から240℃まで熱した。水がその反応から生成されて、その水をディーンスタークにおいて回収/分離した。有機物をディーンスタークからフラスコへ還流した。反応は、酸価が0.5未満になるまで240℃で行った。真空は100mmHgで徐々に適用して、アルカリ値が0.5未満になるまで余分なジ−(2−エチルヘキシル)アミンを剥離した。反応混合物を80℃で冷却して、完全な真空下で濾紙を通じて濾過して、液体アミドとして生成物を得た。
水凝縮器に接続したディーンスターク装置に備え付けた1リットルの丸底フラスコに、2−エチルヘキサン酸(288g、2モル)と、ジイソプロピルアミン(240g、2.4モル)と、ジ亜リン酸ナトリウム(3g、0.028モル)とを入れた。反応混合物を180分間かけて室温から220℃まで熱した。水がその反応から生成されて、その水をディーンスタークにおいて回収/分離した。有機物をディーンスタークからフラスコへ還流した。反応は、酸価が1.0未満になるまで220℃で行った。真空は1時間で250−200mmHgで徐々に適用して、次いで、その後に、塩基価が2未満になるまで35mmHg/240℃で余分なアミンを剥離した。反応混合物を110℃で冷却して、完全な真空下で濾紙を通じて濾過して、液体アミドとして生成物を得た。その試料に以下の結果を生成したQC分析を行った。
水凝縮器に接続したディーンスターク装置に備え付けた1リットルの丸底フラスコに、イソステアリン酸(288g、1モル)と、ジイソプロピルアミン(280g、2.17モル)と、ジ亜リン酸ナトリウム(3g、0.028モル)とを入れた。反応混合物を40分間かけて室温から220℃まで熱した。水がその反応から生成されて、その水をディーンスタークにおいて回収/分離した。有機物をディーンスタークからフラスコへ還流した。反応は、酸価が1.0未満になるまで220℃で行った。真空は1時間で250−200mmHgで徐々に適用して、次いで、その後に、塩基価が2未満になるまで35mmHg/240℃で余分なアミンを剥離した。反応混合物を110℃で冷却して、完全な真空下で濾紙を通じて濾過して、液体アミドとして生成物を得た。
水凝縮器に接続したディーンスターク装置に備え付けた1リットルの丸底フラスコに、ステアリン酸(249g、0.876モル)と、(ジ−2−エチルヘキシル)アミン(259g、0.92モル)と、ジ亜リン酸ナトリウム(3g、0.028モル)とを入れた。反応混合物を40分間かけて室温から240℃まで熱した。水がその反応から生成されて、その水をディーンスタークにおいて回収/分離した。有機物をディーンスタークからフラスコへ還流した。反応は、酸価が1.0未満になるまで240℃で行った。真空は1時間で250−200mmHgで徐々に適用して、次いで、その後に、塩基価が2未満になるまで35mmHg/240℃で余分なジ−(2−エチルヘキシル)アミンを剥離した。反応混合物を110℃で冷却して、完全な真空下で濾紙を通じて濾過して、液体アミドとして生成物を得た。
例1〜9の製造のための上で示した方法を以下の表1に示した反応体で続けて行って、さらにアミドを製造した。
上記の例1〜10で製造したアミドの物性を、工業的標準方法に従って測定して、その結果を以下の表2に表示した。4つの良く知られた潤滑剤基油の性質をまた、比較として表に含めた。
例14:加水分解安定性の評価
加水分解安定性を評価するために、2つのASTM試験、作動流体の加水分解安定性に対するASTM D2619−標準試験方法(飲料ボトル法)と、潤滑剤の加水分解安定性の反映でもある、酸化防止鉱物油の酸化特性に対するASTM D943標準試験方法とを使用した。
10wt%の試験材料
87.35wt%のGR IV素材(PAO)
2.65wt%のHITEC(登録商標)307ギア油添加剤(Afton Chemical)
未希釈の試験材料の揮発度を、熱重量分析器(TGA)ノアック法による、潤滑油の蒸発損失に対する試験方法の、ASTM D6375−09標準試験方法に従って測定した。比較例E(GRII鉱物油(Phillips 66 Co製のPURE PERFORMANCE(登録商標)110N))と、比較例F(PAO4(SPECTRASYN(商標)4、Exxon Chemicals))とを、比較のために試験マトリックスに追加した。その結果を以下の表5に示す。
例1及び2のアミドから選択した第2基油、比較B及びCのエステル、又はPAO4(SPECTRASYN(商標)4、ExxonMobil Chemicalsから入手可能)と共に、各添加剤及び添加剤パッケージをPAO40(SPECTRASYN(商標)40、ExxonMobil Chemicalsから入手可能)の中に混合することで、様々な潤滑剤添加剤の相対溶解性を試験した。600RPMの撹拌を用いて65℃で1時間、潤滑剤基油(PAO40及び第2基油)と、添加剤又は添加剤パッケージとを撹拌することで、混合が容易になった。撹拌が完了した後、得られた油試料を、気密瓶内に密閉して24℃で30日間保存した。1月(30日間)の保存の後、潤滑剤試料を目視で検査して、その外観を記録した。その結果を以下の表6、7及び8に示す。
Claims (16)
- a)分枝状の第2級アミン及びカルボン酸の反応生成物であるアミドと、
b)少なくとも1種の添加剤と
を含む、潤滑剤組成物。 - 前記カルボン酸がモノカルボン酸であり、前記アミドがモノアミドである、請求項1に記載の潤滑剤組成物。
- 前記モノカルボン酸が4〜36個の炭素原子を含む、請求項4に記載の潤滑剤組成物。
- 前記カルボン酸がジカルボン酸であり、前記アミドがジアミドである、請求項1に記載の潤滑剤組成物。
- 前記ジカルボン酸が、2〜14個の炭素原子又は24〜52個の炭素原子を含む、請求項6に記載の潤滑剤組成物。
- 未希釈の前記アミドが、ASTM D943で設定された方法に従って測定して、少なくとも40時間の加水分解安定性を有する、請求項1に記載の方法。
- 前記組成物の総質量に対して、1wt%以上99.9wt%以下のアミドを含む、請求項1に記載の潤滑剤組成物。
- 前記組成物の総質量に対して、0.1wt%以上40wt%以下の前記少なくとも1種の添加剤を含む、請求項1に記載の潤滑剤組成物。
- 追加の基油を含む、請求項1に記載の潤滑剤組成物。
- 前記組成物の総質量に対して、1wt%以上98.9wt%以下の前記追加の基油を含む、請求項11に記載の潤滑剤組成物。
- a)分枝状の第2級アミン及びカルボン酸の反応生成物であるアミドと、
b)少なくとも1種の添加剤と
を潤滑剤組成物に加えることを含む、潤滑剤組成物の添加剤の溶解性又は洗浄性を向上させる方法。 - a)分枝状の第2級アミン及びカルボン酸を反応させてアミドを形成する工程と、
b)少なくとも1種の添加剤を前記アミドに加える工程と
を含む、加水分解に安定である潤滑剤組成物を製造する方法。
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