JP5840222B2 - 摩擦調節剤ブレンドを含有する潤滑組成物 - Google Patents
摩擦調節剤ブレンドを含有する潤滑組成物 Download PDFInfo
- Publication number
- JP5840222B2 JP5840222B2 JP2013540965A JP2013540965A JP5840222B2 JP 5840222 B2 JP5840222 B2 JP 5840222B2 JP 2013540965 A JP2013540965 A JP 2013540965A JP 2013540965 A JP2013540965 A JP 2013540965A JP 5840222 B2 JP5840222 B2 JP 5840222B2
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- JP
- Japan
- Prior art keywords
- lubricating oil
- oil composition
- olefin
- acid
- normal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000000203 mixture Substances 0.000 title claims description 197
- 239000003607 modifier Substances 0.000 title claims description 33
- 230000001050 lubricating effect Effects 0.000 title claims description 23
- 239000010687 lubricating oil Substances 0.000 claims description 108
- -1 hydrocarbyl amine Chemical class 0.000 claims description 83
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 67
- 239000003921 oil Substances 0.000 claims description 61
- 239000004711 α-olefin Substances 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 52
- 150000001336 alkenes Chemical class 0.000 claims description 47
- 150000002148 esters Chemical class 0.000 claims description 35
- 239000007795 chemical reaction product Substances 0.000 claims description 33
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 20
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 claims description 19
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 19
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 claims description 19
- 239000007787 solid Substances 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 238000006735 epoxidation reaction Methods 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
- 150000001735 carboxylic acids Chemical class 0.000 claims description 10
- SPURMHFLEKVAAS-UHFFFAOYSA-N 1-docosene Chemical compound CCCCCCCCCCCCCCCCCCCCC=C SPURMHFLEKVAAS-UHFFFAOYSA-N 0.000 claims description 8
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 8
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 claims description 8
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 claims description 8
- 150000001414 amino alcohols Chemical class 0.000 claims description 8
- 238000002485 combustion reaction Methods 0.000 claims description 8
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 claims description 8
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 claims description 6
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 claims description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229940069096 dodecene Drugs 0.000 claims description 4
- 229940102253 isopropanolamine Drugs 0.000 claims description 4
- FIKTURVKRGQNQD-UHFFFAOYSA-N 1-eicosene Natural products CCCCCCCCCCCCCCCCCC=CC(O)=O FIKTURVKRGQNQD-UHFFFAOYSA-N 0.000 claims description 3
- 229940106006 1-eicosene Drugs 0.000 claims description 3
- VFYFMNCKPJDAPV-UHFFFAOYSA-N 2,2'-(5-oxo-1,3-dioxolan-4,4-diyl)diessigs Chemical compound C1N(C2)CN3CN1CN2C3.OC(=O)CC1(CC(O)=O)OCOC1=O VFYFMNCKPJDAPV-UHFFFAOYSA-N 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 59
- 239000002270 dispersing agent Substances 0.000 description 36
- 239000003599 detergent Substances 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 28
- 229910052751 metal Inorganic materials 0.000 description 28
- 239000002184 metal Substances 0.000 description 28
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 28
- 239000000654 additive Substances 0.000 description 27
- 150000001412 amines Chemical class 0.000 description 26
- 239000002199 base oil Substances 0.000 description 22
- 239000002253 acid Substances 0.000 description 21
- 125000001183 hydrocarbyl group Chemical group 0.000 description 20
- 239000002585 base Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 235000014113 dietary fatty acids Nutrition 0.000 description 17
- 239000000194 fatty acid Substances 0.000 description 17
- 229930195729 fatty acid Natural products 0.000 description 17
- 150000002924 oxiranes Chemical class 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000003963 antioxidant agent Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- 239000000446 fuel Substances 0.000 description 13
- 238000006317 isomerization reaction Methods 0.000 description 13
- 239000010705 motor oil Substances 0.000 description 13
- 229960002317 succinimide Drugs 0.000 description 13
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 235000010338 boric acid Nutrition 0.000 description 11
- 229960002645 boric acid Drugs 0.000 description 11
- 150000005690 diesters Chemical class 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 230000000996 additive effect Effects 0.000 description 10
- 239000004327 boric acid Substances 0.000 description 10
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 229920000768 polyamine Polymers 0.000 description 9
- 239000001993 wax Substances 0.000 description 9
- 239000011701 zinc Substances 0.000 description 9
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 8
- 229910052791 calcium Inorganic materials 0.000 description 8
- 239000011575 calcium Substances 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 229910052750 molybdenum Inorganic materials 0.000 description 8
- 239000011733 molybdenum Substances 0.000 description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 8
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 7
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 7
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 239000005642 Oleic acid Substances 0.000 description 7
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 229910052796 boron Inorganic materials 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 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
- 239000000314 lubricant Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 239000010689 synthetic lubricating oil Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 239000002808 molecular sieve Substances 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 description 4
- 229910020366 ClO 4 Inorganic materials 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 150000002736 metal compounds Chemical class 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 229920013639 polyalphaolefin Polymers 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 229960004889 salicylic acid Drugs 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 235000011044 succinic acid Nutrition 0.000 description 4
- KQIXMZWXFFHRAQ-UHFFFAOYSA-N 1-(2-hydroxybutylamino)butan-2-ol Chemical compound CCC(O)CNCC(O)CC KQIXMZWXFFHRAQ-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005069 Extreme pressure additive Substances 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000001639 boron compounds Chemical class 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 3
- 229940043276 diisopropanolamine Drugs 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000012208 gear oil Substances 0.000 description 3
- 150000002314 glycerols Chemical class 0.000 description 3
- 150000002440 hydroxy compounds Chemical class 0.000 description 3
- 238000005461 lubrication Methods 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920001281 polyalkylene Polymers 0.000 description 3
- 229920001083 polybutene Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 3
- 229960001860 salicylate Drugs 0.000 description 3
- 239000011949 solid catalyst Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 150000005691 triesters Chemical class 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- CIRMGZKUSBCWRL-LHLOQNFPSA-N (e)-10-[2-(7-carboxyheptyl)-5,6-dihexylcyclohex-3-en-1-yl]dec-9-enoic acid Chemical compound CCCCCCC1C=CC(CCCCCCCC(O)=O)C(\C=C\CCCCCCCC(O)=O)C1CCCCCC CIRMGZKUSBCWRL-LHLOQNFPSA-N 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 2
- RLPSARLYTKXVSE-UHFFFAOYSA-N 1-(1,3-thiazol-5-yl)ethanamine Chemical compound CC(N)C1=CN=CS1 RLPSARLYTKXVSE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
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- 239000001569 carbon dioxide Substances 0.000 description 1
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- CJMZLCRLBNZJQR-UHFFFAOYSA-N ethyl 2-amino-4-(4-fluorophenyl)thiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC=C1C1=CC=C(F)C=C1 CJMZLCRLBNZJQR-UHFFFAOYSA-N 0.000 description 1
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
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- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
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- LVZUNTGFCXNQAF-UHFFFAOYSA-N n-nonyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCCC)C1=CC=CC=C1 LVZUNTGFCXNQAF-UHFFFAOYSA-N 0.000 description 1
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- FATBGEAMYMYZAF-UHFFFAOYSA-N oleicacidamide-heptaglycolether Natural products CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
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- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
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- 229920001195 polyisoprene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
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- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003443 succinic acid derivatives Chemical class 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000011275 tar sand Substances 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- MQHSFMJHURNQIE-UHFFFAOYSA-N tetrakis(2-ethylhexyl) silicate Chemical compound CCCCC(CC)CO[Si](OCC(CC)CCCC)(OCC(CC)CCCC)OCC(CC)CCCC MQHSFMJHURNQIE-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical class CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical class CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical class COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical class CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical group [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- PADPILQDYPIHQQ-UHFFFAOYSA-L zinc;diperchlorate;hexahydrate Chemical compound O.O.O.O.O.O.[Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O PADPILQDYPIHQQ-UHFFFAOYSA-L 0.000 description 1
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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
-
- 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/12—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic compound containing atoms of elements not provided for in groups C10M141/02 - C10M141/10
-
- 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
- C10M2203/102—Aliphatic fractions
- C10M2203/1025—Aliphatic fractions used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
-
- 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
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbasedsulfonic acid salts
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
-
- 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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/09—Complexes with metals
-
- 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
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
a)C12〜C30ノルマルαオレフィンを、少なくとも1つの固体又は液体の触媒を用いて異性化し、内部オレフィンを形成し、前記オレフィンをエポキシ化し、そしてモノ又はジヒドロキシヒドロカルビルアミンと反応させることによって調製したアミノアルコール反応生成物、
b)グリセロールと0〜3個の二重結合を含有するC12〜C22カルボン酸とのエステル、
を含有する摩擦調節剤組成物と、を含む上記潤滑油組成物である。
a)C12〜C30ノルマルαオレフィンを、少なくとも1つの固体又は液体の触媒を用いて異性化し、内部オレフィンを形成し、前記オレフィンをエポキシ化し、そしてモノ又はジヒドロキシヒドロカルビルアミンと反応させることによって調製したアミノアルコール反応生成物、
b)グリセロールと0〜3個の二重結合を含有するC12〜C22カルボン酸とのエステル、
を含有する摩擦調節剤組成物と、を供給するステップを含む上記方法に向けられている。
アミノアルコール反応生成物は、C12〜C30ノルマルαオレフィンを、少なくとも1つの固体又は液体の触媒を用いて異性化して本明細書ではインターナライジングと称される内部オレフィン形成をし、前記オレフィンをエポキシ化し、そしてアルカノールアミンと反応させることによって調製される。このアミノアルコール反応生成物は、周囲条件下で液体であり、潤滑油組成物中に容易にブレンドされる。一般的に、本発明の潤滑組成物は、少なくとも0.1、好ましくは0.15〜4.0重量パーセントの該反応生成物を含有する。対応するエポキシドを形成する変換、及びアミノアルカノールによるエポキシドによる開環反応が後に続くαオレフィンのインターナライジングは、液体生成物をもたらす。末端オレフィンは、同様の反応スキームにおいて使用されると固体又はワックス状物質を生成する傾向がある。
実施例中に付されている全ての温度は、摂氏の方式を指し、用語「室温」は、約20〜25℃を指す。用語「パーセント又は%」は、重量パーセントを指し、用語「モル(mole)」又は「モル(moles)」は、グラムモルを指す。用語「当量」は、有限のモル又は有限の重量若しくは体積に関してその例において挙げられた後に続く反応物の先行するもののモル数とモル数が同じである試薬の量を指す。陽子磁気共鳴スペクトル(NMR)は、300mHzで測定された。
調製例1.C12αオレフィンの異性化
αオレフィン(ここでは例としてC12を使用する)が、鉄ペンタカルボニルにより異性化され、出発物質(C12αオレフィン)の二重結合が異性化の結果今や全て炭素鎖に沿って内部に分配される。
130グラムのC20〜24αオレフィンを、窒素下で一晩30グラムの分子篩(15グラムの3A及び15グラムの4A)にかけて乾燥し、次いで1Lの反応フラスコに移した。0.3mLのFe(CO)5をそのフラスコに注入した。その反応混合物を次にオイルバス中153℃で、一晩加熱した。IRは、反応が終了したことを示した。オイルバスの温度を、85℃まで下げた。5グラムのシリカゲル及び10滴のメタンスルホン酸を加え、その混合物を一晩撹拌した。フラスコ中の褐色がかった油をシリカパッドにより濾過し、無色の液体が化合物2として得られた。
調製例3.エポキシ化(例としてC12内部オレフィンを用いる):
92グラムの異性化オレフィンを、1Lフラスコ中の500mLの塩化メチレンに溶解し、その反応混合物の温度を氷/水浴により0℃に冷却し、次いで112グラムのmCPBA(77%)を反応混合物に小分けしてゆっくり加えた。その反応混合物を次に窒素下で22時間撹拌した。次に、反応混合物をヘキサン中で希釈し、シリカパッドにより濾過し、回転蒸発させて乾燥し、所望されたエポキシドとしての無色の液体、化合物3、を生じさせた。NMR(CDCl3)δ2.6〜3.05,(m,2H);1.1〜1.7,(m,16H);0.9〜1,(m,6H)。
122グラムの異性化C20〜24オレフィンを、氷/水浴中の0℃の1Lフラスコ中の500mLの塩化メチレンに溶解し、次いで106グラムのmCPBA(77%)をその反応混合物に過熱を避けるために小分けしてゆっくり加えた。その反応混合物を窒素下で24時間撹拌した。次に、反応混合物をヘキサン中で希釈し、シリカパッドにより濾過し、重炭酸ナトリウムにより洗浄し、硫酸ナトリウムにより脱水し、得られた生成物を次に回転蒸発させて乾燥し、所望されたエポキシドとしての無色の液体、化合物4、を生じさせた。NMR(CDCl3)δ2.6〜2.9,(m,2H);1.1〜1.7,(m,32〜40H);0.9〜1,(m,6H)。
調製例5.エタノールアミンによるエポキシド開環(例としてC12内部エポキシドを用いる):
内部化合物3のC12エポキシド(60グラム、326mmol)の入っているフラスコに、エタノールアミン(20グラム、327mmol)及び2.42グラムのZn(ClO4)2・6H2Oを加えた。その混合物をオイルバス中で一晩、125℃で加熱し、淡褐色の液体を得、その液体を酢酸エチルで希釈し、次いで2回水洗し、硫酸ナトリウムで脱水し、減圧下で乾燥するまで回転蒸発させて化合物5を生じさせた。NMR(CDCl3)δ3.8(m,3H),2.8〜3,(m,3H),1.4〜1.6(m,16H),1〜1.1(m,6H)。
5グラムの調製例1及び3に従って調製したC14内部エポキシド(23.58mmol)及び4.9グラムのジエタノールアミン(47.16mmol)をフラスコに仕込んだ。この混合物に、0.2グラムのZn(ClO4)2・6H2Oを加えた。その混合物を140℃で一晩加熱した。次いで反応混合物を酢酸エチル中に希釈し、水及び塩水で洗浄し、硫酸ナトリウムにより脱水し、乾燥するまで回転蒸発させた。その生成物の化合物6は、いつでも試験できる琥珀色の液体として得られた。
C20〜24の内部エポキシド(15グラム、46.2mmol)の入っているフラスコに、エタノールアミン(2.82グラム、46.2mmol)及びZn(ClO4)2・6H2O(0.34グラム、0.9mmol)を加えた。その混合物をオイルバス中で48時間、170℃で加熱し、淡褐色の液体を得た。反応混合物を酢酸エチルで希釈し、次いで2回水洗し、硫酸ナトリウムで脱水し、減圧下で乾燥するまで回転蒸発させて生成物を生じさせた。NMR(CDCl3)δ3.7(m,3H),2.7〜2.8,(m,3H),1.4〜1.6(m,32H),1〜1.1(m,6H)。最終生成物のTBNは、213.8である。
例A−ベースラインA
5W−30オイル(SAE粘度グレード)がベースラインの潤滑油組成物を以下の添加剤を用いて調製した:ポリアルキルスクシンイミド分散剤のエチレンカーボネートで後処理されている重質ポリアミンを含むおよそ4重量%の2300の平均分子量のポリイソブチレン無水コハク酸、およそ0.6重量%の低過塩基性(17TBN)のアルキルアリールスルホン酸カルシウム、約1重量%の高過塩基性(410TBN)のアルキルトルエンスルホン酸カルシウム、最終潤滑油に約0.07重量%のリンを提供する第一級及び第二級アルコールの混合物から得られるジアルキルジチオリン酸亜鉛、1.2重量%のジフェニルアミン(オクチル化/ブチル化)酸化防止剤、0.5重量%のモリブデン/窒素含有錯体、並びに大部分のグループII基油に対する粘度指数向上剤、流動点降下剤及び発泡防止剤。
潤滑油組成物を性能例Aのベースライン配合を米国特許第5,629,272号に開示されているように0.5重量%のボレート化グリセロールモノオレエートによりトップトリートすることによって調製した。例C(比較)は、性能例Aのベースライン配合を1.0重量%のボレート化グリセロールモノオレエートによりトップトリートすることによって調製した。
なお、下記[1]から[15]は、いずれも本発明の一形態又は一態様である。
[1]
潤滑油組成物であって、主要量の潤滑粘度の油、並びに該潤滑油組成物の全質量に対して0.25〜5重量パーセントの:
a)C 12 〜C 30 ノルマルαオレフィンを、少なくとも1つの固体又は液体の触媒を用いて異性化して内部オレフィンを形成し、該オレフィンをエポキシ化し、そしてモノ又はジヒドロキシヒドロカルビルアミンと反応させることによって調製したアミノアルコール反応生成物と、
b)グリセロールと0〜3個の二重結合を含有するC 12 〜C 22 カルボン酸とのエステルと
を含有する摩擦調節剤組成物、を含む上記潤滑油組成物。
[2]
前記ノルマルαオレフィンが、C 12 〜C 18 ノルマルαオレフィンである[1]に記載の潤滑油組成物。
[3]
前記ノルマルαオレフィンが、C 20 〜C 30 ノルマルαオレフィンである[1]に記載の潤滑油組成物。
[4]
前記摩擦調節剤組成物が、前記潤滑油組成物の全質量に対して0.25〜1.5重量パーセント存在する[1]に記載の潤滑油組成物。
[5]
前記ノルマルαオレフィンが、85重量パーセントを超える、1−ドデセン、1−テトラデセン、1−ヘキサデセン、1−オクタデセン、1−エイコセン、1−ドコセン及び1−テトラコセンの群から選択される単一炭素数画分を含有する[1]に記載の潤滑油組成物。
[6]
前記モノ又はジヒドロキシルアミンが、式HN(R 1 OH) 2−x H x のものであって、式中、R 1 はC 1〜10 の線状又は分枝状アルキレン基であり、xは0又は1である[1]に記載の潤滑油組成物。
[7]
R 1 が、C 2〜5 の線状又は分枝状アルキレン基である[6]に記載の潤滑油組成物。
[8]
前記モノ又はジヒドロキシルヒドロカルビルアミンが、エタノールアミン、プロパノールアミン、イソプロパノールアミン、ブタノールアミン、sec−ブタノールアミン、ジエタノールアミン、ジプロパノールアミン、ジイソプロパノールアミン、ジブタノールアミン、及びジsec−ブタノールアミンからなる群から選択される[1]に記載の潤滑油組成物。
[9]
b)が、グリセロールモノオレエートである[1]に記載の潤滑油組成物。
[10]
成分a)の成分b)に対する比率が、0.9:1〜5:1である[1]に記載の潤滑油組成物。
[11]
成分a)又は成分b)の少なくとも1つが、ボレート化成分である[1]に記載の潤滑油組成物。
[12]
内燃機関を潤滑する方法であって、該機関に潤滑粘度の油、並びに潤滑油組成物の全質量に対して0.25〜5重量パーセントの:
a)C 12 〜C 30 ノルマルαオレフィンを、少なくとも1つの固体又は液体の触媒を用いて異性化して内部オレフィンを形成し、該オレフィンをエポキシ化し、そしてモノ又はジヒドロキシヒドロカルビルアミンと反応させることによって調製したアミノアルコール反応生成物と、
b)グリセロールと0〜3個の二重結合を含有するC 12 〜C 22 カルボン酸とのエステルとを含有する摩擦調節剤組成物、を供給するステップを含む上記方法。
[13]
前記ノルマルαオレフィンが、C 12 〜C 18 ノルマルαオレフィンである[12]に記載の方法。
[14]
b)が、グリセロールモノオレエートである[12]に記載の方法。
[15]
b)が、ボレート化されているグリセロールモノオレエートである[14]に記載の方法。
Claims (15)
- 潤滑油組成物の製造方法であって、
C 12 〜C 30 ノルマルαオレフィンを、少なくとも1つの固体又は液体の触媒を用いて異性化して内部オレフィンを形成し、該オレフィンをエポキシ化し、そしてモノヒドロキシヒドロカルビルアミンと反応させることによってアミノアルコール反応生成物を調製する工程と、
主要量の潤滑粘度の油、並びに該潤滑油組成物の全質量に対して0.25〜5重量パーセントの:
a)該アミノアルコール反応生成物と、
b)グリセロールと0〜3個の二重結合を含有するC12〜C22カルボン酸とのエステルと
を含有する摩擦調節剤組成物、を混合する工程とを含む上記潤滑油組成物の製造方法。 - 前記ノルマルαオレフィンが、C12〜C18ノルマルαオレフィンである請求項1に記載の潤滑油組成物の製造方法。
- 前記ノルマルαオレフィンが、C20〜C30ノルマルαオレフィンである請求項1に記載の潤滑油組成物の製造方法。
- 前記摩擦調節剤組成物を、前記潤滑油組成物の全質量に対して0.25〜1.5重量パーセント混合する請求項1に記載の潤滑油組成物の製造方法。
- 前記ノルマルαオレフィンが、85重量パーセントを超える、1−ドデセン、1−テトラデセン、1−ヘキサデセン、1−オクタデセン、1−エイコセン、1−ドコセン及び1−テトラコセンの群から選択される単一炭素数画分を含有する請求項1に記載の潤滑油組成物の製造方法。
- 前記モノヒドロキシルアミンが、式HN(R1OH)2−xHxのものであって、式中、R1はC1〜10の線状又は分枝状アルキレン基であり、xは1である請求項1に記載の潤滑油組成物の製造方法。
- R1が、C2〜5の線状又は分枝状アルキレン基である請求項6に記載の潤滑油組成物の製造方法。
- 前記モノヒドロキシルヒドロカルビルアミンが、エタノールアミン、プロパノールアミン、イソプロパノールアミン、ブタノールアミン、及びsec−ブタノールアミン、からなる群から選択される請求項1に記載の潤滑油組成物の製造方法。
- b)が、グリセロールモノオレエートである請求項1に記載の潤滑油組成物の製造方法。
- 成分a)の成分b)に対する比率が、0.9:1〜5:1である請求項1に記載の潤滑油組成物の製造方法。
- 成分a)又は成分b)の少なくとも1つが、ボレート化成分である請求項1に記載の潤滑油組成物の製造方法。
- 内燃機関を潤滑する方法であって、
該機関に潤滑粘度の油、並びに潤滑油組成物の全質量に対して0.25〜5重量パーセントの:
a)C12〜C30ノルマルαオレフィンを、少なくとも1つの固体又は液体の触媒を用いて異性化して内部オレフィンを形成し、該オレフィンをエポキシ化し、そしてモノヒドロキシヒドロカルビルアミンと反応させることによって調製したアミノアルコール反応生成物と、
b)グリセロールと0〜3個の二重結合を含有するC12〜C22カルボン酸とのエステルとを含有する摩擦調節剤組成物、を供給するステップを含む上記方法。 - 前記ノルマルαオレフィンが、C12〜C18ノルマルαオレフィンである請求項12に記載の方法。
- b)が、グリセロールモノオレエートである請求項12に記載の方法。
- b)が、ボレート化されているグリセロールモノオレエートである請求項14に記載の方法。
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2011
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- 2011-11-10 EP EP11842713.7A patent/EP2643440A4/en not_active Withdrawn
- 2011-11-10 SG SG2013035902A patent/SG190231A1/en unknown
- 2011-11-10 US US13/293,382 patent/US8703680B2/en not_active Expired - Fee Related
- 2011-11-10 CN CN201180065435.9A patent/CN103314090B/zh not_active Expired - Fee Related
- 2011-11-10 WO PCT/US2011/060199 patent/WO2012071185A2/en active Application Filing
- 2011-11-10 CA CA2818589A patent/CA2818589C/en not_active Expired - Fee Related
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JP2013543927A (ja) | 2013-12-09 |
CN103314090A (zh) | 2013-09-18 |
EP2643440A4 (en) | 2013-10-23 |
WO2012071185A3 (en) | 2012-09-27 |
CN103314090B (zh) | 2016-10-12 |
SG190231A1 (en) | 2013-06-28 |
CA2818589A1 (en) | 2012-05-31 |
WO2012071185A2 (en) | 2012-05-31 |
EP2643440A2 (en) | 2013-10-02 |
US20120129743A1 (en) | 2012-05-24 |
CA2818589C (en) | 2018-04-24 |
US8703680B2 (en) | 2014-04-22 |
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