JP6789994B2 - 舶用ディーゼルエンジン潤滑組成物のための全塩基価ブースターとしてのマイケル付加アミノエステル - Google Patents
舶用ディーゼルエンジン潤滑組成物のための全塩基価ブースターとしてのマイケル付加アミノエステル Download PDFInfo
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- JP6789994B2 JP6789994B2 JP2017564405A JP2017564405A JP6789994B2 JP 6789994 B2 JP6789994 B2 JP 6789994B2 JP 2017564405 A JP2017564405 A JP 2017564405A JP 2017564405 A JP2017564405 A JP 2017564405A JP 6789994 B2 JP6789994 B2 JP 6789994B2
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- 239000000203 mixture Substances 0.000 title claims description 203
- -1 amino ester Chemical class 0.000 title claims description 147
- 238000005461 lubrication Methods 0.000 title description 10
- 230000001050 lubricating effect Effects 0.000 claims description 154
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 239000003921 oil Substances 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 229920000768 polyamine Polymers 0.000 claims description 39
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 239000002270 dispersing agent Substances 0.000 claims description 26
- 125000004122 cyclic group Chemical group 0.000 claims description 23
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 239000003607 modifier Substances 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 239000003963 antioxidant agent Substances 0.000 claims description 11
- 239000012459 cleaning agent Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000010705 motor oil Substances 0.000 claims description 8
- KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims description 7
- 238000006845 Michael addition reaction Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 230000003078 antioxidant effect Effects 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 75
- 235000019198 oils Nutrition 0.000 description 52
- 150000001412 amines Chemical class 0.000 description 28
- 239000002585 base Substances 0.000 description 26
- 150000002148 esters Chemical class 0.000 description 26
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 21
- 239000000654 additive Substances 0.000 description 20
- 239000003599 detergent Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 125000001183 hydrocarbyl group Chemical group 0.000 description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 17
- 239000000314 lubricant Substances 0.000 description 17
- 229910052717 sulfur Inorganic materials 0.000 description 17
- 239000011593 sulfur Substances 0.000 description 17
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 15
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 14
- 239000003925 fat Substances 0.000 description 14
- 235000019197 fats Nutrition 0.000 description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 12
- 229910052750 molybdenum Inorganic materials 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 229960002317 succinimide Drugs 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 239000011733 molybdenum Substances 0.000 description 10
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 239000005078 molybdenum compound Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 229920002367 Polyisobutene Polymers 0.000 description 8
- 235000015278 beef Nutrition 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000002485 combustion reaction Methods 0.000 description 8
- 239000000446 fuel Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000003549 soybean oil Substances 0.000 description 8
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical group NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 8
- 150000003609 titanium compounds Chemical class 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000002199 base oil Substances 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 7
- 150000002752 molybdenum compounds Chemical class 0.000 description 7
- 238000006386 neutralization reaction Methods 0.000 description 7
- 235000012424 soybean oil Nutrition 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 6
- 235000021317 phosphate Nutrition 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 229920000098 polyolefin Polymers 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 229940095064 tartrate Drugs 0.000 description 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- 235000019486 Sunflower oil Nutrition 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 150000003973 alkyl amines Chemical class 0.000 description 5
- 125000005266 diarylamine group Chemical group 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000010685 fatty oil Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical class NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 229920013639 polyalphaolefin Polymers 0.000 description 5
- 229920000193 polymethacrylate Polymers 0.000 description 5
- 239000002600 sunflower oil Substances 0.000 description 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 150000002646 long chain fatty acid esters Chemical class 0.000 description 4
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 235000021313 oleic acid Nutrition 0.000 description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 4
- 229960001860 salicylate Drugs 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000005263 alkylenediamine group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000005265 dialkylamine group Chemical group 0.000 description 3
- 239000002283 diesel fuel Substances 0.000 description 3
- 150000002440 hydroxy compounds Chemical class 0.000 description 3
- 230000000415 inactivating effect Effects 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 150000003873 salicylate salts Chemical class 0.000 description 3
- 238000007655 standard test method Methods 0.000 description 3
- 150000003890 succinate salts Chemical class 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003643 water by type 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
- 150000000180 1,2-diols Chemical group 0.000 description 2
- 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 2
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 2
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- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- VCAFTIGPOYBOIC-UHFFFAOYSA-N phenyl dihydrogen phosphite Chemical class OP(O)OC1=CC=CC=C1 VCAFTIGPOYBOIC-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229920000333 poly(propyleneimine) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 201000008752 progressive muscular atrophy Diseases 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011684 sodium molybdate Substances 0.000 description 1
- 235000015393 sodium molybdate Nutrition 0.000 description 1
- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical class O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 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
- 239000003039 volatile agent Substances 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- PZXFWBWBWODQCS-UHFFFAOYSA-L zinc;2-carboxyphenolate Chemical compound [Zn+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O PZXFWBWBWODQCS-UHFFFAOYSA-L 0.000 description 1
- USEBTXRETYRZKO-UHFFFAOYSA-L zinc;n,n-dioctylcarbamodithioate Chemical compound [Zn+2].CCCCCCCCN(C([S-])=S)CCCCCCCC.CCCCCCCCN(C([S-])=S)CCCCCCCC USEBTXRETYRZKO-UHFFFAOYSA-L 0.000 description 1
Classifications
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- 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
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/48—Heterocyclic nitrogen compounds the ring containing both nitrogen and oxygen
- C10M133/50—Morpholines
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- 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
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
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- 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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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/028—Overbased salts thereof
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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- C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
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- 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
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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Description
本発明は、一般に、舶用ディーゼルエンジンに使用するのに適した潤滑組成物(潤滑剤)に関し、舶用ディーゼルシリンダ潤滑剤の全塩基価(TBN)を上昇させるための添加剤に関連して特定の用途を見出し、および潤滑方法に関する。
MDCLは、シリンダ内を1回だけ通過するので、酸性燃焼生成物を迅速に中和する能力も有するべきである。燃焼生成物の速い中和を可能にしながらMDCLのTBNを上昇させる低灰分添加剤が、依然として求められている。
例示的な実施形態の一態様によれば、潤滑組成物は、潤滑粘度の油と、式(I):
NR1R2−((CHR3)xNR4)n−(CHR5)2−COY
(I)
(式中、
R1およびR2は、独立して、−(CHR6)2−COY’、H、およびC1〜C3アルキルから選択され、R1およびR2の少なくとも1つは、−(CHR6)2−COY’であり;あるいはNR1R2は環状構造であり;
YおよびY’は、独立して、−OR7、−NHR7、および−N(R7)2から選択され;
各R7は、独立して、C6〜C12アルキルおよびC6〜C12アルケニルから選択され;
R3、R5、およびR6は、独立して、HおよびC1〜C4アルキルから選択され;
R4は、H、C1〜C4アルキル、および(CHR3)xNH2から選択され、
xは2から4であり;そして
NR 1 R 2 が環状構造の場合にnが少なくとも0であることを除いて、nは少なくとも1である。)
のアミノカルボキシレート化合物とを含む。
NR1R2−((CHR3)xNR4)n−(CHR5)2−COY
(I)
(式中、
R1およびR2は、独立して、−(CHR6)2−COY’、H、およびC1〜C3アルキルから選択され、R1およびR2の少なくとも1つは、−(CHR6)2−COY’であり;あるいはNR1R2は環状構造であり;
YおよびY’は、独立して、−OR7、−NHR7、および−N(R7)2から選択され;
各R7は、独立して、C6〜C12アルキルおよびC6〜C12アルケニルから選択され;
R3、R5、およびR6は、独立して、HおよびC1〜C4アルキルから選択され;
R4は、H、C1〜C4アルキル、および(CHR3)xNH2から選択され、
xは2から4であり;そして
NR 1 R 2 が環状構造の場合にnが少なくとも0であることを除いて、nは少なくとも1である。)
を有する。
によって表される。ポリアミンは、一般式:
NHR4−((CHR3)xNR4)n−R4
(式中、xは、2から4であり、
R3は、HおよびC1〜C4アルキルから選択され、
R4は、H、C1〜C4アルキル、および(CHR3)xNH2から選択され、そして
nは少なくとも1である。)
によって表される。
例示的な実施形態の態様は、潤滑組成物中のTBNブースターとして使用するのに適したアミノ−カルボキシレート化合物と、潤滑組成物の方法および使用とに関する。
アミノ−カルボキシレート化合物
NR1R2−((CHR3)xNR4)n−(CHR5)2−COY
(I)
(式中、
R1およびR2は、独立して、−(CHR6)2−COY’、H、およびC1〜C3アルキルから選択され、R1およびR2の少なくとも1つは、−(CHR6)2−COY’であり;あるいはNR1R2は環状構造であり、
YおよびY’は、独立して、−OR7、−NHR7、および−N(R7)2から選択され;
各R7は、独立して、C6〜C12アルキルおよびC6〜C12アルケニルから選択され;
R3、R5、およびR6は、独立して、HおよびC1〜C4アルキルから選択され;
R4は、H、C1〜C4アルキル、および(CHR3)xNH2から選択され、
xは2から4であり;そして
NR 1 R 2 が環状構造の場合にnが少なくとも0であることを除いて、nは少なくとも1である。)
を有していてもよい。
a. xが2である。
b. nが、7まで、または6まで、または5まで、または4までである。
c. YおよびY’の少なくとも1つが、−OR7である。
d. 各R7が、C6〜C10アルキルおよびC6〜C10アルケニルから選択される。
e. 各R7が、C8アルキル(例えば分枝状C8アルキル)などのC6〜C8アルキルおよびC6〜C8アルケニルから選択される。
f. R3、R4、R5、およびR6の少なくとも1つがHである。
g. R3、R4、R5、およびR6が全てHである。
h. NR1R2が環状構造であり、
式中:
R1はC1〜C3アルキルであり;
mは少なくとも2であり;
XはHおよび−(CH2)p−Wから選択され;
Wは、COOR8と、NHR8と、末端XがHまたはC1〜C4アルキルであること以外はNR1R2に関して記載された環状構造とから選択され;
R8は、Hと、C6〜C30アルキルと、C6〜C30アルケニルと、−(CH2)p−W’であって、W’は、末端XがHまたはC1〜C4アルキルであること以外はWに関するものと同様であるものとから選択され;
各pは2から4である。
が含まれる。
アミノ−カルボキシレート化合物を形成する方法
スキーム1
により表されるものが含まれる。
NHR4−((CHR3)xNR4)n−R4
(式中、x、n、R3、およびR4は、上述の通りであり、または末端基が互いに結合されて環を形成する。)
によって表されてもよい。
潤滑組成物
潤滑粘度の油
清浄剤
酸化防止剤
分散剤
耐摩耗剤
油溶性チタン化合物
極圧(EP)剤
抑泡剤
粘度調整剤
腐食防止剤および金属不活性化剤
流動点降下剤
摩擦調整剤
によって表されてもよい。ある特定の実施形態では、ヒドロカルビル基R23、R24、およびR25は、直鎖状または主に直鎖状のアルキル基であってもよい。
式中、R32は、10個またはそれ超の炭素原子を有する鎖状ヒドロカルビル基を表し、sは0または1であり、R33および/またはR34は、水素原子、ヒドロカルビル基、アルカノール基、またはアルキルアミノ基であって2から4個の炭素原子を有するものを表し、s=0である場合、R33およびR34は共に水素原子でも炭化水素基でもない。
抗乳化剤
シール膨潤剤
例示的な潤滑組成物
Dean Stark装置および窒素ブランケット(0.5cfh)を備えた2Lの4つ口丸底フラスコに、メタノール(500mL)およびトリエチレンテトラミン(TETA)(11.36g)を投入する。この混合物に、アクリル酸2−(エチルヘキシル)(2−EHAc)(286.4g)を滴下様式で、90分間にわたり添加する。10℃の発熱が観察される。反応混合物をさらに2.5時間撹拌し、その後、減圧下で揮発性物質を除去することにより生成物を単離する。生成物は、そのTBNが、ASTM D2896によれば399mg KOH/gである。
(実施例3)
例示的な化合物の評価
(i)炭化水素置換基、即ち、脂肪族(例えば、アルキルまたはアルケニル)、脂環式(例えば、シクロアルキル、シクロアルケニル)置換基、ならびに芳香族−、脂肪族−、および脂環式−置換芳香族置換基、ならびに環状置換基であって、環が、分子の別の部分を通して完成している環状置換基(例えば、2個の置換基が一緒になって環を形成する);
(ii)置換炭化水素置換基、即ち、本発明の文脈においては置換基の主に炭化水素の性質を変化させない非炭化水素基(例えば、ハロ(特にクロロおよびフルオロ)、ヒドロキシ、アルコキシ、メルカプト、アルキルメルカプト、ニトロ、ニトロソ、およびスルホキシ)を含有する置換基;
(iii)ヘテロ置換基、即ち、主に炭化水素の特徴を有するが、それ以外が炭素原子で構成される環または鎖中に炭素以外を含有していてもよい置換基
が含まれる。
一実施形態において、例えば、以下の項目が提供される。
(項目1)
潤滑粘度の油と、式(I):
NR 1 R 2 −((CHR 3 ) x NR 4 ) n −(CHR 5 ) 2 −COY
(I)
(式中、
R 1 およびR 2 は、独立して、−(CHR 6 ) 2 −COY’、H、およびC 1 〜C 3 アルキルから選択され、R 1 およびR 2 の少なくとも1つは、−(CHR 6 ) 2 −COY’であり;あるいはNR 1 R 2 は環状構造であり、
YおよびY’は、独立して、−OR 7 、−NHR 7 、および−N(R 7 ) 2 から選択され、
各R 7 は、独立して、C 6 〜C 12 アルキルおよびC 6 〜C 12 アルケニルから選択され、
R 3 、R 5 、およびR 6 は、独立して、HおよびC 1 〜C 4 アルキルから選択され、
R 4 は、H、C 1 〜C 4 アルキル、および(CHR 3 ) x NH 2 から選択され、
xは2から4であり;そして
NR 1 R 2 が環状構造の場合にnが少なくとも0であることを除いて、nは少なくとも1である。)
のアミノカルボキシレート化合物と
を含む、潤滑組成物。
(項目2)
xが2である、項目1に記載の潤滑組成物。
(項目3)
R 3 がHである、項目2に記載の潤滑組成物。
(項目4)
nが少なくとも4である、項目2から3のいずれか一項に記載の潤滑組成物。
(項目5)
nが最大7、または最大6、または最大5、または最大4である、項目1から4のいずれか一項に記載の潤滑組成物。
(項目6)
R 3 、R 4 、R 5 、およびR 6 の少なくとも1つがHである、項目1から5のいずれか一項に記載の潤滑組成物。
(項目7)
R 3 、R 4 、R 5 、およびR 6 が全てHである、項目1から6のいずれか一項に記載の潤滑組成物。
(項目8)
YおよびY’の少なくとも1つが−OR 7 である、項目1から7のいずれか一項に記載の潤滑組成物。
(項目9)
各R 7 が、C 6 〜C 8 アルキルおよびC 6 〜C 8 アルケニルから選択される、項目8に記載の潤滑組成物。
(項目10)
前記化合物が、構造(II):
による構造を有する、項目1から9のいずれか一項に記載の潤滑組成物。
(項目11)
nが、少なくとも3または最大6であり、R 7 が、C 6 〜C 8 のアルキルおよびアルケニル基から選択される、項目10に記載の潤滑組成物。
(項目12)
前記化合物が、
(式中、各R 7 は、C 10 〜C 12 アルキルである。)
(式中、各R 7 は、C 10 〜C 12 アルキルである。)
およびこれらの混合物
のいずれか1つによる構造を有する、項目10または11に記載の潤滑組成物。
(項目13)
NR 1 R 2 が環状構造であり、式中、
R 1 はC 1 〜C 3 アルキルであり、
mは少なくとも2であり、
Xは、Hおよび−(CH 2 ) p −Wから選択され、
Wは、COOR 8 と、NHR 8 と、末端XがHまたはC 1 〜C 4 アルキルであること以外はNR 1 R 2 に関して記載された環状構造とから選択され、
R 8 は、Hと、C 6 〜C 30 アルキルと、C 6 〜C 30 アルケニルと、−(CH 2 ) p −W’(式中、W’は、末端XがHまたはC 1 〜C 4 アルキルであること以外はWに関するものと同様である。)とから選択され、
各pは2から4である、項目1から7のいずれか一項に記載の潤滑組成物。
(項目14)
前記化合物が、構造(III)
による構造を有する、項目13に記載の潤滑組成物。
(項目15)
前記化合物が、
およびこれらの混合物
のいずれか1つによる構造を有する、項目10に記載の潤滑組成物。
(項目16)
前記化合物が、最大700または最大650の重量平均分子量を有する、項目1から15のいずれか一項に記載の潤滑組成物。
(項目17)
前記化合物が、少なくとも275または少なくとも300の重量平均分子量を有する、項目16に記載の潤滑組成物。
(項目18)
前記アミノ−カルボキシレート化合物が、少なくとも200mg KOH/g、または少なくとも250mg KOH/g、または少なくとも300mg KOH/g、または少なくとも350mg KOH/g、または少なくとも400mg KOH/g、または最大600mg KOH/g、または最大500mg KOH/gの全塩基価(TBN)を有する、項目1から17のいずれか一項に記載の潤滑組成物。
(項目19)
前記アミノ−カルボキシレート化合物が、少なくとも180mg KOH/g、または少なくとも200mg KOH/g、または少なくとも240mg KOH/g、または最大400mg KOH/gの塩基価(BN)を有する、項目1から18のいずれか一項に記載の潤滑組成物。
(項目20)
前記アミノ−カルボキシレート化合物が、前記潤滑組成物の全塩基価を少なくとも20、または少なくとも30、または少なくとも40、または少なくとも50mg KOH/g、または最大60mg KOH/g、または最大55mg KOH/g増加させるのに十分な濃度で存在する、項目1から19のいずれか一項に記載の潤滑組成物。
(項目21)
エンジン油の最終的な全塩基価が少なくとも70である、項目20に記載の方法。
(項目22)
前記アミノ−カルボキシレート化合物が、前記潤滑組成物の少なくとも1wt.%、または少なくとも5wt.%、または少なくとも10wt.%である、項目1から21のいずれか一項に記載の潤滑組成物。
(項目23)
前記潤滑粘度の油が、前記潤滑組成物の少なくとも5wt.%、または少なくとも10wt.%、または少なくとも20wt.%、または少なくとも30wt.%、または少なくとも40wt.%、または少なくとも60wt.%である、項目1から21のいずれか一項に記載の潤滑組成物。
(項目24)
前記組成物が、過塩基化清浄剤、粘度調整剤、摩擦調整剤、酸化防止剤、および分散剤の少なくとも1種をさらに含む、項目1から23のいずれか一項に記載の潤滑組成物。
(項目25)
項目1から24のいずれか一項に記載の潤滑組成物の有効量を、エンジンに投与することを含む、エンジンを潤滑する方法。
(項目26)
前記エンジンが2行程舶用ディーゼルエンジンである、項目25に記載の方法。
(項目27)
有効量のアミノカルボキシレート化合物を潤滑組成物に添加することを含む、潤滑組成物の全塩基価を増加させる方法であって、前記アミノカルボキシレート化合物が、式(I):
NR 1 R 2 −((CHR 3 ) x NR 4 ) n −(CHR 5 ) 2 −COY
(I)
(式中、
R 1 およびR 2 は、独立して、−(CHR 6 ) 2 −COY’、H、およびC 1 〜C 3 アルキルから選択され、R 1 およびR 2 の少なくとも1つは、−(CHR 6 ) 2 −COY’であり;あるいはNR 1 R 2 は環状構造であり、
YおよびY’は、独立して、−OR 7 、−NHR 7 、および−N(R 7 ) 2 から選択され、
各R 7 は、独立して、C 6 〜C 12 アルキルおよびC 6 〜C 12 アルケニルから選択され、
R 3 、R 5 、およびR 6 は、独立して、HおよびC 1 〜C 4 アルキルから選択され、
R 4 は、H、C 1 〜C 4 アルキル、および(CHR 3 ) x NH 2 から選択され、
xは2から4であり;そして
NR 1 R 2 が環状構造の場合にnが少なくとも0であることを除いて、nは少なくとも1である。)
を有するものである、方法。
(項目28)
前記潤滑組成物中の前記アミノカルボキシレート化合物の濃度が、0.1重量%から15重量%である、項目27に記載の方法。
(項目29)
前記アミノカルボキシレート化合物が、前記全塩基価を少なくとも15mg KOH/g増加させる、項目27または28に記載の方法。
(項目30)
前記全塩基価の前記増加が少なくとも30mg KOH/gである、項目29に記載の方法。
(項目31)
潤滑粘度の油と、アシル化剤およびポリアミンのマイケル付加によって形成されたアミノカルボキシレート化合物とを含む、潤滑組成物であって、
前記アシル化剤は、一般式:
(式中、R 13 は、水素またはメチルであり、
R 11 およびR 12 は、それぞれ独立して、水素、1から12個の炭素原子を有するアルキル基、および式−COOR 14 (式中、R 14 は、水素、または1から12個もしくは1〜6個の炭素原子を有するアルキル基である。)を有する基からなる群から選択される。)
によって表され、
前記ポリアミンは、一般式:
NHR 4 −((CHR 3 ) x NR 4 ) n −R 4
(式中、xは、2から4であり、
R 3 は、HおよびC 1 〜C 4 アルキルから選択され、
R 4 は、H、C 1 〜C 4 アルキル、および(CHR 3 ) x NH 2 から選択され、そして
nは少なくとも1である。)
によって表される、潤滑組成物。
Claims (32)
- 潤滑粘度の油と、過塩基化金属含有清浄剤と、式(I):
NR1R2−((CHR3)xNR4)n−(CHR5)2−COY
(I)
(式中、
R1およびR2は、独立して、−(CHR6)2−COY’、H、およびC1〜C3アルキルから選択され、R1およびR2の少なくとも1つは、−(CHR6)2−COY’であり;あるいはNR1R2は、窒素ならびに酸素および窒素から選択される追加のヘテロ原子を含有する、任意に置換された複素環式構造であり、
YおよびY’は、独立して、−OR7、−NHR7、および−N(R7)2から選択され、
各R7は、独立して、C6〜C12アルキルおよびC6〜C12アルケニルから選択され、
R3、R5、およびR6は、独立して、HおよびC1〜C4アルキルから選択され、
R4は、H、C1〜C4アルキル、および(CHR3)xNH2から選択され、
xは2から4であり;そして
NR1R2が複素環式構造の場合にnが少なくとも0であることを除いて、nは少なくとも1である。)
のアミノカルボキシレート化合物と
を含む、潤滑組成物。 - xが2である、請求項1に記載の潤滑組成物。
- R3がHである、請求項2に記載の潤滑組成物。
- nが少なくとも4である、請求項2から3のいずれか一項に記載の潤滑組成物。
- nが最大7、または最大6、または最大5、または最大4である、請求項1から4のいずれか一項に記載の潤滑組成物。
- R3、R4、R5、およびR6の少なくとも1つがHである、請求項1から5のいずれか一項に記載の潤滑組成物。
- R3、R4、R5、およびR6が全てHである、請求項1から6のいずれか一項に記載の潤滑組成物。
- YおよびY’の少なくとも1つが−OR7である、請求項1から7のいずれか一項に記載の潤滑組成物。
- 各R7が、C6〜C8アルキルおよびC6〜C8アルケニルから選択される、請求項8に記載の潤滑組成物。
- nが、少なくとも3または最大6であり、R7が、C6〜C8のアルキルおよびアルケニル基から選択される、請求項10に記載の潤滑組成物。
- 前記化合物が、最大700または最大650の重量平均分子量を有する、請求項1から15のいずれか一項に記載の潤滑組成物。
- 前記化合物が、少なくとも275または少なくとも300の重量平均分子量を有する、請求項16に記載の潤滑組成物。
- 前記アミノ−カルボキシレート化合物が、少なくとも200mg KOH/g、または少なくとも250mg KOH/g、または少なくとも300mg KOH/g、または少なくとも350mg KOH/g、または少なくとも400mg KOH/g、または最大600mg KOH/g、または最大500mg KOH/gの、ASTM D2896−11により測定された全塩基価(TBN)を有する、請求項1から17のいずれか一項に記載の潤滑組成物。
- 前記アミノ−カルボキシレート化合物が、少なくとも180mg KOH/g、または少なくとも200mg KOH/g、または少なくとも240mg KOH/g、または最大400mg KOH/gの、ASTM D4739−11により測定された塩基価(BN)を有する、請求項1から18のいずれか一項に記載の潤滑組成物。
- 前記アミノ−カルボキシレート化合物が、前記潤滑組成物の、ASTM D2896−11により測定された全塩基価を少なくとも20、または少なくとも30、または少なくとも40、または少なくとも50mg KOH/g、または最大60mg KOH/g、または最大55mg KOH/g増加させるのに十分な濃度で存在する、請求項1から19のいずれか一項に記載の潤滑組成物。
- エンジン油の、ASTM D2896−11により測定された最終的な全塩基価が少なくとも70である、請求項20に記載の潤滑組成物。
- 前記アミノ−カルボキシレート化合物が、前記潤滑組成物の少なくとも1wt.%、または少なくとも5wt.%、または少なくとも10wt.%である、請求項1から21のいずれか一項に記載の潤滑組成物。
- 前記潤滑粘度の油が、前記潤滑組成物の少なくとも5wt.%、または少なくとも10wt.%、または少なくとも20wt.%、または少なくとも30wt.%、または少なくとも40wt.%、または少なくとも60wt.%である、請求項1から21のいずれか一項に記載の潤滑組成物。
- 前記組成物が、過塩基化清浄剤、粘度調整剤、摩擦調整剤、酸化防止剤、および分散剤の少なくとも1種をさらに含む、請求項1から23のいずれか一項に記載の潤滑組成物。
- 請求項1から24のいずれか一項に記載の潤滑組成物を、エンジンに投与することを含む、エンジンを潤滑する方法。
- 前記エンジンが2行程舶用ディーゼルエンジンである、請求項25に記載の方法。
- アミノカルボキシレート化合物を潤滑組成物に添加することを含む、潤滑組成物の全塩基価を増加させるためのアミノカルボキシレート化合物の使用であって、前記アミノカルボキシレート化合物が、式(I):
NR1R2−((CHR3)xNR4)n−(CHR5)2−COY
(I)
(式中、
R1およびR2は、独立して、−(CHR6)2−COY’、H、およびC1〜C3アルキルから選択され、R1およびR2の少なくとも1つは、−(CHR6)2−COY’であり;あるいはNR1R2は環状構造であり、
YおよびY’は、独立して、−OR7、−NHR7、および−N(R7)2から選択され、
各R7は、独立して、C6〜C12アルキルおよびC6〜C12アルケニルから選択され、
R3、R5、およびR6は、独立して、HおよびC1〜C4アルキルから選択され、
R4は、H、C1〜C4アルキル、および(CHR3)xNH2から選択され、
xは2から4であり;そして
NR1R2が環状構造の場合にnが少なくとも0であることを除いて、nは少なくとも1である。)
を有するものである、使用。 - 前記潤滑組成物中の前記アミノカルボキシレート化合物の濃度が、0.1重量%から15重量%である、請求項27に記載の使用。
- 前記アミノカルボキシレート化合物が、前記ASTM D2896−11により測定された全塩基価を少なくとも15mg KOH/g増加させる、請求項27または28に記載の使用。
- 前記ASTM D2896−11により測定された全塩基価の前記増加が少なくとも30mg KOH/gである、請求項29に記載の使用。
- 潤滑粘度の油と、アシル化剤およびポリアミンのマイケル付加によって形成されたアミノカルボキシレート化合物とを含む、潤滑組成物であって、
前記アシル化剤は、一般式:
R 7 は、独立して、C 6 〜C 12 アルキルおよびC 6 〜C 12 アルケニルから選択され、
R11およびR12は、それぞれ独立して、水素、1から12個の炭素原子を有するアルキル基、および式−COOR14(式中、R14は、水素、または1から12個もしくは1〜6個の炭素原子を有するアルキル基である。)を有する基からなる群から選択される。)
によって表され、
前記ポリアミンは、一般式:
NHR4−((CHR3)xNR4)n−R4
(式中、xは、2から4であり、
R3は、HおよびC1〜C4アルキルから選択され、
R4は、H、C1〜C4アルキル、および(CHR3)xNH2から選択され、そして
nは少なくとも1である。)
によって表される、潤滑組成物。
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