CA2552671A1 - Lubricating oil additive and lubricating oil composition containing same - Google Patents
Lubricating oil additive and lubricating oil composition containing same Download PDFInfo
- Publication number
- CA2552671A1 CA2552671A1 CA002552671A CA2552671A CA2552671A1 CA 2552671 A1 CA2552671 A1 CA 2552671A1 CA 002552671 A CA002552671 A CA 002552671A CA 2552671 A CA2552671 A CA 2552671A CA 2552671 A1 CA2552671 A1 CA 2552671A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- group
- lubricating oil
- oil
- quaternary ammonium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 54
- 239000000203 mixture Substances 0.000 title claims abstract description 39
- 239000000654 additive Substances 0.000 title claims abstract description 29
- 230000000996 additive effect Effects 0.000 title claims abstract description 27
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 20
- 239000002199 base oil Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000129 anionic group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000002485 combustion reaction Methods 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004327 boric acid Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 229910052751 metal Inorganic materials 0.000 abstract description 37
- 239000002184 metal Substances 0.000 abstract description 37
- 238000004140 cleaning Methods 0.000 abstract description 8
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 7
- 229910052791 calcium Inorganic materials 0.000 abstract description 7
- 239000011575 calcium Substances 0.000 abstract description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052749 magnesium Inorganic materials 0.000 abstract description 5
- 239000011777 magnesium Substances 0.000 abstract description 5
- 125000005207 tetraalkylammonium group Chemical group 0.000 abstract description 4
- 150000001450 anions Chemical class 0.000 abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract description 2
- 239000003093 cationic surfactant Substances 0.000 abstract description 2
- -1 phenate Chemical compound 0.000 description 69
- 239000002585 base Substances 0.000 description 35
- 239000003921 oil Substances 0.000 description 27
- 235000019198 oils Nutrition 0.000 description 26
- 239000002253 acid Substances 0.000 description 24
- 125000001931 aliphatic group Chemical group 0.000 description 20
- 239000012459 cleaning agent Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000003963 antioxidant agent Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000002480 mineral oil Substances 0.000 description 10
- 239000010802 sludge Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 150000003512 tertiary amines Chemical class 0.000 description 9
- 230000003078 antioxidant effect Effects 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 8
- 235000010446 mineral oil Nutrition 0.000 description 8
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 150000003141 primary amines Chemical group 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000003472 neutralizing effect Effects 0.000 description 6
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 6
- 239000003760 tallow Substances 0.000 description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
- SIOLDWZBFABPJU-UHFFFAOYSA-N isotridecanoic acid Chemical compound CC(C)CCCCCCCCCC(O)=O SIOLDWZBFABPJU-UHFFFAOYSA-N 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000012188 paraffin wax Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 4
- MHPUGCYGQWGLJL-UHFFFAOYSA-N 5-methyl-hexanoic acid Chemical compound CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 description 4
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 150000008050 dialkyl sulfates Chemical class 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052750 molybdenum Inorganic materials 0.000 description 4
- 239000010705 motor oil Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 4
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000007112 amidation reaction Methods 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 235000015278 beef Nutrition 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000010495 camellia oil Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 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 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 235000014593 oils and fats Nutrition 0.000 description 3
- 239000013618 particulate matter Substances 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Chemical class 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003335 secondary amines Chemical group 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 229960002317 succinimide Drugs 0.000 description 3
- GWHCXVQVJPWHRF-KTKRTIGZSA-N (15Z)-tetracosenoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-KTKRTIGZSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- 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 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- QJRRBVNPIKYRQJ-UHFFFAOYSA-N 10-methylundecanoic acid Chemical compound CC(C)CCCCCCCCC(O)=O QJRRBVNPIKYRQJ-UHFFFAOYSA-N 0.000 description 2
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- OXDRRSIWCCBLOE-UHFFFAOYSA-N 3-methylbutanoic acid Chemical compound CC(C)CC(O)=O.CC(C)CC(O)=O OXDRRSIWCCBLOE-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 2
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 description 2
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000004166 Lanolin Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 235000019774 Rice Bran oil Nutrition 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 244000299461 Theobroma cacao Species 0.000 description 2
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 2
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 230000009435 amidation Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- PASOAYSIZAJOCT-UHFFFAOYSA-N butanoic acid Chemical compound CCCC(O)=O.CCCC(O)=O PASOAYSIZAJOCT-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 235000001046 cacaotero Nutrition 0.000 description 2
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
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- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 1
- ICZKASVWFUJTEI-UHFFFAOYSA-N n,n-dimethyldocosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN(C)C ICZKASVWFUJTEI-UHFFFAOYSA-N 0.000 description 1
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- IDFANOPDMXWIOP-UHFFFAOYSA-N n,n-dimethylpentan-1-amine Chemical compound CCCCCN(C)C IDFANOPDMXWIOP-UHFFFAOYSA-N 0.000 description 1
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- DDCVREGVKUIOSZ-UHFFFAOYSA-N n,n-dimethylprop-1-en-2-amine Chemical compound CN(C)C(C)=C DDCVREGVKUIOSZ-UHFFFAOYSA-N 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- PFPFHPHPGFCJND-UHFFFAOYSA-N n,n-dimethyltetracosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCN(C)C PFPFHPHPGFCJND-UHFFFAOYSA-N 0.000 description 1
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- ZEBPQFOCKZMJBV-UHFFFAOYSA-N n-dec-1-enyl-n-methyldec-1-en-1-amine Chemical compound CCCCCCCCC=CN(C)C=CCCCCCCCC ZEBPQFOCKZMJBV-UHFFFAOYSA-N 0.000 description 1
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- UWHRNIXHZAWBMF-UHFFFAOYSA-N n-dodecyl-n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)CCCCCCCCCCCC UWHRNIXHZAWBMF-UHFFFAOYSA-N 0.000 description 1
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- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- ILEBRBCUTWOWCM-UHFFFAOYSA-N n-hex-1-enyl-n-methylhex-1-en-1-amine Chemical compound CCCCC=CN(C)C=CCCCC ILEBRBCUTWOWCM-UHFFFAOYSA-N 0.000 description 1
- YBKFZZZSEOBTSI-UHFFFAOYSA-N n-hexacosyl-n-methylhexacosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCCCCCCCCCC YBKFZZZSEOBTSI-UHFFFAOYSA-N 0.000 description 1
- KCMTVIZYKDBFFS-UHFFFAOYSA-N n-hexadecyl-n-methylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCC KCMTVIZYKDBFFS-UHFFFAOYSA-N 0.000 description 1
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- POMGZMHIXYRARC-UHFFFAOYSA-N n-hexyl-n-methylhexan-1-amine Chemical compound CCCCCCN(C)CCCCCC POMGZMHIXYRARC-UHFFFAOYSA-N 0.000 description 1
- CWAIAZCEPCBUON-UHFFFAOYSA-N n-icosyl-n-methylicosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCCCC CWAIAZCEPCBUON-UHFFFAOYSA-N 0.000 description 1
- QZTDBEZGINZUDE-UHFFFAOYSA-N n-methyl-2-phenyl-n-(2-phenylethenyl)ethenamine Chemical compound C=1C=CC=CC=1C=CN(C)C=CC1=CC=CC=C1 QZTDBEZGINZUDE-UHFFFAOYSA-N 0.000 description 1
- XXHGARJZQUANMR-UHFFFAOYSA-N n-methyl-2-propan-2-yl-n-(2-propan-2-ylphenyl)aniline Chemical compound CC(C)C1=CC=CC=C1N(C)C1=CC=CC=C1C(C)C XXHGARJZQUANMR-UHFFFAOYSA-N 0.000 description 1
- WDQDHROPTFGYNF-UHFFFAOYSA-N n-methyl-3-phenyl-n-(3-phenylprop-2-enyl)prop-2-en-1-amine Chemical compound C=1C=CC=CC=1C=CCN(C)CC=CC1=CC=CC=C1 WDQDHROPTFGYNF-UHFFFAOYSA-N 0.000 description 1
- XGJKKPNMPYTVLZ-UHFFFAOYSA-N n-methyl-n-non-1-enylnon-1-en-1-amine Chemical compound CCCCCCCC=CN(C)C=CCCCCCCC XGJKKPNMPYTVLZ-UHFFFAOYSA-N 0.000 description 1
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- VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 description 1
- DFHKPRZWSRIWQW-UHFFFAOYSA-N n-methyl-n-pent-1-enylpent-1-en-1-amine Chemical compound CCCC=CN(C)C=CCCC DFHKPRZWSRIWQW-UHFFFAOYSA-N 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- YAGKCBZESGTUJX-UHFFFAOYSA-N n-methyl-n-prop-1-en-2-ylprop-1-en-2-amine Chemical compound CC(=C)N(C)C(C)=C YAGKCBZESGTUJX-UHFFFAOYSA-N 0.000 description 1
- GZSPGEZRIUWWJA-UHFFFAOYSA-N n-methyl-n-prop-1-enylprop-1-en-1-amine Chemical compound CC=CN(C)C=CC GZSPGEZRIUWWJA-UHFFFAOYSA-N 0.000 description 1
- HVZCVNRPXWJWHM-UHFFFAOYSA-N n-methyl-n-tetracosyltetracosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCCCCCCCC HVZCVNRPXWJWHM-UHFFFAOYSA-N 0.000 description 1
- KBIKNCRGZMEZLQ-UHFFFAOYSA-N n-methyl-n-tetradec-1-enyltetradec-1-en-1-amine Chemical compound CCCCCCCCCCCCC=CN(C)C=CCCCCCCCCCCCC KBIKNCRGZMEZLQ-UHFFFAOYSA-N 0.000 description 1
- KUFYUMSBZMUWAN-UHFFFAOYSA-N n-methyl-n-tetradecyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCC KUFYUMSBZMUWAN-UHFFFAOYSA-N 0.000 description 1
- SKSVCKGZZUFGGC-UHFFFAOYSA-N n-methylmethanamine;propanoic acid Chemical compound C[NH2+]C.CCC([O-])=O SKSVCKGZZUFGGC-UHFFFAOYSA-N 0.000 description 1
- QANXKUOOYFKWAH-UHFFFAOYSA-N n-tridecylaniline Chemical compound CCCCCCCCCCCCCNC1=CC=CC=C1 QANXKUOOYFKWAH-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 235000019488 nut oil Nutrition 0.000 description 1
- 239000010466 nut oil Substances 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl 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])=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 1
- 229940113162 oleylamide Drugs 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- HISQRFFCSVGSGI-UHFFFAOYSA-N pentadecane-1,2,3-triol Chemical compound CCCCCCCCCCCCC(O)C(O)CO HISQRFFCSVGSGI-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001296 polysiloxane 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
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012430 stability testing Methods 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
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- WFLJHDLVVWUGGZ-UHFFFAOYSA-N triacontan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCN WFLJHDLVVWUGGZ-UHFFFAOYSA-N 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-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
- 239000002383 tung oil Substances 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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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
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- 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
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Abstract
Disclosed is a lubricating oil additive with excellent cleaning performance which does not include a metal component such as calcium or magnesium. Also disclosed is a lubricating oil composition containing such a lubricating oil additive. The lubricating oil additive is characterized by containing a quaternary ammonium salt having a base number of at least 10 mgKOH/g. Examples of such a quaternary ammonium salt include quaternary ammonium salts obtained through salt-exchange of counter anions contained in cationic surfactants such as tetraalkylammonium chloride and tetraalkylammonium sulfate.
Description
DESCRIPTION
LUBRICATING OIL ADDITIVE AND LUBRICATING OIL COMPOSITION CONTAINING
THE SAME
TECHNICAL FIELD
[0001]
The present invention relates to a lubricating oil additive and a lubricating oil composition containing the same.
BACKGROUND ART
LUBRICATING OIL ADDITIVE AND LUBRICATING OIL COMPOSITION CONTAINING
THE SAME
TECHNICAL FIELD
[0001]
The present invention relates to a lubricating oil additive and a lubricating oil composition containing the same.
BACKGROUND ART
[0002]
A metal-based cleaning agent has been conventionally added to engine oil for the purpose of lengthening the lifetime of the engine oil. The metal-based cleaning agent functions to prevent the deposition of sludge in an engine and to neutralize acid substances as by-products of the burning of fuel or as products obtained as a result of deterioration of the engine oil. Perbasic sulfonate, phenate, salicylate, or the like has been used in such metal-based cleaning agents. Of those, a metal-based cleaning agent composed of perbasic calcium sulfonate, calcium salicylate, magnesium sulfonate, or the like has been most generally used because it is relatively inexpensive and has excellent cleaning performance.
However, part of a metal-based cleaning agent is burnt together with fuel, and metal components in the metal-based cleaning agent cause various problems. To be specific, there arises the following problem: metal components released together with exhaust gas adhere to an exhaust gas catalyst to reduce exhaust gas clarifying performance, and, in a diesel engine, reduces the particulate matter (PM) removal performance of a diesel particulate filter (DPF) and inhibits the reuse of the DPF. Therefore, a reduction in amount of a metal-based cleaning agent to be added is of great concern.
A metal-based cleaning agent has been conventionally added to engine oil for the purpose of lengthening the lifetime of the engine oil. The metal-based cleaning agent functions to prevent the deposition of sludge in an engine and to neutralize acid substances as by-products of the burning of fuel or as products obtained as a result of deterioration of the engine oil. Perbasic sulfonate, phenate, salicylate, or the like has been used in such metal-based cleaning agents. Of those, a metal-based cleaning agent composed of perbasic calcium sulfonate, calcium salicylate, magnesium sulfonate, or the like has been most generally used because it is relatively inexpensive and has excellent cleaning performance.
However, part of a metal-based cleaning agent is burnt together with fuel, and metal components in the metal-based cleaning agent cause various problems. To be specific, there arises the following problem: metal components released together with exhaust gas adhere to an exhaust gas catalyst to reduce exhaust gas clarifying performance, and, in a diesel engine, reduces the particulate matter (PM) removal performance of a diesel particulate filter (DPF) and inhibits the reuse of the DPF. Therefore, a reduction in amount of a metal-based cleaning agent to be added is of great concern.
[0003]
In view of the foregoing, with a view to reducing the amount of a metal-based cleaning agent to be added, there have been proposed a lubricating oil composition blended with an ashless dispersant and a phenol-based ashless antioxidant (see, for example, Patent Document 1) and a lubricating oil composition blended with a specific amine compound (see, for example, Patent Documents 2 and 3) . There has been also proposed a lubricating oil composition blended with an ashless dispersant, an oil-soluble antioxidant, and an oil-soluble dihydrocarbyl dithiophosphorate and containing a small total sulfated ash content (see, for example, Patent Document 4).
In view of the foregoing, with a view to reducing the amount of a metal-based cleaning agent to be added, there have been proposed a lubricating oil composition blended with an ashless dispersant and a phenol-based ashless antioxidant (see, for example, Patent Document 1) and a lubricating oil composition blended with a specific amine compound (see, for example, Patent Documents 2 and 3) . There has been also proposed a lubricating oil composition blended with an ashless dispersant, an oil-soluble antioxidant, and an oil-soluble dihydrocarbyl dithiophosphorate and containing a small total sulfated ash content (see, for example, Patent Document 4).
[0004]
Patent Document l: JP 2000-256690 A
Patent Document 2: JP 09-100485 A
Patent Document 3: JP 09-013067 A
Patent Document 4: JP 2877887 B
DISCLOSURE OF THE INVENTION
PROBLEMS TO BE SOLVED BY THE INVENTION
Patent Document l: JP 2000-256690 A
Patent Document 2: JP 09-100485 A
Patent Document 3: JP 09-013067 A
Patent Document 4: JP 2877887 B
DISCLOSURE OF THE INVENTION
PROBLEMS TO BE SOLVED BY THE INVENTION
[0005]
In recent years, there has been a growing demand for a reduction in amount of metal components in lubricating oil compositions such as engine oil from the viewpoint of alleviating the load on the environment. However, it has been difficult to additionally reduce the amount of metal components in any one of the above lubricating oil compositions while maintaining cleaning performance such as sludge dispersibility or acid neutralizing property.
The present invention has been made with a view to solving such problems as described above, and an object of the present invention is to provide a lubricating oil additive which is free of metal components such as calcium or magnesium and is excellent incleaning performance and alubricating oilcomposition containing the same.
MEANS FOR SOLVING THE PROBLEMS
In recent years, there has been a growing demand for a reduction in amount of metal components in lubricating oil compositions such as engine oil from the viewpoint of alleviating the load on the environment. However, it has been difficult to additionally reduce the amount of metal components in any one of the above lubricating oil compositions while maintaining cleaning performance such as sludge dispersibility or acid neutralizing property.
The present invention has been made with a view to solving such problems as described above, and an object of the present invention is to provide a lubricating oil additive which is free of metal components such as calcium or magnesium and is excellent incleaning performance and alubricating oilcomposition containing the same.
MEANS FOR SOLVING THE PROBLEMS
[0006]
The inventors of the present invention, through intensive studies on the above problems, have found that a quaternary ammonium salt having a specific base number and containing no metal components has cleaning performance comparable to or higher than that of a conventionalmetal-based cleaning agent, to complete the invention.
That is, the present invention relates to a lubricating oil additive containing a quaternary ammonium salt having a base number of at least 10 mgKOH/g.
Further, the present invention provides a lubricating oil composition containing 0 . I to 10 o by mass of the above lubricating oil additive based on a base oil.
The term "metal" as used in the present invention refers to a "typical metal element" and a "transition metal element".
EFFECT OF THE INVENTION
The inventors of the present invention, through intensive studies on the above problems, have found that a quaternary ammonium salt having a specific base number and containing no metal components has cleaning performance comparable to or higher than that of a conventionalmetal-based cleaning agent, to complete the invention.
That is, the present invention relates to a lubricating oil additive containing a quaternary ammonium salt having a base number of at least 10 mgKOH/g.
Further, the present invention provides a lubricating oil composition containing 0 . I to 10 o by mass of the above lubricating oil additive based on a base oil.
The term "metal" as used in the present invention refers to a "typical metal element" and a "transition metal element".
EFFECT OF THE INVENTION
[0007) According to the present invention, a lubricating oil additive containing a quaternary ammonium salt having a base number of at least 10 mgKOH/g can provide a lubricating oil composition having an extremely small amount of metal components such as calcium or magnesium and excellent cleaning performance.
BEST MODE FOR CARRYING OUT THE INVENTION
BEST MODE FOR CARRYING OUT THE INVENTION
[0008) The lubricating oil additive according to the present invention contains a quaternary ammonium salt having a base number of at least mgKOH/g. The quaternary ammonium salt may be directly used as the lubricating oil additive, or may be mixed with base oil or any other additive to be used in a lubricating oil composition described later before being used as the lubricating oil additive.
The base number of the quaternary ammonium salt is preferably high from the viewpoint of sludge dispersibility or acid neutralizing properties. However, an excessively high base number is not preferable because such base number may increase the frictional coefficient of lubricating oil, or may deteriorate solubility into base oil. Therefore, the base number of the quaternary ammonium salt is preferably 30 to 600 mgKOH/g, or more preferably 50 to 300 mgKOH/g.
Here, the term "base number" as used in the present invention refers to the number of milligrams (mg) of potassium hydroxide in an amount equivalent to that of hydrochloric acid needed for neutralizing a basic component in 1 g of a quaternary ammonium salt.
The base number can be measured by means of the total base number measuring method of JIS K2501 (petroleum product and lubricating oil-neutralization number testing method).
The base number of the quaternary ammonium salt is preferably high from the viewpoint of sludge dispersibility or acid neutralizing properties. However, an excessively high base number is not preferable because such base number may increase the frictional coefficient of lubricating oil, or may deteriorate solubility into base oil. Therefore, the base number of the quaternary ammonium salt is preferably 30 to 600 mgKOH/g, or more preferably 50 to 300 mgKOH/g.
Here, the term "base number" as used in the present invention refers to the number of milligrams (mg) of potassium hydroxide in an amount equivalent to that of hydrochloric acid needed for neutralizing a basic component in 1 g of a quaternary ammonium salt.
The base number can be measured by means of the total base number measuring method of JIS K2501 (petroleum product and lubricating oil-neutralization number testing method).
[0009]
Examples of such quaternary ammonium salt include quaternary ammonium salts obtained by subjecting counter anions in cationic surfactants such as tetraalkylammonium chloride and tetraalkylammonium sulfate to salt-exchange. Among them, a quaternary ammonium salt represented by the following general formula (1) is preferable.
[00101 [Chemical formula 1]
/N\ ' X- C1) (Where R1 to Rq each independently represent a hydrocarbon group having 1 to 30 carbon atoms, -R90-CO-R1°, or -R~1NH-CO-R~' (provided that at least one of R1 to R9 represents a hydrocarbon group having 1 to 30 carbon atoms ) , R9 and R11 each represent a hydrocarbon group having 1 to 4 carbon atoms, R1° and R12 each represent a hydrocarbon group having 1 to 30 carbon atoms or a hydrogen atom, and X- represents an anionic group.) [0011]
Examples of a hydrocarbon group having 1 to 30 carbon atoms represented by each of R1 to R9, R1°, and R12 include: alkyl groups such as a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, secondary butyl group, tertiary butyl group, pentyl group, isopentyl group, secondary pentyl group, neopentyl group,tertiary pentylgroup, hexylgroup, secondary hexyl group, heptyl group, secondary heptyl group, octyl group, 2-ethylhexyl group, secondary octyl group, nonyl group, secondary nonyl group, decyl group, secondary decyl group, undecyl group, secondary undecyl group, dodecyl group, secondary dodecyl group, tridecyl group, isotridecyl group, secondary tridecyl group, tetradecyl group, secondary tetradecyl group, hexadecyl group, secondary hexadecyl group, stearyl group, eicosyl group, docosyl group, tetracosyl group, triacontyl group, 2-butyloctyl group, 2-butyldecyl group, 2-hexyloctyl group, 2-hexyldecyl group, 2-octyldecyl group, 2-hexyldodecyl group, 2-octyldodeCyl group, 2-decyltetradecyl group, 2-dodecylhexadecyl group, or monomethyl-branchedisostearylgroup;alkenylgroupssuchasa vinyl group, allylgroup, propenylgroup, isopropenylgroup, butenylgroup, isobutenylgroup, pentenyl group, isopentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, tetradecenyl group, or oleyl group; aryl groups such as a phenyl group, toluyl group, xylyl group, cumenyl group, mesityl group, benzyl group, phenethyl group, styryl group, cinnamyl group, benzhydryl group, trityl group, ethylphenyl group, propylphenyl group, butylphenyl group, pentylphenyl group, hexylphenyl group, heptylphenyl group, octylphenyl group, nonylphenyl group, decylphenyl group, undecylphenyl group, dodecylphenylgroup, octadecylphenylgroup, styrenated phenylgroup, p-cumylphenyl group, phenylphenyl group, benzylphenyl group, a-naphthyl group, or ~-naphthyl group; and cycloalkyl groups or cycloalkenyl groups such as a cyclopentyl group, cyclohexyl group, cycloheptylgroup, methylcyclopentylgroup, methylcyclohexylgroup, methylcycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, methylcyclopentenyl group, methylcyclohexenyl group, or methylcycloheptenyl group.
[0012]
Examples of a hydrocarbon group having 1 to 4 carbon atoms represented by each of R9 and R1~ includes a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, or secondary butyl group. Of those, a linear alkyl group is preferable, and an ethyl group, propyl group, and isopropyl group are more preferable because of easy availability of raw materials for them.
[0013 In the above-described general formula ( 1 ) , X- represents an anionic group . X- as an anionic group may have a value of pka (equilibrium constant) that is an index of acidity of more than 0 when X- is represented as an acidic compound HX.
Examples of such anionic group include groups derived from:
inorganic compounds such as carbonic acid, boric acid, and silicic acid; carbonates such as monomethyl carbonate and monoethyl carbonate; and organic carboxylic acids such as formic acid, acetic acid, propionic acid, butanoic acid (butyric acid) , pentanoic acid (valeric acid), isopentanoic acid (isovaleric acid), hexanoic acid (capronic acid), heptanoic acid, isoheptanoic acid, octanoic acid (caprylic acid) , 2-ethylhexanoic acid, isooctanoic acid, nonanoic acid (pelargonic acid), isononanoic acid, decanoic acid (capric acid), isodecanoic acid, undecylic acid, isoundecylic acid, dodecanoic acid(lauric acid),isododecanoic acid,tridecanoicacid, isotridecanoic acid, tetradecanoic acid (myristic acid), hexadecanoic acid(palmitic acid),octadecanoic acid(stearic acid), isostearic acid, eicosanoic acid (arachic acid), docosanoic acid (behenic acid), tetracosanoic acid (lignoceric acid), hexacosanoic acid (cerotic acid), octacosanoic acid (montanic acid), 10-undecenoic acid, zoomaric acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, gadoleic acid, erucic acid, selacholeic acid, a mixed aliphatic acid obtained from natural oils and fats, malonic acid, succinic acid, malefic acid, benzoic acid, methylbenzoic acid, ethylbenzoic acid, butylbenzoic acid, hydroxybenzoic acid, naphthalenecarboxylic acid, diphenylcarboxylic acid, terephthalic acid, naphthalenedicarboxylic acid, trimellitic acid, and pyromellitic acid, and a hydroxyl group. Of those, groups derived from carbonic acid, carbonate, boric acid and an organic carboxylic acid, and a hydroxyl group are preferable because of easy availability of raw materials for them and solubility into oil.
[0014]
A quaternary ammonium salt represented by the general formula (1) of the present invention can be manufactured as follows. At least one tertiary amine selected from the group consisting of tertiary amine compounds, tertiary amineamide compounds, tertiary amine ester compounds, and tertiary amineamide ester compounds is used as a starting material . Then, the tertiary amine is quaternized with a quaterni zing agent . It should be noted that wel l-known methods may be used for salt-exchange when a counter anion of the compound obtained by quaternization is a group other than the above-described anionic groups . In addition, when an anionic group of the quaternary ammonium salt obtained by quaternization or salt-exchange is a hydroxyl group, the hydroxyl group is neutralized with the above-described acidic compound HX and produced waterisdehydrated.
As a result, the hydroxyl group can be replaced with an anionic group derived from an organic carboxylic acid.
[0015) Examples of a tertiary amine compound which is a starting material include: alkyl tertiary amines such as trimethylamine, triethylamine, tripropylamine, tributylamine, triamylamine, trihexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, tridodecylamine, tritetradecylamine, trihexadecylamine, trioctadecylamine, trieicosylamine, tridocosylamine, tritetracosylamine, trihexacosylamine, trioctacosylamine, triacontylamine, monomethyldiethylamine, monomethyldibutylamine, monomethyldihexylamine, monomethyldioctylamine, monomethyldidecylamine, monomethyldidodecylamine, monomethylditetradecylamine, monomethyldihexadecylamine, monomethyldioctadecylamine, monomethyldieicosylamine, monomethyldidocosylamine, monomethylditetracosylamine, monomethyldihexacosylamine, monomethyldioctacosylamine, monomethyldiacontylamine, dimethylmonoethylamine, dimethylmonoethylamine, dimethylmonopropylamine, dimethylmonobutylamine, dimethylmonoamylamine, dimethylmonohexylamine, dimethylmonoheptylamine, dimethylmonooctylamine, dimethylmonononylamine, dimethylmonodecylamine, dimethylmonododecylamine, dimethylmonotetradecylamine, dimethylmonohexadecylamine, dimethylmonooctadecylamine, dimethylmonoeicosylamine, dimethylmonodocosylamine, dimethylmonotetracosylamine, dimethylmonohexacosylamine, dimethylmonooctacosylamine, and dimethylmonoacontylamine;
tertiary amines each having an alkenyl group such as triallylamine, tripropenylamine, triisopropenylamine, tributenylamine, triisobutenylamine, tripentenylamine, triisopentenylamine, trihexenylamine, triheptenylamine, trioctenylamine, trinonenylamine, tridecenylamine, tridodecenylamine, tritetradecenylamine, trioleylamine, monomethyldiallylamine, monomethyldipropenylamine, monomethyldiisopropenylamine, monomethyldibutenylamine, monomethyldiisobutenylamine, monomethyldipentenylamine, monomethyldiisopentenylamine, monomethyldihexenylamine, monomethyldiheptenylamine, monomethyldioctenylamine, monomethyldinonenylamine, monomethyldidecenylamine, monomethyldidodecenylamine, monomethylditetradecenylamine, monomethyldioleylamine, dimethylmonoallylamine, dimethylmonopropenylamine, dimethylmonoisopropenylamine, dimethylmonobutenylamine, dimethylmonoisobutenylamine, dimethylmonopentenylamine, dimethylmonoisopentenylamine, dimethylmonohexenylamine, dimethylmonoheptenylamine, dimethylmonooctenylamine, dimethylmonononenylamine, dimethylmonodecenylamine, dimethylmonododecenylamine, dimethylmonotetradecenylamine, and dimethylmonooleylamine; tertiary amines each having an aryl group such as triphenylamine, tritoluylamine, trixylylamine, tricumenylamine,tribenzylamine,tristyrylamine,tricinnamylamine, tribenzhydrylamine, triethylphenylamine, tripropylphenylamine, tributylphenylamine, trihexylphenylamine, trioctylphenylamine, trinonylphenylamine, tridecylphenylamine, tridodecylphenylamine, tristyrenated phenylamine, tri-p-curnylphenylamine, tribenzylphenylamine, tri-a-naphthylamine, tri-~-naphthylamine, monomethyldiphenylamine, monomethylditoluylamine, monomethyldixylylamine, monomethyldicumenylamine, monomethyldibenzylamine, monomethyldistyrylamine, monomethyldicinnamylamine, monomethyldibenzhydrylamine, monomethyldiethylphenylamine, monomethyldipropylphenylamine, monomethyldibutylphenylamine, monomethyldihexylphenylamine, monomethyldioctylphenylamine, monomethyldinonylphenylamine, monomethyldidecylphenylamine, monomethyldidodecylphenylamine, monomethyldistyrenated phenylamine, monomethyldi-p-cumylphenylamine, monomethyldibenzylphenylamine, monomethyldi-a-naphthylamine, monomethyldi-~-naphthylamine, dimethylmonophenylamine, dimethylmonotoluylamine, dimethylmonoxylylamine, dimethylmonocumenylamine, dimethylmonobenzylamine, dimethylmonostyrylamine, dimethylmonocinnamylamine, dimethylmonobenzhydrylamine, dimethylmonoethylphenylamine, dimethylmonopropylphenylamine, dimethylmonobutylphenylamine, dimethylmonohexylphenylamine, dimethylmonooctylphenylamine, dimethylmonononylphenylamine, dimethylmonodecylphenylamine, dimethylmonododecylphenylamine, dimethylmonostyrenated phenylamine, dimethylmono-p-cumylphenylamine, dimethylmonobenzylphenylamine, dimethylmono-a-naphthylamine, and dimethylmono-(3-naphthylamine;
and tertiary amines derived from a raw material aliphatic acid obtained from natural oils and fats such as vegetable oils, for example, a linseed oil, olive oil, cacao oil, sesame oil, rice bran oil, safflower oil, soybean oil, camellia oil, corn oil, rapeseed oil, palm oil, palm kernel oil, castor oil, sunflower oil, cotton oil, and coconut oil and animal oils and fats, for example, beef tallow, lard, milk fat, fish oil, and whale oil.
[0016) A tertiary amineamide compound which is a starting material can be manufactured by the following method. An amine compound such as : triamine having two primary amine groups and one secondary amine group such as diethylenetriamine, dipropylenetriamine, or ethylenepropylenetriamine; a triamine having two primary amine groups and one tertiary amine group such as bis(3-aminopropyl)methylamine, bis(3-aminopropyl)ethylamine, bis(3-aminopropyl)propylamine, bis(3-aminopropyl)butylamine, or bis(3-arninopropyl)benzylamine;oradiamine having one primaryamine group such as N,N-dimethylethylenediamine, N,N-diethylethylenediamine, N,N-dipropylethylenediamine, N,N-dibutylethylenediamine, N,N-dimethylpropylenediamine, N,N-diethylpropylenediamine, N,N-dipropylpropylenediamine, or N,N-dibutylpropylenediamineisallowed to react with aliphaticacid, aliphatic acid chloride, or aliphatic acid ester to amidate a primary amine group of the amine compound. As a result, an amineamide compound is obtained. When the obtained compound is a secondary amineamide compound, the secondary amine group can be tertiarized with halogenated hydrocarbon, dialkylsulfate, or thelike to thereby obtain a tertiary amineamide compound.
[0017]
Examples of a tertiary amine ester compound which is a starting material include tertiary alkanolamines such as triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, N-propyldiethanolamine, N-isopropyldiethanolamine, N-butyldiethanolamine, N,N-dimethylethanolamine, N,N-diethylethanolamine, N,N-dipropylethanolamine, N,N-dibutylethanolamine, N-cyclohexyldiethanolamine, N-benzyldiethanolamine, tripropanolamine, triisopropanolamine, N-cyclohexyldiisopropanolamine, N-benzyldiisopropanolamine, and tributanolamine.
In addition, the tertiary amine ester compound can also be obtained as follows. A primary alkanolamine or secondary alkanolamine such as monoethanolamine, diethanolamine, N-methylethanolamine, N-ethylethanolamine, N-propylethanolamine, N-isopropylethanolamine, N-butylethanolamine, N-cyclohexylethanolamine, N-benzylethanolamine, monopropanolamine, dipropanolamine, monoisopropanolamine, diisopropanolamine, N-cyclohexylisopropanolamine, N-benzylisopropanolamine, monobu~tanolamine, or dibutanolamine is tertiarized with halogenated hydrocarbon, dialkylsulfate, or the like. After that, the resultant is allowed to react with aliphatic acid, aliphatic acid chloride, or aliphatic acid ester to esterify a hydroxyl group of the amine compound.
[0018]
A tertiary amineamide ester compound which is a starting material can be manufactured by the following method. An alcanoldiamine such as N-methanolethylenediamine, N-ethanolethylenediamine, N-propanolethylenediamine, N-butanolethylenediamine, N,N-dimethanolethylenediamine, N,N-diethanolethylenediamine, N,N-dipropanolethylenediamine, N,N-dibutanolethylenediamine, N-methanolpropylenediamine, N-ethanolpropylenediamine, N-propanolpropylenediamine, N-butanolpropylenediamine, N,N-dimethanolpropylenediamine, N,N-diethanolpropylenediamine, N,N-dipropanolpropylenediamine, or N,N-dibutanolpropylenediamineisallowedto react with aliphatic acid, aliphatic acid chloride, or aliphatic acid ester. Then, a primary amine group and a hydroxyl group of the alcanoldiamine are subjected to an amidation reaction and an esterification reaction.
As a result, an amineamide ester compound can be obtained. When the obtained compound is a secondary amineamide ester compound, the secondary amine group can be tertiarized with halogenated hydrocarbon, dialkylsulfate, or the like to thereby obtain a tertiary amineamide ester compound.
[0019]
Examples of an aliphatic acid to be used in the amidation of a primary amine group or in the amidation and esterification of a primary amine group and a hydroxyl group include formic acid, acetic acid, propionic acid, butanoic acid (butyric acid) , pentanoic acid (valeric acid), isopentanoic acid (isovaleric acid), hexanoic acid (capronic acid), heptanoic acid, isoheptanoic acid, octanoic acid (caprylic acid), 2-ethylhexanoic acid, isooctanoic acid, nonanoic acid (pelargonic acid), isononanoic acid, decanoic acid (capric acid), isodecanoic acid, undecanoic acid, isoundecanoic acid,dodecanoic acid(lauricacid),isododecanoic acid,tridecanoic acid, isotridecanoic acid, tetradecanoic acid (myristic acid), hexadecanoic acid(palmiticacid),octadecanoic acid(stearic acid), isostearic acid, eicosanoic acid (arachic acid), docosanoic acid (behenic acid), tetracosanoic acid (lignoceric acid), hexacosanoic acid (cerotic acid), octacosanoic acid (montanic acid), 10-undecenoic acid, zoomaric acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, gadoleic acid, erucic acid, and selacholeic acid. Mixed aliphatic acids producedfrom naturalfats and oils are also available. Examples of the natural fats and oils include: vegetable fats and oils such as linseed oil, perilla oil, oiticica oil, olive oil, cacao oil, kapok oil, white mustard oil, sesame oil, rice bran oil, safflower oil, shea nut oil, china wood oil, soybean oil, tea oil, camellia oil, corn oil, rapeseed oil, palm oil, palm kernel oil, castor oil, sunflower oil, cottonseed oil, coconut oil, haze wax, and peanut oil; and animal fats and oils such as horse tallow, beef tallow, hoof oil, ghee, lard, goat tallow, mutton tallow, milk fat, fish oil, and whale oil.
~0020~
A known method can be used as a reaction method for quaternarization. Generally,the methodinvolves:loading tertiary amine into an autoclave; adding a quaternarizing agent at 60°C to 200°C; and aging the resultant till the completion of a reaction.
Pressurization may be performed in an inert gas such as nitrogen or helium with a view to increasing a reaction velocity or a reaction rate. The amount of the quaternarizing agent to be added is 1.0 to 9.0 mol, preferably 1.1 to 2.5 mol, or more preferably 1.1 to 1.8 mol with respect to 1 mol of the tertiary amine. An excessively small amount of the quaternarizing agent to be added may fail to complete the reaction. An excessively large amount of the quaternarizing agent to be added may cause a large amount of an unreacted quaternarizing agent to remain to have an adverse effect on an environment such as the release of the agent to the atmosphere.
[0021]
Examples of a quaternarizing agent to be used for quaternarization include: organic halides such as methyl chloride, benzylchloride,cyclohexylchloride,methylbromide,benzylbromide, and cyclohexyl bromide; dialkyl sulfates such as dimethyl sulfate and diethyl sulfate; dialkyl carbonates such as dimethyl carbonate and diethyl carbonate; and trialkyl phosphates such as trimethyl phosphate and triethyl phosphate. Of those, methyl chloride and dimethyl carbonate are preferably used because of easy availability of raw materials for them and their ease of handling.
[0022]
Known methods can be used as a method for salt-exchange without any limitation. Examples of such amethod include: amethod involving synthesizing quaternary ammonium hydroxide from a quaternary ammonium halide salt, which is obtained by reacting a tertiary amine and an alkyl halide, by means of an electrolytic method (JP 45-28569 B), an ion-exchange resin method (JP 52-3009 A), or the like, neutralizing the quaternary ammonium hydroxide with an acid compound HX, and removing produced water; and a method involving reacting a quaternary ammonium halide salt and an inorganic alkali such as sodium hydroxide or potassium hydroxide, removing the produced inorganic salt to provide quaternary ammonium hydroxide, and neutralizing the quaternary ammonium hydroxide with an acid compound HX.
[0023]
Meanwhile, an organic solvent can be used in a quaternarization reaction and a salt-exchange reaction as long as the solvent does not inhibit any one of the reactions. The organic solvent that can be used in the reactions is not particularly limited. Specific examples of such solvent include: aliphatic, alicyclic, aromatic, and heterocyclic compounds, or a mixture of them; and general lubricating oil. More specific examples of such solvent include:
alkanessuch aspentane,hexane,heptane,cyclopentane,cyclohexane, ligroin, and petroleum ether; alcohols such as methanol, ethanol, propanol, 2-propanol, butanol, 2-butanol, pentanol, hexanol, heptanol, octanol, and2-ethylhexanol;alkyletherssuch asdimethyl ether, ethylmethyl ether, diethyl ether, methyl isobutyl ether, and ethyl isopropyl ether; ketones such as acetone, ethyl methyl ketone, and methyl isobutyl ketone; aromatic compounds such as benzene, toluene, xylene, and ethylbenzene; synthetic oils such as poly-a-olefin, an ethylene-a-olefin copolymer, polybutene, an alkylbenzene, an alkylnaphthalene, polyalkylene glycol, polyphenyl ether, an alkyl-substituted diphenyl ether, a polyol ester, a dibasic ester, silicone oil, and fluorinated oil; and paraffin-based mineral oil and naphthene-based mineral oil, or purified mineral oils obtained by purifying them. Of those, alkanes (such as hexane, heptane, and petroleum ether), alcohols (such as methanol, ethanol, propanol, and 2-propanol), aromatic compounds (such as benzene, toluene, and xylene), paraffin-based mineral oil, naphthene-based mineral oil, and the like are preferable from the viewpoints of thesolubilityand handleability ofareaction product. In addition, adding any one of those solvents is preferable for effectively removing by-products and impurities and for dissolving solid reaction products.
[0029]
The lubricating oil composition according to the present invention contains 0.1 to 100, or preferably 0.2 to 8% by mass of the above lubricating oil additive based on a base oil. Within the content range, cleaning performance such as sludge dispersibility or acid neutralizing property can be improved without any impairment of lubricity.
The base oil has only to be a base oil generally used in lubricating oil. Specific examples of the base oil include mineral oil, hydrocarbon-based synthetic oil, and a mixture of them. More specific examples of the base oil include: synthetic oils such as poly-a-olefin, ethylene-a-olefin copolymers, polybutene, alkylbenzene, alkylnaphthalene, polyalkylene glycol, polyphenyl ether, an alkyl-substituted diphenyl ether, polyol ester, dibasic ester, phosphate, phosphate, carbonate, silicone oil, and fluorinated oil; and paraffin-based mineral oil and naphthene-based mineral oil, or purified mineral oils obtained by purifying them.
[0025]
The lubricating oil composition of the present invention does not inhibit the addition of any known lubricating oil additive.
The composition may be added with, for example, antioxidants, organic molybdenum-based additives, extreme pressure agents, oiliness improvers, metal-based cleaning agents, dispersants, viscosity index improvers, pour depressants, rust inhibitors, corrosion inhibitors, or defoaming agents for an intended purpose.
[0026]
Examples of the antioxidant include a zinc dithiophosphate-based antioxidant, aphenol-based antioxidant, and an amine-based antioxidant . The preferable loading of any one of those antioxidants is 0.1 to 5o by mass based on the base oil.
[0027]
Examples of the organic molybdenum-based additive include:
oxymolybdenum dithiocarbamate sulfide; oxymolybdenum dithiophosphatesulfide; aliphatic molybdenumsalts; oxymolybdenum xanthate sulfide; reaction products between molybdenum trioxide and acid phosphate; reaction products between molybdenum trioxide and aliphatic diethanolamide; reaction productsbetween molybdenum trioxide and glycerin monoaliphatic acid ester; reaction products between succinimide, amide carboxylate, Mannich base, or a boride of any one of them and molybdenum trioxide; and reaction products between amine and a molybdenum compound having a pentavalent or hexavalent molybdenum atom. The preferable loading of any one of those organic molybdenum-based additives is 0.001 to 5o by mass based on the base oil.
[0028]
Examples of the extreme pressure agent include: sulfur-based compounds such as sulfurized fats and oils, olefin polysulfide, and dibenzyl sulfide; phosphor compounds such as monooctyl phosphate, tributyl phosphate, triphenyl phosphate, tributyl phosphate, and thiophosphate; and organometallic compounds such as metal thiophosphates, metal thiocarbamates, and acid metal phosphates.
The preferable loading of any one of those extreme pressure agents is 0.1 to 10o by mass based on the base oil.
[0029]
Examples of the oiliness improver include: higher alcohols such as oleyl alcohol and stearyl alcohol; aliphatic acids such as oleic acid and stearic acid; esters such as oleyl glycerin ester, lauryl glycerin ester, oleyl sorbitan ester, and oleyl trimethylolpropane ester; amides such as laurylamide, oleylamide, and stearylamide; amines such as laurylamine, oleylamine, and stearylamine; and ethers such as lauryl glycerin ether and oleyl glycerin ether. The preferable loading of any one of those oiliness improvers is 0.1 to 10o by mass based on the base oil.
[0030]
Examples of the metal-based cleaning agent include the sulfonates,phenates,salicylates,phosphonates,and perbasicsalts of calcium, magnesium, barium, and the like. The loading of any one of those metal-based cleaning agents is preferably small from the viewpoint of the alleviation of the load on the environment.
When the lubricating oil composition needs to have additional cleaning properties, the composition may be blended with 0 to 10 0, or preferably 0 to 5% by mass of any one of those metal-based cleaning agents based on the base oil.
[0031) Examples of the dispersant include succinimide, benzylamine, succinate, and boron-denatured products of them. The preferable loading of any one of those dispersants is 0. 5 to 10 o by mass based on the base oil.
[0032) Examples of the viscosity index improver include: polyalkyl methacrylate (having 1 to 18 carbon atoms) , alkyl acrylate (having 1 to 18 carbon atoms)/alkyl methacrylate (having 1 to 18 carbon atoms) copolymers; diethylaminoethyl methacrylate/alkyl methacrylate (having 1 to 18 carbon atoms) copolymers;
ethylene/alkyl methacrylate (having 1 to 18 carbon atoms) copolymers;polyisobutylene;polyalkylstyrene;ethylene/propylene copolymers; styrene/maleate copolymers; styrene/maleic acid amide copolymers; styrene/butadiene hydrogenated copolymers; and styrene/isoprene hydrogenated copolymers. Each of those viscosity index improvers has an average molecular weight of about 10,000 to l, 500, 000. The preferable loading of any one of those viscosity index improvers is 0.1 to 20o by mass based on the base oil.
[0033) Examples of the pour depressant include polyalkyl methacrylate, polyalkyl acrylate, polyalkylstyrene, and polyvinyl acetate. Each of those pour depressants has an average molecular weight of about 1, 000 to 100, D00. The preferable loading of any one of those pour depressants is 0.005 to 3o by mass based on the base oil.
[0034]
Examples of the rust inhibitor include: sodium nitrite;
oxidized paraffin waxcalciumsalts;oxidized paraffin wax magnesium salts; beef tallow aliphatic acid alkali metal salts, alkali earth metal salts, or amine salts; alkenyl succinic acid or alkenyl succinic acid half esters (in which an alkenyl group has a molecular weight of about 100 to 300); sorbitan monoesters; pentaerythritol monoesters;nonylphenolethoxylates;lanolin aliphatic acid esters;
and lanolin aliphatic acid calcium salts. The preferable loading of any one of those rust inhibitors is 0.01 to 5o by mass based on the base oil.
[0035) Examples of the corrosion inhibitor include benzotriazole, benzoimidazole, benzothiazole, and tetraalkylthiuram disulfide.
The preferable loading of any one of those corrosion inhibitors is 0.01 to 3o by mass based on the base oil.
[ 0036]
Examples of the defoaming agent include polydimethyl silicone, trifluoropropylmethyl silicone, colloidal silica, polyalkyl acrylate, polyalkyl methacrylate, alcohol ethoxy/propoxylate, aliphatic acid ethoxy/propoxylate, and sorbitan partial aliphatic acid ester. The preferable loading of any one of those defoaming agents is 0.001 to to by mass based on the base oil.
[0037]
The lubricating oil composition of the present invention can be suitably used in any one of automobile and industrial greases typified by internal combustion engine lubricating oil, driving system lubricating oil (such as manual transmission oil, differential gear oil, or automatic transmission oil), lubricating oil for metal working, and grease for constant velocity joints.
Of those, the composition can be suitably used in lubricating oil for internal combustion engines such as gasoline engines, diesel engines, or jet engines.
EXAMPLES
[0038]
~-iereinafter, the present invention will be described more specifically by way of examples. In the following examples, the term "o" means "o by mass" unless otherwise stated.
At first, a reference oil having the formulation shown below was prepared. Next, a lubrication oil composition of each of Examples 1 to 5 and Comparative Examples 1 to 5 was prepared by means of the following reference oil and each additive according to the formulation shown in Table 1 below. In each of Examples 1 to 5 and Comparative Examples 1 to 4, an additive was added in such a manner that the total base number of a lubricating oil composition would be 5 mgKOH/g.
<Base oil>
Mineral oil-based high-viscosity-index (VI) oil Dynamic viscosity 4 . 1 mmz/s (at 100°C) , 18. 3 mmz/s (at 40°C) , viscosity index (VI) - 126 [Reference oil formulation) Base oil 100 parts by mass Succinimide-based dispersant 5.0 parts by mass Phenol-based antioxidant 0.3 part by mass Amine-based antioxidant 0.3 part by mass Zinc dithiophosphate 1.0 part by mass [0039]
<Additive>
(A-1: product of the present invention) Dioleyl dimethyl ammonium bicarbonate Base number: 92 mgKOH/g Metal component: Oo (A-2: product of the present invention) Dioleyl dimethyl ammonium propionate Base number: 90 mgKOH/g Metal component: Oo (A-3: product of the present invention) Tridecyl monomethyl ammonium bicarbonate Base number: 93 mgKOH/g Metal component: Oo (A-4: product of the present invention) [0040) [Chemical formula 2]
I I
HC03 H3C~N~C2H4 0'C-Cl~Hs3 H3C C2H4 -0-~-CoH3a Base number: 77 mgKOH/g Metal component: Oo (A-5: product of the present invention) [0041) [Chemical formula 3) HsCv ~iC2Ha N-~'C12H25 H3C C2H4--~ ~ ~12H25 Base number: 95 mgKOH/g Metal component: Oo (B-1: product of comparative example) Calcium sulfonate Base number: 300 mgKOH/g Metal component: 12.60 (B-2: product of comparative example) Calcium sulfonate Base number: 100 mgKOH/g Metal component: 4.30 (B-3: product of comparative example) Magnesium salicylate Base number: 200 mgKOH/g Metal component: 3.10 (B-4: product of comparative example) Dioleyl dimonomethyl amine Base number: 105 mgKOH/g Metal component: Oo (B-5: product of comparative example) Dioleyl dimethyl ammonium chloride Base number: 0 mgKOH/g Metal component: Oo [0042].
<Test of sample oil for oxidation stability>
In conformance with JIS K-2514 (lubricating oil-oxidation stability testing method), 250 ml of a sample were placed into a glass vessel having incorporated therein a copper plate and an iron plate as catalysts, and the whole was heated at 165.5°C for one week while the sample was stirred at 1,300 rpm in such a manner that air would be involved. The dynamic viscosity (40°C) and total base number of a lubricating oil composition were measured before and after the test . A difference in dynamic viscosity was determined from the dynamic viscosity before the test and the dynamic viscosity after the test. The amount of a reduction in total base number was determined from the total base number before the test and the total base number after the test. The lubricating oil composition after the test was filtered, washed with toluene, and dried. Then, the amount of produced sludge was measured.
Oxidation stability is higher as a difference between the dynamic viscosity before the test and the dynamic viscosity after the test is smaller and the amount of a reduction in total base number is smaller. The corrosion of a metal is reduced and dispersibility is higher as the amount of produced sludge is smaller.
Table 1 shows the results.
.-. 0 0 ~ N O
L~ O O O O O O l0 I~ N O O
O
~1a N . lq f1~
~
'' ,~ r-i O
U
N N r-100 h M I~ ri N ri M V' +~
is ~'N M Ol O l0 N ~ N N
~
TS M ~ M M ~' M ~' ~' ~t~~ O
~
~
N O O O O O O O O r-I N
c!~ O O O O O O O O O O O
r0 4-i O
O
'-1 f~ ,~ ~-~IX17r1 01 M ~ N
01 O O O Ol Ol O O
~ I . . . . . . . . ' I
U
r1 N N N ~ ~ N N
n N
~
Z
T
a~
x (>) y -I c-I N ,-IO ~' O OJ
O
~ O ri O O O r1 O O Ol O O
.Q +~
b~ v v v M M M M M M M N
b O
H
S-I l0~ N M lfl~-I ~C7M l0 N t~
O O O O O O O O r-i Ol y~
N O ~ ~ ~ ~ ~ ~ ~ ~ ~ O
N
U
f~a1 ~ ~ ~ L9 u~ oo ~ o ao 0 0 0 0 0 0 o O ~ t~
-.~w ~
u~ ''-I
U
p f~
a U
O
.,1 ~ OOlflt~ V~ oW -1 O O e1~M N
N
U W n ~ ~ tm o r ~ o o~ .-I ao v -'-I4-I ~ l0 l~ l0 lfllfl l9 I~ l0 l9 N
r, S-I ~ ~ M 4D N f ~ 00 r-1M O
p 4-~ O t~ OJ (~ I~ (~ Ol O O ~ l0 l0l0 t0 l0 l0 l0 l0 I~ I~ lfl l0 P~l N
5 _ _ _ _ _ _ _ _ _ ~ _ N M ~' ~
o t ~-IN M V' N '-IO O 00 O
~' ~ M N ! M ! ! ! 1 I I
ov I I I ~ r~ !Y1f~q f~ C~ fr) .O r.>;~ ~ u7 V r-I~' N M
~r v~ ~
~--IN M ~ ~ rl N M
M .-1 p ~ O N
p .-1 N -r1 U
N t<3 U
N ~ S1 ~
H w r0 ~
tb m x o x fxW U
W
3~
* The term "additive ( o) " represents an addition ratio of an additive to the reference oil.
* A metal component shown is derived from a cleaning agent.
* The difference in total base number of each of the reference oil and B-5 is not written because the total base number of each of them before the test is about 1 and the total base number of each of them after the test is equal to or less than 0.
[0044]
As is apparent from Table 1, the lubricating oil composition of the present invention had a difference in dynamic viscosity of 0.4 to 0.9 mm2/S and an amount of a reduction in total base number of 1.91 to 2.05 mgKOH/g. That is, the composition showed excellent oxidation stability. In addition, the composition had a sludge amount of 0.0338 to 0.0421 g. That is, the composition showed excellent sludge dispersibility. Tn addition, the composition was comparable to or better than any one of the lubricating oil compositionswiththe conventionalmetal-based cleaning agentsadded (B-1 to B-3) in terms of all of a difference in dynamic viscosity, a sludge amount, and the amount of a reduction in total base number.
Furthermore, the lubricating oil composition of the present invention does not reduce the exhaust gas clarifying performance of an exhaust gas catalyst or the particulate matter removing performance of a diesel particulate filter even when the composition is used in internal combustion engine lubricating oiI because the composition does not contain any metal components derived from a cleaning agent.
In contrast, each of the lubricating oil compositions of Comparative Example 4 added with the tertiary amine compound (B-4 ) having a base number of 205 mgKOH/g and the lubricating oil composition of Comparative Example 5 added with the quaternary ammonium salt (B-5) having a base number of 0 mgKOH/g was poor in oxidation stability and sludge dispersibility.
Examples of such quaternary ammonium salt include quaternary ammonium salts obtained by subjecting counter anions in cationic surfactants such as tetraalkylammonium chloride and tetraalkylammonium sulfate to salt-exchange. Among them, a quaternary ammonium salt represented by the following general formula (1) is preferable.
[00101 [Chemical formula 1]
/N\ ' X- C1) (Where R1 to Rq each independently represent a hydrocarbon group having 1 to 30 carbon atoms, -R90-CO-R1°, or -R~1NH-CO-R~' (provided that at least one of R1 to R9 represents a hydrocarbon group having 1 to 30 carbon atoms ) , R9 and R11 each represent a hydrocarbon group having 1 to 4 carbon atoms, R1° and R12 each represent a hydrocarbon group having 1 to 30 carbon atoms or a hydrogen atom, and X- represents an anionic group.) [0011]
Examples of a hydrocarbon group having 1 to 30 carbon atoms represented by each of R1 to R9, R1°, and R12 include: alkyl groups such as a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, secondary butyl group, tertiary butyl group, pentyl group, isopentyl group, secondary pentyl group, neopentyl group,tertiary pentylgroup, hexylgroup, secondary hexyl group, heptyl group, secondary heptyl group, octyl group, 2-ethylhexyl group, secondary octyl group, nonyl group, secondary nonyl group, decyl group, secondary decyl group, undecyl group, secondary undecyl group, dodecyl group, secondary dodecyl group, tridecyl group, isotridecyl group, secondary tridecyl group, tetradecyl group, secondary tetradecyl group, hexadecyl group, secondary hexadecyl group, stearyl group, eicosyl group, docosyl group, tetracosyl group, triacontyl group, 2-butyloctyl group, 2-butyldecyl group, 2-hexyloctyl group, 2-hexyldecyl group, 2-octyldecyl group, 2-hexyldodecyl group, 2-octyldodeCyl group, 2-decyltetradecyl group, 2-dodecylhexadecyl group, or monomethyl-branchedisostearylgroup;alkenylgroupssuchasa vinyl group, allylgroup, propenylgroup, isopropenylgroup, butenylgroup, isobutenylgroup, pentenyl group, isopentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, tetradecenyl group, or oleyl group; aryl groups such as a phenyl group, toluyl group, xylyl group, cumenyl group, mesityl group, benzyl group, phenethyl group, styryl group, cinnamyl group, benzhydryl group, trityl group, ethylphenyl group, propylphenyl group, butylphenyl group, pentylphenyl group, hexylphenyl group, heptylphenyl group, octylphenyl group, nonylphenyl group, decylphenyl group, undecylphenyl group, dodecylphenylgroup, octadecylphenylgroup, styrenated phenylgroup, p-cumylphenyl group, phenylphenyl group, benzylphenyl group, a-naphthyl group, or ~-naphthyl group; and cycloalkyl groups or cycloalkenyl groups such as a cyclopentyl group, cyclohexyl group, cycloheptylgroup, methylcyclopentylgroup, methylcyclohexylgroup, methylcycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, methylcyclopentenyl group, methylcyclohexenyl group, or methylcycloheptenyl group.
[0012]
Examples of a hydrocarbon group having 1 to 4 carbon atoms represented by each of R9 and R1~ includes a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, or secondary butyl group. Of those, a linear alkyl group is preferable, and an ethyl group, propyl group, and isopropyl group are more preferable because of easy availability of raw materials for them.
[0013 In the above-described general formula ( 1 ) , X- represents an anionic group . X- as an anionic group may have a value of pka (equilibrium constant) that is an index of acidity of more than 0 when X- is represented as an acidic compound HX.
Examples of such anionic group include groups derived from:
inorganic compounds such as carbonic acid, boric acid, and silicic acid; carbonates such as monomethyl carbonate and monoethyl carbonate; and organic carboxylic acids such as formic acid, acetic acid, propionic acid, butanoic acid (butyric acid) , pentanoic acid (valeric acid), isopentanoic acid (isovaleric acid), hexanoic acid (capronic acid), heptanoic acid, isoheptanoic acid, octanoic acid (caprylic acid) , 2-ethylhexanoic acid, isooctanoic acid, nonanoic acid (pelargonic acid), isononanoic acid, decanoic acid (capric acid), isodecanoic acid, undecylic acid, isoundecylic acid, dodecanoic acid(lauric acid),isododecanoic acid,tridecanoicacid, isotridecanoic acid, tetradecanoic acid (myristic acid), hexadecanoic acid(palmitic acid),octadecanoic acid(stearic acid), isostearic acid, eicosanoic acid (arachic acid), docosanoic acid (behenic acid), tetracosanoic acid (lignoceric acid), hexacosanoic acid (cerotic acid), octacosanoic acid (montanic acid), 10-undecenoic acid, zoomaric acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, gadoleic acid, erucic acid, selacholeic acid, a mixed aliphatic acid obtained from natural oils and fats, malonic acid, succinic acid, malefic acid, benzoic acid, methylbenzoic acid, ethylbenzoic acid, butylbenzoic acid, hydroxybenzoic acid, naphthalenecarboxylic acid, diphenylcarboxylic acid, terephthalic acid, naphthalenedicarboxylic acid, trimellitic acid, and pyromellitic acid, and a hydroxyl group. Of those, groups derived from carbonic acid, carbonate, boric acid and an organic carboxylic acid, and a hydroxyl group are preferable because of easy availability of raw materials for them and solubility into oil.
[0014]
A quaternary ammonium salt represented by the general formula (1) of the present invention can be manufactured as follows. At least one tertiary amine selected from the group consisting of tertiary amine compounds, tertiary amineamide compounds, tertiary amine ester compounds, and tertiary amineamide ester compounds is used as a starting material . Then, the tertiary amine is quaternized with a quaterni zing agent . It should be noted that wel l-known methods may be used for salt-exchange when a counter anion of the compound obtained by quaternization is a group other than the above-described anionic groups . In addition, when an anionic group of the quaternary ammonium salt obtained by quaternization or salt-exchange is a hydroxyl group, the hydroxyl group is neutralized with the above-described acidic compound HX and produced waterisdehydrated.
As a result, the hydroxyl group can be replaced with an anionic group derived from an organic carboxylic acid.
[0015) Examples of a tertiary amine compound which is a starting material include: alkyl tertiary amines such as trimethylamine, triethylamine, tripropylamine, tributylamine, triamylamine, trihexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, tridodecylamine, tritetradecylamine, trihexadecylamine, trioctadecylamine, trieicosylamine, tridocosylamine, tritetracosylamine, trihexacosylamine, trioctacosylamine, triacontylamine, monomethyldiethylamine, monomethyldibutylamine, monomethyldihexylamine, monomethyldioctylamine, monomethyldidecylamine, monomethyldidodecylamine, monomethylditetradecylamine, monomethyldihexadecylamine, monomethyldioctadecylamine, monomethyldieicosylamine, monomethyldidocosylamine, monomethylditetracosylamine, monomethyldihexacosylamine, monomethyldioctacosylamine, monomethyldiacontylamine, dimethylmonoethylamine, dimethylmonoethylamine, dimethylmonopropylamine, dimethylmonobutylamine, dimethylmonoamylamine, dimethylmonohexylamine, dimethylmonoheptylamine, dimethylmonooctylamine, dimethylmonononylamine, dimethylmonodecylamine, dimethylmonododecylamine, dimethylmonotetradecylamine, dimethylmonohexadecylamine, dimethylmonooctadecylamine, dimethylmonoeicosylamine, dimethylmonodocosylamine, dimethylmonotetracosylamine, dimethylmonohexacosylamine, dimethylmonooctacosylamine, and dimethylmonoacontylamine;
tertiary amines each having an alkenyl group such as triallylamine, tripropenylamine, triisopropenylamine, tributenylamine, triisobutenylamine, tripentenylamine, triisopentenylamine, trihexenylamine, triheptenylamine, trioctenylamine, trinonenylamine, tridecenylamine, tridodecenylamine, tritetradecenylamine, trioleylamine, monomethyldiallylamine, monomethyldipropenylamine, monomethyldiisopropenylamine, monomethyldibutenylamine, monomethyldiisobutenylamine, monomethyldipentenylamine, monomethyldiisopentenylamine, monomethyldihexenylamine, monomethyldiheptenylamine, monomethyldioctenylamine, monomethyldinonenylamine, monomethyldidecenylamine, monomethyldidodecenylamine, monomethylditetradecenylamine, monomethyldioleylamine, dimethylmonoallylamine, dimethylmonopropenylamine, dimethylmonoisopropenylamine, dimethylmonobutenylamine, dimethylmonoisobutenylamine, dimethylmonopentenylamine, dimethylmonoisopentenylamine, dimethylmonohexenylamine, dimethylmonoheptenylamine, dimethylmonooctenylamine, dimethylmonononenylamine, dimethylmonodecenylamine, dimethylmonododecenylamine, dimethylmonotetradecenylamine, and dimethylmonooleylamine; tertiary amines each having an aryl group such as triphenylamine, tritoluylamine, trixylylamine, tricumenylamine,tribenzylamine,tristyrylamine,tricinnamylamine, tribenzhydrylamine, triethylphenylamine, tripropylphenylamine, tributylphenylamine, trihexylphenylamine, trioctylphenylamine, trinonylphenylamine, tridecylphenylamine, tridodecylphenylamine, tristyrenated phenylamine, tri-p-curnylphenylamine, tribenzylphenylamine, tri-a-naphthylamine, tri-~-naphthylamine, monomethyldiphenylamine, monomethylditoluylamine, monomethyldixylylamine, monomethyldicumenylamine, monomethyldibenzylamine, monomethyldistyrylamine, monomethyldicinnamylamine, monomethyldibenzhydrylamine, monomethyldiethylphenylamine, monomethyldipropylphenylamine, monomethyldibutylphenylamine, monomethyldihexylphenylamine, monomethyldioctylphenylamine, monomethyldinonylphenylamine, monomethyldidecylphenylamine, monomethyldidodecylphenylamine, monomethyldistyrenated phenylamine, monomethyldi-p-cumylphenylamine, monomethyldibenzylphenylamine, monomethyldi-a-naphthylamine, monomethyldi-~-naphthylamine, dimethylmonophenylamine, dimethylmonotoluylamine, dimethylmonoxylylamine, dimethylmonocumenylamine, dimethylmonobenzylamine, dimethylmonostyrylamine, dimethylmonocinnamylamine, dimethylmonobenzhydrylamine, dimethylmonoethylphenylamine, dimethylmonopropylphenylamine, dimethylmonobutylphenylamine, dimethylmonohexylphenylamine, dimethylmonooctylphenylamine, dimethylmonononylphenylamine, dimethylmonodecylphenylamine, dimethylmonododecylphenylamine, dimethylmonostyrenated phenylamine, dimethylmono-p-cumylphenylamine, dimethylmonobenzylphenylamine, dimethylmono-a-naphthylamine, and dimethylmono-(3-naphthylamine;
and tertiary amines derived from a raw material aliphatic acid obtained from natural oils and fats such as vegetable oils, for example, a linseed oil, olive oil, cacao oil, sesame oil, rice bran oil, safflower oil, soybean oil, camellia oil, corn oil, rapeseed oil, palm oil, palm kernel oil, castor oil, sunflower oil, cotton oil, and coconut oil and animal oils and fats, for example, beef tallow, lard, milk fat, fish oil, and whale oil.
[0016) A tertiary amineamide compound which is a starting material can be manufactured by the following method. An amine compound such as : triamine having two primary amine groups and one secondary amine group such as diethylenetriamine, dipropylenetriamine, or ethylenepropylenetriamine; a triamine having two primary amine groups and one tertiary amine group such as bis(3-aminopropyl)methylamine, bis(3-aminopropyl)ethylamine, bis(3-aminopropyl)propylamine, bis(3-aminopropyl)butylamine, or bis(3-arninopropyl)benzylamine;oradiamine having one primaryamine group such as N,N-dimethylethylenediamine, N,N-diethylethylenediamine, N,N-dipropylethylenediamine, N,N-dibutylethylenediamine, N,N-dimethylpropylenediamine, N,N-diethylpropylenediamine, N,N-dipropylpropylenediamine, or N,N-dibutylpropylenediamineisallowed to react with aliphaticacid, aliphatic acid chloride, or aliphatic acid ester to amidate a primary amine group of the amine compound. As a result, an amineamide compound is obtained. When the obtained compound is a secondary amineamide compound, the secondary amine group can be tertiarized with halogenated hydrocarbon, dialkylsulfate, or thelike to thereby obtain a tertiary amineamide compound.
[0017]
Examples of a tertiary amine ester compound which is a starting material include tertiary alkanolamines such as triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, N-propyldiethanolamine, N-isopropyldiethanolamine, N-butyldiethanolamine, N,N-dimethylethanolamine, N,N-diethylethanolamine, N,N-dipropylethanolamine, N,N-dibutylethanolamine, N-cyclohexyldiethanolamine, N-benzyldiethanolamine, tripropanolamine, triisopropanolamine, N-cyclohexyldiisopropanolamine, N-benzyldiisopropanolamine, and tributanolamine.
In addition, the tertiary amine ester compound can also be obtained as follows. A primary alkanolamine or secondary alkanolamine such as monoethanolamine, diethanolamine, N-methylethanolamine, N-ethylethanolamine, N-propylethanolamine, N-isopropylethanolamine, N-butylethanolamine, N-cyclohexylethanolamine, N-benzylethanolamine, monopropanolamine, dipropanolamine, monoisopropanolamine, diisopropanolamine, N-cyclohexylisopropanolamine, N-benzylisopropanolamine, monobu~tanolamine, or dibutanolamine is tertiarized with halogenated hydrocarbon, dialkylsulfate, or the like. After that, the resultant is allowed to react with aliphatic acid, aliphatic acid chloride, or aliphatic acid ester to esterify a hydroxyl group of the amine compound.
[0018]
A tertiary amineamide ester compound which is a starting material can be manufactured by the following method. An alcanoldiamine such as N-methanolethylenediamine, N-ethanolethylenediamine, N-propanolethylenediamine, N-butanolethylenediamine, N,N-dimethanolethylenediamine, N,N-diethanolethylenediamine, N,N-dipropanolethylenediamine, N,N-dibutanolethylenediamine, N-methanolpropylenediamine, N-ethanolpropylenediamine, N-propanolpropylenediamine, N-butanolpropylenediamine, N,N-dimethanolpropylenediamine, N,N-diethanolpropylenediamine, N,N-dipropanolpropylenediamine, or N,N-dibutanolpropylenediamineisallowedto react with aliphatic acid, aliphatic acid chloride, or aliphatic acid ester. Then, a primary amine group and a hydroxyl group of the alcanoldiamine are subjected to an amidation reaction and an esterification reaction.
As a result, an amineamide ester compound can be obtained. When the obtained compound is a secondary amineamide ester compound, the secondary amine group can be tertiarized with halogenated hydrocarbon, dialkylsulfate, or the like to thereby obtain a tertiary amineamide ester compound.
[0019]
Examples of an aliphatic acid to be used in the amidation of a primary amine group or in the amidation and esterification of a primary amine group and a hydroxyl group include formic acid, acetic acid, propionic acid, butanoic acid (butyric acid) , pentanoic acid (valeric acid), isopentanoic acid (isovaleric acid), hexanoic acid (capronic acid), heptanoic acid, isoheptanoic acid, octanoic acid (caprylic acid), 2-ethylhexanoic acid, isooctanoic acid, nonanoic acid (pelargonic acid), isononanoic acid, decanoic acid (capric acid), isodecanoic acid, undecanoic acid, isoundecanoic acid,dodecanoic acid(lauricacid),isododecanoic acid,tridecanoic acid, isotridecanoic acid, tetradecanoic acid (myristic acid), hexadecanoic acid(palmiticacid),octadecanoic acid(stearic acid), isostearic acid, eicosanoic acid (arachic acid), docosanoic acid (behenic acid), tetracosanoic acid (lignoceric acid), hexacosanoic acid (cerotic acid), octacosanoic acid (montanic acid), 10-undecenoic acid, zoomaric acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, gadoleic acid, erucic acid, and selacholeic acid. Mixed aliphatic acids producedfrom naturalfats and oils are also available. Examples of the natural fats and oils include: vegetable fats and oils such as linseed oil, perilla oil, oiticica oil, olive oil, cacao oil, kapok oil, white mustard oil, sesame oil, rice bran oil, safflower oil, shea nut oil, china wood oil, soybean oil, tea oil, camellia oil, corn oil, rapeseed oil, palm oil, palm kernel oil, castor oil, sunflower oil, cottonseed oil, coconut oil, haze wax, and peanut oil; and animal fats and oils such as horse tallow, beef tallow, hoof oil, ghee, lard, goat tallow, mutton tallow, milk fat, fish oil, and whale oil.
~0020~
A known method can be used as a reaction method for quaternarization. Generally,the methodinvolves:loading tertiary amine into an autoclave; adding a quaternarizing agent at 60°C to 200°C; and aging the resultant till the completion of a reaction.
Pressurization may be performed in an inert gas such as nitrogen or helium with a view to increasing a reaction velocity or a reaction rate. The amount of the quaternarizing agent to be added is 1.0 to 9.0 mol, preferably 1.1 to 2.5 mol, or more preferably 1.1 to 1.8 mol with respect to 1 mol of the tertiary amine. An excessively small amount of the quaternarizing agent to be added may fail to complete the reaction. An excessively large amount of the quaternarizing agent to be added may cause a large amount of an unreacted quaternarizing agent to remain to have an adverse effect on an environment such as the release of the agent to the atmosphere.
[0021]
Examples of a quaternarizing agent to be used for quaternarization include: organic halides such as methyl chloride, benzylchloride,cyclohexylchloride,methylbromide,benzylbromide, and cyclohexyl bromide; dialkyl sulfates such as dimethyl sulfate and diethyl sulfate; dialkyl carbonates such as dimethyl carbonate and diethyl carbonate; and trialkyl phosphates such as trimethyl phosphate and triethyl phosphate. Of those, methyl chloride and dimethyl carbonate are preferably used because of easy availability of raw materials for them and their ease of handling.
[0022]
Known methods can be used as a method for salt-exchange without any limitation. Examples of such amethod include: amethod involving synthesizing quaternary ammonium hydroxide from a quaternary ammonium halide salt, which is obtained by reacting a tertiary amine and an alkyl halide, by means of an electrolytic method (JP 45-28569 B), an ion-exchange resin method (JP 52-3009 A), or the like, neutralizing the quaternary ammonium hydroxide with an acid compound HX, and removing produced water; and a method involving reacting a quaternary ammonium halide salt and an inorganic alkali such as sodium hydroxide or potassium hydroxide, removing the produced inorganic salt to provide quaternary ammonium hydroxide, and neutralizing the quaternary ammonium hydroxide with an acid compound HX.
[0023]
Meanwhile, an organic solvent can be used in a quaternarization reaction and a salt-exchange reaction as long as the solvent does not inhibit any one of the reactions. The organic solvent that can be used in the reactions is not particularly limited. Specific examples of such solvent include: aliphatic, alicyclic, aromatic, and heterocyclic compounds, or a mixture of them; and general lubricating oil. More specific examples of such solvent include:
alkanessuch aspentane,hexane,heptane,cyclopentane,cyclohexane, ligroin, and petroleum ether; alcohols such as methanol, ethanol, propanol, 2-propanol, butanol, 2-butanol, pentanol, hexanol, heptanol, octanol, and2-ethylhexanol;alkyletherssuch asdimethyl ether, ethylmethyl ether, diethyl ether, methyl isobutyl ether, and ethyl isopropyl ether; ketones such as acetone, ethyl methyl ketone, and methyl isobutyl ketone; aromatic compounds such as benzene, toluene, xylene, and ethylbenzene; synthetic oils such as poly-a-olefin, an ethylene-a-olefin copolymer, polybutene, an alkylbenzene, an alkylnaphthalene, polyalkylene glycol, polyphenyl ether, an alkyl-substituted diphenyl ether, a polyol ester, a dibasic ester, silicone oil, and fluorinated oil; and paraffin-based mineral oil and naphthene-based mineral oil, or purified mineral oils obtained by purifying them. Of those, alkanes (such as hexane, heptane, and petroleum ether), alcohols (such as methanol, ethanol, propanol, and 2-propanol), aromatic compounds (such as benzene, toluene, and xylene), paraffin-based mineral oil, naphthene-based mineral oil, and the like are preferable from the viewpoints of thesolubilityand handleability ofareaction product. In addition, adding any one of those solvents is preferable for effectively removing by-products and impurities and for dissolving solid reaction products.
[0029]
The lubricating oil composition according to the present invention contains 0.1 to 100, or preferably 0.2 to 8% by mass of the above lubricating oil additive based on a base oil. Within the content range, cleaning performance such as sludge dispersibility or acid neutralizing property can be improved without any impairment of lubricity.
The base oil has only to be a base oil generally used in lubricating oil. Specific examples of the base oil include mineral oil, hydrocarbon-based synthetic oil, and a mixture of them. More specific examples of the base oil include: synthetic oils such as poly-a-olefin, ethylene-a-olefin copolymers, polybutene, alkylbenzene, alkylnaphthalene, polyalkylene glycol, polyphenyl ether, an alkyl-substituted diphenyl ether, polyol ester, dibasic ester, phosphate, phosphate, carbonate, silicone oil, and fluorinated oil; and paraffin-based mineral oil and naphthene-based mineral oil, or purified mineral oils obtained by purifying them.
[0025]
The lubricating oil composition of the present invention does not inhibit the addition of any known lubricating oil additive.
The composition may be added with, for example, antioxidants, organic molybdenum-based additives, extreme pressure agents, oiliness improvers, metal-based cleaning agents, dispersants, viscosity index improvers, pour depressants, rust inhibitors, corrosion inhibitors, or defoaming agents for an intended purpose.
[0026]
Examples of the antioxidant include a zinc dithiophosphate-based antioxidant, aphenol-based antioxidant, and an amine-based antioxidant . The preferable loading of any one of those antioxidants is 0.1 to 5o by mass based on the base oil.
[0027]
Examples of the organic molybdenum-based additive include:
oxymolybdenum dithiocarbamate sulfide; oxymolybdenum dithiophosphatesulfide; aliphatic molybdenumsalts; oxymolybdenum xanthate sulfide; reaction products between molybdenum trioxide and acid phosphate; reaction products between molybdenum trioxide and aliphatic diethanolamide; reaction productsbetween molybdenum trioxide and glycerin monoaliphatic acid ester; reaction products between succinimide, amide carboxylate, Mannich base, or a boride of any one of them and molybdenum trioxide; and reaction products between amine and a molybdenum compound having a pentavalent or hexavalent molybdenum atom. The preferable loading of any one of those organic molybdenum-based additives is 0.001 to 5o by mass based on the base oil.
[0028]
Examples of the extreme pressure agent include: sulfur-based compounds such as sulfurized fats and oils, olefin polysulfide, and dibenzyl sulfide; phosphor compounds such as monooctyl phosphate, tributyl phosphate, triphenyl phosphate, tributyl phosphate, and thiophosphate; and organometallic compounds such as metal thiophosphates, metal thiocarbamates, and acid metal phosphates.
The preferable loading of any one of those extreme pressure agents is 0.1 to 10o by mass based on the base oil.
[0029]
Examples of the oiliness improver include: higher alcohols such as oleyl alcohol and stearyl alcohol; aliphatic acids such as oleic acid and stearic acid; esters such as oleyl glycerin ester, lauryl glycerin ester, oleyl sorbitan ester, and oleyl trimethylolpropane ester; amides such as laurylamide, oleylamide, and stearylamide; amines such as laurylamine, oleylamine, and stearylamine; and ethers such as lauryl glycerin ether and oleyl glycerin ether. The preferable loading of any one of those oiliness improvers is 0.1 to 10o by mass based on the base oil.
[0030]
Examples of the metal-based cleaning agent include the sulfonates,phenates,salicylates,phosphonates,and perbasicsalts of calcium, magnesium, barium, and the like. The loading of any one of those metal-based cleaning agents is preferably small from the viewpoint of the alleviation of the load on the environment.
When the lubricating oil composition needs to have additional cleaning properties, the composition may be blended with 0 to 10 0, or preferably 0 to 5% by mass of any one of those metal-based cleaning agents based on the base oil.
[0031) Examples of the dispersant include succinimide, benzylamine, succinate, and boron-denatured products of them. The preferable loading of any one of those dispersants is 0. 5 to 10 o by mass based on the base oil.
[0032) Examples of the viscosity index improver include: polyalkyl methacrylate (having 1 to 18 carbon atoms) , alkyl acrylate (having 1 to 18 carbon atoms)/alkyl methacrylate (having 1 to 18 carbon atoms) copolymers; diethylaminoethyl methacrylate/alkyl methacrylate (having 1 to 18 carbon atoms) copolymers;
ethylene/alkyl methacrylate (having 1 to 18 carbon atoms) copolymers;polyisobutylene;polyalkylstyrene;ethylene/propylene copolymers; styrene/maleate copolymers; styrene/maleic acid amide copolymers; styrene/butadiene hydrogenated copolymers; and styrene/isoprene hydrogenated copolymers. Each of those viscosity index improvers has an average molecular weight of about 10,000 to l, 500, 000. The preferable loading of any one of those viscosity index improvers is 0.1 to 20o by mass based on the base oil.
[0033) Examples of the pour depressant include polyalkyl methacrylate, polyalkyl acrylate, polyalkylstyrene, and polyvinyl acetate. Each of those pour depressants has an average molecular weight of about 1, 000 to 100, D00. The preferable loading of any one of those pour depressants is 0.005 to 3o by mass based on the base oil.
[0034]
Examples of the rust inhibitor include: sodium nitrite;
oxidized paraffin waxcalciumsalts;oxidized paraffin wax magnesium salts; beef tallow aliphatic acid alkali metal salts, alkali earth metal salts, or amine salts; alkenyl succinic acid or alkenyl succinic acid half esters (in which an alkenyl group has a molecular weight of about 100 to 300); sorbitan monoesters; pentaerythritol monoesters;nonylphenolethoxylates;lanolin aliphatic acid esters;
and lanolin aliphatic acid calcium salts. The preferable loading of any one of those rust inhibitors is 0.01 to 5o by mass based on the base oil.
[0035) Examples of the corrosion inhibitor include benzotriazole, benzoimidazole, benzothiazole, and tetraalkylthiuram disulfide.
The preferable loading of any one of those corrosion inhibitors is 0.01 to 3o by mass based on the base oil.
[ 0036]
Examples of the defoaming agent include polydimethyl silicone, trifluoropropylmethyl silicone, colloidal silica, polyalkyl acrylate, polyalkyl methacrylate, alcohol ethoxy/propoxylate, aliphatic acid ethoxy/propoxylate, and sorbitan partial aliphatic acid ester. The preferable loading of any one of those defoaming agents is 0.001 to to by mass based on the base oil.
[0037]
The lubricating oil composition of the present invention can be suitably used in any one of automobile and industrial greases typified by internal combustion engine lubricating oil, driving system lubricating oil (such as manual transmission oil, differential gear oil, or automatic transmission oil), lubricating oil for metal working, and grease for constant velocity joints.
Of those, the composition can be suitably used in lubricating oil for internal combustion engines such as gasoline engines, diesel engines, or jet engines.
EXAMPLES
[0038]
~-iereinafter, the present invention will be described more specifically by way of examples. In the following examples, the term "o" means "o by mass" unless otherwise stated.
At first, a reference oil having the formulation shown below was prepared. Next, a lubrication oil composition of each of Examples 1 to 5 and Comparative Examples 1 to 5 was prepared by means of the following reference oil and each additive according to the formulation shown in Table 1 below. In each of Examples 1 to 5 and Comparative Examples 1 to 4, an additive was added in such a manner that the total base number of a lubricating oil composition would be 5 mgKOH/g.
<Base oil>
Mineral oil-based high-viscosity-index (VI) oil Dynamic viscosity 4 . 1 mmz/s (at 100°C) , 18. 3 mmz/s (at 40°C) , viscosity index (VI) - 126 [Reference oil formulation) Base oil 100 parts by mass Succinimide-based dispersant 5.0 parts by mass Phenol-based antioxidant 0.3 part by mass Amine-based antioxidant 0.3 part by mass Zinc dithiophosphate 1.0 part by mass [0039]
<Additive>
(A-1: product of the present invention) Dioleyl dimethyl ammonium bicarbonate Base number: 92 mgKOH/g Metal component: Oo (A-2: product of the present invention) Dioleyl dimethyl ammonium propionate Base number: 90 mgKOH/g Metal component: Oo (A-3: product of the present invention) Tridecyl monomethyl ammonium bicarbonate Base number: 93 mgKOH/g Metal component: Oo (A-4: product of the present invention) [0040) [Chemical formula 2]
I I
HC03 H3C~N~C2H4 0'C-Cl~Hs3 H3C C2H4 -0-~-CoH3a Base number: 77 mgKOH/g Metal component: Oo (A-5: product of the present invention) [0041) [Chemical formula 3) HsCv ~iC2Ha N-~'C12H25 H3C C2H4--~ ~ ~12H25 Base number: 95 mgKOH/g Metal component: Oo (B-1: product of comparative example) Calcium sulfonate Base number: 300 mgKOH/g Metal component: 12.60 (B-2: product of comparative example) Calcium sulfonate Base number: 100 mgKOH/g Metal component: 4.30 (B-3: product of comparative example) Magnesium salicylate Base number: 200 mgKOH/g Metal component: 3.10 (B-4: product of comparative example) Dioleyl dimonomethyl amine Base number: 105 mgKOH/g Metal component: Oo (B-5: product of comparative example) Dioleyl dimethyl ammonium chloride Base number: 0 mgKOH/g Metal component: Oo [0042].
<Test of sample oil for oxidation stability>
In conformance with JIS K-2514 (lubricating oil-oxidation stability testing method), 250 ml of a sample were placed into a glass vessel having incorporated therein a copper plate and an iron plate as catalysts, and the whole was heated at 165.5°C for one week while the sample was stirred at 1,300 rpm in such a manner that air would be involved. The dynamic viscosity (40°C) and total base number of a lubricating oil composition were measured before and after the test . A difference in dynamic viscosity was determined from the dynamic viscosity before the test and the dynamic viscosity after the test. The amount of a reduction in total base number was determined from the total base number before the test and the total base number after the test. The lubricating oil composition after the test was filtered, washed with toluene, and dried. Then, the amount of produced sludge was measured.
Oxidation stability is higher as a difference between the dynamic viscosity before the test and the dynamic viscosity after the test is smaller and the amount of a reduction in total base number is smaller. The corrosion of a metal is reduced and dispersibility is higher as the amount of produced sludge is smaller.
Table 1 shows the results.
.-. 0 0 ~ N O
L~ O O O O O O l0 I~ N O O
O
~1a N . lq f1~
~
'' ,~ r-i O
U
N N r-100 h M I~ ri N ri M V' +~
is ~'N M Ol O l0 N ~ N N
~
TS M ~ M M ~' M ~' ~' ~t~~ O
~
~
N O O O O O O O O r-I N
c!~ O O O O O O O O O O O
r0 4-i O
O
'-1 f~ ,~ ~-~IX17r1 01 M ~ N
01 O O O Ol Ol O O
~ I . . . . . . . . ' I
U
r1 N N N ~ ~ N N
n N
~
Z
T
a~
x (>) y -I c-I N ,-IO ~' O OJ
O
~ O ri O O O r1 O O Ol O O
.Q +~
b~ v v v M M M M M M M N
b O
H
S-I l0~ N M lfl~-I ~C7M l0 N t~
O O O O O O O O r-i Ol y~
N O ~ ~ ~ ~ ~ ~ ~ ~ ~ O
N
U
f~a1 ~ ~ ~ L9 u~ oo ~ o ao 0 0 0 0 0 0 o O ~ t~
-.~w ~
u~ ''-I
U
p f~
a U
O
.,1 ~ OOlflt~ V~ oW -1 O O e1~M N
N
U W n ~ ~ tm o r ~ o o~ .-I ao v -'-I4-I ~ l0 l~ l0 lfllfl l9 I~ l0 l9 N
r, S-I ~ ~ M 4D N f ~ 00 r-1M O
p 4-~ O t~ OJ (~ I~ (~ Ol O O ~ l0 l0l0 t0 l0 l0 l0 l0 I~ I~ lfl l0 P~l N
5 _ _ _ _ _ _ _ _ _ ~ _ N M ~' ~
o t ~-IN M V' N '-IO O 00 O
~' ~ M N ! M ! ! ! 1 I I
ov I I I ~ r~ !Y1f~q f~ C~ fr) .O r.>;~ ~ u7 V r-I~' N M
~r v~ ~
~--IN M ~ ~ rl N M
M .-1 p ~ O N
p .-1 N -r1 U
N t<3 U
N ~ S1 ~
H w r0 ~
tb m x o x fxW U
W
3~
* The term "additive ( o) " represents an addition ratio of an additive to the reference oil.
* A metal component shown is derived from a cleaning agent.
* The difference in total base number of each of the reference oil and B-5 is not written because the total base number of each of them before the test is about 1 and the total base number of each of them after the test is equal to or less than 0.
[0044]
As is apparent from Table 1, the lubricating oil composition of the present invention had a difference in dynamic viscosity of 0.4 to 0.9 mm2/S and an amount of a reduction in total base number of 1.91 to 2.05 mgKOH/g. That is, the composition showed excellent oxidation stability. In addition, the composition had a sludge amount of 0.0338 to 0.0421 g. That is, the composition showed excellent sludge dispersibility. Tn addition, the composition was comparable to or better than any one of the lubricating oil compositionswiththe conventionalmetal-based cleaning agentsadded (B-1 to B-3) in terms of all of a difference in dynamic viscosity, a sludge amount, and the amount of a reduction in total base number.
Furthermore, the lubricating oil composition of the present invention does not reduce the exhaust gas clarifying performance of an exhaust gas catalyst or the particulate matter removing performance of a diesel particulate filter even when the composition is used in internal combustion engine lubricating oiI because the composition does not contain any metal components derived from a cleaning agent.
In contrast, each of the lubricating oil compositions of Comparative Example 4 added with the tertiary amine compound (B-4 ) having a base number of 205 mgKOH/g and the lubricating oil composition of Comparative Example 5 added with the quaternary ammonium salt (B-5) having a base number of 0 mgKOH/g was poor in oxidation stability and sludge dispersibility.
Claims (5)
- [1] A lubricating oil additive comprising a quaternary ammonium salt having a base number of at least 10 mgKOH/g.
- [2] A lubricating oil additive according to Claim 1, wherein the quaternary ammonium salt is represented by the following general formula (1) where R1 to R4 each independently represent a hydrocarbon group having 1 to 30 carbon atoms, -R9O-CO-R10, or -R11NH-CO-R12 (provided that at least one of R1 to R9 represents a hydrocarbon group having 1 to 30 carbon atoms), R9 and R11 each represent a hydrocarbon group having 1 to 4 carbon atoms, R10 and R12 each represent a hydrocarbon group having 1 to 30 carbon atoms or a hydrogen atom, and X- represents an anionic group.
- [3] A lubricating oil additive according to Claim 1 or 2, wherein X is selected from the group consisting of anionic groups derived from carbonic acid, a carbonate, boric acid and an organic carboxylic acid, and a hydroxyl group.
- [4] A lubricating oil additive according to any one of Claims 1 to 3, which is used for internal combustion engine lubricating oil or for driving system lubricating oil.
- [5] A lubricating oil composition comprising 0.1 to 10% by mass of the lubricating oil additive according to any one of Claims 1 to 4 based on a base oil.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004024309A JP4594626B2 (en) | 2004-01-30 | 2004-01-30 | Lubricating oil composition for internal combustion engine lubricating oil or drive system lubricating oil |
JP2004-024309 | 2004-01-30 | ||
PCT/JP2005/000913 WO2005073351A1 (en) | 2004-01-30 | 2005-01-25 | Lubricating oil additive and lubricating oil composition containing same |
Publications (1)
Publication Number | Publication Date |
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CA2552671A1 true CA2552671A1 (en) | 2005-08-11 |
Family
ID=34823927
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA002552671A Abandoned CA2552671A1 (en) | 2004-01-30 | 2005-01-25 | Lubricating oil additive and lubricating oil composition containing same |
Country Status (5)
Country | Link |
---|---|
US (1) | US20070155636A1 (en) |
EP (1) | EP1717298A4 (en) |
JP (1) | JP4594626B2 (en) |
CA (1) | CA2552671A1 (en) |
WO (1) | WO2005073351A1 (en) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
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JP4927349B2 (en) * | 2005-05-11 | 2012-05-09 | 出光興産株式会社 | Refrigerator oil composition, compressor and refrigeration apparatus using the same |
BRPI0711265A2 (en) * | 2006-05-03 | 2011-08-30 | Shell Int Research | lube oil composition, deposit reduction method in an internal combustion engine, and use of a lube oil composition |
EP1970432A1 (en) * | 2006-12-19 | 2008-09-17 | Castrol Limited | Lubricating oil compositions and uses |
JP2010053352A (en) * | 2008-07-31 | 2010-03-11 | Sanyo Chem Ind Ltd | Lubricating oil additive and lubricating oil composition |
SG176084A1 (en) | 2009-05-15 | 2011-12-29 | Lubrizol Corp | Quaternary ammonium amide and/or ester salts |
US20120010112A1 (en) | 2010-07-06 | 2012-01-12 | Basf Se | Acid-free quaternized nitrogen compounds and use thereof as additives in fuels and lubricants |
JP5808775B2 (en) * | 2013-07-05 | 2015-11-10 | 株式会社椿本チエイン | Lubricant composition for chain and chain |
US9677020B2 (en) | 2014-06-25 | 2017-06-13 | Afton Chemical Corporation | Hydrocarbyl soluble quaternary ammonium carboxylates and fuel compositions containing them |
US10358616B2 (en) | 2015-04-09 | 2019-07-23 | The Lubrizol Corporation | Lubricants containing quaternary ammonium compounds |
CA2993016A1 (en) * | 2015-07-20 | 2017-03-09 | The Lubrizol Corporation | Zinc-free lubricating composition |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2344886A (en) * | 1941-01-02 | 1944-03-21 | Standard Oil Dev Co | Lubricant composition |
US2820006A (en) * | 1953-03-02 | 1958-01-14 | Shell Dev | Process for the preparation of grease compositions |
GB1445993A (en) * | 1973-06-27 | 1976-08-11 | Exxon Research Engineering Co | Lubricating oil compositions |
US4253980A (en) * | 1979-06-28 | 1981-03-03 | Texaco Inc. | Quaternary ammonium salt of ester-lactone and hydrocarbon oil containing same |
JPS5966575A (en) * | 1982-10-06 | 1984-04-16 | 帝人株式会社 | Spinning oil composition for polyestr fiber |
JPS59227982A (en) * | 1983-06-10 | 1984-12-21 | Kao Corp | Metal working oil composition |
GB8712442D0 (en) * | 1987-05-27 | 1987-07-01 | Exxon Chemical Patents Inc | Diesel fuel composition |
US5486316A (en) * | 1987-06-01 | 1996-01-23 | Henkel Corporation | Aqueous lubricant and surface conditioner for formed metal surfaces |
US4902437A (en) * | 1987-12-09 | 1990-02-20 | Exxon Research And Engineering Company | Engine lubricating oil comprising a quaternary ammonium hydroxide |
US5124054A (en) * | 1988-12-29 | 1992-06-23 | Exxon Research And Engineering Company | Method of improving the thermal stability of quaternary ammonium hydroxides (PNE-539) |
US5264082A (en) * | 1992-04-09 | 1993-11-23 | Procter & Gamble Company | Soft absorbent tissue paper containing a biodegradable quaternized amine-ester softening compound and a permanent wet strength resin |
TW269709B (en) * | 1992-07-08 | 1996-02-01 | Lubrizol Corp | |
JPH07305083A (en) * | 1994-05-10 | 1995-11-21 | Hitachi Ltd | Lubricating oil composition and operating medium containing the same composition |
JPH10195476A (en) * | 1996-11-15 | 1998-07-28 | Lion Corp | Low foaming frictional resistance reducing agent for aqueous medium and reduction in fictional resistance for aqueous medium using the same |
JP3126339B2 (en) * | 1997-12-29 | 2001-01-22 | 三洋化成工業株式会社 | Sterilizable conveyor lubricant for container transport |
JP3126338B2 (en) * | 1997-12-29 | 2001-01-22 | 三洋化成工業株式会社 | Sterilizable conveyor lubricant for container transport |
-
2004
- 2004-01-30 JP JP2004024309A patent/JP4594626B2/en not_active Expired - Fee Related
-
2005
- 2005-01-25 EP EP05709314A patent/EP1717298A4/en not_active Withdrawn
- 2005-01-25 WO PCT/JP2005/000913 patent/WO2005073351A1/en not_active Application Discontinuation
- 2005-01-25 CA CA002552671A patent/CA2552671A1/en not_active Abandoned
- 2005-01-25 US US10/587,020 patent/US20070155636A1/en not_active Abandoned
Also Published As
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JP2005213452A (en) | 2005-08-11 |
EP1717298A4 (en) | 2012-07-11 |
US20070155636A1 (en) | 2007-07-05 |
WO2005073351A1 (en) | 2005-08-11 |
EP1717298A1 (en) | 2006-11-02 |
JP4594626B2 (en) | 2010-12-08 |
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