CN101343591B - Lubricating oils having improved friction stability - Google Patents
Lubricating oils having improved friction stability Download PDFInfo
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- CN101343591B CN101343591B CN2008101319413A CN200810131941A CN101343591B CN 101343591 B CN101343591 B CN 101343591B CN 2008101319413 A CN2008101319413 A CN 2008101319413A CN 200810131941 A CN200810131941 A CN 200810131941A CN 101343591 B CN101343591 B CN 101343591B
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- China
- Prior art keywords
- friction
- oil
- alkyl
- friction modifiers
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000010687 lubricating oil Substances 0.000 title claims abstract description 35
- 239000003921 oil Substances 0.000 claims abstract description 59
- 239000003607 modifier Substances 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 41
- 229920000768 polyamine Polymers 0.000 claims abstract description 33
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 28
- 229920001281 polyalkylene Polymers 0.000 claims abstract description 13
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 230000005540 biological transmission Effects 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 26
- 239000000654 additive Substances 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 20
- 230000010933 acylation Effects 0.000 claims description 14
- 238000005917 acylation reaction Methods 0.000 claims description 14
- 230000000996 additive effect Effects 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000002199 base oil Substances 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 230000001050 lubricating effect Effects 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 125000005466 alkylenyl group Chemical group 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 15
- 239000011574 phosphorus Substances 0.000 abstract description 15
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001408 amides Chemical class 0.000 abstract description 4
- -1 phosphorus compound Chemical class 0.000 description 53
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 239000000463 material Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 18
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 16
- 239000002585 base Substances 0.000 description 15
- 230000008878 coupling Effects 0.000 description 13
- 238000010168 coupling process Methods 0.000 description 13
- 238000005859 coupling reaction Methods 0.000 description 13
- 239000012530 fluid Substances 0.000 description 13
- 238000006317 isomerization reaction Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 229960002317 succinimide Drugs 0.000 description 10
- 125000002769 thiazolinyl group Chemical group 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000002480 mineral oil Substances 0.000 description 8
- 235000010446 mineral oil Nutrition 0.000 description 8
- 238000010926 purge Methods 0.000 description 8
- 229940014800 succinic anhydride Drugs 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 230000004087 circulation Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 0 *C(CC(N1*)=O)C1=O Chemical compound *C(CC(N1*)=O)C1=O 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 5
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 5
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 4
- RJWUMFHQJJBBOD-UHFFFAOYSA-N 2-methylheptadecane Chemical compound CCCCCCCCCCCCCCCC(C)C RJWUMFHQJJBBOD-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- UZEFVQBWJSFOFE-UHFFFAOYSA-N dibutyl hydrogen phosphite Chemical class CCCCOP(O)OCCCC UZEFVQBWJSFOFE-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- CIRMGZKUSBCWRL-LHLOQNFPSA-N (e)-10-[2-(7-carboxyheptyl)-5,6-dihexylcyclohex-3-en-1-yl]dec-9-enoic acid Chemical compound CCCCCCC1C=CC(CCCCCCCC(O)=O)C(\C=C\CCCCCCCC(O)=O)C1CCCCCC CIRMGZKUSBCWRL-LHLOQNFPSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- LEEDMQGKBNGPDN-UHFFFAOYSA-N 2-methylnonadecane Chemical compound CCCCCCCCCCCCCCCCCC(C)C LEEDMQGKBNGPDN-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000010696 ester oil Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
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- 150000004665 fatty acids Chemical class 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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- 150000003141 primary amines Chemical group 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
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- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000010909 process residue Substances 0.000 description 1
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- 230000035807 sensation Effects 0.000 description 1
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- 238000010008 shearing Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
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- 239000011275 tar sand Substances 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 230000003685 thermal hair damage Effects 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/048—Mixtures of base-materials and additives the additives being a mixture of compounds of unknown or incompletely defined constitution, non-macromolecular and macromolecular compounds
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- 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
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/12—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/14—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds a condensation reaction being involved
- C10M149/22—Polyamines
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
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- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/086—Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
- C10M2215/224—Imidazoles
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/28—Amides; Imides
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- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbased sulfonic acid salts
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/106—Thiadiazoles
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/049—Phosphite
-
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/045—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for continuous variable transmission [CVT]
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
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- Chemical & Material Sciences (AREA)
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Abstract
Lubricating oil compositions having excellent friction stability comprise a base lubricating oil, an oil soluble source of phosphorus and a defined polyalkylene polyamine-based friction modifier that has been reacted with an acylating agent to convert at least one secondary amine group into an amide.
Description
The present invention relates to compositions of additives, described composition can be lubricating oil splendid friction stability is provided, especially to picture automatic transmission fluid (hereinafter referred to as " ATF "), continuously variable transmission fluid (" CVTF "), with double-clutch automatic transmission liquid (" DCTF ") homenergic transmission fluid, more particularly, described composition can be liquid carrying for splendid nature of friction when clutch coupling at a high speed engages.
The present invention comprises on the other hand makes this kind lubricating oil have the method for friction stability, comprises the compositions of additives that uses in the lubricating oil, with the improvement friction stability, and other aspects as described below.
The transmission mechanism that the present invention is suitable for refers to that those contain the transmission mechanism of the lubricated humid clutch that uses under the high-energy Dissipative condition.The device of these types comprises the clutch coupling that is used for ratio or speed change on the automatic driver; At automatic driver, vari-speed drive, or the wet starting clutch in the double clutch transmissions; Or be used in clutch coupling on torque orientation (torque vectoring) or the shaft space difference speed.The characteristics of these clutch couplinges are that very high velocity contrast is arranged between the two elements of clutch coupling, and " joint " of clutch coupling (engagement) or " locking " (lock up) very high waste of energy is arranged.
Therefore, another aspect of the present invention also relates to energy driver, described device contains by transmission ofenergy liquid of the present invention lubricated veneer or multi-plate clutch device, wherein clutch coupling uses under the high-energy condition, namely about 500rpm (rpm) more than speed engage, particularly engage in the speed greater than 500rpm.
Automaker's common objective all is to produce the automobile of more durable within its working life and more reliable performance.The weather resistance that improves and reliability are to produce to need as far as possible few automobile of repairing within working life on the one hand.Second aspect is automobile to be showed stablize in its whole " life-span " process.For automatic driver, transmission mechanism does not only have fault within the life-span of automobile, and its gear shift character does not occur significantly to change during this period yet.Because the gear shift character of automatic driver depends on the rubbing characteristics of ATF to a great extent, so As time goes on liquid need with the increase of mileage very stable frictional behaviour to be arranged.This performance of ATF is exactly friction stability.Present many automakers turn to the automatic transmission fluid of " using throughout one's life "; This trend has further increased the needs to the ATF friction stability, because will no longer change liquid 15,000 to 50,000 miles service intervals in the time.
The method that is commonly used to measure ATF friction weather resistance is to use SAE#2 friction testing instrument.This instrument is by making its energy that absorbs specified quantitative come the high velocity engagement of simulated clutch with clutch coupling as brake.System capacity is equal to clutch coupling and finishes the energy that once conversion absorbs in the automobilism of reality.This machine uses specific bonding speed, 3600rpm normally, the inertia that calculates to test clutch coupling and liquid carrying for required energy.Clutch coupling lubricates with evaluated liquid, and each deceleration of system (i.e. brake) is defined as a circulation.Assess friction stability by continuous a plurality of circulations.OEM (OEM) to hammering at of friction stability impel to show the good circulation sum of friction weather resistance from the hundreds of in the 1980's bring up to present some standards 10,000 or even higher.Specific examples is referring to Ford MERCON
V automatic transmission fluid service standard.
Estimate improved friction weather resistance two kinds of methods are arranged.The first is to keep specific rubbing characteristics in the longer time cycle (i.e. more circulations).The second is to allow each friction parameter that less variation occurs in through the process of same loop number.Two kinds of methods illustrate that all the gear shift character of automobile can keep constant in long mileage.
ATF, the friction control in CVTF or the DCTF homenergic transmission fluid is the major function of friction modifiers in the liquid.Yet, be used in the degraded that the suffered heat of liquid in the transmission mechanism and oxidative stress can cause additive, therefore can cause the change of liquid property.The oxidation of friction modifiers or cause thermal damage at first show as the rising of stiction in the liquid usually.The stiction rising can cause stiff gearshift, and when whole gearshift was finished, the people in the automobile had the sensation of jolting or tilting.It is the common form that transmission ofenergy liquid lost efficacy that stiction rises.Yet in some cases, the oxidation of friction modifiers can convert them to active higher form.In these situations, stiction was actually and can reduces in the maintenance period.Although the reduction of stiction is not the problem that owner is concerned about usually, it can reduce the hold facility (holding capacity) of clutch coupling in the transmission mechanism.The reduction of hold facility then can cause clutch coupling in high loading lower slip such as traction or quick acceleration, thereby this can make their that overheated ultimate failure occurs easily.Therefore best transmission ofenergy liquid has the stiction level that in use can keep well stabilizer pole.
Usually, there is dual mode can improve transmission ofenergy liquid friction stability.First kind of way is by increasing the content of friction modifiers in the liquid.Although the reserves that improve friction modifiers in oil can be obtained the effect of the improvement friction stability of expection, but the increase of friction modified agent content has but brought the undesirable side effect of people, and the frictional coefficient (particularly static friction coefficient) that is about to liquid is reduced under the aspiration level.The second way is the oxidation-resistance of improving liquid with the oxidation suppressant additive by working in coordination with, particularly reduces the generation that can compete with friction modifiers the polarity oxidation products of friction surface.Therefore, the oxidation that reduces liquid might improve long-term friction control.
United States Patent (USP) the 5th, 750,476 and 5,840, disclosed antioxidant No. 662, the composition of oil soluble phosphorus compound and special low effect friction modifiers can provide outstanding friction weather resistance for ATF.In case the characteristics of these low effect friction modifiers are that the concentration of friction modifiers reaches capacity in the liquid, continue to increase its concentration and can not further reduce the friction level of measuring before.Therefore, can come treatment liq increasing the reserves of additive in the oil with the low effect friction modifiers of this class of high density, and liquid still show satisfied friction level.Believe when the friction modified agent molecule of low effect is consumed by shearing or oxidation, on friction surface, also always have the friction modifiers of enough high densitys to substitute the part that consumes.Be used for preventing that the oil soluble P contained compound of system wear from also being necessary.
Yet this type of solution requires to use a large amount of additives certainly.This class solution need to more effectively utilize chemical resource and more economically.
Similarly, the extra demand of oxidation retarder caused more complicated prescription, development prospect and cost of use.
We have had been found that a class friction modifiers now; it is polyalkylene polyamine base friction modifiers; the acylations that partly goes up at least one secondary amino group by its polyamines obtains, and this friction modifiers has more high thermal stability and oxidative stability, and the ability of its control friction is not subjected to any loss.When having an above secondary amino group in the polyamines chain, secondary amino group carries out acylations can make it have particularly preferred stability to the great majority in the friction modifiers (all preferred).
This type of friction modifiers demonstrates the improvement character that surpasses existing approach, and it is for solving in the oil, and particularly the problem of friction weather resistance provides more economical approach in the transmission ofenergy liquid.
On the one hand; the present invention relates to lubricating oil (particularly transmission ofenergy liquid) composition; comprise the oil soluble P contained compound and with the polyalkylene polyamine base friction modifiers of at least one hydrocarbyl substituent; this hydrocarbyl substituent or each hydrocarbyl substituent contain 6 to 30 carbon atoms, and wherein at least one secondary amino group on the friction modifiers polyamines chain is changed into corresponding amide group by acyl group.
More specifically, the present invention relates to lubricating oil (particularly transmission ofenergy liquid) composition, comprising:
(a) account for the lubricating oil of main amount; With
(b) friction stability improves the compositions of additives of significant quantity, comprising:
(i) contain acylation agent R
3COX (R wherein
3Be alkyl, X is leavings group) be selected from compound (I), (II) and the friction modifiers of the reaction product of one or more compounds in the group (III), wherein (I), (II) He (III) structure is as follows:
Wherein:
R is C
6To C
30Alkyl or alkenyl; R
1The polyalkylene polyamine group shown in structure (IV):
N and m each integer of from 1 to 6 independently naturally respectively wherein; R
2Be the heteroatomic derivative that contains of alkyl or aryl or they, or be selected from following V, the structure shown in VI and the VII;
(ii) oil soluble P contained compound.
In the embodiment of back; structure I; the secondary nitrogen-atoms of on the structure I V among II and the III at least one (preferably each) respectively by being transformed into acid amides with the acylting agent reaction, obtains corresponding structure (VIII), (IX) and (X):
R wherein, R
1, R
2, R
3With n as defined above, wherein p+q=m (wherein m is as defined above) and p 〉=1.It is q=0 and p=m that yet choosing is arranged most.
In above all structures, R
3Preferred C
1To C
20Hydrocarbyl substituent, more preferably wherein a kind of in the heteroatomic analogue contained in alkyl or aryl or they.Even R
3More preferably C
1To C
10Alkyl or aryl, R
3C most preferably
1To C
6Alkyl or aryl, particularly methyl, ethyl, propyl group or butyl.
Other side of the present invention comprises itself, and polyalkylene polyamine base friction modifiers (b) is (i) as defined above; Contain the as defined above compositions of additives of friction modifiers and oil soluble P contained compound combination; For lubricating oil provides the method for friction stability, be included in and use the as defined above additive combination that friction stability is improved significant quantity in the lubricating oil; And the as defined above compositions of additives that uses significant quantity in lubricating oil is to improve its friction stability.
Other aspects of the present invention and embodiment specify by following description.
Embodiment
The method that the present invention relates to improve the lubricating oil friction stability and do not reduce the shortcoming of frictional coefficient.Described method is included in unites the self-defining polyalkylene polyamine friction modifiers in use source and oil-soluble phosphorus source in the oil.This combination of additive can be lubricating oil (especially transmission fluid) splendid friction stability is provided.
Although expectability benefit of the present invention is applicable to the lubricating oil (such as crankcase machine oil etc.) of various use friction modifiers, but it is transmission ofenergy liquid that particularly preferred composition divides, especially automatic transmission fluid (ATF), continuously variable transmission fluid (CVTF), and double-clutch automatic transmission liquid (DCTF).The example that comprises the transmission ofenergy liquid of other less preferred type within the scope of the present invention is gear oil, hydraulic efficiency oil, used with tractor oil, all-purpose tractor oil and analogue.These transmission ofenergy liquid can be by additive and the preparation of base oil structure of various additional properties.
Polyalkylene polyamine base friction modifiers of the present invention
The preferred friction modifiers of the present invention can be made by the succinimide with at least one hydrocarbyl substituent, and wherein this hydrocarbyl substituent or each hydrocarbyl substituent contain 6 to 30 carbon atoms, and preferably thiazolinyl or fully saturated alkyl analogue; Perhaps can be made by the carboxylic acid amides with at least one thiazolinyl or alkyl chain, described thiazolinyl or alkyl chain contain 6 to 30 carbon atoms, and have one or more structures that formed by corresponding thiazolinyl or alkyl carboxylic acid and polyalkylene polyamine reaction.
Most preferred friction modifiers type at first is by alkyl or alkenyl succinyl oxide and one or more polyalkylene polyamines, and preferably with one or more polyethylene polyamines reaction preparations, the alkyl or alkenyl substituting group on the described succinyl oxide is the isomery chain.In this type of preferred material, the isomery chain is combined with the alpha-carbon atom of succinimide ring, so that two substitution in side chain bases link to each other by tertiary carbon atom and the upper alpha-carbon atom of ring, and the alkenyl substituted structure of reacting with the polyethylene polyamines shown in the following structure for example:
Wherein x and y are respectively integers independently, and they and be to be from 1 to 10 integer from 1 to 25, z.
The preparation method of isomerization alkenyl succinic anhydride is well known, and is described in such as United States Patent (USP) the 3rd, 382, in No. 172.The common preparation method of these materials makes its pair key move on to interior location by alpha-olefin is heated under the condition that has an acidic catalyst to exist.The mixture of alkene (2-alkene, 3-alkene etc.) carries out thermal response with maleic anhydride subsequently.Usually use from C
6(1-hexene) is to C
30The alkene of (1-30 alkene).Suitable isomerization alkenyl succinic anhydride such as structure (I) comprises isodecyl succinyl oxide (x+y=5 in the following formula), Permethyl 99A. base succinyl oxide (x+y=7), different tetradecyl succinyl oxide (x+y=9), isocetyl succinyl oxide (x+y=11), isooctadecane base succinyl oxide (x+y=13), and Isoeicosane base succinyl oxide (x+y=15).Preferred isocetyl succinyl oxide and isooctadecane base succinyl oxide, they all demonstrate good performance.
All contain a two key (thiazolinyl) on the alkyl chain of the material for preparing by described technique.The succinyl oxide of alkenyl substituted can be easy to by being hydroconverted into its saturated alkyl analogue.
The succinyl oxide that isomerization thiazolinyl or isomerization alkyl replace can generate with suitable amine reaction the friction modifiers such as structure (I) shown type subsequently, and this friction modifiers can pass through R subsequently
3The acylations of COX forms friction modifiers of the present invention (b) (i).
Surrogate as isomerization thiazolinyl or isomerization alkyl succinic anhydride, also can select with the carboxylic acid of at least one thiazolinyl or alkyl chain and suitable amine reaction to generate such as structure (II) and (III) friction modifiers of shown type, described thiazolinyl or alkyl chain contain 6 to 30 carbon atoms.This type of acid preferably contains 12 to 22 carbon atoms, particularly contains the alkyl or alkenyl acid of 16 to 20 carbon atoms.Friction modifiers of the present invention passes through R subsequently
3The acylations of COX forms.
Be suitable for preparation such as structure (I), (II) with (III) shown in the amine of friction modifiers shown in structure (XI):
Wherein n and m are respectively from 1 to 6 integers independently, R
2As defined above.
And the amine shown in structure XI can make by the reaction of uncle's polyamines.In this type of amine useful especially a kind of be polyalkylene polyamine shown in general formula (XII), general formula (XII) is:
Wherein a is from 1 to 5 integer, preferably from 2 to 4; Each n is from 1 to 6 integer independently, preferably from 1 to 4.
The non-limiting example of suitable polyamine compounds comprises: diethylenetriamine, triethylene tetramine, tetraethylene pentamine, and five ethene hexamines.The low-cost polyamine mixture that per molecule contains 5 to 7 nitrogen-atoms can be the Polyamine H of Dow Chemical Co., Polyamine 400 and Polyamine E-300.
This class polyamines can be by reacting generating structure I with the succinyl oxide of above-mentioned alkenyl substituted or their complete saturated alkyl analogue; Perhaps generate II or III with above-mentioned thiazolinyl or alkyl carboxylic acid reaction.Generate or III.
The preferred friction modifiers of the present invention is usually by heating above-mentioned isomerized alkenyl succinic anhydride (or its saturated alkyl analogue) and above-mentioned polyamines, and the water of removing generation prepares.Yet also can use other known preparation method.The ratio of primary amine group and succinic anhydride group normally 1 to 1.Be in the situation of the diamines that stops with primary amine or polyamines at the molecule two ends, the amino at molecule two ends is all wished and the succinyl oxide reaction that replaces generates material shown in structure (XIII):
R wherein, a and n are as defined above.
Acylting agent of the present invention refers to secondary amine to be converted to those materials of acid amides.The general formula of this class material is R
3COX, wherein R
3Be alkyl, X is leavings group, described leavings group also can with the R of acylting agent
3Group connects to form ring structure.
R
3Preferably from C
1To C
20Hydrocarbyl substituent, the wherein a kind of of heteroatomic analogue contained in preferred alkyl or aryl or they.R
3More preferably from C
1To C
10Alkyl or aryl, R
3Most preferably from C
1To C
6Alkyl or aryl.Most preferred alkyl can be methyl, ethyl, propyl group or butyl.
Especially, acylting agent preferably uses diacetyl oxide, propionic anhydride, butyryl oxide, trifluoroacetic anhydride, Acetyl Chloride 98Min., propionyl chloride, butyryl bromide, butyrolactone, caprolactone, methyl acetate, ethyl acetate, butylacetate, butyl propionate, and butyl butyrate.Most preferably use diacetyl oxide.
The preferred anti-friction composition of the present invention be alkenyl succinic anhydride at first with polyamines (XI) reaction, make with acetic anhydride more subsequently.The most preferred product of the present invention be the isomerization alkenyl succinic anhydride at first with polyamines (XII) reaction, make with acetic anhydride more subsequently.
The most preferred friction modifiers of the present invention (b) structure (i) is as follows:
It can obtain by the reaction product of diethylenetriamine and essential isomerization octadecylene base succinyl oxide is carried out acylations.This material demonstrates splendid performance in the present invention.The friction modified agent addition agent and the described compound itself that contain described compound have all further embodied the present invention.
Although can use in the present invention the friction modifiers of any significant quantity, this friction modifiers is processed ratio (treat rate) and usually is about 0.1 to 10% of lubricating composition minute weight, and is preferred 0.5 to 7%, most preferably 1.0 to 5.0%.
Below provide the embodiment of the present invention typical case friction modifiers material preparation.The purpose of these embodiment is explanation, and the present invention is not subjected to the restriction of detail among the embodiment.
Preparation Example
Embodiment A (preparation of isomerization succinimide)
In one liter of round-bottomed flask that mechanical stirrer, nitrogen purging device, Dean-Stark separator and condenser have been installed, place the different octadecylene base succinyl oxide of 352gm (1.00 moles) (ODSA that DixieChemical Co. produces).Begin slowly nitrogen purging, start agitator and heat this material to 130 ℃.Subsequently, in the different octadecylene base succinyl oxide of heat agitated, slowly add 95gm (0.50 mole) commodity tetraethylene pentamine by dropping funnel immediately.Mixture is warming up to 150 ℃, and under this temperature, kept two hours.In heat-processed, collect 10mL water (be approximately theoretical yield 50%) by the Dean-Stark separator.The cooling flask is to obtain product.Output: 435gm.Nitrogen per-cent: 8.1.
Embodiment B (preparation of isomerization succinimide)
Except using following amount, use with embodiment A in identical step: different octadecylene base succinyl oxide, 700gm (2.0 moles), and diethylenetriamine 103gm (1.0 moles).Recycle-water 32mL.Output: 765gm.Nitrogen per-cent: 5.5.
Embodiment C (preparation of acylations isomerization succinimide of the present invention)
Place the product of 765gm (1.0 moles) Embodiment B in one liter of round-bottomed flask that mechanical stirrer, nitrogen purging device, Dean-Stark separator and condenser have been installed.Begin slowly nitrogen purging, start agitator and heat this material to 90 ℃.Drip 102gm (1.0 moles) diacetyl oxide by dropping funnel.Namely be warming up to 140 ℃ after being added dropwise to complete, and kept 3 hours.Under the condition of 150 ℃ and 50mmHg, remove remaining acetic acid by distillation.Output: 805gm.Nitrogen per-cent: 5.2.
Embodiment D (preparation of acylations isomerization succinimide of the present invention)
Except using following amount, use with Embodiment C in identical step: the product of Embodiment B, 765gm (1.0 moles); With caprolactone 131gm (1.15 moles).With mixture heating up to 170 ℃ and kept 6 hours, add subsequently the 2ml stannous octoate.Octylate adds and to be warming up to 180 ℃ and kept 4 hours after finishing.Output: 895gm.Nitrogen per-cent: 4.7.
Embodiment E (preparation of acylations isomerization succinimide of the present invention)
Place the product of 429gm (0.5 mole) embodiment A in one liter of round-bottomed flask that mechanical stirrer, nitrogen purging device, Dean-Stark separator and condenser have been installed.Begin slowly nitrogen purging, start agitator and heat this material to 90 ℃.Drip 61gm (0.5 mole) diacetyl oxide by dropping funnel.Namely be warming up to 140 ℃ after being added dropwise to complete, and kept 3 hours.Under the condition of 150 ℃ and 50mmHg, remove remaining acetic acid by distillation.Output: 485gm.Nitrogen per-cent: 7.1.
Embodiment F (preparation of the acylations product of Unimac 5680-TEPA)
In one liter of round-bottomed flask that mechanical stirrer, nitrogen purging device, Dean-Stark separator and condenser have been installed, place 402gm (1.37 moles) Unimac 5680.Begin slowly nitrogen purging, start agitator and heat this material to 100 ℃.In one hour, drip 130gm (0.69 mole) tetraethylene pentamine (TEPA) by dropping funnel.Add and namely to be warming up to 160 ℃ after finishing, and kept 6 hours, during this period recycle-water 24gm (theoretical 98%).Raw material is cooled to 100 ℃, and drips 71gm (0.69 mole) diacetyl oxide by dropping funnel.Namely be warming up to 140 ℃ after being added dropwise to complete, and kept 3 hours.Under the condition of 130 ℃ and 50mmHg, remove remaining acetic acid.Output: 560gm.Nitrogen per-cent: 8.8%.
The oil soluble P contained compound
On wide significance, can be used for oil soluble P contained compound of the present invention can in wide in range scope, select, and be not subject to chemical type.Unique restriction is that this material should be oil soluble, so that P contained compound disperses in lubricating oil system and is transported to its action site.The example of the phosphorus compound that is fit to is: phosphorous acid ester and thiophosphite (analogue of monoalkyl, two alkyl, trialkyl and its partial hydrolysis); Phosphoric acid ester and thiophosphatephosphorothioate; Amine through inorganic phosphorus (for example, phosphorous acid, phosphoric acid or their thip-analogues) processing; Dithio bisphosphate zinc; Phosphamide (amine phosphate).The example of particularly suitable phosphorus compound comprises: single normal-butyl H-Phosphonate (mono-n-butyl-hydrogen-acid-phosphite); Di-n-butyl H-Phosphonate (di-n-butyl-hydrogen phosphite); The triphenyl phosphorous acid ester; The triphenyl thiophosphite; Three normal-butyl phosphoric acid ester; Dimethyl octadecylene base phosphonic acid ester is through H
3PO
3And H
3BO
3900MW polyisobutenyl succinic anhydride (PIBSA) the polyamines dispersion agent (for example referring to United States Patent (USP) the 4th, 857, No. 214) of aftertreatment; Two (2-ethylhexyl) zinc dithiophosphate.
Preferred oil soluble phosphorus compound is the ester of phosphoric acid and phosphorous acid.These materials should comprise dialkyl group, trialkyl and triarylphosphite and phosphoric acid ester.The alkylthio phosphorous acid ester of preferred oil soluble phosphorus compound for mixing for example, lists in that United States Patent (USP) in this paper reference produces for the 5th, 314, No. 633.Most preferred phosphorus compound is the alkylthio phosphorous acid ester, and for example following embodiment G is described.
Phosphorus compound of the present invention can use in lubricating oil with any significant quantity.Yet the typical effective concentration of these compounds should be for providing about 5 concentration to about 5000ppm phosphorus in lubricating oil.Preferred concentration range is to contain about 10 to about 1000ppm phosphorus in processed oil, and most preferred concentration range is about 50 to about 500ppm.
Embodiment
Embodiment G
194 gram (1 mole) hydrogen dibutyl phosphites (dibutyl hydrogen phosphite) are placed and are equipped with reflux exchanger, in the flask with four necks,round bottom of agitator and nitrogen bubble device with preparation alkyl phosphite mixture.With this flask nitrogen wash, sealing also starts agitator.Vacuum (90kPa) under the condition, heating hydrogen dibutyl phosphite to 150 ℃, and in about a hour, add 190 gram (1 mole) hydroxyethyl n-octyl sulphur by dropping funnel.In adding procedure, use the trap of cooling to reclaim about 35mL butanols.Finish the interpolation of hydroxyethyl n-octyl sulphur, do not have extra butanols to distribute after, continue about one hour of heating.Reaction mixture, and its p and s analyzed.The TAN of end product is 115, and contains 8.4% phosphorus and 9.1% sulphur.
Other additive as known in the art also can join in the lubricating oil of the present invention, perhaps can contain these additives in the compositions of additives of the present invention.These additives comprise dispersion agent, anti-wear agent, inhibiter, washing agent, extreme-pressure additive and similar additive.They for example usually be disclosed in C.V.Smallheer and R.Kennedy Smith show " Lubricant Additives " (1967, pp.1-11) and in No. the 4th, 105,571, the United States Patent (USP).
The typical content of these additives is summarized as follows among the ATF:
| Additive | % by weight (wide region) | % by weight (preferably) |
| The VI improving agent | 1-12 | 1-4 |
| Inhibiter | 0.01-3 | 0.02-1 |
| Dispersion agent | 0.10-10 | 2-5 |
| Defoamer | 0.001-5 | 0.001-0.5 |
| Washing agent | 0.01-6 | 0.01-3 |
| Anti-wear agent | 0.001-5 | 0.2-3 |
| Pour point depressant | 0.01-2 | 0.01-1.5 |
| Sealed expander | 0.1-8 | 0.5-5 |
| Lubricating oil | Surplus | Surplus |
The dispersion agent that is fit to comprises hydrocarbyl succinic imide and the hydrocarbon succinic amide that long-chain (namely more than 40 carbon atoms) replaces, long-chain (namely more than 40 carbon atoms) alkyl replaces the mixed ester/acid amides of succsinic acid, this alkyl replaces the hydroxy ester of succsinic acid, and the phenol of long-chain (namely more than 40 carbon atoms) alkyl replacement, the Mannich condensation product of formaldehyde and polyamines.Also can use the mixture of these dispersion agents.
Preferred dispersion agent is long chain alkenyl succinimides.They comprise and extensively are disclosed in the succinimide that acyclic hydrocarbon group in the patent documentation and that various kinds of amine or sulfonamide derivatives form replaces.Also be suitable for composition of the present invention through the mineral acid (or its acid anhydrides) of phosphorus and the alkenyl succinimide of boronation agent treated because they and better by the consistency between the elastic sealed body of making such as the material of fluoroelastomer and silicon-containing elastomer etc.What especially be fit to by polyisobutenyl succinic anhydride and alkylene polyamines (for example is, triethylene tetramine or tetraethylene pentamine) polyisobutenyl succinimide that forms, wherein, the polyisobutenyl substituting group is derived from the polyisobutene of number-average molecular weight in 500 to 5000 (preferred 800 to 2500) scope.Can use a lot of reagent well known to those skilled in the art to dispersion agent carry out aftertreatment (referring to, for example United States Patent (USP) the 3rd, 254, No. 025, the 3rd, 502, No. 677 and the 4th, 857, No. 214).
Compositions of additives of the present invention can make up to form enriched material with other required lubricating oil additive.Typical activity composition (a.i.) horizontal extent of this enriched material is 20 to 90%, is preferably 25 to 80%, most preferably the enriched material of 35 to 75 % by weight.The surplus of this enriched material is common thinner by lubricating oil or solvent composition.
Be used for lubricating oil of the present invention derived from natural lubricating oil, ucon oil and its mixture.Usually, natural and ucon oil all has from about 1 to about 100mm in the time of 100 ℃ separately
2The kinematic viscosity of/s (cSt) scope, although typically used needs each lubricating oil in the time of 100 ℃, kinematic viscosity about 2 to 8mm
2In/s (cSt) scope.
Natural lubricating oil comprises the oil of animal oil, vegetables oil (for example, Viscotrol C and lard), oil, mineral oil and derive coal or shale.Preferred natural lubricating oil is mineral oil.
The mineral oil that is fit to comprises all common minerals oil base oils.This comprises that chemical structure is the oils of cycloalkanes or alkane.These oil can be to use acid, and alkali and clay or other reagent (for example aluminum chloride) is by the refining oil of traditional method, or the extraction oil that uses solvent (for example, phenol, sulfurous gas, furfural, dichloroethyl ether etc.) for example to produce by solvent extraction.Can carry out hydrotreatment or hydrofining to these oil, dewax by cooling or catalytic dewaxing process, or carry out hydrocracking.Mineral oil can originate from natural origin, or is comprised of isomery wax material or other treating process residue.
Usually, mineral oil has from 2.0mm in the time of 100 ℃
2/ s (cSt) is to 8.0mm
2The kinematic viscosity of/s (cSt) scope.Preferred mineral oil has from 2 to 6mm
2The kinematic viscosity of/s (cSt) scope, most preferred mineral oil has from 3 to 5mm in the time of 100 ℃
2The kinematic viscosity of/s (cSt) scope.
Synthetic lubricating oil comprises hydrocarbon ils and halo hydrocarbon ils, for example oligomeric, alkene polymerization and that gather mutually (for example, polybutene, polypropylene, propylene, isobutylene copolymers, chlorination polylactone (chlorinatedpolylactene), poly-(1-hexene), poly-(1-octene), poly-(1-decene) etc., and composition thereof); Alkylbenzene (for example, dodecylbenzene, Tetradecylbenzene, dinonyl benzene, two (2-ethylhexyl) benzene etc.); Polyphenyl (for example, biphenyl, terphenyl, alkylation polyphenyl etc.); With alkylation phenyl ether, alkylation diphenyl sulfide, and their derivative, analogs and homologue, and analogue.Preferred oil is the oligopolymer of the oligopolymer of alpha-olefin, particularly 1-decene in this class synthetic oil.
Ucon oil also comprises alkylene oxide polymer, interpretation, multipolymer and derivative thereof, and its terminal hydroxyl is through over-churning, the modifications such as etherificate.The example of this class synthetic oil has: the polyoxyalkylene polymers by oxyethane or Polymerization of Propylene Oxide preparation is arranged; The alkyl oxide of this class polyoxyalkylene polymers and aryl ethers (for example, molecular-weight average is 1000 methyl-poly-Isopropanediol ether, and molecular-weight average is 1000 to 1500 polypropylene glycol phenyl ether); With its monocarboxylate and polycarboxylate (for example, the C of acetic ester, mixing
3-C
8Fatty acid ester, and the C of Tetraglycol 99
12The oxygen acid diester).
Another kind of suitable ucon oil comprises that dicarboxylic acid (for example, phthalic acid, succsinic acid, alkyl succinic acid and alkenyl succinic acid, toxilic acid, nonane diacid, suberic acid, sebacic acid, fumaric acid, hexanodioic acid, linoleic acid dimer, propanedioic acid, alkyl propanedioic acid, thiazolinyl propanedioic acid etc.) and the formed ester of multiple alcohol (for example, butanols, hexanol, dodecanol, 2-ethylhexyl alcohol, ethylene glycol, Diethylene Glycol monoether, propylene glycol etc.).The specific examples of these esters comprises two (2-ethylhexyl) ester of Polycizer W 260, two (2-ethylhexyl) sebate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, two different decayl esters of azelaic acid, dioctyl phthalate (DOP), didecyl phthalate, two (eicosyl) sebate, linoleic acid dimer, with by one mole of sebacic acid and two moles of TEGs and two moles of complex ester that the 2 ethyl hexanoic acids reaction forms, and its analogue.Preferred kind is C in this class synthetic oil
4-C
12The adipic acid ester of alcohol.
Ester class for the synthesis of lubricating oil also comprises by C
5-C
12Those of monocarboxylic acid and polyvalent alcohol and polyol ethers (for example neopentyl glycol, TriMethylolPropane(TMP), tetramethylolmethane, TriMethylolPropane(TMP) tetramethylolmethane, Dipentaerythritol, tripentaerythritol and analogue) preparation.
Silicon-based oil (for example, poly-alkyl-, poly-aryl-, poly-alkoxyl group-or poly-aryloxy-silicone oil and silicic acid ester oil) consist of another kind of useful ucon oil.These oil comprise tetraethyl orthosilicate, silicic acid four isopropyl esters, four (2-ethylhexyl) silicon ester, four (4-methyl-2-ethylhexyl) silicon ester, four (to tert-butyl-phenyl) silicon ester, six (4-methyl-2-pentyloxy)-sily oxide, polymethyl siloxane and poly-(aminomethyl phenyl) siloxanes and analogue thereof.Other ucon oil comprises liquid ester (for example, Tritolyl Phosphate, trioctyl phosphate and decylphosphonic acid diethyl ester), polytetrahydrofuran, poly-(alpha-olefin) of phosphorous acid, and analogue.
Lubricating oil can be derived from refining oil, the oil of re-refining and their mixture.Unrefined oil refers to that those directly do not pass through the oil that is further purified or processes from natural or synthetic source (for example, coal, shale or tar sand, pitch).The example of unrefined oil comprises the shale oil that is directly obtained by destructive distillation, by the petroleum oil that directly obtains of distillation, or the ester oil that is directly obtained by esterification technique, every kind of unrefined oil namely uses without further processing subsequently.Treated oil is similar to unrefined oil, just they through a step or more the purification process of multistep improve one or more character.Purification technique is known in the art, comprises distillation, hydrotreatment, dewaxing, solvent extraction, acid or alkaline extraction, filtration and diafiltration.Rerefined oils is by producing with the similar art breading used oil of technique that obtains treated oil.These rerefined oils also refer to the oil of regenerating or reprocessing, and they usually will be through removing the additional processing of useless additive and oil decomposition product.
Another kind of suitable lubricating oil refers to the prepared base oil of isomery of the oligomeric or wax that those pass through gas material.These base oils can be found in a lot of methods, but they are commonly called solution-air (GTL) or fischer-tropsch base oil.
When lubricating oil is the mixture (being partial synthesis) of natural lubricating oil and ucon oil, the one-tenth component selections of partial synthesis oil can be quite extensive, yet useful especially combination contains mineral oil and gathers (alpha-olefin) (PAO), particularly the oligopolymer of 1-decene.
Following examples are used for illustrating claim of the present invention.It should be understood, however, that the present invention is not subject to the detail that proposes among the embodiment.Except as otherwise noted, all umbers and per-cent are all calculated by weight.
Embodiment
Select the Ford of change
Friction testing (
AutomaticTransmission Fluid Specification for Service, on September 1st, 1992, the 3.8th joint) the friction weather resistance of liquid of the present invention is described.The Ford test is by giving prominence to the friction weather resistance with small volumes of liquids and the high test of every circulation energy.Repeatedly with this high-energy by dissipate in this small volume test liquid appraisal procedure of effort of the ability that is liquid-retentive constant friction characteristic of 10,000 circulations.
The following change of this Ford test process:
Test mode:
Friction materials: Borg Warner 6100 (unslotted)
Probe temperature: 115 ℃
Total test loop: 10,000
Cpm: 3
The total energy of each circulation: 20,400J
Use piston pressure: 275kPa
Stiction is measured:
Speed: 4.37rpm
Application pressure: 275kPa
Stiction: rotate afterwards test in 2 seconds
Because the main task of friction modifiers of the present invention is to reduce stiction and keep the level of liquid within work-ing life, comes static friction coefficient (Mu-s or the μ of comparison product of the present invention and non-acylations sample by above-mentioned SAE#2 friction testing
s) stability.
Use identical lubricating base oils, dispersion agent, antioxidant and viscosity modifier mix three kinds of test liquids.The test mixing thing contains most preferred oil soluble phosphorus source (above-described embodiment G), presses United States Patent (USP) the 5th, 314, No. 633 description preparation.By following mode, add 3.0 quality % friction modifiers in each liquid:
Fluid A contains the product of Embodiment B
Fluid B contains the product of Embodiment C
Fluid C contains the product of embodiment D
The composition of test liquid and the summary of test result are shown in the following table 1.
As seen from Table 1, the stiction of the common friction modifiers (liquid A) of Embodiment B in 500 to 10,000 loop cycles reduces to be changed to 0.013.In containing the liquid of product of the present invention, the product of Embodiment C and D shows less stiction to be changed: reduce 0.002 for liquid B, C reduces 0.003 for liquid.
Therefore, obviously the friction modifiers based on alkylene amine is carried out acylations and process the improvement that causes its friction stability in test process.
Table 1
Test formulations and test result
Mixture
Composition 123
Boronation PIBSA/PAM dispersion agent 3.60 3.60 3.60
Non-boronation PIBSA/PAM dispersion agent 1.50 1.50 1.50
Alkylated diphenylamine antioxidant 0.75 0.75 0.75
Hindered phenol antioxidant 0.25 0.25 0.25
Alkyl thiol thiadiazoles 0.09 0.09 0.09
The product 0.40 0.40 0.40 of embodiment G
The product 0.30 0.30 0.30 of embodiment A
The product 3.30 of Embodiment B
The product of Embodiment C-3.30-
The product of embodiment D--3.30
Alkylthio ester 0.10 0.10 0.10
Longer chain fatty acid 0.10 0.10 0.10
Higher fatty acid amide 0.10 0.10 0.10
Calcium sulphonate, 300TBN 0.20 0.20 0.20
Tetramethylene sulfone base sealed expander 1.5 1.5 1.50
Polymethacrylate viscosity modifiers 3.00 3.00 3.00
III class base oil 84.81 84.81 84.81
Amount to 100.00 100.00 100.00
Stiction changes
500 to 10,000 loop cycles interior 0.013 0.002 0.003
Above specification sheets has been described principle of the present invention, preferred embodiment and operator scheme.Yet the invention that is protected of expectation herein should not limited by particular forms disclosed, and is unrestricted because these should be understood to be explanation that the present invention is made.Those skilled in the art can improve under the prerequisite that does not break away from spirit of the present invention and change.
Claims (5)
1. method of improving the frictional behaviour of lubricating oil composition; comprise mixing (a) lubricating base oils; (b) at least a oil soluble P contained compound; (c) with the polyalkylene polyamine base friction modifiers of at least one hydrocarbyl substituent; wherein said hydrocarbyl substituent or each hydrocarbyl substituent contain 6 to 30 carbon atoms; and at least one secondary amino group on the friction modifiers polyamines chain is changed into corresponding amide group by acyl group, thereby has improved the friction stability of lubricating oil composition.
2. method of improving the frictional behaviour of composition comprises and mixes following (a) and (b):
(a) account for the lubricating base oils of main amount; With
(b) friction stability improves the additive combination of significant quantity, comprises:
(i) at least a friction modifiers, described friction modifiers contains acylation agent R
3COX be selected from compound (I), (II) and the reaction product of one or more compounds in the group (III), wherein R
3Be alkyl, X is leavings group, wherein (I), and (II) He (III) structure is as follows:
Wherein R is C
6To C
30Alkyl or alkenyl; R
1The polyalkylene polyamine group shown in structure (IV):
Wherein n and m are from 1 to 6 integer independently of one another; R
2Be the heteroatomic derivative that contains of alkyl or aryl or they, or be selected from following V, the structure shown in VI and the VII;
(ii) at least a oil soluble P contained compound, thus the friction stability of composition improved.
3. method as claimed in claim 2, wherein friction modifiers (b) (i) comprises such as structure (VIII), the reaction product of one or more (IX) and (X):
R wherein, R
2, R
3, n and m such as claim 2 definition, p+q=m, and p 〉=1.
4. the method for claim 1, wherein composition is transmission ofenergy liquid.
5. method of improving the frictional behaviour of composition, by mixing following (a) and (b) forming:
(a) account for the lubricating base oils of main amount; With
(b) friction stability improves the additive combination of significant quantity, comprises:
(i) at least a friction modifiers, described friction modifiers contains acylation agent R
3COX be selected from compound (I), (II) and the reaction product of one or more compounds in the group (III), wherein R
3Be alkyl, X is leavings group, wherein (I), and (II) He (III) structure is as follows:
Wherein R is C
6To C
30Alkyl or alkenyl; R
1The polyalkylene polyamine group shown in structure (IV):
Wherein n and m are from 1 to 6 integer independently of one another; R
2Be the heteroatomic derivative that contains of alkyl or aryl or they, or be selected from following V, the structure shown in VI and the VII;
(ii) at least a oil soluble P contained compound, thus the friction stability of composition improved.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/770,966 US20090005277A1 (en) | 2007-06-29 | 2007-06-29 | Lubricating Oils Having Improved Friction Stability |
| US11/770,966 | 2007-06-29 |
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| Publication Number | Publication Date |
|---|---|
| CN101343591A CN101343591A (en) | 2009-01-14 |
| CN101343591B true CN101343591B (en) | 2013-03-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008101319413A Active CN101343591B (en) | 2007-06-29 | 2008-06-27 | Lubricating oils having improved friction stability |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20090005277A1 (en) |
| EP (1) | EP2028256B1 (en) |
| JP (1) | JP5541850B2 (en) |
| KR (1) | KR101545743B1 (en) |
| CN (1) | CN101343591B (en) |
| CA (1) | CA2635151C (en) |
| SG (2) | SG148979A1 (en) |
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| DE112010000769T5 (en) * | 2009-01-26 | 2012-07-26 | Baker Hughes Incorporated | Additives for the improvement of engine oil properties |
| BRPI1008704B1 (en) | 2009-02-18 | 2018-05-08 | Lubrizol Corp | bis-amides or oxalic acid ester amides as friction modifiers in lubricants |
| CN102395661B (en) * | 2009-02-18 | 2017-03-15 | 路博润公司 | In the lubricant as the amine derivative of friction improver |
| EP2406358B1 (en) | 2009-02-18 | 2013-08-21 | The Lubrizol Corporation | Amine derivatives as friction modifiers in lubricants |
| EP2430134B1 (en) | 2009-05-13 | 2016-03-16 | The Lubrizol Corporation | Method using imides and bis-amides as friction modifiers in lubricants |
| JP5642360B2 (en) * | 2009-06-16 | 2014-12-17 | シェブロンジャパン株式会社 | Lubricating oil composition |
| JP5385830B2 (en) | 2010-03-16 | 2014-01-08 | Ｊｘ日鉱日石エネルギー株式会社 | Lubricating oil additive and lubricating oil composition |
| KR101951396B1 (en) | 2011-05-12 | 2019-02-22 | 더루우브리졸코오포레이션 | Aromatic imides and esters as lubricant additives |
| KR101526769B1 (en) * | 2013-12-30 | 2015-06-05 | 현대자동차주식회사 | Automatic Transmission Oil Composition for Enhanced Fuel Efficiency |
| US20170015931A1 (en) | 2015-07-16 | 2017-01-19 | Infineum International Limited | Method of improving vehicle transmission operation through use of specific lubricant compositions |
| EP3736318B1 (en) | 2019-05-09 | 2022-03-09 | Infineum International Limited | Transmission fluid composition for improved wear protection |
| CN111019736B (en) * | 2019-11-15 | 2022-04-15 | 山西潞安矿业(集团)有限责任公司 | A kind of sulfur-free phosphorus type organic friction modifier and preparation method thereof |
| US11365273B2 (en) | 2019-12-16 | 2022-06-21 | Infineum International Limited | High viscosity index comb polymer viscosity modifiers and methods of modifying lubricant viscosity using same |
| US11384311B2 (en) | 2019-12-16 | 2022-07-12 | Infineum International Limited | High viscosity index comb polymer viscosity modifiers and methods of modifying lubricant viscosity using same |
| US11685874B2 (en) | 2019-12-16 | 2023-06-27 | Infineum International Limited | High viscosity index comb polymer viscosity modifiers and methods of modifying lubricant viscosity using same |
| US11441094B2 (en) | 2020-10-02 | 2022-09-13 | Jatco Ltd | Rejuvenation and/or extension of the lifetime of frictional performance in transmission fluids |
| US11905488B2 (en) | 2020-10-16 | 2024-02-20 | Infineum International Limited | Transmission fluid compositions for hybrid and electric vehicle applications |
| WO2022136384A1 (en) | 2020-12-24 | 2022-06-30 | Infineum International Limited | Thermally responsive brush polymers having a copolymer backbone and copolymer arms |
| CN115584293B (en) * | 2021-07-06 | 2023-09-15 | 中国石油化工股份有限公司 | Lubricating oil friction improver and preparation method and application thereof |
| EP4194531A1 (en) | 2021-12-09 | 2023-06-14 | Infineum International Limited | Borated detergents and their lubricating applications |
| CN118516154A (en) | 2023-02-17 | 2024-08-20 | 英菲诺姆国际有限公司 | Multi-purpose oxypyridones and their functional uses |
| JP2024117719A (en) | 2023-02-17 | 2024-08-29 | インフィニューム インターナショナル リミテッド | Multipurpose oxypyridinones and their functional uses |
| KR20240128569A (en) | 2023-02-17 | 2024-08-26 | 인피늄 인터내셔날 리미티드 | Multipurpose oxypyridinones and their functional use |
| CN118516152A (en) | 2023-02-17 | 2024-08-20 | 英菲诺姆国际有限公司 | Multipurpose oxypyridones and their functional use |
| CN120484018A (en) * | 2024-02-06 | 2025-08-15 | 广州汽车集团股份有限公司 | Friction modifier, preparation method thereof, and lubricating oil |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20090004532A (en) | 2009-01-12 |
| EP2028256A2 (en) | 2009-02-25 |
| SG148979A1 (en) | 2009-01-29 |
| SG182148A1 (en) | 2012-07-30 |
| JP2009013408A (en) | 2009-01-22 |
| CA2635151C (en) | 2015-08-11 |
| JP5541850B2 (en) | 2014-07-09 |
| KR101545743B1 (en) | 2015-08-19 |
| US20090005277A1 (en) | 2009-01-01 |
| EP2028256A3 (en) | 2012-06-20 |
| CA2635151A1 (en) | 2008-12-29 |
| CN101343591A (en) | 2009-01-14 |
| EP2028256B1 (en) | 2019-08-28 |
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