CA2086757C - Synergystic blend of amine/amide and ester/alcohol friction modifying agents for improved fuel economy of an internal combustion engine - Google Patents
Synergystic blend of amine/amide and ester/alcohol friction modifying agents for improved fuel economy of an internal combustion engine Download PDFInfo
- Publication number
- CA2086757C CA2086757C CA002086757A CA2086757A CA2086757C CA 2086757 C CA2086757 C CA 2086757C CA 002086757 A CA002086757 A CA 002086757A CA 2086757 A CA2086757 A CA 2086757A CA 2086757 C CA2086757 C CA 2086757C
- Authority
- CA
- Canada
- Prior art keywords
- friction modifier
- alcohol
- group
- carbon atoms
- alkylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 191
- 150000001412 amines Chemical class 0.000 title claims abstract description 74
- 150000002148 esters Chemical class 0.000 title claims abstract description 57
- 150000001408 amides Chemical class 0.000 title claims abstract description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 239000000446 fuel Substances 0.000 title claims abstract description 40
- 238000002485 combustion reaction Methods 0.000 title claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 title abstract description 15
- 239000010687 lubricating oil Substances 0.000 claims abstract description 49
- 239000003607 modifier Substances 0.000 claims description 124
- 125000004432 carbon atom Chemical group C* 0.000 claims description 57
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 54
- 239000000654 additive Substances 0.000 claims description 52
- -1 1,3-propylene Chemical group 0.000 claims description 51
- 229920000768 polyamine Polymers 0.000 claims description 50
- 239000002253 acid Substances 0.000 claims description 47
- 239000003921 oil Substances 0.000 claims description 46
- 150000005846 sugar alcohols Polymers 0.000 claims description 32
- 229920006395 saturated elastomer Polymers 0.000 claims description 30
- 235000011187 glycerol Nutrition 0.000 claims description 21
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 20
- 150000001414 amino alcohols Chemical class 0.000 claims description 18
- 230000001050 lubricating effect Effects 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 17
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 17
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 17
- 239000005642 Oleic acid Substances 0.000 claims description 17
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 17
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 17
- 239000010705 motor oil Substances 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 14
- 230000000996 additive effect Effects 0.000 claims description 14
- 239000012141 concentrate Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 12
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 12
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 12
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 9
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 9
- 239000004386 Erythritol Substances 0.000 claims description 9
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 9
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 9
- 235000019414 erythritol Nutrition 0.000 claims description 9
- 229940009714 erythritol Drugs 0.000 claims description 9
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims description 9
- 229960003656 ricinoleic acid Drugs 0.000 claims description 9
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 9
- 239000000600 sorbitol Substances 0.000 claims description 9
- 239000002270 dispersing agent Substances 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 230000006872 improvement Effects 0.000 claims description 8
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 8
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 7
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 7
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 7
- 229930195725 Mannitol Natural products 0.000 claims description 7
- 239000000594 mannitol Substances 0.000 claims description 7
- 235000010355 mannitol Nutrition 0.000 claims description 7
- URKBBEIOEBOBIY-UHFFFAOYSA-N pentane-1,1,1,2-tetrol Chemical compound CCCC(O)C(O)(O)O URKBBEIOEBOBIY-UHFFFAOYSA-N 0.000 claims description 7
- 229960001124 trientine Drugs 0.000 claims description 7
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 7
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 7
- 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 claims description 6
- 239000005700 Putrescine Substances 0.000 claims description 6
- DZZRNEZNZCRBOT-UHFFFAOYSA-N hexane-1,2,4-triol Chemical compound CCC(O)CC(O)CO DZZRNEZNZCRBOT-UHFFFAOYSA-N 0.000 claims description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 6
- XMMDVXFQGOEOKH-UHFFFAOYSA-N n'-dodecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCNCCCN XMMDVXFQGOEOKH-UHFFFAOYSA-N 0.000 claims description 6
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 6
- 238000012935 Averaging Methods 0.000 claims description 5
- 125000006539 C12 alkyl 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 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 8
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000002195 synergetic effect Effects 0.000 abstract description 12
- 235000019198 oils Nutrition 0.000 description 41
- 238000009472 formulation Methods 0.000 description 32
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- 238000012360 testing method Methods 0.000 description 17
- 235000014113 dietary fatty acids Nutrition 0.000 description 16
- 239000000194 fatty acid Substances 0.000 description 16
- 229930195729 fatty acid Natural products 0.000 description 16
- 150000007513 acids Chemical class 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 229920005862 polyol Polymers 0.000 description 11
- 150000001298 alcohols Chemical class 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 10
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- 230000003647 oxidation Effects 0.000 description 8
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- 230000001603 reducing effect Effects 0.000 description 7
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- 230000000694 effects Effects 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
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- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
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- 238000010348 incorporation Methods 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
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- 150000003839 salts Chemical class 0.000 description 4
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
- C10M2223/121—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy of alcohols or phenols
-
- 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
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
-
- 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
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
- C10M2225/041—Hydrocarbon polymers
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/12—Groups 6 or 16
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/251—Alcohol-fuelled engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
- C10N2040/253—Small diesel engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/28—Rotary engines
-
- 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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Liquid Carbonaceous Fuels (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56083990A | 1990-07-31 | 1990-07-31 | |
| US560,839 | 1990-07-31 | ||
| PCT/US1991/005392 WO1992002602A1 (en) | 1990-07-31 | 1991-07-30 | Synergystic blend of amine/amide and ester/alcohol friction modifying agents for improved fuel economy of an internal combustion engine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2086757A1 CA2086757A1 (en) | 1992-02-01 |
| CA2086757C true CA2086757C (en) | 2000-03-28 |
Family
ID=24239571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002086757A Expired - Lifetime CA2086757C (en) | 1990-07-31 | 1991-07-30 | Synergystic blend of amine/amide and ester/alcohol friction modifying agents for improved fuel economy of an internal combustion engine |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0553100B1 (ja) |
| JP (1) | JP2777750B2 (ja) |
| CA (1) | CA2086757C (ja) |
| DE (1) | DE69116697T2 (ja) |
| WO (1) | WO1992002602A1 (ja) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993021288A1 (en) * | 1992-04-15 | 1993-10-28 | Exxon Chemical Patents Inc. | Lubricant composition containing mixed friction modifiers |
| CA2132523C (en) * | 1992-04-15 | 1999-08-03 | Ricardo Alfredo Bloch | Lubricant compositions containing alkoxylated amine and sulfurized hydrocarbyl phenol friction modifiers |
| US5520831A (en) * | 1993-12-20 | 1996-05-28 | Exxon Chemical Patents Inc. | Increasing the friction durability of power transmission fluids through the use of oil soluble competing additives |
| JP3555844B2 (ja) | 1999-04-09 | 2004-08-18 | 三宅 正二郎 | 摺動部材およびその製造方法 |
| GB2359092A (en) * | 2000-02-14 | 2001-08-15 | Exxonmobil Res & Eng Co | Lubricating oils having improved fuel economy retention properties |
| US6589302B1 (en) | 2000-05-09 | 2003-07-08 | Texaco Inc. | Friction modifier for poor lubricity fuels |
| US6739238B2 (en) | 2000-11-20 | 2004-05-25 | Nissan Motor Co., Ltd. | Sliding structure for a reciprocating internal combustion engine and a reciprocating internal combustion engine using the sliding structure |
| JP2003184883A (ja) | 2001-12-20 | 2003-07-03 | Nissan Motor Co Ltd | 軸受摺動部材 |
| JP3555891B2 (ja) * | 2002-02-22 | 2004-08-18 | 新日本石油株式会社 | 低摩擦摺動材料及びこれに用いる潤滑油組成物 |
| US6803350B2 (en) * | 2002-05-22 | 2004-10-12 | Chevron Oronite Company Llc | Lubricating compositions for friction material interfaces |
| JP2004360649A (ja) * | 2003-06-06 | 2004-12-24 | Nissan Motor Co Ltd | エンジン用ピストンピン |
| EP1666572B1 (en) * | 2003-08-06 | 2017-05-17 | Nippon Oil Corporation | System having dlc contacting faces, method for lubricating the system and lubricating oil for the system |
| WO2005014761A2 (ja) * | 2003-08-06 | 2005-02-17 | Nissan Motor Co., Ltd. | 低摩擦摺動機構、低摩擦剤組成物及び摩擦低減方法 |
| EP1661971A4 (en) * | 2003-08-06 | 2008-12-03 | Nippon Oil Corp | SYSTEM HAVING DLC CONTACT FACES, METHOD FOR LUBRICATING THIS SYSTEM, AND LUBRICATING OIL FOR THIS SYSTEM |
| JP4973971B2 (ja) * | 2003-08-08 | 2012-07-11 | 日産自動車株式会社 | 摺動部材 |
| CN100485232C (zh) * | 2003-08-08 | 2009-05-06 | 日产自动车株式会社 | 滑动件及其生产方法 |
| JP2005090738A (ja) * | 2003-08-13 | 2005-04-07 | Nissan Motor Co Ltd | 転がり軸受 |
| US7771821B2 (en) * | 2003-08-21 | 2010-08-10 | Nissan Motor Co., Ltd. | Low-friction sliding member and low-friction sliding mechanism using same |
| US20060183652A1 (en) * | 2004-12-10 | 2006-08-17 | Takashi Fujitsu | Lubricating oil composition |
| US7550415B2 (en) | 2004-12-10 | 2009-06-23 | Shell Oil Company | Lubricating oil composition |
| KR20080094958A (ko) | 2006-02-21 | 2008-10-27 | 셀 인터나쵸나아레 레사아치 마아츠샤피 비이부이 | 윤활유 조성물 |
| IN2009CN02056A (ja) * | 2006-10-17 | 2015-08-07 | Idemitsu Kosan Co | |
| JP5203590B2 (ja) * | 2006-10-27 | 2013-06-05 | 出光興産株式会社 | 潤滑油組成物 |
| EP2441818A1 (en) * | 2010-10-12 | 2012-04-18 | Shell Internationale Research Maatschappij B.V. | Lubricating composition |
| JP6907461B2 (ja) * | 2016-02-29 | 2021-07-21 | 出光興産株式会社 | 潤滑油組成物、潤滑方法、及び変速機 |
| RU2675632C1 (ru) * | 2017-11-22 | 2018-12-21 | Игорь Васильевич Мухортов | Противоизносная композиция к смазочным материалам |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1390948A (fr) * | 1962-09-28 | 1965-03-05 | Shell Int Research | Préparation d'additifs pour lubrifiants et lubrifiants contenant ces additifs |
| US4201684A (en) * | 1978-11-13 | 1980-05-06 | Ethyl Corporation | Lubricant composition of improved friction reducing properties |
| US4208293A (en) * | 1978-11-13 | 1980-06-17 | Ethyl Corporation | Improved crankcase lubricant composition |
| CA1157846A (en) * | 1978-12-18 | 1983-11-29 | Thomas V. Liston | Fuel economy |
| GB2097813B (en) * | 1981-05-06 | 1985-09-25 | Exxon Research Engineering Co | Glycerol esters in lubricating oils as fuel economy additives |
| US4724091A (en) * | 1983-03-31 | 1988-02-09 | The Lubrizol Corporation | Alkyl phenol and amino phenol compositions and two-cycle engine oils and fuels containing same |
| WO1988006616A1 (en) * | 1987-03-02 | 1988-09-07 | Idemitsu Kosan Company Limited | Lubricating oil composition |
| US4960530A (en) * | 1988-03-31 | 1990-10-02 | Ethyl Petroleum Additives, Inc. | Lubricating oil composition |
| CA1325420C (en) * | 1988-03-31 | 1993-12-21 | Armgard Kohler Everett | Lubricating oil composition |
-
1991
- 1991-07-30 WO PCT/US1991/005392 patent/WO1992002602A1/en active IP Right Grant
- 1991-07-30 EP EP91914651A patent/EP0553100B1/en not_active Expired - Lifetime
- 1991-07-30 DE DE69116697T patent/DE69116697T2/de not_active Expired - Fee Related
- 1991-07-30 JP JP3514276A patent/JP2777750B2/ja not_active Expired - Lifetime
- 1991-07-30 CA CA002086757A patent/CA2086757C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69116697D1 (de) | 1996-03-07 |
| WO1992002602A1 (en) | 1992-02-20 |
| DE69116697T2 (de) | 1996-05-30 |
| JPH05509125A (ja) | 1993-12-16 |
| JP2777750B2 (ja) | 1998-07-23 |
| EP0553100A1 (en) | 1993-08-04 |
| EP0553100B1 (en) | 1996-01-24 |
| CA2086757A1 (en) | 1992-02-01 |
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| EEER | Examination request | ||
| MKEX | Expiry |