CA2534902A1 - Biodegradable lubricants containing complex polyol esters - Google Patents
Biodegradable lubricants containing complex polyol esters Download PDFInfo
- Publication number
- CA2534902A1 CA2534902A1 CA002534902A CA2534902A CA2534902A1 CA 2534902 A1 CA2534902 A1 CA 2534902A1 CA 002534902 A CA002534902 A CA 002534902A CA 2534902 A CA2534902 A CA 2534902A CA 2534902 A1 CA2534902 A1 CA 2534902A1
- Authority
- CA
- Canada
- Prior art keywords
- composition
- weight
- present
- polyol ester
- complex polyol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 229920005862 polyol Polymers 0.000 title claims abstract description 30
- -1 polyol esters Chemical class 0.000 title claims abstract description 22
- 239000000314 lubricant Substances 0.000 title claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims abstract description 6
- 125000003158 alcohol group Chemical group 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 13
- 150000003077 polyols Chemical class 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 239000005069 Extreme pressure additive Substances 0.000 claims description 3
- 239000002518 antifoaming agent Substances 0.000 claims description 3
- 238000005536 corrosion prevention Methods 0.000 claims description 3
- 239000003599 detergent Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims 1
- 239000002253 acid Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 239000012530 fluid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 230000003292 diminished effect Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- BNJOQKFENDDGSC-UHFFFAOYSA-N octadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCC(O)=O BNJOQKFENDDGSC-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000004610 Internal Lubricant Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical group 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- QQWAKSKPSOFJFF-UHFFFAOYSA-N oxiran-2-ylmethyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC1CO1 QQWAKSKPSOFJFF-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
-
- 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
- C10N2030/26—Waterproofing or water resistance
-
- 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
- C10N2030/64—Environmental friendly compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49653503P | 2003-08-20 | 2003-08-20 | |
| US60/496,535 | 2003-08-20 | ||
| US10/901,578 | 2004-07-29 | ||
| US10/901,578 US8183190B2 (en) | 2003-08-20 | 2004-07-29 | Complex polyol esters with improved performance |
| PCT/US2004/025816 WO2005019395A1 (en) | 2003-08-20 | 2004-08-10 | Complex polyol esters with improved performance |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2534902A1 true CA2534902A1 (en) | 2005-03-03 |
Family
ID=34221414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002534902A Abandoned CA2534902A1 (en) | 2003-08-20 | 2004-08-10 | Biodegradable lubricants containing complex polyol esters |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8183190B2 (enExample) |
| EP (1) | EP1656437A4 (enExample) |
| JP (1) | JP5129960B2 (enExample) |
| AU (1) | AU2004267410B2 (enExample) |
| CA (1) | CA2534902A1 (enExample) |
| NO (1) | NO20061250L (enExample) |
| WO (1) | WO2005019395A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019087205A1 (en) | 2017-11-03 | 2019-05-09 | Council Of Scientific & Industrial Research | Ecofriendly and biodegradable lubricant formulation and process for preparation thereof |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080317964A1 (en) * | 2005-02-10 | 2008-12-25 | Rocco Vincent Burgo | High Temperature Lubricant Compositions and Methods of Making the Same |
| WO2006134173A2 (en) | 2005-06-17 | 2006-12-21 | Novo Nordisk Health Care Ag | Selective reduction and derivatization of engineered proteins comprising at least one non-native cysteine |
| EP2163669B1 (de) | 2008-09-12 | 2011-11-23 | Karl Mayer Textilmaschinenfabrik GmbH | Musterkettenschärmaschine und Drehgatter für eine Musterkettenschärmaschine |
| US8419968B2 (en) * | 2008-11-13 | 2013-04-16 | Chemtura Corporation | Lubricants for refrigeration systems |
| GB0822256D0 (en) * | 2008-12-05 | 2009-01-14 | Croda Int Plc | Gear oil additive |
| EP2486112B1 (en) | 2009-10-07 | 2015-10-21 | Chemtura Corporation | Polyolester lubricants for refrigeration systems |
| EP2345710A1 (en) * | 2010-01-18 | 2011-07-20 | Cognis IP Management GmbH | Lubricant with enhanced energy efficiency |
| EP2444473B1 (de) * | 2010-10-25 | 2016-07-13 | Dako Ag | Mehrdimensionaler Polyester, seine Herstellung und seine Verwendung als Basisöl für Schmierstoffe |
| JP6669343B2 (ja) * | 2015-02-27 | 2020-03-18 | 出光興産株式会社 | 生分解性潤滑油組成物 |
| CN114525162B (zh) * | 2021-12-27 | 2023-12-29 | 广州米奇化工有限公司 | 一种润滑剂、包含其的全合成切削液及润滑剂的制备方法 |
| CN115353919A (zh) * | 2022-09-07 | 2022-11-18 | 新乡市瑞丰新材料股份有限公司 | 一种难燃液压油基础油多元醇油酸酯的制备方法 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3240703A (en) * | 1961-12-27 | 1966-03-15 | Universal Oil Prod Co | Stabilization of organic substances |
| US3778454A (en) * | 1970-02-18 | 1973-12-11 | Ethyl Corp | Complex ester |
| FR2187894A1 (en) * | 1972-06-12 | 1974-01-18 | Inst Francais Du Petrole | Lubricants for 2-stroke and rotary engines - contg high-viscosity simple, complex or ether esters as base lubricant |
| DE2262266C2 (de) * | 1972-12-20 | 1982-04-01 | Neynaber Chemie Gmbh, 2854 Loxstedt | Verwendung eines Estergemisches als Gleitmittel für die formgebende Verarbeitung thermoplastischer Massen |
| US3956154A (en) * | 1974-02-11 | 1976-05-11 | Stauffer Chemical Company | Hydraulic fluid system |
| US4155924A (en) * | 1977-01-24 | 1979-05-22 | Petrolite Corporation | Quality improvement process for organic liquid |
| JPS53127970A (en) * | 1977-04-14 | 1978-11-08 | Nippon Oil & Fats Co Ltd | Synthetic lubricating oil compound |
| DE3061696D1 (en) * | 1979-02-03 | 1983-03-03 | Dynamit Nobel Ag | Fluid, biodegradable ester mixtures resistant to oxidation, with low cloud points, and their preparation |
| DE2904164A1 (de) * | 1979-02-03 | 1980-08-07 | Dynamit Nobel Ag | Biologisch abbaubare, oxidationsstabile, fluessige estergemische mit niedrigen truebungspunkten |
| US4617134A (en) | 1980-11-10 | 1986-10-14 | Exxon Research And Engineering Company | Method and lubricant composition for providing improved friction reduction |
| US4459223A (en) | 1982-05-05 | 1984-07-10 | Exxon Research And Engineering Co. | Lubricant oil composition with improved friction reducing properties |
| JPS59164393A (ja) * | 1983-03-10 | 1984-09-17 | Nippon Oil & Fats Co Ltd | エステル系冷凍機油 |
| JPS60112895A (ja) * | 1983-11-24 | 1985-06-19 | Nippon Oil & Fats Co Ltd | 金属圧延用潤滑油 |
| JP2579502B2 (ja) * | 1987-11-26 | 1997-02-05 | 日清製油株式会社 | 潤滑油 |
| JPH0245595A (ja) * | 1988-08-05 | 1990-02-15 | Kao Corp | 合成潤滑油 |
| US5254466A (en) | 1989-11-06 | 1993-10-19 | Henkel Research Corporation | Site-specific modification of the candida tropicals genome |
| JPH05331482A (ja) * | 1992-05-29 | 1993-12-14 | Tonen Corp | ２サイクルエンジン用潤滑油組成物 |
| DE4222341A1 (de) * | 1992-07-08 | 1994-01-13 | Henkel Kgaa | Grundöle mit hohem Viskositätsindex und verbessertem Kälteverhalten |
| KR100245894B1 (ko) * | 1992-08-28 | 2000-03-02 | 웨인 씨 제쉬크 | 자연 분해성 2-사이클 엔진 오일 조성물 및 에스테르 기본 원료 |
| US5411672A (en) * | 1992-09-15 | 1995-05-02 | Nippon Oil Co., Ltd. | Lubrication oil composition |
| DE4437007A1 (de) * | 1994-10-15 | 1996-04-18 | Roehm Gmbh | Biologisch abbaubare, als Schmierstoff geeignete Oligoester |
| AU717620B2 (en) | 1995-08-22 | 2000-03-30 | Henkel Corporation | Smokeless two-cycle engine lubricants |
| US5994278A (en) | 1996-09-06 | 1999-11-30 | Exxon Chemical Patents Inc. | Blends of lubricant basestocks with high viscosity complex alcohol esters |
| ATE246239T1 (de) * | 1997-10-01 | 2003-08-15 | Unichema Chemie Bv | Komplexaster, diese enthaltende zusammensetzungen und ihre verwendung |
| GB9911592D0 (en) | 1999-05-19 | 1999-07-21 | Exxon Research Engineering Co | Lubrication system for internal combustion engines |
-
2004
- 2004-07-29 US US10/901,578 patent/US8183190B2/en not_active Expired - Fee Related
- 2004-08-10 AU AU2004267410A patent/AU2004267410B2/en not_active Ceased
- 2004-08-10 CA CA002534902A patent/CA2534902A1/en not_active Abandoned
- 2004-08-10 WO PCT/US2004/025816 patent/WO2005019395A1/en not_active Ceased
- 2004-08-10 JP JP2006523911A patent/JP5129960B2/ja not_active Expired - Fee Related
- 2004-08-10 EP EP04780623A patent/EP1656437A4/en not_active Ceased
-
2006
- 2006-03-17 NO NO20061250A patent/NO20061250L/no not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019087205A1 (en) | 2017-11-03 | 2019-05-09 | Council Of Scientific & Industrial Research | Ecofriendly and biodegradable lubricant formulation and process for preparation thereof |
| US11142718B2 (en) | 2017-11-03 | 2021-10-12 | Council Of Scientific & Industrial Research | Ecofriendly and biodegradable lubricant formulation and process for preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5129960B2 (ja) | 2013-01-30 |
| AU2004267410B2 (en) | 2009-08-06 |
| US20050049153A1 (en) | 2005-03-03 |
| EP1656437A1 (en) | 2006-05-17 |
| NO20061250L (no) | 2006-03-17 |
| AU2004267410A1 (en) | 2005-03-03 |
| WO2005019395A1 (en) | 2005-03-03 |
| JP2007502887A (ja) | 2007-02-15 |
| US8183190B2 (en) | 2012-05-22 |
| EP1656437A4 (en) | 2010-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140812 |