EP0489809A1 - Neues basisöl für die schmierstoffindustrie. - Google Patents
Neues basisöl für die schmierstoffindustrie.Info
- Publication number
- EP0489809A1 EP0489809A1 EP90913144A EP90913144A EP0489809A1 EP 0489809 A1 EP0489809 A1 EP 0489809A1 EP 90913144 A EP90913144 A EP 90913144A EP 90913144 A EP90913144 A EP 90913144A EP 0489809 A1 EP0489809 A1 EP 0489809A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- lubricant compositions
- ester oils
- lubricant
- compositions according
- viscosity
- 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.)
- Granted
Links
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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/68—Esters
- C10M129/72—Esters of polycarboxylic acids
-
- 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
- C10M105/36—Esters of polycarboxylic acids
-
- 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
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- 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
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- 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
-
- 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
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- 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
- C10N2040/20—Metal working
-
- 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
- C10N2040/30—Refrigerators lubricants or compressors lubricants
-
- 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
- C10N2040/32—Wires, ropes or cables lubricants
-
- 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
- C10N2040/34—Lubricating-sealants
-
- 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
- C10N2040/36—Release agents or mold release agents
-
- 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
- C10N2040/38—Conveyors or chain belts
-
- 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
- C10N2040/40—Generators or electric motors in oil or gas winning field
-
- 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
- C10N2040/42—Flashing oils or marking oils
-
- 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
- C10N2040/44—Super vacuum or supercritical use
-
- 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
- C10N2040/50—Medical uses
Definitions
- the invention relates to a high and low temperature stable, low viscosity ester oil based on an aliphatic dicarboxylic acid and a correspondingly selected Guerbet alcohol.
- ester oils goes back more than 50 years, in which ever more powerful ester oils have developed due to the special requirements of the lubricant industry.
- the first generation of synthetic aviation turbine oils based on diesters of adipic, azelaic and sebacic acid with aliphatic alcohols played a particularly important role in civil and military aviation (see: M. Wildersohn, Tribologie und Schm michtechnik, Volume 32, page 70 to 75, 1985 and. Ullmann, volume 20, pages 457 to 671, 1984).
- ester oils are characterized by better viscosity / temperature behavior, a significantly better load-bearing capacity at high temperatures coupled with a lower vaporizability and in particular by significantly lower pour points. Nevertheless, there is still marked interest in new synthetic ester oils, the use of which in the field of motor vehicle oils and industrial lubricants is particularly in demand when the load limit of the previously known ester and mineral oils is exceeded.
- the invention is based on the object of providing new synthetic diesters of dibasic carboxylic acids with monohydric alcohols which, compared to the known ester oils, have an improved temperature / viscosity behavior, expressed by a higher viscosity index and improved low-temperature properties, and a lower one Evaporation loss and a higher flash point.
- the technical solution to this problem according to the invention is based on the selection of a specific alcohol component and combines this selection of the hydroxyl group component with the selection of a specific dicarboxylic acid on the acid side to produce a new ester oil with surprising properties.
- the present invention now relates to high and low temperature stable, low viscosity lubricant compositions based on ester oils, produced from the known esterification of a dicarboxylic acid with a fatty alcohol, characterized in that the ester oils are the esterification product of aliphatic dicarboxylic acids with 8 and / or Contain 9 C atoms and branched Guerbet alcohols or Guerbet alcohol mixtures with at least 12 to 20 C atoms.
- ester oils composed of aliphatic dicarboxylic acid components are already known from the prior art, so that the selection according to the invention of corkic acid and / or azelaic acid, preferably of azelaic acid, can be described as known per se.
- the core of the action according to the invention turns out to be the selection of the alcohol component which is derived from a Guerbet alcohol or a Guerbet alcohol mixture with at least 12 to 20 C atoms.
- the trivial name Guerbet alcohol means 2-alkyl-substituted 1-alkanols, their technical synthesis, for example, in H. Mache er, Angewandte Chemie, Volume 64, pages 213-220 (1952) and in G. Dieckelmann and HJ Heinz in "The Basics of Industrie” ! Oleochemistry ", pages 145-146 (1988).
- the Guerbet alcohol content of the ester oils is derived at least in part from 2-hexyldecanol, 2-hexyldodecanol, 2-0ctyldecanol and / or 2-octyldodecanol, the use of 2-hexyldecanol in particular being preferred.
- the actual esterification reaction takes place according to a known method by the reaction of a one-molar amount of dicarboxylic acid with at least 2 mol of Guerbet alcohol in the presence of an esterification catalyst with distillation of the water formed in the reaction.
- Ester oils preferred according to the invention have a kinematic viscosity in the range from about 7 to 50 mm 2 / s, preferably from about 15 to 40 mm 2 / s, at 40 ° C. according to DIN 51 562. These low Viscosity values are somewhat surprising in view of the relatively high molecular weight, since comparable polyol esters with a lower molecular weight, such as, for example, triethylolpropane esterified with adipic acid, give substantially higher-viscosity ester oils.
- the ester oils according to the invention have excellent viscosity / temperature behavior, which is also found in the pour points determined according to DIN ISO 3016 of about -40 down to -65 ° C, preferably below -55 ° C.
- the high-temperature behavior in addition to the low-temperature behavior, the high-temperature behavior also plays an important role.
- the new ester oils according to the invention are particularly suitable for temperature-resistant applications.
- the evaporation losses determined by thermogravimetric analysis at a heating rate of 1 ° C./min are also 0% by weight at 200 ° C., approximately 1% by weight at 250 ° C. and approximately 5 to 10% by weight 300 ° C is important.
- the dicarboxylic acid ester oils according to the invention are particularly well suited as lubricant compositions in industrial gear oil, hydraulic and / or cooling lubricants in metal, plastic and textile processing, and as additives with lubricant properties in one of the areas mentioned.
- additives such as oxidation and Corrosion inhibitors, dispersants, high-pressure additives, anti-foaming agents, metal deactivators are used in the usual effective amounts.
- the corresponding dicarboxylic acid and the selected Guerbet alcohol were esterified in the presence of 0.1% by weight of tin (II) oxalate at about 160 to 240 ° C. for 6 to 8 hours while distilling off the water formed in the reaction .
- further esterification was carried out at the same temperature under reduced pressure. After cooling to 90 ° C., about 0.5 to 1% of bleaching earth was added for wet bleaching and the reaction product was filtered off after cooling.
- ester oils according to the invention described in Table 1 now surprisingly have, compared to the viscosity-compliant comparative bonds, in particular the mineral oils, significantly higher flash points with excellent cold properties.
- Comparable ester oils with the same or larger molecular weights based on aliphatic dicarboxylic acids, such as adipic or sebacic acid also by no means achieve the low-temperature properties of the ester oils according to the invention.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Lubricants (AREA)
- Arc Welding Control (AREA)
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3929069A DE3929069A1 (de) | 1989-09-01 | 1989-09-01 | Neues basisoel fuer die schmierstoffindustrie |
DE3929069 | 1989-09-01 | ||
PCT/EP1990/001404 WO1991003531A1 (de) | 1989-09-01 | 1990-08-23 | Neues basisöl für die schmierstoffindustrie |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0489809A1 true EP0489809A1 (de) | 1992-06-17 |
EP0489809B1 EP0489809B1 (de) | 1994-12-07 |
Family
ID=6388435
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP90913144A Expired - Lifetime EP0489809B1 (de) | 1989-09-01 | 1990-08-23 | Neues basisöl für die schmierstoffindustrie |
Country Status (9)
Country | Link |
---|---|
US (1) | US5286397A (de) |
EP (1) | EP0489809B1 (de) |
JP (1) | JP2848702B2 (de) |
AT (1) | ATE115175T1 (de) |
AU (1) | AU6298490A (de) |
CA (1) | CA2066444A1 (de) |
DE (2) | DE3929069A1 (de) |
ES (1) | ES2064758T3 (de) |
WO (1) | WO1991003531A1 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5749947A (en) * | 1994-10-14 | 1998-05-12 | Henkel Kommanditgesellschaft Auf Aktien | Use of guanidinium salts of unsaturated fatty acids as corrosion inhibitors |
US8921289B2 (en) | 2006-01-12 | 2014-12-30 | Cognis Ip Management Gmbh | Esters comprising branched alkyl groups as lubricants |
RU2668975C2 (ru) * | 2013-09-16 | 2018-10-05 | Басф Се | Сложный полиэфир и применение сложного полиэфира в смазочных материалах |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993007240A1 (en) * | 1991-10-03 | 1993-04-15 | Exxon Chemical Patents Inc. | Process for producing fluids of enhanced thermal stability |
DE4202034A1 (de) * | 1992-01-25 | 1993-07-29 | Rwe Dea Ag | Hydraulikfluessigkeiten |
DE4313948A1 (de) * | 1993-04-28 | 1994-11-03 | Henkel Kgaa | Hydrauliköle mit verbesserter Dichtungsverträglichkeit |
US5578642A (en) * | 1994-08-17 | 1996-11-26 | Henkel Corporation | Self-emulsifying and/or emollient agents |
US5998340A (en) * | 1997-03-07 | 1999-12-07 | Hitachi Maxell, Ltd. | Lubricant and magnetic recording medium using the same |
EP0890634A1 (de) * | 1997-07-09 | 1999-01-13 | Voith Turbo GmbH & Co. KG | Betriebsmedium für eine hydrodynamische Maschine |
DE19830240C1 (de) * | 1998-07-07 | 2000-02-17 | Chemtec Leuna Ges Fuer Chemie | Wachsester mit vaselineähnlicher Konsistenz, Verfahren und Verwendung |
US6362265B1 (en) * | 1998-12-04 | 2002-03-26 | Rhodia Inc | Additives with reduced residual tin content and thermoplastic compositions containing the same |
JP4028982B2 (ja) * | 2001-12-27 | 2008-01-09 | 新日鐵化学株式会社 | 流体軸受ユニット及び軸受用潤滑油組成物 |
JP5033419B2 (ja) * | 2003-09-13 | 2012-09-26 | エクソンモービル・ケミカル・パテンツ・インク | 自動車用ギアのための潤滑組成物 |
EP1958932A1 (de) * | 2007-02-16 | 2008-08-20 | Cognis IP Management GmbH | Ester und deren Mischungen sowie deren Verwendung als Schmiermittel oder in Hydraulikölen |
EP2009289A1 (de) * | 2007-06-25 | 2008-12-31 | Siemens Aktiengesellschaft | Winterfeste Turboverdichtereinheit und Verfahren zur Winterfestmachung der Turboverdichtereinheit |
JP5334421B2 (ja) * | 2008-02-07 | 2013-11-06 | コスモ石油ルブリカンツ株式会社 | 潤滑油用エステル基油及び潤滑油 |
JP5334432B2 (ja) * | 2008-03-17 | 2013-11-06 | コスモ石油ルブリカンツ株式会社 | グリース組成物 |
KR20120112666A (ko) * | 2009-12-28 | 2012-10-11 | 이데미쓰 고산 가부시키가이샤 | 기기 냉각용 기유, 상기 기유를 배합하여 이루어지는 기기 냉각유, 상기 냉각유에 의해 냉각되는 기기, 및 상기 냉각유에 의한 기기 냉각 방법 |
GB201508971D0 (en) * | 2015-05-26 | 2015-07-01 | Croda Int Plc | Hair care formulation |
WO2018063602A1 (en) * | 2016-09-27 | 2018-04-05 | Exxonmobil Research And Engineering Company | Processes for preparing vinylidene dimer derivatives |
EP3601500A1 (de) * | 2017-03-28 | 2020-02-05 | ExxonMobil Chemical Patents Inc. | Schmierbasis zur verringerung der viskosität für einen kaltstartsimulator und schmierölformulierungen damit |
JP2019119838A (ja) * | 2018-01-11 | 2019-07-22 | Emgルブリカンツ合同会社 | 潤滑油組成物 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2921089A (en) * | 1957-11-27 | 1960-01-12 | Eastman Kodak Co | 2-propylheptanol and its esters |
US4425458A (en) * | 1982-04-09 | 1984-01-10 | Henkel Corporation | Polyguerbet alcohol esters |
US4830769A (en) * | 1987-02-06 | 1989-05-16 | Gaf Corporation | Propoxylated guerbet alcohols and esters thereof |
US4731190A (en) * | 1987-02-06 | 1988-03-15 | Alkaril Chemicals Inc. | Alkoxylated guerbet alcohols and esters as metal working lubricants |
AU2785789A (en) * | 1987-10-28 | 1989-05-23 | Gaf Corporation | Polycarbonate internal lubricants |
-
1989
- 1989-09-01 DE DE3929069A patent/DE3929069A1/de not_active Withdrawn
-
1990
- 1990-08-23 ES ES90913144T patent/ES2064758T3/es not_active Expired - Lifetime
- 1990-08-23 JP JP2512143A patent/JP2848702B2/ja not_active Expired - Fee Related
- 1990-08-23 AT AT90913144T patent/ATE115175T1/de not_active IP Right Cessation
- 1990-08-23 DE DE59007953T patent/DE59007953D1/de not_active Expired - Lifetime
- 1990-08-23 AU AU62984/90A patent/AU6298490A/en not_active Abandoned
- 1990-08-23 WO PCT/EP1990/001404 patent/WO1991003531A1/de active IP Right Grant
- 1990-08-23 US US07/836,333 patent/US5286397A/en not_active Expired - Lifetime
- 1990-08-23 CA CA002066444A patent/CA2066444A1/en not_active Abandoned
- 1990-08-23 EP EP90913144A patent/EP0489809B1/de not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
See references of WO9103531A1 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5749947A (en) * | 1994-10-14 | 1998-05-12 | Henkel Kommanditgesellschaft Auf Aktien | Use of guanidinium salts of unsaturated fatty acids as corrosion inhibitors |
US8921289B2 (en) | 2006-01-12 | 2014-12-30 | Cognis Ip Management Gmbh | Esters comprising branched alkyl groups as lubricants |
RU2668975C2 (ru) * | 2013-09-16 | 2018-10-05 | Басф Се | Сложный полиэфир и применение сложного полиэфира в смазочных материалах |
US10150928B2 (en) | 2013-09-16 | 2018-12-11 | Basf Se | Polyester and use of polyester in lubricants |
Also Published As
Publication number | Publication date |
---|---|
DE59007953D1 (de) | 1995-01-19 |
WO1991003531A1 (de) | 1991-03-21 |
DE3929069A1 (de) | 1991-03-07 |
CA2066444A1 (en) | 1991-03-02 |
US5286397A (en) | 1994-02-15 |
ES2064758T3 (es) | 1995-02-01 |
AU6298490A (en) | 1991-04-08 |
ATE115175T1 (de) | 1994-12-15 |
JP2848702B2 (ja) | 1999-01-20 |
JPH05500382A (ja) | 1993-01-28 |
EP0489809B1 (de) | 1994-12-07 |
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