EP0489809B1 - Nouvelle huile de base pour la production de lubrifiants - Google Patents

Nouvelle huile de base pour la production de lubrifiants Download PDF

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Publication number
EP0489809B1
EP0489809B1 EP90913144A EP90913144A EP0489809B1 EP 0489809 B1 EP0489809 B1 EP 0489809B1 EP 90913144 A EP90913144 A EP 90913144A EP 90913144 A EP90913144 A EP 90913144A EP 0489809 B1 EP0489809 B1 EP 0489809B1
Authority
EP
European Patent Office
Prior art keywords
lubricant compositions
ester oils
viscosity
carbon atoms
dicarboxylic acid
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
Application number
EP90913144A
Other languages
German (de)
English (en)
Other versions
EP0489809A1 (fr
Inventor
Karl Schmid
Frank Bongardt
Reinhold Wüst
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cognis IP Management GmbH
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0489809A1 publication Critical patent/EP0489809A1/fr
Application granted granted Critical
Publication of EP0489809B1 publication Critical patent/EP0489809B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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 an appropriately selected Guerbet alcohol.
  • ester oils go back more than 50 years, in which ever more powerful ester oils have developed due to the special requirements of the lubricant industry.
  • synthetic aviation turbine oils based on diesters of adipic, azelaic and sebacic acid with aliphatic alcohols played an important role (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.
  • the invention is based on the object of providing new synthetic diesters of dibasic carboxylic acids with monohydric alcohols which, compared with the known ester oils, have improved temperature / viscosity behavior, expressed by a higher viscosity index and improved low-temperature properties, as well as a lower evaporation loss and a higher one Flash point, mark.
  • 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 9 carbon atoms and branched Guerbet alcohols or Guerbet alcohol mixtures containing at least 12 to 20 carbon atoms.
  • ester oils which are composed of aliphatic dicarboxylic acid components are already known from the prior art, so that the selection according to the invention of suberic 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 carbon atoms.
  • the trivial name Guerbet alcohol means 2-alkyl-substituted 1-alkanols, their technical synthesis, for example, in H. Machemer, Angewandte Chemie, Volume 64, pages 213-220 (1952) and in G. Dieckelmann and HJ Heinz in "The Basics of Industrial Oleochemistry ", Pages 145-146 (1988) is described in detail.
  • the Guerbet alcohol content of the ester oils is derived at least in part from 2-hexyldecanol, 2-hexyldodecanol, 2-octyldecanol and / or 2-octyldodecanol, with the use of 2-hexyldecanol being particularly preferred.
  • the actual esterification reaction is carried out according to a known method by reacting a one-molar amount of dicarboxylic acid with at least 2 moles of Guerbet alcohol in the presence of an esterification catalyst while distilling off 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, trimethylolpropane esterified with adipic acid, give significantly more viscous 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 from 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. important at 300 ° C.
  • the dicarboxylic acid ester oils according to the invention are particularly suitable 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.

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)

Claims (7)

  1. Compositions lubrifiantes à basse viscosité, stables à haute et basse températures, à base d'huiles-ester, produites par l'estérification connue d'un acide dicarboxylique avec un alcool gras, caractérisées en ce que les huiles-ester contiennent le produit de l'estérification d'acides dicarboxyliques aliphatiques ayant 8 et/ou 9 atomes de carbone et d'alcools de Guerbet ramifiés ou de mélanges d'alcools de Guerbet ayant au moins 12 à 20 atomes de C.
  2. Compositions lubrifiantes selon la revendication 1, caractérisées en ce que la proportion d'acide dicarboxylique aliphatique des huiles-ester dérive de l'acide subérique et/ou de l'acide azélaïnique.
  3. Compositions lubrifiantes selon les revendications 1 à 2, caractérisées en ce que la proportion d'alcool de Guerbet des huiles-ester dérive au moins partiellement des 2-hexyldécanol, 2-hexyldodécanol, 2-octyldécanol et/ou 2-octyldodécanol, mais l'utilisation de 2-hexyldécanol est particulièrement préférée.
  4. Compositions lubrifiantes selon les revendications 1 à 3, caractérisées en ce qu'elles présentent à 40°C une viscosité cinématique (DIN 51562) dans la zone de 7 à 50 mm²/s, de préférence environ de 15 à 40 mm²/s et un indice de viscosité (DIN ISO 2909) au moins environ 150 et de préférence au moins 160.
  5. Compositions lubrifiantes selon les revendications 1 à 4, caractérisées en ce qu'elles comportent un point d'écoulement (DIN ISO 3016) environ de -40 à -65°C, de préférence en dessous de -55°C environ.
  6. Compositions lubrifiantes selon la revendication 1 à 5, caractérisées en ce qu'elles présentent un point d'inflammation (DIN ISO 2592) au moins 250 jusqu'à environ 300°C, de préférence supérieur à 270°C.
  7. Utilisation des compositions lubrifiantes décrites dans les revendications 1 à 6 comme lubrifiants d'engrenages industriels, liquides lubrifiants en hydraulique et/ou liquides lubrifiants de réfrigération lors du façonnage des métaux, des matières plastiques et des textiles ainsi que comme additifs avec des propriétés de lubrifiant dans un des secteurs nommés.
EP90913144A 1989-09-01 1990-08-23 Nouvelle huile de base pour la production de lubrifiants Expired - Lifetime EP0489809B1 (fr)

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 (fr) 1989-09-01 1990-08-23 Nouvelle huile de base pour la production de lubrifiants

Publications (2)

Publication Number Publication Date
EP0489809A1 EP0489809A1 (fr) 1992-06-17
EP0489809B1 true EP0489809B1 (fr) 1994-12-07

Family

ID=6388435

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90913144A Expired - Lifetime EP0489809B1 (fr) 1989-09-01 1990-08-23 Nouvelle huile de base pour la production de lubrifiants

Country Status (9)

Country Link
US (1) US5286397A (fr)
EP (1) EP0489809B1 (fr)
JP (1) JP2848702B2 (fr)
AT (1) ATE115175T1 (fr)
AU (1) AU6298490A (fr)
CA (1) CA2066444A1 (fr)
DE (2) DE3929069A1 (fr)
ES (1) ES2064758T3 (fr)
WO (1) WO1991003531A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015036293A1 (fr) * 2013-09-16 2015-03-19 Basf Se Polyester et utilisation d'un polyester dans des lubrifiants

Families Citing this family (21)

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Publication number Priority date Publication date Assignee Title
WO1993007240A1 (fr) * 1991-10-03 1993-04-15 Exxon Chemical Patents Inc. Procede de production de fluides ayant une stabilite thermique amelioree
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
DE4436764A1 (de) * 1994-10-14 1996-04-18 Henkel Kgaa Verwendung von Guanidiniumsalzen ungesättigter Fettsäuren als Korrosionsschutzwirkstoff
US5998340A (en) * 1997-03-07 1999-12-07 Hitachi Maxell, Ltd. Lubricant and magnetic recording medium using the same
EP0890634A1 (fr) * 1997-07-09 1999-01-13 Voith Turbo GmbH & Co. KG Fluide de travail pour machine hydrodynamique
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
DE102006001768A1 (de) * 2006-01-12 2007-07-19 Cognis Ip Management Gmbh Verwendung von Estern mit verzweigten Alkylgruppen als Schmiermittel
EP1958932A1 (fr) * 2007-02-16 2008-08-20 Cognis IP Management GmbH Ester et ses mélanges tout comme leur utilisation comme lubrifiant ou dans des huiles hydrauliques
EP2009289A1 (fr) * 2007-06-25 2008-12-31 Siemens Aktiengesellschaft Unité de turbocompresseur résistant à l'hiver et procédé destiné à la création de résistance à l'hiver de l'unité de turbocompresseur
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 (fr) * 2016-09-27 2018-04-05 Exxonmobil Research And Engineering Company Procédés de préparation de dérivés de dimère de vinylidène
EP3601500A1 (fr) * 2017-03-28 2020-02-05 ExxonMobil Chemical Patents Inc. Huiles de base réduisant la viscosité d'un simulateur de démarrage à froid et formulations d'huile lubrifiante les contenant
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

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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

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015036293A1 (fr) * 2013-09-16 2015-03-19 Basf Se Polyester et utilisation d'un polyester dans des lubrifiants
KR20160058864A (ko) * 2013-09-16 2016-05-25 바스프 에스이 폴리에스테르 및 윤활제에서의 폴리에스테르의 용도

Also Published As

Publication number Publication date
DE59007953D1 (de) 1995-01-19
EP0489809A1 (fr) 1992-06-17
WO1991003531A1 (fr) 1991-03-21
DE3929069A1 (de) 1991-03-07
CA2066444A1 (fr) 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

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