EP2049630B1 - Schmierstoffzusammensetzung - Google Patents

Schmierstoffzusammensetzung Download PDF

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Publication number
EP2049630B1
EP2049630B1 EP20070787797 EP07787797A EP2049630B1 EP 2049630 B1 EP2049630 B1 EP 2049630B1 EP 20070787797 EP20070787797 EP 20070787797 EP 07787797 A EP07787797 A EP 07787797A EP 2049630 B1 EP2049630 B1 EP 2049630B1
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EP
European Patent Office
Prior art keywords
tert
butyl
bis
straight
alkyl 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.)
Not-in-force
Application number
EP20070787797
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English (en)
French (fr)
Other versions
EP2049630A2 (de
Inventor
David Eliezer Chasan
Patricia Roberta Wilson
Marc Ribeaud
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.)
BASF SE
Original Assignee
BASF SE
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Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to PL07787797T priority Critical patent/PL2049630T3/pl
Publication of EP2049630A2 publication Critical patent/EP2049630A2/de
Application granted granted Critical
Publication of EP2049630B1 publication Critical patent/EP2049630B1/de
Not-in-force legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • 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
    • C10N2030/36—Seal compatibility, e.g. with rubber
    • 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

Definitions

  • the present invention relates to lubricant compositions stabilized against oxidative degradation via the incorporation of certain sterically hindered amine stabilizers.
  • the lubricant compositions exhibit excellent results regarding seal swell.
  • U.S. Pat. Nos. 5,073,278 and 5,273,669 teach the stabilization of lubricant compositions with a certain aromatic amine and at least one sterically hindered amine.
  • U.S. Pat. No. 5,268,113 discloses lubricants stabilized by the addition of a sterically hindered amine and a phenol.
  • EP 0356677 discloses lubricants comprising a mineral or synthetic base oil, an aromatic amine and at least one sterically hindered amine.
  • International Application WO 02/04578 discloses lubricant compositions including blends of Group II and/or Group III base oils and alkylated aromatic compositions which exhibit excellent additive solvency, thermo-oxidative stability, hydrolytic stability, and seal swell characteristics.
  • Oxidative degradation of lubricants plays a significant role especially in motor oils because of the high temperatures prevailing in the combustion chambers of the engines and the presence, in addition to oxygen, of oxides of nitrogen which act as oxidation catalysts.
  • Hindered amine compounds are effective stabilizers for lubricants. However, they are generally not employed due to detrimental effects such as seal swell.
  • the present invention relates to the stabilization of lubricant compositions with a specific class of hindered amine compounds.
  • the present lubricant compositions are non-aggressive towards seals.
  • the present invention relates to a stabilized lubricant composition which comprises
  • the sterically hindered amines are known and are prepared according to methods known in the art.
  • the present hindered amines are 2,2,6,6-tetramethylpiperidin-4-ol esters of aliphatic carboxylic acids, for example the esters of lauric acid or stearic acid.
  • the invention relates to compositions wherein the hindered amines of the formula is present.
  • Lubricants according to the present invention are functional fluids, that is lubricants, hydraulic fluids or metal working fluids.
  • Lubricants are in particular mineral oil based (API classifications Groups I, II, III, Group IV including gas to liquid (GTL) oils) or synthetic base oils, such as is normally used for the production of lubricants.
  • Synthetic oils may be, for example, esters of polycarboxylic acids or of polyols; they may also be aliphatic polyesters or poly- ⁇ -olefins, silicones, phosphoric acid esters or polalkylene glycols.
  • the lubricant may also be a grease based on an oil and a thickener. Such lubricants are described, for example in D. Klamann "Schmierstoffe und artverwandte Producte", Verlag Chemie, Weinheim, 1982 .
  • Examples are lubricants and hydraulic fluids based on mineral oil or synthetic lubricants or hydraulic fluids, in particular those which are derivatives of carboxylic esters and which are used at temperatures of 200°C and above.
  • Examples of synthetic lubricants embrace lubricants based on a diester of a dibasic acid with a monovalent alcohol, for example dioctyl sebacate or dinonyl adipate, a triester of trimethylolpropane with a monobasic acid or a mixture of such acids, for example trimethylolpropane tripelargonate, trimethylolpropane tricaprylate or mixtures of these, a tetraester of pentaerythritol with a monobasic acid or with a mixture of such acids, for example pentaerythritol tetracaprylate, or a complex ester of monobasic and dibasic acids with polyhydric alcohols, for example a complex ester of trimethylolpropane with caprylic and sebacic acid or a mixture of these.
  • a diester of a dibasic acid with a monovalent alcohol for example dioctyl sebacate or dinon
  • mineral oils for example poly- ⁇ -olefins, lubricants based on esters, or phosphates, glycols, polyglycols and polalkyene glycols and mixtures of these with water.
  • the sterically hindered amines of this invention are in particular non-aggressive toward elastomeric seals.
  • the seals are in particular a fluoropolymer elastomer used in O-rings and other goods.
  • the "fluoroelastomers” are categorized under ASTM D1418 and ISO 1629 designation of FKM for example.
  • the fluoroelastomers comprise copolymers of hexafluoropropylene (HFP) and vinylidene fluoride (VDF of VF2), terpolymers of tetrafluoroethylene (TFE), vinylidene fluoride and hexafluoropropylene, perfluoromethylvinylether (PMVE), copolymers of TFE and propylene and copolymers of TFE, PMVE and ethylene.
  • the fluorine content varies for example between about 66 to about 70% by weight.
  • FKM is fluoro rubber of the polymethylene type having substituent fluoro and perflouroalkyl or perfluoroalkoxy groups on the polymer chain.
  • a preferred subject of the invention is a method which comprises contacting a fluoroelastomer with a stabilized lubricant composition, which comprises At least one mineral or a synthetic base oil or a mixture of a mineral and a synthetic base oil and At least one or more sterically hindered amine compounds of the formula (I), where R is a straight or branched alkyl group of 7, 8, 9, 10, 11, 12, 13, 14, 15 or 16.
  • the sterically hindered amines according to this invention are admixed with the lubricants in an amount of about 0.01 to about 5% by weight, for example from about 0.05 to about 3% by weight, for instance from about 0.1 to about 2% by weight, based on the weight of the lubricant.
  • the lubricants can additionally comprise other additives which are added to improve the basic properties of lubricants even further; these include antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressors, dispersants, detergents, high pressure additives, antifriction additives and antiwear additives.
  • additives which are added to improve the basic properties of lubricants even further; these include antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressors, dispersants, detergents, high pressure additives, antifriction additives and antiwear additives.
  • metal deactivators for example for copper, are:
  • rust inhibitors and friction modifiers are:
  • viscosity index improvers examples are:
  • pour-point depressants are:
  • dispersants/surfactants examples are:
  • antiwear additives are:
  • a 5W-30 engine oil containing 0.08 %P is supplemented with sufficient sterically hindered amine additive to raise the total base number, as measured by ASTM D 4739 by two units.
  • Amine additive A is added at a treat level of 1.0 weight percent and amine additive B is added at a treat level of 1.2%.
  • the oils are stirred at 60°C for one hour to insure homogeneity.
  • the formulations are tested according to elastomer compatibility procedure CEC- L-39-T-96. The results of the CEC- L-39-T-96 testing of these formulations with an FKM fluorinated rubber are found below.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)

Claims (15)

  1. Stabilisierte Schmiermittelzusammensetzung, die ein mineralisches oder synthetisches Grundöl oder eine Mischung aus einem mineralischen und einem synthetischen Grundöl und
    mindestens eine sterisch gehinderte Aminverbindung der Formel
    Figure imgb0008
     wobei R für eine gerade oder verzweigte Alkylgruppe mit 7, 8, 9, 10, 11, 12, 13, 14, 15 oder 16 Kohlenstoffatomen steht,
    umfasst.
  2. Zusammensetzung nach Anspruch 1, wobei R für eine gerade oder verzweigte Alkylgruppe mit 11 Kohlenstoffatomen steht.
  3. Zusammensetzung nach Anspruch 1, wobei das gehinderte Amin die Formel
    Figure imgb0009
     aufweist.
  4. Zusammensetzung nach Anspruch 1, wobei das gehinderte Amin in einer Menge von etwa 0,01 bis etwa 5 Gew.-%, bezogen auf das Gewicht des Schmiermittels, vorliegt.
  5. Zusammensetzung nach Anspruch 1, wobei das gehinderte Amin in einer Menge von etwa 0,05 bis etwa 3 Gew.-%, bezogen auf das Gewicht des Schmiermittels, vorliegt.
  6. Zusammensetzung nach Anspruch 1, wobei das gehinderte Amin in einer Menge von etwa 0,1 bis etwa 2 Gew.-%, bezogen auf das Gewicht des Schmiermittels, vorliegt.
  7. Verfahren, bei dem man
    ein Fluorelastomer mit einer stabilisierten Schmiermittelzusammensetzung, die
    mindestens ein mineralisches oder synthetisches Grundöl oder eine Mischung aus einem mineralischen und einem synthetischen Grundöl und
    mindestens eine sterisch gehinderte Aminverbindung der Formel
    Figure imgb0010
     wobei R für eine gerade oder verzweigte Alkylgruppe mit 7, 8, 9, 10, 11, 12, 13, 14, 15 oder 16 Kohlenstoffatomen steht,
    umfasst, in Berührung bringt.
  8. Zusammensetzung nach Anspruch 1, wobei R für eine gerade oder verzweigte Alkylgruppe mit 8, 9, 10, 11, 12, 13 oder 14 Kohlenstoffatomen steht.
  9. Zusammensetzung nach Anspruch 1, wobei R für eine gerade oder verzweigte Alkylgruppe mit 10, 11, 12, 13 oder 14 Kohlenstoffatomen steht.
  10. Zusammensetzung nach Anspruch 1, wobei R für eine gerade oder verzweigte Alkylgruppe mit 10, 11 oder 12 Kohlenstoffatomen steht.
  11. Zusammensetzung nach Anspruch 1, wobei R für eine gerade oder verzweigte Alkylgruppe mit 11 Kohlenstoffatomen steht.
  12. Verfahren nach Anspruch 7, wobei R für eine gerade oder verzweigte Alkylgruppe mit 8, 9, 10, 11, 12, 13 oder 14 Kohlenstoffatomen steht.
  13. Verfahren nach Anspruch 7 wobei R für eine gerade oder verzweigte Alkylgruppe mit 10, 11, 12 oder 13 Kohlenstoffatomen steht.
  14. Verfahren nach Anspruch 7, wobei R für eine gerade oder verzweigte Alkylgruppe mit 10, 11 oder 12 Kohlenstoffatomen steht.
  15. Verfahren nach Anspruch 7, wobei R für eine gerade oder verzweigte Alkylgruppe mit 11 Kohlenstoffatomen steht.
EP20070787797 2006-07-31 2007-07-23 Schmierstoffzusammensetzung Not-in-force EP2049630B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL07787797T PL2049630T3 (pl) 2006-07-31 2007-07-23 Kompozycja smarowa

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US83438306P 2006-07-31 2006-07-31
PCT/EP2007/057552 WO2008015116A2 (en) 2006-07-31 2007-07-23 Lubricant composition

Publications (2)

Publication Number Publication Date
EP2049630A2 EP2049630A2 (de) 2009-04-22
EP2049630B1 true EP2049630B1 (de) 2015-04-29

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ID=38895958

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Country Status (12)

Country Link
EP (1) EP2049630B1 (de)
JP (2) JP5546858B2 (de)
KR (1) KR101433140B1 (de)
CN (1) CN101495605B (de)
AU (1) AU2007280548B2 (de)
BR (1) BRPI0714961B1 (de)
CA (1) CA2657382C (de)
IL (1) IL196250A (de)
MX (1) MX2009001124A (de)
PL (1) PL2049630T3 (de)
RU (1) RU2462505C2 (de)
WO (1) WO2008015116A2 (de)

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JP5546858B2 (ja) * 2006-07-31 2014-07-09 チバ ホールディング インコーポレーテッド 潤滑剤組成物
US8236204B1 (en) 2011-03-11 2012-08-07 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles solubilized in activating solvents and methods for using same
US8236205B1 (en) 2011-03-11 2012-08-07 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles and other triazoles and methods for using same
US9969950B2 (en) * 2012-07-17 2018-05-15 Infineum International Limited Lubricating oil compositions containing sterically hindered amines as ashless TBN sourcces
KR20150042831A (ko) * 2012-08-14 2015-04-21 바스프 에스이 비-시클릭 장애 아민을 포함하는 윤활제 조성물
BR112015008109A2 (pt) * 2012-10-12 2018-04-24 Basf Se composição lubrificante, e, pacote de aditivo para uma composição lubrificante.
JP2016501284A (ja) * 2012-11-16 2016-01-18 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ フルオロポリマーシール適合性向上のためのエポキシ化合物含有潤滑油組成物
FR3000103B1 (fr) * 2012-12-21 2015-04-03 Total Raffinage Marketing Composition lubrifiante a base d'ether de polyglycerol
US10066186B2 (en) 2013-04-22 2018-09-04 Basf Se Lubricating oil compositions containing a halide seal compatibility additive and a second seal compatibility additive
KR20160003716A (ko) * 2013-04-22 2016-01-11 바스프 에스이 윤활제 조성물의 플루오로중합체 씰 상용성을 개선하기 위한 씰 상용성 첨가제
RU2528833C1 (ru) * 2013-05-15 2014-09-20 Открытое акционерное общество "Нефтяная компания "Роснефть" Редукторное масло
EP3000866A4 (de) 2013-05-20 2017-01-18 Idemitsu Kosan Co., Ltd Schmiermittelzusammensetzung
EP2816097A1 (de) * 2013-06-18 2014-12-24 Shell Internationale Research Maatschappij B.V. Schmierölzusammensetzung
US9309205B2 (en) 2013-10-28 2016-04-12 Wincom, Inc. Filtration process for purifying liquid azole heteroaromatic compound-containing mixtures
WO2015066690A1 (en) 2013-11-04 2015-05-07 Basf Se Lubricant composition
EP3164473A4 (de) * 2014-07-02 2018-01-03 Basf Se Sulfonatester zur verbesserung der fluorpolymerdichtungsverträglichkeit von schmiermittelzusammensetzungen
CN106604980B (zh) * 2014-09-04 2020-04-17 范德比尔特化学品有限责任公司 用于润滑组合物的液体无灰抗氧化剂添加剂
JP6863557B2 (ja) * 2016-12-05 2021-04-21 出光興産株式会社 潤滑油組成物及びその製造方法

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Also Published As

Publication number Publication date
RU2462505C2 (ru) 2012-09-27
CN101495605B (zh) 2014-03-05
IL196250A0 (en) 2009-09-22
BRPI0714961A2 (pt) 2013-07-30
CA2657382A1 (en) 2008-02-07
EP2049630A2 (de) 2009-04-22
KR20090033358A (ko) 2009-04-02
CN101495605A (zh) 2009-07-29
KR101433140B1 (ko) 2014-08-22
WO2008015116A2 (en) 2008-02-07
CA2657382C (en) 2014-09-09
BRPI0714961B1 (pt) 2016-11-22
RU2009106723A (ru) 2010-09-10
PL2049630T3 (pl) 2015-10-30
MX2009001124A (es) 2009-03-05
WO2008015116A3 (en) 2008-03-20
JP2009545640A (ja) 2009-12-24
JP5546858B2 (ja) 2014-07-09
JP2014139313A (ja) 2014-07-31
IL196250A (en) 2013-10-31
AU2007280548B2 (en) 2012-04-05
AU2007280548A1 (en) 2008-02-07

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