EP0735128A2 - Korrosions- und Oxidationsöle mit verlängerter Lebensdauer - Google Patents

Korrosions- und Oxidationsöle mit verlängerter Lebensdauer Download PDF

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Publication number
EP0735128A2
EP0735128A2 EP96302164A EP96302164A EP0735128A2 EP 0735128 A2 EP0735128 A2 EP 0735128A2 EP 96302164 A EP96302164 A EP 96302164A EP 96302164 A EP96302164 A EP 96302164A EP 0735128 A2 EP0735128 A2 EP 0735128A2
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EP
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Prior art keywords
formula
weight percent
oxidation
carbon atoms
dithiocarbamate
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Granted
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EP96302164A
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English (en)
French (fr)
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EP0735128B1 (de
EP0735128A3 (de
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Ramnath Iyer
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Ethyl Corp
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Ethyl Corp
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    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
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    • 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
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
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    • C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
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    • C10M2207/02—Hydroxy compounds
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    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2215/064—Di- and triaryl amines
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    • C10M2215/066—Arylene diamines
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    • C10M2223/10—Phosphatides, e.g. lecithin, cephalin

Definitions

  • This invention relates to the field of improved thermal and oxidative stability of lubricating fluids.
  • Lubricating oils such as circulating oils, turbine oils, hydraulic fluids and transformer oils as well as others require good oxidation stability and good rust inhibition properties. Extended life for such fluids where desired rust and oxidation (R&O) inhibition properties are maintained for extended periods of use is demanded by industrial users and provides important economic benefit.
  • R&O oils are widely used in turbine and compressor circulating systems. Their thermal and oxidative stability are of particular importance.
  • R&O oils provide rust protection, corrosion protection and metal passivation. Antiwear protection is sometimes needed.
  • U. S. Patent 4,125,479 to Chesluk et al. discloses an oxidation inhibited lubricating oil with a combination of additives comprising methylenebis(di-n-butyldithiocarbamate) and 4-methyl-2,6-ditertiary butyl phenol, said to provide enhanced oxidation inhibition.
  • U. S. Patent 4,125,479 to Chesluk et al. discloses an oxidation inhibited lubricating oil with a combination of additives comprising methylenebis(di-n-butyldithiocarbamate) and 4-methyl-2,6-ditertiary butyl phenol, said to provide enhanced oxidation inhibition.
  • U. S. Patent 4,125,479 to Chesluk et al. discloses an oxidation inhibited lubricating oil with a combination of additives comprising methylenebis(di-n-butyldithiocarbamate) and 4-methyl-2
  • Patent 4,880,551 to Doe discloses an antioxidant composition consisting of a 1-(di(4-octylphenyl) aminomethyl)tolutriazole and at least one antioxidant selected from the group consisting essentially of methylenebis(di-n-butyldithiocarbamate); 2,6-di-t-butyl-4-sec-butylphenol; 2,6-di-t-butyl-4-methylphenol and butylated phenol mixture.
  • R&O lubricant concentrate packages typically contain phenolic, amino and other antioxidants, rust inhibitor(s), a metal deactivator, and a demulsifying agent. They may include additional components such as an antiwear agent depending on the final performance properties desired.
  • the principle function of the antioxidants is the inhibition of oxidative degradation of R&O oils that are obtained by blending the R&O lubricant concentrate package in a particular basestock oil of choice. Basestock oils have varying degrees of thermal and oxidative stability.
  • This invention will serve to improve the thermal and oxidative properties of even those basestock oils that are known to have less than satisfactory stability.
  • the current invention relates to the use of certain components. that contribute directly to prolonging the life of R&O oils.
  • a rust and oxidation (R&O) inhibited lubricant composition comprising a base oil and rust and oxidation inhibitors
  • said lubricant composition comprises (a) a dithiocarbamate compound represented by the formula wherein R 4 is a hydrocarbylene group having 1 to 10 carbon atoms, each R 5 is a hydrogen or a hydrocarbyl group having 1 to 18 carbon atoms, and each R 3 is a hydrocarbyl group having 1 to 18 carbon atoms; and (b) an alkylphenyl- ⁇ -naphthylamine.
  • the lubricant composition further optionally comprises (c) a hydrocarbyl phosphite represented by the formula (R 6 O) 3 P where each R 6 is independently C 1 to C 18 alkyl, C 2 to C 18 alkenyl, or C 6 to C 18 aryl.
  • Each component (a) and (b), or (a), (b) and (c) is present in an amount sufficient to provide improved inhibition of oxidation to the R&O lubricant composition.
  • the additive combinations of this invention may be used in any lubricating oil where oxidation inhibition is required.
  • This may include circulating oils used in compressor and turbine circulating systems, transformer oils, engine oils and other oils which are subjected to conditions where oxidation is a problem. It has been found that a dithiocarbamate compound in combination with an alkylphenyl- ⁇ -naphthylamine, in effective amounts, and that combination in further combination with an effective amount of hydrocarbyl phosphite, provide important and unexpected enhancement of thermal and oxidation stability, with resulting improvement in the life of the R&O oil.
  • the additive combinations of this invention can be incorporated in a wide variety of lubricants and functional fluids in effective amounts to provide suitable active ingredient concentrations.
  • the base oils useful herein can be hydrocarbon oils of suitable viscosities; synthetic oils such as hydrogenated polyolefin oils; poly- ⁇ -olefin oligomers (such as hydrogenated poly-1-decene) ; alkyl esters of dicarboxylic acids; complex esters of dicarboxylic acid, polyglycol and alcohol; alkyl esters of carbonic or phosphoric acids; polysilicones; fluorohydrocarbon oils; and mixtures of mineral, natural and/or synthetic oils in any proportion, etc.
  • base oil for this disclosure includes all the foregoing and mixtures thereof.
  • the dithiocarbamate compound to be included in the combination of the invention is represented by the formula wherein R 4 is a hydrocarbylene group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms.
  • R 4 is an alkylene group, most preferably a methylene or ethylene group.
  • Each R 5 is a hydrogen or a hydrocarbyl group having 1 to 18 carbon atoms, preferably 2 to 10, more preferably 2 to 6.
  • Each R 3 is a hydrocarbyl group having 1 to 18 carbon atoms, preferably 2 to 10, more preferably 2 to 6.
  • a commercially available dithiocarbamate compound appropriate for use in the invention is VANLUBE° 7723, methylenebis(di-n-butyldithiocarbamate).
  • dithiocarbamate compound may start hurting or interfering with relevent bench tests other than R&O tests. Higher levels of dithiocarbamate compound may result in deterioration of thermal stability, causing undesired sludge in thermal stability tests. Also rust problems may occur at higher dithiocarbamate compound levels, which may result in failure of specified rust tests.
  • An effective amount of dithiocarbamate compound is up to 1.0 weight percent of the finished lubricant composition, for example 0.01 to 1.0 weight percent, 0.02 to 0.5 preferred, 0.03-0.2 most preferred.
  • alkylphenyl- ⁇ -naphthylamine for use in the invention is represented by the formula wherein R 1 and R 2 are independently hydrogen or C 1 to C 18 alkyl.
  • alkylphenyl- ⁇ -naphthylamine includes phenyl- ⁇ -naphthylamine (PANA), where both R 1 and R 2 are hydrogen.
  • An effective amount of alkylphenyl- ⁇ -naphthylamine for use in the invention is up to 0.15 weight percent of the finished lubricant composition, for example 0.025 to 0.15 weight percent, 0.03 to 0.125 weight percent preferred.
  • the hydrocarbyl phosphite compound for use in the invention is represented by the formula: (R 6 O) 3 P where each R 6 is independently C 1 to C 18 alkyl, C 2 to C 18 alkenyl, or C 6 to C 18 aryl. In preferred compounds, each R 6 is independently C 3 to C 12 alkyl or C 6 to C 18 aryl. In most preferred compounds, R 6 is C 6 to C 18 aryl, including triphenylphosphite, tricresylphos-phite, trinonylphenylphosphite (C15), tridodecylphenylphosphite, and mixtures thereof.
  • An effective amount of the hydrocarbyl phosphite compound for use in the invention is up to 0.075 weight percent of the finished lubricant composition, for example 0.005 to 0.075 weight percent, 0.01 to 0.06 preferred.
  • R&O oils will typically contain a conventional quantity of one or more antioxidants in order to protect the composition from premature degradation in the presence of air, especially at elevated temperatures.
  • Typical antioxidants include various alkylated phenols, hindered phenols and phenol derivatives such as t-butyl hydroquinone, butylated hydroxyanisole, polybutylated bisphenol A, butylated hydroxy toluene, alkylated hydroquinone, 2,5-ditertaryl hydroquinone; 2,6-ditert-butyl-para-cresol; 2,2'-methylenebis(6-tert-butyl-p-cresol); 1,5-naphthalenediol; 4,4'-thiobis(t-tert-butyl-m-cresol); p,p-biphenol; 4,4'-butylidenebis(6-tert-butyl-m-cresol); 4-methoxy-2,6-di-tert-butylphenol; and the
  • Phenolic antioxidants are known and may be represented by the general formula: where R 7 is hydrogen or an alkyl group with 1 to 4 carbons, R 8 is an alkyl group with 1 to 4 carbons or a benzylic group, and R 9 is hydrogen, an alkyl group with 1 to 6 carbons, or an alkoxy group with 1 to 6 carbons.
  • R 7 is hydrogen
  • R 8 is an alkyl group with 1 to 4 carbons
  • R 9 is an alkyl group with 1 to 6 carbons; most preferably both R 8 and R 9 are t-butyl.
  • R 9 is hydrogen, R 7 is an alkyl group with 1 to 4 carbons, and R 8 is an alkyl group with 1 to 4 carbons; most preferably both R 7 and R 8 are t-butyl.
  • the R&O oil compositions useful herein will also typically comprise a rust inhibitor and a metal deactivator. These are commonly selected from alkenyl succinic acid esters and from triazoles and triazole derivatives, known for these purposes.
  • a corrosion inhibitor This may be a single compound or a mixture of compounds having the property of inhibiting corrosion of metallic surfaces.
  • One type of such additives are inhibitors of copper corrosion.
  • Such compounds include thiazoles, triazoles and thiadizoles.
  • Examples of such compounds include benzotriazole, tolytriazole, octyltriazole, decyltriazole, dodecyltriazole, 2-mercaptobenzothiazole, 2, 5-dimercapto-1, 3, 4-thiadiazole, 2-mercapto-5-hydrocarbylthio-1,3,4-thiadiazoles, 2-mercapto-5-hydrocarbyldithio-1, 3, 4-thiadiazoles, 2, 5-bis(hydrocarbylthio)-1, 3, 4-thiadiazoles, and 2, 5-(bis)hydrocarbyldithio), 1, 3, 4-thiadiazoles.
  • the preferred compounds are the 1, 3, 4-thiadiazoles, a number of which are available as articles of commerce.
  • Such compounds are generally synthesized from hydrazine and carbon disulfide by known procedures. See for example U.S. Pat. Nos. 2,765,289; 2,749, 311; 2,760,933; 2,850,453; 2,910,439; 3,663,561; 3,862,798; and 3,840,549.
  • Other types of corrosion inhibitors are known and suitable for use in the compositions of this invention. Suitable corrosion inhibitors include ether amines; acid phosphates; amines; polyethoxylated compounds such as ethoxylated amines, ethoxylated and/or propoxylated phenols, and ethoxylated alcohols; imidazolines; and the like. Materials of these types are well known to those skilled in the art and a number of such materials are available as articles of commerce.
  • the lubricating composition of the present invention may further contain other additives such as extreme pressure agents and/or antiwear agents.
  • the additives of the present invention can be incorporated into a lubricating oil in any convenient way.
  • the compounds, or mixtures thereof, can be added directly to the oil at the desired level or by adding concentrates of the additive to the oil.
  • the additive compounds can be blended with a suitable oil soluble solvent such as mineral spirits and/or base oil to form a concentrate and then the concentrate may be blended with lubricating oil to obtain a final formulation.
  • a complete R&O lubricant concentrate package can be prepared containing antioxidants, rust inhibitor, metal, deactivator, demulsifier, additional desired components as well as the components of the invention, i.e.
  • the components are present in the lubricant concentrate package at a level sufficient to provide an effective level in the finished composition to provide the enhanced oxidation inhibition properties.
  • HiTec 575® Ashless Rust & Oxidation Inhibitor is a lubricant additive concentrate package commercially available from Ethyl Corporation. This is fully formulated for high-performance, turbine-quality hydraulic fluids. It provides extended oxidation life, excellent rust control, demulsibility and filterability, and is compatible with other additives commonly used in hydraulic fluids.
  • HiTec 575 lubricant additive represents a typical R&O package and has been used in the studies reported herein to demonstrate the improved oxidation properties obtained with the present invention.
  • Texaco ISO 46 basestock oil was used in preparing the formulation of the examples below. In Example 1, HiTec 575 lubricant additive was blended with the basestock oil at its recommended dosage, 0.80 weight percent.
  • HiTec 575 lubricant additive contains PANA in an amount that provides 0.10 weight percent to the blended lubricant composition at this recommended dosage.
  • the PANA was removed from the HiTec 575 lubricant additive.
  • the HiTec 575 lubricant additive without PANA was blended with the Texaco ISO 46 basestock oil at 0.80 weight percent dosage, and the dithiocarbamate compound and triphenylphosphite were added in the amounts indicated.
  • commercially available HiTec 575 lubricant additive was blended with the basestock at 0.80 weight percent dosage, and the dithiocarbamate compound and triphenylphosphite were added in the amounts indicated.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
EP96302164A 1995-03-28 1996-03-28 Korrosions- und Oxidationsöle mit verlängerter Lebensdauer Expired - Lifetime EP0735128B1 (de)

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0994175A2 (de) * 1998-10-16 2000-04-19 Ethyl Corporation Turbineölenmit ausgezeigneter Oxidationsstabilität bei hoher Temperatur
US6207623B1 (en) 2000-01-14 2001-03-27 Exxonmobil Research And Engineering Company Industrial oils of enhanced resistance to oxidation
EP1104800A2 (de) * 1999-12-02 2001-06-06 Oronite Japan Limited Schmiermittelzusammensetzung für Gasmotoren
CN1067714C (zh) * 1998-08-27 2001-06-27 中国石油化工集团公司 用于透平油的复合添加剂
WO2011153178A2 (en) 2010-06-02 2011-12-08 The Lubrizol Corporation Lubricating composition containing a carboxylic functionalised polymer
RU2493243C2 (ru) * 2009-02-02 2013-09-20 Ар.Ти. ВАНДЕРБИЛТ КОМПАНИ, ИНК. Беззольная смазывающая композиция
CN103517972A (zh) * 2011-05-16 2014-01-15 卢布里佐尔公司 用于涡轮机和水力系统的具有改进抗氧化性的润滑组合物
CN107573987A (zh) * 2017-09-29 2018-01-12 中国石油化工股份有限公司 涡轮机油添加剂组合物及其用途
EP3189125A4 (de) * 2014-09-04 2018-01-24 Vanderbilt Chemicals, LLC Flüssiges aschefreies antioxidierendes additiv für schmiermittelzusammensetzungen
CN107653025A (zh) * 2017-09-29 2018-02-02 中国石油化工股份有限公司 涡轮机油组合物及其用途

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2679663C1 (ru) * 2018-04-06 2019-02-12 Федеральное государственное бюджетное образовательное учреждение высшего образования "Казанский государственный энергетический университет" (ФГБОУ ВО "КГЭУ") Способ замедления окисления трансформаторного масла

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US3230168A (en) * 1964-12-08 1966-01-18 Shell Oil Co Lubricant compositions
US4119551A (en) * 1977-06-28 1978-10-10 Texaco Inc. Synthetic aircraft turbine lubricating oil compositions
US4125479A (en) * 1975-12-22 1978-11-14 Texaco Inc. Oxidation inhibited lubricating oil
US4226732A (en) * 1978-06-30 1980-10-07 Texaco Inc. Synthetic aircraft turbine oil
EP0528610A1 (de) * 1991-08-09 1993-02-24 Oronite Japan Limited Motorölzusammensetzung mit niedrigem Phosphongehalt und Additivzusammensetzungen
US5236610A (en) * 1992-02-03 1993-08-17 The United States Of America As Represented By The Secretary Of The Commerce Stable high temperature liquid lubricant blends and antioxidant additives for use therewith

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GB810741A (en) * 1956-05-28 1959-03-25 Wakefield & Co Ltd C C Improvements in or relating to lubricating oil compositions
US3230168A (en) * 1964-12-08 1966-01-18 Shell Oil Co Lubricant compositions
US4125479A (en) * 1975-12-22 1978-11-14 Texaco Inc. Oxidation inhibited lubricating oil
US4119551A (en) * 1977-06-28 1978-10-10 Texaco Inc. Synthetic aircraft turbine lubricating oil compositions
US4226732A (en) * 1978-06-30 1980-10-07 Texaco Inc. Synthetic aircraft turbine oil
EP0528610A1 (de) * 1991-08-09 1993-02-24 Oronite Japan Limited Motorölzusammensetzung mit niedrigem Phosphongehalt und Additivzusammensetzungen
US5236610A (en) * 1992-02-03 1993-08-17 The United States Of America As Represented By The Secretary Of The Commerce Stable high temperature liquid lubricant blends and antioxidant additives for use therewith

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1067714C (zh) * 1998-08-27 2001-06-27 中国石油化工集团公司 用于透平油的复合添加剂
EP0994175A3 (de) * 1998-10-16 2001-10-31 Ethyl Corporation Turbineölenmit ausgezeigneter Oxidationsstabilität bei hoher Temperatur
CN1100859C (zh) * 1998-10-16 2003-02-05 乙基公司 具有优异的高温氧化稳定性的汽轮机油
US6326336B1 (en) 1998-10-16 2001-12-04 Ethyl Corporation Turbine oils with excellent high temperature oxidative stability
EP0994175A2 (de) * 1998-10-16 2000-04-19 Ethyl Corporation Turbineölenmit ausgezeigneter Oxidationsstabilität bei hoher Temperatur
EP1104800A3 (de) * 1999-12-02 2001-06-20 Oronite Japan Limited Schmiermittelzusammensetzung für Gasmotoren
EP1104800A2 (de) * 1999-12-02 2001-06-06 Oronite Japan Limited Schmiermittelzusammensetzung für Gasmotoren
US6207623B1 (en) 2000-01-14 2001-03-27 Exxonmobil Research And Engineering Company Industrial oils of enhanced resistance to oxidation
RU2493243C2 (ru) * 2009-02-02 2013-09-20 Ар.Ти. ВАНДЕРБИЛТ КОМПАНИ, ИНК. Беззольная смазывающая композиция
WO2011153178A2 (en) 2010-06-02 2011-12-08 The Lubrizol Corporation Lubricating composition containing a carboxylic functionalised polymer
US8969266B2 (en) 2010-06-02 2015-03-03 The Lubrizol Corporation Lubricating composition containing a carboxylic functionalised polymer
CN103517972A (zh) * 2011-05-16 2014-01-15 卢布里佐尔公司 用于涡轮机和水力系统的具有改进抗氧化性的润滑组合物
EP3189125A4 (de) * 2014-09-04 2018-01-24 Vanderbilt Chemicals, LLC Flüssiges aschefreies antioxidierendes additiv für schmiermittelzusammensetzungen
CN107573987A (zh) * 2017-09-29 2018-01-12 中国石油化工股份有限公司 涡轮机油添加剂组合物及其用途
CN107653025A (zh) * 2017-09-29 2018-02-02 中国石油化工股份有限公司 涡轮机油组合物及其用途

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EP0735128B1 (de) 2000-08-23
EP0735128A3 (de) 1997-06-11
CA2171924C (en) 2007-03-13

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