EP0819754A1 - Des lubrifiants contenant un acide propionique bèta-dithiophosphorylé - Google Patents

Des lubrifiants contenant un acide propionique bèta-dithiophosphorylé Download PDF

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Publication number
EP0819754A1
EP0819754A1 EP97810446A EP97810446A EP0819754A1 EP 0819754 A1 EP0819754 A1 EP 0819754A1 EP 97810446 A EP97810446 A EP 97810446A EP 97810446 A EP97810446 A EP 97810446A EP 0819754 A1 EP0819754 A1 EP 0819754A1
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EP
European Patent Office
Prior art keywords
tert
butyl
bis
composition according
lubricants
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
Application number
EP97810446A
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German (de)
English (en)
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EP0819754B1 (fr
Inventor
Hugo Camenzind
Marc Ribeaud
Michael Fletschinger
Peter Rohrbach
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.)
Novartis AG
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
Ciba Spezialitaetenchemie Holding AG
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    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
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    • C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol fueled engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines

Definitions

  • the present invention relates to compositions which contain a lubricant (preferably an industrial oil or a fat), a metal working or a hydraulic fluid and at least one ⁇ -dithiophosphorylated propionic acid of the formula I described below.
  • a lubricant preferably an industrial oil or a fat
  • a metal working or a hydraulic fluid and at least one ⁇ -dithiophosphorylated propionic acid of the formula I described below.
  • Additives are added to modern lubricants, which perform tasks such as high-pressure and wear protection, corrosion protection and antioxidation effects [WJ Bartz (Editor), et al., "Additives for lubricants” (expert-Verlag 1994)].
  • Zinc dialkyldithiophosphates which combine antioxidative and high-pressure and wear protection effects, are of particular importance.
  • efforts have been made to largely replace these heavy metal additives with metal-free compounds, because this is environmentally friendly and has a positive effect on the service life of the exhaust gas catalysts of internal combustion engines.
  • Type of ester are available under the trade name lrgalube TM 63.
  • US 4,333,841 dithiophosphorylated mercaptoacetic acids and their salts are described as lubricant additives.
  • R 1 and R 2 are, independently of one another, C 3 -C 18 alkyl, C 5 -C 6 cycloalkyl or C 7 -C 18 alkylphenyl.
  • R 1 and R 2 are particularly preferably i-propyl, i-butyl or 2-ethylhexyl, and R 3 is hydrogen.
  • IR 1 and R 2 are C 3 -C 18 -alkyl in the above formula, these are branched or unbranched radicals. Examples include propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, isopentyl, hexyl, heptyl, 3-heptyl, octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl , Heptadecyl, octadecyl, 2-ethylbutyl, 1-methylpentyl, 1,3-dimethylbutyl, 1,1,3,3-tetramethylbutyl, 1-methylhexyl, isoheptyl, 1-methylheptyl, 1,1,3-trimethylhexyl or
  • R 1 and R 2 as C 5 -C 12 cycloalkyl can be, for example, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl or cyclododecyl. Cyclopentyl and cyclohexyl are preferred, especially cyclohexyl.
  • R 1 and R 2 are C 5 -C 6 -cycloalkyl-methyl, this means cyclopentylmethyl and especially cyclohexylmethyl.
  • R 1 and R 2 are C 5 -C 6 -cycloalkyl-methyl, this means cyclopentylmethyl and especially cyclohexylmethyl.
  • R 1 and R 2 are, for example, decalinylmethyl as C 9 -C 10 bicycloalkylmethyl. As C 9 -C 10 tricycloalkylmethyl, R 1 and R 2 preferably have the meaning of a group of the formula
  • alkylphenyl examples include methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, isopropylphenyl, t-butylphenyl, di-t-butylphenyl or 2,6 di-t-butyl-4-methylphenyl.
  • the invention also relates to the use of component B) as additives in lubricants (industrial oils or greases), hydraulic or metalworking fluids, preferably in hydraulic and gear oils.
  • lubricants industrial oils or greases
  • hydraulic or metalworking fluids preferably in hydraulic and gear oils.
  • the use according to the invention includes the protection of the metal parts to be lubricated against mechanical wear (high pressure and wear protection) and an anti-corrosion effect.
  • the present invention therefore also relates to a process for improving the performance properties of lubricants, metalworking and hydraulic fluids, characterized in that compounds of the formula I are added to these.
  • the lubricants or fuels mentioned are based, for example, on mineral or synthetic oils or mixtures thereof.
  • the lubricants are familiar to the person skilled in the art and are found in the relevant specialist literature, for example in Dieter Klamann, "Lubricants and Related Products” (Verlag Chemie, Weinheim, 1982), in Schewe-Kobek, "The Lubricant Pocket Book” (Dr. Alfred Hüthig- Verlag, Heidelberg, 1974) and in "Ullmann's Encyclopedia of Technical Chemistry", Vol. 13, pages 85-94 (Verlag Chemie, Weinheim, 1977).
  • the lubricants are in particular oils and fats, for example based on a mineral oil. Oils are preferred.
  • lubricants that can be used are vegetable or animal oils, fats, tallow and waxes or their mixtures with one another or mixtures with the mineral or synthetic oils mentioned.
  • Vegetable and animal oils, fats, tallow and waxes are for example Tree nut oil and mixtures thereof, fish oils, tallow from slaughter animals such as beef tallow, claw fat and bone oil and their modified, epoxidized and sulfoxidized forms, for example epoxidized soybean oil.
  • the mineral oils are based in particular on hydrocarbon compounds.
  • Examples of synthetic lubricants include lubricants based on the aliphatic or aromatic carboxyl esters, the polymeric esters, the polyalkylene oxides, the phosphoric acid esters, the poly- ⁇ -olefins or the silicones, a diester of a dibasic acid with a monohydric alcohol, e.g. Dioctyl sebacate or dinonyl adipate, a triester of trimethylolpropane with a monohydric acid or with a mixture of such acids, e.g.
  • mineral oils e.g. Poly- ⁇ -olefins, ester-based lubricants, phosphates, glycols, polyglycols and polyalkylene glycols, and mixtures thereof with water.
  • Industrial oils, greases, metalworking fluids and hydraulic fluids can be produced on the basis of the same substances as described above for the lubricants. Often these are emulsions of such substances in water or other liquids.
  • Lubricant compositions according to the invention find e.g. Use in internal combustion engines, e.g. in motor vehicles, e.g. with engines of the Otto, Diesel, two-stroke, Wankel or orbital type.
  • Component B is also suitable as an additive for fuels in motor vehicles which are equipped with the engines of the type mentioned.
  • the compounds of the formula I are readily soluble in lubricants, fuels, metalworking and hydraulic fluids and are therefore particularly suitable as additives to lubricants, metalworking and hydraulic fluids.
  • compositions advantageously contain 0.005 to 1.0% by weight of a compound of the formula I, preferably 0.005-0.1% by weight, in particular 0.005-0.05% by weight.
  • compositions advantageously contain 0.005 to 1.0% by weight of a compound of the formula I, preferably 0.005-0.1% by weight, in particular 0.005-0.05% by weight.
  • the compounds of the formula I can be added to the lubricants or fuels in a manner known per se.
  • the compounds are readily soluble in oils, for example. It is also possible to produce a so-called master batch, which can be diluted with the appropriate lubricant to the required concentration depending on the consumption. In such cases, concentrations above 1% by weight are also possible.
  • the lubricants or fuels, metalworking and hydraulic fluids stabilized according to the invention can additionally contain other additives which are added in order to further improve their basic properties; these include: antioxidants, metal passivators, other rust inhibitors, viscosity index improvers, pour point depressants, solid lubricants, dispersants, detergents, anti-foaming agents, other high-pressure additives, anti-wear additives and friction coefficient reducers.
  • additives are added in the amounts customary for this in the range from about 0.01 to 10.0% by weight.
  • viscosity index improvers examples are:
  • Polyacrylates polymethacrylates, vinyl pyrrolidone / methacrylate copolymers, polyvinyl pyrrolidones, polybutenes, olefin copolymers, styrene / acrylate copolymers, polyethers.
  • pour point depressants examples are:
  • dispersants / surfactants examples are :
  • anti-foaming agents examples include:
  • solid lubricants are:
  • Teflon TM or molybdenum sulfide Teflon TM or molybdenum sulfide.
  • wear protection additives are:
  • Sulfur and / or phosphorus and / or halogen-containing compounds such as sulfurized olefins and vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, tricresyl phosphate, chlorinated paraffins, alkyl- and aryldi- and trisulfides, amine salts of mono- and dialkyl phosphates, amine salts of methylphosphonic acid, diethanolaminomethyltolyltriazole , Di (2-ethylhexyl) aminomethyltolyltriazole, derivatives of 2,5-dimercapto-1,3,4-thiadiazole, 3 - [(bis-isopropyloxy-phosphinothioyl) thio] propionic acid ethyl ester, triphenylthiophosphate (triphenylphosphorothioate), tris (alkylphenyl ) phosphorothioates and mixtures thereof (
  • the compounds according to the invention are prepared, for example, according to the following scheme: CA 90: 120801s] and in LA Belova, et al, Zh. Obshch. Khim 51 (9) (1981) 1982-88 (Russian) [CA 96: 103597 m].
  • compositions are good wear protection and especially the very good load-bearing properties - especially for hydraulic and gear oils, whereby surprisingly relatively small amounts of ⁇ -dithiophosphorylated propionic acids are sufficient. This can minimize any negative side effects such as corrosivity to Cu and incompatibility with any Ca compounds (precipitation reactions). There is also additional corrosion protection potential.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Lubricants (AREA)
  • Liquid Carbonaceous Fuels (AREA)
EP97810446A 1996-07-15 1997-07-07 Des lubrifiants contenant un acide propionique bèta-dithiophosphorylé Expired - Lifetime EP0819754B1 (fr)

Applications Claiming Priority (3)

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CH1769/96 1996-07-15
CH176996 1996-07-15
CH176996 1996-07-15

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EP0819754A1 true EP0819754A1 (fr) 1998-01-21
EP0819754B1 EP0819754B1 (fr) 2001-04-25

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US (1) US5922657A (fr)
EP (1) EP0819754B1 (fr)
JP (1) JP3882154B2 (fr)
KR (1) KR100441550B1 (fr)
BR (1) BR9703974A (fr)
CA (1) CA2210216C (fr)
DE (1) DE59703420D1 (fr)
ES (1) ES2157549T3 (fr)
SG (1) SG84506A1 (fr)
SK (1) SK283148B6 (fr)
ZA (1) ZA976208B (fr)

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SG85234A1 (en) * 2000-03-31 2001-12-19 Chevron Oronite Co Lubricant composition for air-cooled two-stroke cycle engines
WO2002079358A2 (fr) * 2001-03-29 2002-10-10 Shell Internationale Research Maatschappij B.V. Composition d'huile lubrifiante
WO2002092735A1 (fr) * 2001-05-11 2002-11-21 Shell International Research Maatschappij B.V. Composition d'huile lubrifiante comprenant une combinaison d'addition composee d'un acide carboxylique et d'une amine en tant qu'agent antirouille
EP1816182A1 (fr) * 2004-11-24 2007-08-08 Nippon Oil Corporation Composition d'huile lubrifiante
EP2653528A1 (fr) * 2010-11-19 2013-10-23 JX Nippon Oil & Energy Corporation Composition d'huile lubrifiante pour section coulissante comportant un matériau d'aluminium, et procédé de lubrification
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Cited By (10)

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Publication number Priority date Publication date Assignee Title
SG85234A1 (en) * 2000-03-31 2001-12-19 Chevron Oronite Co Lubricant composition for air-cooled two-stroke cycle engines
WO2002079358A2 (fr) * 2001-03-29 2002-10-10 Shell Internationale Research Maatschappij B.V. Composition d'huile lubrifiante
WO2002079358A3 (fr) * 2001-03-29 2007-10-25 Shell Int Research Composition d'huile lubrifiante
WO2002092735A1 (fr) * 2001-05-11 2002-11-21 Shell International Research Maatschappij B.V. Composition d'huile lubrifiante comprenant une combinaison d'addition composee d'un acide carboxylique et d'une amine en tant qu'agent antirouille
EP1816182A1 (fr) * 2004-11-24 2007-08-08 Nippon Oil Corporation Composition d'huile lubrifiante
EP1816182A4 (fr) * 2004-11-24 2008-04-23 Nippon Oil Corp Composition d'huile lubrifiante
US9157046B2 (en) 2004-11-24 2015-10-13 Nippon Oil Corporation Lubricating oil composition
EP2653528A1 (fr) * 2010-11-19 2013-10-23 JX Nippon Oil & Energy Corporation Composition d'huile lubrifiante pour section coulissante comportant un matériau d'aluminium, et procédé de lubrification
EP2653528A4 (fr) * 2010-11-19 2015-04-22 Jx Nippon Oil & Energy Corp Composition d'huile lubrifiante pour section coulissante comportant un matériau d'aluminium, et procédé de lubrification
WO2021198420A1 (fr) * 2020-04-03 2021-10-07 Shell Internationale Research Maatschappij B.V. Fluide hydraulique à base d'eau/de glycol

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JP3882154B2 (ja) 2007-02-14
DE59703420D1 (de) 2001-05-31
BR9703974A (pt) 1998-11-17
SK94997A3 (en) 1998-02-04
KR980009432A (ko) 1998-04-30
ZA976208B (en) 1998-01-15
CA2210216C (fr) 2006-01-31
KR100441550B1 (ko) 2004-11-20
JPH1067993A (ja) 1998-03-10
EP0819754B1 (fr) 2001-04-25
SG84506A1 (en) 2001-11-20
CA2210216A1 (fr) 1998-01-15
SK283148B6 (sk) 2003-03-04
ES2157549T3 (es) 2001-08-16
US5922657A (en) 1999-07-13
MX9705300A (es) 1998-08-30

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