EP0819754B1 - Beta-Dithiophosphorylierte Propionsäure in Schmierstoffen - Google Patents

Beta-Dithiophosphorylierte Propionsäure in Schmierstoffen Download PDF

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Publication number
EP0819754B1
EP0819754B1 EP97810446A EP97810446A EP0819754B1 EP 0819754 B1 EP0819754 B1 EP 0819754B1 EP 97810446 A EP97810446 A EP 97810446A EP 97810446 A EP97810446 A EP 97810446A EP 0819754 B1 EP0819754 B1 EP 0819754B1
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EP
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Prior art keywords
tert
butyl
bis
composition according
lubricants
Prior art date
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EP97810446A
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German (de)
English (en)
French (fr)
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EP0819754A1 (de
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.)
BASF Schweiz AG
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Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
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Definitions

  • the present invention relates to compositions containing a lubricant (preferably an industrial oil or a grease), a metalworking or a Hydraulic fluid and at least one ⁇ -dithiophosphorylated propionic acid Formula I described below.
  • a lubricant preferably an industrial oil or a grease
  • metalworking or a Hydraulic fluid preferably an industrial oil or a grease
  • at least one ⁇ -dithiophosphorylated propionic acid Formula I described below preferably an industrial oil or a grease
  • 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, preferred in hydraulic and gear oils.
  • Lubricants industrial oils or greases
  • the use according to the invention closes the protection of the metal parts to be lubricated from mechanical Wear (high pressure and wear protection) and an anti-corrosion effect on. Therefore, the present invention also relates to a method for improvement the performance characteristics of lubricants, metalworking and Hydraulic fluids, characterized in that these compounds of Formula I can be added.
  • the lubricants or fuels mentioned are based for example on mineral or synthetic oils or mixtures thereof.
  • the lubricants are familiar to the specialist and in the relevant specialist literature, as for example in Dieter Klamann, "Lubricants and related Products “(Verlag Chemie, Weinheim, 1982), in Schewe-Kobek,” The Lubricant Paperback “ (Dr. Alfred Wilsonhig-Verlag, Heidelberg, 1974) and in “Ullmanns Encyclopedia of Technical Chemistry ", Vol. 13, pages 85-94 (Verlag Chemie, Weinheim, 1977).
  • the lubricants are especially 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 each other 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 as well as 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 based lubricants the aliphatic or aromatic carboxyl esters, the polymeric esters, the Polyalkylene oxides, phosphoric acid esters, poly- ⁇ -olefins or silicones, a diester of a dihydric acid with a monohydric alcohol, e.g. Dioctyl sebacate or dinonyl adipate, a triester of trimethylolpropane with a monovalent acid or with a mixture of such acids, e.g.
  • Trimethylolpropane tripelargonate Trimethylolpropane tricaprylate or mixtures thereof, one Pentaerythritol tetraesters with a monovalent acid or with a mixture such acids, e.g. Pentaerythritol tetracaprylate, or a complex ester of monohydric and dihydric acids with polyhydric alcohols, e.g. on complex ester of trimethylolpropane with caprylic and sebacic acid or of a mixture of them.
  • mineral oils e.g. Poly- ⁇ -olefins, Ester based lubricants, phosphates, glycols, polyglycols and Polyalkylene glycols and their mixtures with water.
  • Industrial oils, greases, metalworking fluids and hydraulic fluids can be produced on the basis of the same substances as for the above Lubricant described. Often these are also emulsions 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 motors of the Otto, diesel, two-stroke, Wankel or orbital types.
  • Component B is also suitable as an additive for fuels in motor vehicles, which are equipped with motors of the type mentioned.
  • the compounds of the formula I are used in lubricants, fuels, metalworking and hydraulic fluids well soluble and therefore as additives Lubricants, metalworking and hydraulic fluids are particularly suitable.
  • compositions advantageously contain 0.005 to 1.0% by weight of one 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 one Compound of the formula I, preferably 0.005-0.1% by weight, in particular 0.005- 0.05% by weight.
  • the compounds of formula I can the lubricants or fuels per se be mixed in a known manner.
  • the compounds are in oils, for example readily soluble. It is also possible to produce a so-called master batch that in accordance with the consumption to use concentrations with the corresponding Lubricant can be diluted. In such cases there are also concentrations over 1% by weight possible.
  • the lubricants or fuels, metalworking and hydraulic fluids can additionally contain other additives that be added to further improve their basic properties; to 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 coefficient of friction.
  • additives are used in the usual way Amounts in the range of about 0.01 to 10.0% by weight each.
  • viscosity index improvers examples include: polyacrylates, polymethacrylates, vinyl pyrrolidone / methacrylate copolymers, polyvinyl pyrrolidones, polybutenes, olefin copolymers, styrene / acrylate copolymers, polyethers.
  • pour point depressants are: polymethacrylate, alkylated naphthalene derivatives.
  • dispersants / surfactants are: polybutenylsuccinic acid amides or - imides, polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sulfonates and phenolates.
  • anti-foaming agents silicone oils and polymethacrylene.
  • solid lubricants examples include 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 aryl di- and tri-sulfides, 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] -prophosphate-ethyl-propionate (Triphenylphosphorothioate), tris (alkylphenyl) phosphorothioate 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 carrying properties - especially for hydraulic and Gear oils, with surprisingly relatively small amounts of ⁇ -dithiophosphorylated Sufficient propionic acids. This can cause any negative Accompanying effects such as corrosiveness to Cu and incompatibility with any existing ones Ca compounds (precipitation reactions) can be minimized. Furthermore, a additional corrosion protection potential available.

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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 Beta-Dithiophosphorylierte Propionsäure in Schmierstoffen Expired - Lifetime EP0819754B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH176996 1996-07-15
CH176996 1996-07-15
CH1769/96 1996-07-15

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

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ZA976208B (en) 1998-01-15
CA2210216A1 (en) 1998-01-15
JPH1067993A (ja) 1998-03-10
SK283148B6 (sk) 2003-03-04
BR9703974A (pt) 1998-11-17
KR980009432A (ko) 1998-04-30
DE59703420D1 (de) 2001-05-31
KR100441550B1 (ko) 2004-11-20
SG84506A1 (en) 2001-11-20
EP0819754A1 (de) 1998-01-21
JP3882154B2 (ja) 2007-02-14
ES2157549T3 (es) 2001-08-16
SK94997A3 (en) 1998-02-04
US5922657A (en) 1999-07-13
CA2210216C (en) 2006-01-31

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