EP0819754B1 - Des lubrifiants contenant un acide propionique bèta-dithiophosphorylé - Google Patents
Des lubrifiants contenant un acide propionique bèta-dithiophosphorylé Download PDFInfo
- 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
- Authority
- 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.)
- Expired - Lifetime
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- NXTFOHPUXYZDOH-UHFFFAOYSA-N CCC(C)C1(C)CC23C=CC2C3C1 Chemical compound CCC(C)C1(C)CC23C=CC2C3C1 NXTFOHPUXYZDOH-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- 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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- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
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- C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
- C10L1/265—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) oxygen and/or sulfur bonds
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- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
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- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/28—Rotary engines
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.
Landscapes
- 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)
Claims (13)
- Composition contenantA) un lubrifiant ou carburant, un fluide d'usinage des métaux ou un fluide hydraulique;B) au moins un composé de formule oùR1 et R2 représentent indépendamment l'un de l'autre, des groupes alkyle en C3-C18, cycloalkyle en C5-C12, (cycloalkyl en en C5-C6)méthyle, bi(cycloalkyl en C9-C10) méthyle, tri(cycloalkyl en C9-C10) -méthyle, phényle, (alkyl en C7-C24)phényle ou conjointement représentent un groupe (CH3)2C(CH2)2, etR3 représente un atome d'hydrogène ou un groupe méthyle, et éventuellementC) d'autres addititifs d'huiles usuelles.
- Composition selon la revendication 1 contenant de 0,005 à 0,01 % en masse d'un composé de formule.I.
- Composition selon la revendication 1 contenant de 0,005 à 0,05 % en masse d'un composé de formule I.
- Composition selon la revendication 1, où le composant A) est une huile industrielle ou une graisse.
- Composition selon la revendication 1, où le composant A) est une huile de base prise dans le groupe des huiles minérales, végétales ou synthétiques.
- Composition selon la revendication 1, où R1 et R2 représentent, indépendamment l'un de l'autre, des groupes alkyle en C3-C18, cycloalkyle en C5-C12 ou (alkyl en C7-C18) phényle.
- Composition selon la revendication 1, où R1 et R2 représente des groupes i-propyle, i-butyle ou 2-éthylhexyle, et R3 représente un atome d'hydrogène.
- Composition selon la revendication 1 qui contient de plus C) d'autres additifs d'huiles pris dans le groupe des antioxydants, désactivateurs de métaaux, inhibiteurs de la rouille, dispersants, détergents, additifs de résistance au moussage, graisses, additifs améliorant l'indice de la viscosité, additifs d'abaissement du point de figeage et additifs de protection contre l'usure.
- Procédé pour améliorer les propriétés d'utilisation des lubrifiants, des fluides hydrauliques ou des fluides d'usinage des métaux, caractérisé en ce qu'on leur ajoute au moins un composé de formule I comme décrit à la revendication 1.
- Procédé selon la revendication 9 pour l'amélioration des propriétés d'utilisation de fluides hydrauliques ou d'huiles à engrenage.
- Composition selon la revendication 1 sans zinc.
- Composition essentiellement sans cendres selon la revendication 1.
- Utilisation du composant B) décrit à la revendication 1 en tant qu'additif de lubrifiants, de fluides hydrauliques ou de fluides d'usinage des métaux.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1769/96 | 1996-07-15 | ||
CH176996 | 1996-07-15 | ||
CH176996 | 1996-07-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0819754A1 EP0819754A1 (fr) | 1998-01-21 |
EP0819754B1 true EP0819754B1 (fr) | 2001-04-25 |
Family
ID=4218165
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP97810446A Expired - Lifetime EP0819754B1 (fr) | 1996-07-15 | 1997-07-07 | Des lubrifiants contenant un acide propionique bèta-dithiophosphorylé |
Country Status (11)
Country | Link |
---|---|
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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JP5976836B2 (ja) | 2011-12-22 | 2016-08-24 | 昭和シェル石油株式会社 | 潤滑組成物 |
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JP6887758B2 (ja) * | 2016-05-10 | 2021-06-16 | 日本グリース株式会社 | グリース組成物 |
JP2018009106A (ja) * | 2016-07-14 | 2018-01-18 | コスモ石油ルブリカンツ株式会社 | 非亜鉛系油圧作動油組成物 |
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WO2018236592A1 (fr) * | 2017-06-20 | 2018-12-27 | The Lubrizol Corporation | Composition lubrifiante |
JP6951272B2 (ja) * | 2018-02-08 | 2021-10-20 | Eneos株式会社 | 潤滑油用添加剤組成物及び潤滑油組成物 |
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-
1997
- 1997-07-07 EP EP97810446A patent/EP0819754B1/fr not_active Expired - Lifetime
- 1997-07-07 ES ES97810446T patent/ES2157549T3/es not_active Expired - Lifetime
- 1997-07-07 SG SG9702390A patent/SG84506A1/en unknown
- 1997-07-07 DE DE59703420T patent/DE59703420D1/de not_active Expired - Lifetime
- 1997-07-11 KR KR1019970032255A patent/KR100441550B1/ko not_active IP Right Cessation
- 1997-07-11 CA CA002210216A patent/CA2210216C/fr not_active Expired - Fee Related
- 1997-07-11 SK SK949-97A patent/SK283148B6/sk not_active IP Right Cessation
- 1997-07-14 ZA ZA9706208A patent/ZA976208B/xx unknown
- 1997-07-15 US US08/892,781 patent/US5922657A/en not_active Expired - Lifetime
- 1997-07-15 BR BR9703974A patent/BR9703974A/pt not_active IP Right Cessation
- 1997-07-15 JP JP20529597A patent/JP3882154B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP0819754A1 (fr) | 1998-01-21 |
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 |
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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