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EP0557839B1 - Additifs anticorrosion à bas et haut poids moléculaire à base d'époxides - Google Patents

Additifs anticorrosion à bas et haut poids moléculaire à base d'époxides Download PDF

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Publication number
EP0557839B1
EP0557839B1 EP93102317A EP93102317A EP0557839B1 EP 0557839 B1 EP0557839 B1 EP 0557839B1 EP 93102317 A EP93102317 A EP 93102317A EP 93102317 A EP93102317 A EP 93102317A EP 0557839 B1 EP0557839 B1 EP 0557839B1
Authority
EP
European Patent Office
Prior art keywords
acids
molecular weight
oils
low
epoxides
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
Application number
EP93102317A
Other languages
German (de)
English (en)
Other versions
EP0557839A1 (fr
Inventor
Volker Dr. Schäfer
Robert Kohler
Alfred Dr. Pauli
Achim Dr. Fessenbecker
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.)
Rhein Chemie Rheinau GmbH
Original Assignee
Rhein Chemie Rheinau GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Rhein Chemie Rheinau GmbH filed Critical Rhein Chemie Rheinau GmbH
Publication of EP0557839A1 publication Critical patent/EP0557839A1/fr
Application granted granted Critical
Publication of EP0557839B1 publication Critical patent/EP0557839B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/66—Epoxidised acids or esters
    • 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or derivatives thereof
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/24—Epoxidised acids; Ester derivatives thereof
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • 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
    • C10N2040/02—Bearings
    • 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
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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
    • C10N2040/135—Steam engines or turbines

Definitions

  • oxidizing inhibitors are sodium nitrite or lithium nitrite, which can be finely divided as solid salts in the fat, and also certain organic nitrites or chromates.
  • adsorption inhibitors which often consist of nitrogen or sulfur compounds. This subheading also includes the amines, which are used either as such or as salts of lower alkane-carboxylic acids.
  • the most important inhibitors used in oil are the alkali and alkaline earth salts of high molecular weight sulfonic acids, which are obtained by neutralizing sulfonated oils (petroleum sulfonates, synthesis sulfonates). These are higher molecular weight compounds that are adsorbed on the entire metal surface via their polar sulfonic acid group. They generally work in two ways; that is, they delay both the anodic and cathodic reactions. The lipophilic part of such compounds contributes to better solubility in mineral oils.
  • alkaline earth metal sulfonates A disadvantage of the alkaline earth metal sulfonates is that, when combined with other additives, poorly soluble alkaline earth metal salts can form, which can impair the tribological effectiveness due to deposits on the metal surfaces. Even at high processing temperatures at which the oils evaporate or burn, inorganic salts may remain on the metal surface, e.g. are annoying when rolling thin sheets.
  • Another disadvantage is that heavy metal residues such as barium sulfate and zinc sulfate are produced in the production of metal-containing sulfonates.
  • metal-containing corrosion inhibitors in particular in open tribosystems, is restricted because, owing to their high metal content, the biodegradability can be delayed by interfering with microbial degradation processes.
  • the object of the invention is to provide sulfonate-like compounds which, as additives to mineral oils, fats and in particular native oils such as rapeseed oil, provide good corrosion protection.
  • reaction products of epoxidized fatty acid esters preferably the methyl esters of such fatty acids with higher molecular weight sulfonic acids, have the required properties.
  • EP-A 0 335 429 mentions special amine salts of alkyl aromatic sulfonic acids as lubricant additives, but does not specify how these products can be produced in detail.
  • the invention therefore relates to the use of epoxidized fatty acid esters and subsequently reacted with low or higher molecular weight sulfonic acids, in particular methyl esters of unsaturated fatty acids, as a corrosion-inhibiting additive to lubricating oils, in particular lubricating oils of vegetable origin.
  • reaction products used according to the invention can be prepared as follows: Suitable sulfonic acids for the reaction are, for example, higher molecular weight monoalkylbenzenesulfonic acids or dialkylbenzenesulfonic acids.
  • Suitable sulfonic acids for the reaction are, for example, higher molecular weight monoalkylbenzenesulfonic acids or dialkylbenzenesulfonic acids.
  • the epoxidized methyl esters of unsaturated fatty acids or fatty acid mixtures for example rapeseed oil, linseed oil, soybean oil or fish oil, are preferred as epoxidized fatty acid esters Fatty acids used.
  • the sulfonic acids mentioned with the epoxidized fatty acid esters which have epoxide contents of 1.5-15% by weight (% by weight of oxygen, based on epoxidized methyl ester), preferably 4-8% by weight, in amounts of 10-60 % By weight (based on epoxidized fatty acid esters) at temperatures of 20-120 ° C., preferably at 30-60 ° C., to give liquid products.
  • the amount of sulfonic acids is such that there is about one mole of reactive sulfonic acid group per mole of epoxy groups. If the stoichiometric conversion is not complete, the reaction product should preferably also contain epoxy groups.
  • Preferred sulfonic acids are higher molecular weight dialkylbenzenesulfonic acids.
  • the reaction products obtained are added to oils, in particular native oils, in amounts of 0.01-70% by weight, preferably 0.05 to 5% by weight, based on pure oil, and give them significantly better corrosion protection properties than conventional corrosion inhibitors such as metal sulfonates and metal naphthenates.
  • demulsifying or emulsifying products can be obtained.
  • demulsifying or emulsifying products can be obtained for hydraulic, gear and steam turbine oils where HLP and CLP requirements are prescribed.
  • the use of lubricants with good demulsifying behavior is necessary for hydraulic, gear and steam turbine oils where HLP and CLP requirements.
  • Hydraulic oils HLP according to DIN 51 524 part 2 are hydraulic fluids made from mineral oils with active ingredients to increase corrosion protection, aging resistance and reduce seizure wear.
  • Lubricating oils CLP according to DIN 51 517 Part 3 are mineral oils with active substances to increase the protection against corrosion and the aging resistance as well as effects to reduce the wear.
  • hydraulic oils must be easy to filter through extremely fine filters (eg 3 ⁇ m).
  • the reaction products according to the invention contain no metal compounds which often interfere with the filterability or even make it impossible, and are therefore particularly easy to filter.
  • reaction products according to the invention are suitable as an additive to dewatering fluids based on low-boiling hydrocarbons.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Paints Or Removers (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Epoxy Compounds (AREA)

Claims (2)

  1. Procédé pour la préparation d'acides gras modifiés, caractérisé en ce qu'on fait réagir des esters d'acides gras époxydés possédant des teneurs en époxydes de 1,5 à 15% en poids, à une température de 20 à 120°C, avec des acides monoalkylbenzènesulfoniques ou avec des acides dialkylbenzènesulfoniques.
  2. Utilisation d'acides gras époxydés et soumis à une mise en réaction ultérieure avec des acides sulfoniques à bas poids moléculaires ou à poids moléculaires plus élevés, en particulier avec les esters méthyliques d'acides gras insaturés, comme additif inhibant la corrosion à des huiles de graissage, en particulier des huiles de graissage d'origine végétale.
EP93102317A 1992-02-27 1993-02-15 Additifs anticorrosion à bas et haut poids moléculaire à base d'époxides Expired - Lifetime EP0557839B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4206047 1992-02-27
DE4206047A DE4206047A1 (de) 1992-02-27 1992-02-27 Nieder- und hochmolekulare korrosionsschutzadditive auf basis von epoxiden

Publications (2)

Publication Number Publication Date
EP0557839A1 EP0557839A1 (fr) 1993-09-01
EP0557839B1 true EP0557839B1 (fr) 1997-04-09

Family

ID=6452731

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93102317A Expired - Lifetime EP0557839B1 (fr) 1992-02-27 1993-02-15 Additifs anticorrosion à bas et haut poids moléculaire à base d'époxides

Country Status (6)

Country Link
EP (1) EP0557839B1 (fr)
JP (1) JPH0625687A (fr)
AT (1) ATE151449T1 (fr)
DE (2) DE4206047A1 (fr)
DK (1) DK0557839T3 (fr)
ES (1) ES2099852T3 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4079830A1 (fr) 2021-04-19 2022-10-26 Marteen Sports World, S.L. Composition lubrifiante biodégradable

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2763615A (en) * 1953-04-16 1956-09-18 Monsanto Chemicals Carboxylic acid derivatives and lubricants containing them
US3096357A (en) * 1960-05-04 1963-07-02 Bohme Fettchemie Gmbh Novel reaction products of a sulfuric acid and epoxides
US3485754A (en) * 1967-06-30 1969-12-23 Emery Industries Inc Lubricant composition and method of refining
DE3617550A1 (de) * 1986-05-24 1987-11-26 Henkel Kgaa Verwendung von salzen von estern langkettiger fettalkohole mit (alpha)-sulfofettsaeuren
ATE76894T1 (de) * 1988-03-22 1992-06-15 King Industries Inc Amindinonylnaphthalinsulfonate mit korrosionshemmenden eigenschaften.

Also Published As

Publication number Publication date
DE59306079D1 (de) 1997-05-15
JPH0625687A (ja) 1994-02-01
ATE151449T1 (de) 1997-04-15
EP0557839A1 (fr) 1993-09-01
ES2099852T3 (es) 1997-06-01
DE4206047A1 (de) 1993-09-02
DK0557839T3 (da) 1997-10-13

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