WO2015024561A2 - Additif pour lubrifiants à base d'huile présentant de meilleures propriétés extrême pression - Google Patents

Additif pour lubrifiants à base d'huile présentant de meilleures propriétés extrême pression Download PDF

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Publication number
WO2015024561A2
WO2015024561A2 PCT/DE2014/100298 DE2014100298W WO2015024561A2 WO 2015024561 A2 WO2015024561 A2 WO 2015024561A2 DE 2014100298 W DE2014100298 W DE 2014100298W WO 2015024561 A2 WO2015024561 A2 WO 2015024561A2
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Prior art keywords
formula
derivative
alternative
dimeric
iii
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PCT/DE2014/100298
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German (de)
English (en)
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WO2015024561A3 (fr
Inventor
Helmut Fackler
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Hkp Heiz- Und Kraftstoffe Pflanzenöl Gmbh
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Application filed by Hkp Heiz- Und Kraftstoffe Pflanzenöl Gmbh filed Critical Hkp Heiz- Und Kraftstoffe Pflanzenöl Gmbh
Priority to PL14793006T priority Critical patent/PL3036313T3/pl
Priority to DK14793006.9T priority patent/DK3036313T3/en
Priority to DE112014003817.2T priority patent/DE112014003817A5/de
Priority to ES14793006T priority patent/ES2705064T3/es
Priority to EP14793006.9A priority patent/EP3036313B1/fr
Priority to JP2016535346A priority patent/JP6339201B2/ja
Priority to US14/912,668 priority patent/US20160201001A1/en
Publication of WO2015024561A2 publication Critical patent/WO2015024561A2/fr
Publication of WO2015024561A3 publication Critical patent/WO2015024561A3/fr

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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
    • 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
    • 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
    • C10M127/00—Lubricating compositions characterised by the additive being a non- macromolecular hydrocarbon
    • C10M127/02—Lubricating compositions characterised by the additive being a non- macromolecular hydrocarbon well-defined aliphatic
    • 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
    • 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
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
    • C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/024—Well-defined aliphatic compounds unsaturated
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
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    • 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
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28—Amides; Imides
    • 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
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/40—Low content or no content compositions
    • C—CHEMISTRY; METALLURGY
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/62—Food grade properties
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/70—Soluble oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—Bearings
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/135—Steam engines or turbines
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/16—Dielectric; Insulating oil or insulators
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/243—Cold working
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses
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    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • the present invention relates to a novel additive for oil-based lubricants having improved extreme pressure properties, a process for making this novel additive, oil-based lubricants containing this novel additive and uses of this novel additive.
  • lubricants serves to significantly reduce the wear of the material due to abrasion, which accompanies dry friction.
  • a lubricant additive One of the most important requirements of a lubricant additive is the surface protection of the materials, which prevents or at least greatly reduces abrasive wear and micro-welding between metal surfaces. This property is ensured by so-called anti-wear (AW) and extreme pressure (EP) agents.
  • AW anti-wear
  • EP extreme pressure
  • C14-C17 medium-chain chloroparaffins
  • EP extreme pressure
  • Due to these negative properties of chloroparaffins there is a considerable need for ecologically and toxicologically harmless substitutes for the various applications.
  • chlorine paraffins have so far not been able to be completely displaced from many applications because they have excellent performance, especially at extreme pressures.
  • the main application for chlorinated paraffins is the forming technique (deep drawing, thread forming, etc.).
  • chloroparaffins have been partially replaced by ecologically more acceptable zinc compounds, for example by zinc dialkyl dithiophosphates, zinc complexes of alkyl dithiophosphorus (RO) 2P (S) SH having the general empirical formula Zn [(RO) 2PS2] 2.
  • RO alkyl dithiophosphorus
  • S alkyl dithiophosphorus
  • thiadiazoles which are known as additives with good release effect and high pressure absorption capacity (EP) and Moreover, they offer a very good corrosion protection, especially for non-ferrous metals.
  • the monomeric thiadiazoles also referred to as dimercaptothiadiazole, are therefore used mainly as non-ferrous metal deactivators, as described in EP2228425A1, and marketed, for example, under the name "Additin RC8210" or "Additin RC 5201" by RheinChemie Rheinau GmbH.
  • the monomeric thiadiazoles are usually colorless, clear liquids which are soluble in oily hydrophobic media.
  • the EP properties of the monomeric thiadiazole are still behind those of the abovementioned zinc compounds, such as zinc dithiophosphate or zinc dithiocarbamate.
  • Dimer 2,5-dimercapto-1, 3,4-thiadiazole is commercially available under the name "Vanlube 829" from the Vanderbilt Company, USA, and unlike the monomers has very good EP properties
  • the reason for the very limited use is that the powdery substance is insoluble in hydrophobic systems and due to the relatively high density (2.09 g / cm 3
  • the finest possible distribution of 2,5-dimercapto-1, 3,4-thiadiazole in the matrix is a prerequisite for effective performance.
  • the present invention is therefore based on the object to develop a lubricant system which avoids the above-mentioned disadvantages of the prior art.
  • This object is achieved according to the invention by a process for the preparation of a lubricant additive, which is characterized in that
  • a dimeric thiadiazole compound in particular a bis (2-alkyl- 1, 3,4 - thiadiazolyl) -5.5 x disulfide derivative of the formula I)
  • n 1 or 2
  • R 1 and R 2 independently of one another represent hydrogen, linear or branched alkyl groups having 1 to 12 carbon atoms, in particular thioalkyl groups (-SR) having 1 to 12 carbon atoms, aromatic radicals or heteroaromatic radicals,
  • n is an integer from 1 to 15, in particular an integer from 3 to 8, and
  • R 1 and R 2 independently of one another represent hydrogen, -NH 2, linear or branched alkyl groups having 1 to 12 carbon atoms or represent a modified or unmodified succinimide group, and
  • the solution obtained is a compound of the formula (IV) in which n is an integer from 1 to 8, in particular an integer from 3 to 8, preferably 6,
  • a dimeric thiadiazole compound in particular a bis (2-alkyl- 1, 3,4 - thiadiazolyl) -5.5 x disulfide derivative of the formula (I)
  • R 1 and R 2 independently of one another represent hydrogen, linear or branched alkyl groups having 1 to 12 carbon atoms, in particular
  • Thioalkyl groups having 1 to 12 carbon atoms, aromatic radicals or heteroaromatic radicals,
  • a polyol in particular a polyether polyol having a high propylene oxide content, d. H. with a low etyloxide / propylene oxide ratio, and / or a triglyceride with hydroxyfatty acid component dissolves and
  • a dimeric thiadiazole compound which can likewise be used according to the invention is bis [2,5-dithio-1,3,4-thiodiozol] (formula VIII), which is described, for example, in EP1702918 A2 of RHEIN-CHEMIE RHEINAU GmbH.
  • Also usable according to the invention are compounds of the formulas (I) and (II) whose radicals R are alkyl or thioalkyl groups.
  • R are alkyl or thioalkyl groups.
  • R1 and R2 As the chain length of the alkyl groups on R1 and R2 increases, the solubility in hydrophobic media gradually increases. Although these side groups contribute more to reducing the coefficient of friction with increasing chain length, they can have a negative effect on the EP properties.
  • the load bearing capacity tends to increase with the number of sulfur atoms in the molecule, the solubility in hydrophobic media at the same time.
  • R is a polyisobutylene radical having a molecular weight in the range of 500-2500.
  • R is a polyisobutylene radical having a molecular weight in the range of 500-2500.
  • Bissuccinimid- derivative with the CAS No .: 84605-20-9 which is represented in the formula (VI)
  • n is an integer from 1 to 8 and R is a polyisobutylene radical having a molecular weight in the range 500-2500.
  • the compounds of the formula (III) are used in alternative a) according to the invention with a weight fraction of 30% to 95%, preferably 40% to 60%, any mixtures of compounds of the formulas (III), (IV) and (V) Preferably, (IV) and (V) are possible.
  • said polyamine-based compound types are ecologically, toxicologically and harmless to health.
  • the compounds of the formula (IV) are used in alternative a) according to the invention with a proportion by weight of 10% to 60%, preferably 30% to 50%.
  • additive solutions with more than 10% by weight active ingredient content can be produced whose consistency remains within the manageable liquid range above 10 ° C and that in hydrophobic esters (vegetable oils or synthetic esters) as a base oil in each case from a professional point of view meaningful relationship results in clear solutions.
  • preferably usable polyols are, for example, hydrophobic polyether polyols of the formula (VII) having an ethylene oxide / propylene oxide ratio ⁇ 1
  • ns esonere is from 6 to 10.
  • Particularly preferably usable polyols have an ethylene oxide / propylene oxide ratio (EO / PO ratio) of ⁇ 0.5.
  • preferably usable triglycerides with Hydroxyfett- acid component are selected from those which are obtainable from renewable raw materials, in particular with ricinoleic acid (12- (fl) -hydroxy-9-cis-octadecenoic acid), lesquerelolic acid (14- (fl ) -Hydroxy-1-cis-eicosenoic acid), 9- (S) -hydroxy-10,12-cis, cis-octadecadienoic acid (obtainable from the seed oil of Dimorphotheca pluvialis), phloic acid (meso-9,10-dihydroxy - octadecanoic acid) and aleuritic acid
  • castor oil which typically contains from about 85% to 92% of ricinoleic acid.
  • the compounds of the formulas (I) or (II) are used in alternative b) according to the invention with a weight fraction of 3% to 6%, preferably 4% to 5%.
  • polyols and / or triglycerides with hydroxy fatty acid component are used in alternative b) according to the invention with a weight fraction of 40% to 96%, preferably 50% to 80%.
  • the additive obtainable according to b) it is also possible with the additive obtainable according to b) to add relevant quantities of additive without precipitations in media on a paraffinic basis.
  • the non-polar media should preferably contain at least 10% by volume of polyglycol or castor oil in order to achieve the required stability.
  • iii) preferably usable hydrophobic phenol derivatives are selected from anacardic acid, cardol, cardanol.
  • iii) preferably usable unsaturated fatty alcohols are selected from hexadecenol, octadecenol.
  • hydrophobic phenol derivatives and / or unsaturated fatty alcohols are used in alternative b) according to the invention with a weight fraction of 40 to 96%, preferably 50% to 80%.
  • a dimeric thiadiazole is homogeneously distributed with a proportion by weight of 4% with stirring at a maximum of 140 °, slowly forming a dark red liquid .
  • Other additives such as benzotriazole (as a preservative not as a non-ferrous metal deactivator) are added at up to 0.5% by weight. After cooling, a stable viscous liquid is obtained, to which a base oil based on rapeseed oil is mixed up to a weight proportion of 5%.
  • Tributoxyalkyl phosphate (AW1 1 Schfer Chemie) 200ml and 270ml paraffin (thin liquid) is heated in a round bottomed flask to 90 ° C. Dimer Thiadiazole 40g is added in several portions until a clear solution is obtained. In order to ensure the durability (bacterial attack) a small amount (per thousand range) benzotriazole, which was previously dissolved in a small amount Tributoxyalkylphosphat, stirred into the still hot solution. After cooling, the solution can be used.
  • a further subject of the invention is a lubricant additive which is obtainable by the process according to the invention.
  • Another object of the invention is a lubricant additive comprising a dimeric I. thiadiazole compound, in particular a bis (2-alkyl- 1, 3,4 - thiadiazolyl) - x disulfide derivative of the formula (I)
  • n 1 or 2
  • R 1 and R 2 independently of one another represent hydrogen, linear or branched alkyl groups having 1 to 12 carbon atoms, in particular
  • Thioalkyl groups having 1 to 12 carbon atoms, aromatic radicals or heteroaromatic radicals,
  • n is an integer from 1 to 15, in particular an integer from 3 to 8, and
  • R 1 and R 2 independently of one another represent hydrogen, -NH 2, linear or branched alkyl groups having 1 to 12 carbon atoms or a modified or unmodified succinimide group, and
  • n is an integer from 1 to 8, in particular an integer from 3 to 8, preferably 6.
  • Another object of the invention is a lubricant additive comprising a dimeric I. thiadiazole compound, in particular a bis (2-alkyl- 1, 3,4 - thiadiazolyl) -5.5 x disulfide derivative of the formula I)
  • n 1 or 2
  • R 1 and R 2 independently of one another represent hydrogen, linear or branched alkyl groups having 1 to 12 carbon atoms, in particular thioalkyl groups (-SR) having 1 to 12 carbon atoms, aromatic radicals or heteroaromatic radicals,
  • a polyol in particular a polyether polyol with a high Propyle- noxid share, d. H. with a low etyloxide / propylene oxide ratio, and / or a triglyceride with hydroxyfatty acid component, and
  • the parts by weight of the constituents of the additives according to the invention correspond to those specified for the preparation process.
  • Another object of the invention is a lubricant, in particular a lubricating oil, comprising an additive according to the invention, preferably in a concentration of 0.2% to 10 wt.%.
  • Another object of the invention is the use of an additive according to the invention in lubricants, in particular for plain bearings, bearings, gears, chains, precision engineering, slideways, motors, hydraulics, tools, machinery, metalworking processes, metal cutting and cold forming. Accordingly, a distinction according to the invention lubricant depending on the application z.
  • As engine lubricating oils cylinder oils, turbine oils, engine oils, gear oils, compressor oils, circulating oils, hydraulic oils, insulating oils, heat transfer oils, process oils, metalworking oils, coolants, cutting oils and greases.
  • the use according to the invention is preferred in lubricating oils, in particular in mineral oil-free forming lubricants.
  • an additive according to the invention in lubricants which are used in the foodstuffs sector, in medical technology or also for lubrication in the "offshore offshore sector” (deep-sea windmills).
  • the lubricants according to the invention in particular lubricating oils, generally consist of a base oil and the additives according to the invention and possible further additives.
  • base oils are used in particular mineral oils, eg. B. petroleum distillate fractions; Synthetic oils, e.g. B. polyethers such as polyglycols and polyphenyl ethers; Carbonklareester; Phosphoric and phosphonic acid esters; Silicon; Silicate esters and polyolefins or mixtures thereof.
  • Phosphoric acid esters which are likewise preferred according to the invention are phosphoric acid esters having oleyl ethoxylate radicals, as shown in formula IX, in which R is hydrogen or
  • oxidation inhibitors for. Hindered phenols, amines, zinc dithiophosphates; Corrosion and rust inhibitors, z. Amine phosphates, alkyl succinic acids, fatty acids; Friction Modifier, eg. Fatty acids, fatty amines; Detergents, e.g. Normal or basic Ca, Ba-Mg sulfonates or phosphonates; Dispersants, e.g. For example, polymers such as nitrogen-containing polymethacrylates, alkyl succinimides, succinate esters - pour point depressants, e.g.
  • Viscosity index improvers e.g. Polyisobutylenes, polyacrylates, hydrogenated styrene-butadiene copolymers
  • Foam inhibitors e.g. Silicone polymers, tributyl phosphate
  • Adhesive z. Soap, polyacrylates
  • Emulsifiers e.g. For example, sodium salts of organic sulfonic acids, fatty amine salts; Bactericides, z. As phenols or formaldehyde derivatives.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)

Abstract

L'invention concerne un nouvel additif pour lubrifiants à base d'huile présentant de meilleures propriétés extrême pression, un procédé de fabrication de ce nouvel additif, des lubrifiants à base d'huile contenant ce nouvel additif ainsi que des utilisations de ce nouvel additif.
PCT/DE2014/100298 2013-08-21 2014-08-21 Additif pour lubrifiants à base d'huile présentant de meilleures propriétés extrême pression WO2015024561A2 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
PL14793006T PL3036313T3 (pl) 2013-08-21 2014-08-21 Dodatek do opartych na oleju środków smarowych o ulepszonych skrajnych właściwościach nacisku
DK14793006.9T DK3036313T3 (en) 2013-08-21 2014-08-21 ADDITIVE TO OIL-BASED LUBRICANTS WITH IMPROVED EXTREME PRESSURE PROPERTIES
DE112014003817.2T DE112014003817A5 (de) 2013-08-21 2014-08-21 Additiv für ölbasierte Schmiermittel mit verbesserten Extreme-Pressure-Eigenschaften
ES14793006T ES2705064T3 (es) 2013-08-21 2014-08-21 Aditivo para lubricantes a base de aceite con propiedades de extrema presión mejoradas
EP14793006.9A EP3036313B1 (fr) 2013-08-21 2014-08-21 Additif pour lubrifiants à base d'huile présentant de meilleures propriétés extrême pression
JP2016535346A JP6339201B2 (ja) 2013-08-21 2014-08-21 向上した極圧特性を有するオイルベースの潤滑剤用の添加剤
US14/912,668 US20160201001A1 (en) 2013-08-21 2014-08-21 Additive for oil-based lubricants having improved extreme pressure properties

Applications Claiming Priority (2)

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DE102013109064.8 2013-08-21
DE201310109064 DE102013109064A1 (de) 2013-08-21 2013-08-21 Additiv für ölbasierte Schmiermittel mit verbesserten Extreme- Pressure-Eigenschaften

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WO2015024561A2 true WO2015024561A2 (fr) 2015-02-26
WO2015024561A3 WO2015024561A3 (fr) 2015-06-04

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DE (2) DE102013109064A1 (fr)
DK (1) DK3036313T3 (fr)
ES (1) ES2705064T3 (fr)
PL (1) PL3036313T3 (fr)
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CA3161842A1 (fr) 2019-12-20 2021-06-24 Hyungsoo KIM Composition lubrifiante contenant un detergent derive d'un liquide de coque de noix de cajou
CN111154542B (zh) * 2020-01-19 2021-11-02 上海贝能环保科技有限公司 一种环保微量润滑剂及制备方法
CN113121468A (zh) * 2021-04-22 2021-07-16 青岛中科润美润滑材料技术有限公司 一种噻二唑蓖麻油衍生物及其应用
CN115960666B (zh) * 2021-10-11 2024-07-09 中国石油化工股份有限公司 空气压缩机润滑油组合物及其制备方法
CN114316097B (zh) * 2021-12-08 2023-05-23 深圳市优宝新材料科技有限公司 一类噻唑基衍生物及一种润滑脂组合物

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EP2228425A1 (fr) 2009-02-27 2010-09-15 Dako Ag Lubrifiant

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EP3036313B1 (fr) 2018-10-10
JP6339201B2 (ja) 2018-06-06
TR201900126T4 (tr) 2019-02-21
DE112014003817A5 (de) 2016-05-04
ES2705064T3 (es) 2019-03-21
EP3036313A2 (fr) 2016-06-29
DK3036313T3 (en) 2019-02-04
US20160201001A1 (en) 2016-07-14
DE102013109064A1 (de) 2015-02-26
JP2016531182A (ja) 2016-10-06
PL3036313T3 (pl) 2019-05-31
WO2015024561A3 (fr) 2015-06-04

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