EP3036313B1 - Additiv für ölbasierte schmiermittel mit verbesserten extreme-pressure-eigenschaften - Google Patents

Additiv für ölbasierte schmiermittel mit verbesserten extreme-pressure-eigenschaften Download PDF

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Publication number
EP3036313B1
EP3036313B1 EP14793006.9A EP14793006A EP3036313B1 EP 3036313 B1 EP3036313 B1 EP 3036313B1 EP 14793006 A EP14793006 A EP 14793006A EP 3036313 B1 EP3036313 B1 EP 3036313B1
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EP
European Patent Office
Prior art keywords
iii
formula
additive
thiadiazole
polyamine
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.)
Not-in-force
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EP14793006.9A
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German (de)
English (en)
French (fr)
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EP3036313A2 (de
Inventor
Helmut Fackler
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Terralub GmbH
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Terralub GmbH
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Priority to PL14793006T priority Critical patent/PL3036313T3/pl
Publication of EP3036313A2 publication Critical patent/EP3036313A2/de
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Publication of EP3036313B1 publication Critical patent/EP3036313B1/de
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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
    • 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
    • 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
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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
    • C10M2207/021—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
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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
    • C10M2207/023—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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    • 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
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    • 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
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • 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
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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
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    • 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
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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
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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
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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
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—Bearings
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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
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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
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    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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    • C10N2040/135—Steam engines or turbines
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    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/16—Dielectric; Insulating oil or insulators
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    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
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    • 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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    • C10N2040/243—Cold working
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    • C10N2040/30—Refrigerators lubricants or compressors lubricants
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    • C10N2040/50—Medical uses
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    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; 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 lubricating oil such as the viscosity as a hydrodynamic characteristic
  • 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
  • chloroparaffins have been partially replaced by ecologically more acceptable zinc compounds, for example by zinc dialkyl dithiophosphates, zinc complexes of dithiophosphoric acid (RO) 2P (S) SH having the general molecular formula Zn [(RO) 2PS2] 2.
  • RO dithiophosphoric acid
  • S dithiophosphoric acid
  • Zn Zn [(RO) 2PS2] 2.
  • 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 known as dimercaptothiadiazole - are therefore used mainly as non-ferrous metal deactivators, as in EP2228425A1 described and sold, 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.
  • Dimeric 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. It is a compound mainly used in fats or pastes, but not in liquid oily (hydrophobic) media. The reason for the very limited use is that the powdery substance is insoluble in hydrophobic systems and can not be effectively dispersed because of the relatively high density (2.09 g / cm 3 ). However, the finest possible distribution of 2,5-dimercapto-1,3,4-thiadiazole in the matrix is a prerequisite for effective performance.
  • EP 0 196 362 A2 discloses polymeric thiadiazole lubricant additives. In summary, it can be stated that the known from the prior art lubricant additives are either ecologically and toxicologically questionable, have insufficient EP performance or can not be used meaningfully in liquid oily (hydrophobic) media.
  • the present invention is therefore based on the object to develop a lubricant system which avoids the above-mentioned disadvantages of the prior art.
  • dimeric thiadiazole compound is bis- [2,5-dithio-1,3,4-thiodiozol] (formula VIII), for example, in the EP1702918 A2 the RHEIN-CHEMIE RHEINAU GmbH is described.
  • 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.
  • the compounds of the formulas (I) and (II) are used according to the invention with a proportion by weight of 4% to 13%, preferably 8% to 10%.
  • Polyamines or polyamine derivatives of the formula (III) which are preferred according to the invention are those which, instead of R 1 or R 2, independently of one another, contain a succinimide group.
  • Particularly preferred is the monosuccinimide derivative with the CAS No .: 67762-72-5, which is represented in the formula (V), where R is a polyisobutylene radical having a molecular weight in the range of 500-2500.
  • the Bissuccinimidderivat with the CAS No .: 84605-20-9 which is represented in the formula (VI) wherein n is an integer from 1 to 8 and R is a polyisobutylene radical having a molecular weight in the range 500-2500.
  • a likewise usable according to the invention modification of succinimide-polyamine compounds is in the U.S. Patent 6569819
  • suitable solvents for dimeric thiadiazoles are polyamine compounds which are terminal (R1 / R2) phenyl groups or hetero ring compounds, such as thiadiazoles or succinimide in combination with thiadiazoles. Such compounds are for example in the US Patent 5597785 described.
  • the compounds of the formula (III) are used according to the invention in an amount by weight of 30% to 95%, preferably 40% to 60%, with any mixtures of squalene and compounds of the formulas (III) and (V), preferably squalene and compounds of the formula (V) are possible.
  • said polyamine-based compound types are ecologically, toxicologically and harmless to health.
  • Polyamines as well as the corresponding Succinimidderivate have a honey-like consistency at room temperature, when heated above 70 ° C, they are thin and then able to slowly dissolve dimeric 2,5-dimercapto-1,3,4-thiadiazoles residue.
  • the inventive method is therefore preferably carried out at a temperature in the range of about 70 ° C to about 140 ° C, more preferably at a temperature in the range of about 80 ° C to about 130 ° C, most preferably at a temperature in the range of about 80 ° C to about 120 ° C.
  • temperatures between 120 ° C and 140 ° C - higher temperatures may u.U. lead to decomposition reactions - arise brownish red solutions, which, however, after cooling due to rubbery consistency are no longer usable.
  • Squalene is used according to the invention with a proportion by weight of 10% to 60%, preferably 30% to 50%.
  • additive solutions can be produced with more than 10% by weight of active ingredient, the consistency from 10 ° C in the manageable liquid range and in hydrophobic esters (vegetable oils or synthetic esters) as a base oil in any meaningful ratio from a professional point of view give clear solutions.
  • Stable sols can also be prepared to produce stable microfine dispersions.
  • a dimeric thiadiazole is homogeneously distributed at a weight fraction 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%.
  • a flask is charged with a proportion of 60% squalene, 30% polyisobutylene succinimide (CAS 84605-20-9) and about 10% dimeric 2,5-dimercapto-1,3,4-thiadiazole (CAS No .: 72676-55 -2) and heated to about 135 ° C.
  • the thiadiazole is completely dissolved to form a reddish brown liquid.
  • preservatives are added. After cooling, a viscous liquid which is easy to handle and can be used as an EP additive remains.
  • This additive was added to the hydraulic oil Flexon 845 ISO VG 32 (available from Esso) in varying concentrations, and the samples subjected to a four-ball test.
  • Example of the preparation of a thiadiazole solution with the aid of phosphoric acid ester Tributoxyalkyl phosphate (AW11 Schulfer Chemie) 200ml and 270ml paraffin (thin liquid) is heated to 90 ° C in a round bottomed flask. Dimer Thiadiazole 40g is added in several portions until a clear solution is obtained. To ensure the shelf life (bacterial attack) a small amount (per thousand range) of 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.
  • the proportions by weight of the constituents of the additive 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.
  • lubricant depending on the application z.
  • 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 else for lubrication in the "offshore offshore sector” (deep-sea wind wheels).
  • 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; silicones; Silicate esters and polyolefins or mixtures thereof.
  • dialkylphosphoric acid esters having chain lengths of 8 to 12, as well as alkoxylated dialkylphosphoric acid esters.
  • Thiadiazole solutions with tributoxyalkyl phosphate can be incorporated in almost all media (especially on mineral oil basis) without large miscibility gaps.
  • phosphoric esters are phosphoric acid ester with Oleylethoxylatresten, as shown in formula IX, in the R for hydrogen or stands.
  • 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)
EP14793006.9A 2013-08-21 2014-08-21 Additiv für ölbasierte schmiermittel mit verbesserten extreme-pressure-eigenschaften Not-in-force EP3036313B1 (de)

Priority Applications (1)

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PL14793006T PL3036313T3 (pl) 2013-08-21 2014-08-21 Dodatek do opartych na oleju środków smarowych o ulepszonych skrajnych właściwościach nacisku

Applications Claiming Priority (2)

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DE201310109064 DE102013109064A1 (de) 2013-08-21 2013-08-21 Additiv für ölbasierte Schmiermittel mit verbesserten Extreme- Pressure-Eigenschaften
PCT/DE2014/100298 WO2015024561A2 (de) 2013-08-21 2014-08-21 Additiv für ölbasierte schmiermittel mit verbesserten extreme-pressure-eigenschaften

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EP3036313A2 EP3036313A2 (de) 2016-06-29
EP3036313B1 true EP3036313B1 (de) 2018-10-10

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EP (1) EP3036313B1 (pl)
JP (1) JP6339201B2 (pl)
DE (2) DE102013109064A1 (pl)
DK (1) DK3036313T3 (pl)
ES (1) ES2705064T3 (pl)
PL (1) PL3036313T3 (pl)
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US11999922B2 (en) 2019-12-20 2024-06-04 The Lubrizol Corporation Lubricant composition containing a detergent derived from cashew nut shell liquid
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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Publication number Publication date
DK3036313T3 (en) 2019-02-04
DE102013109064A1 (de) 2015-02-26
ES2705064T3 (es) 2019-03-21
DE112014003817A5 (de) 2016-05-04
JP6339201B2 (ja) 2018-06-06
PL3036313T3 (pl) 2019-05-31
TR201900126T4 (tr) 2019-02-21
US20160201001A1 (en) 2016-07-14
JP2016531182A (ja) 2016-10-06
WO2015024561A3 (de) 2015-06-04
WO2015024561A2 (de) 2015-02-26
EP3036313A2 (de) 2016-06-29

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