US20140200169A1 - High Temperature Oil - Google Patents

High Temperature Oil Download PDF

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Publication number
US20140200169A1
US20140200169A1 US14/119,015 US201214119015A US2014200169A1 US 20140200169 A1 US20140200169 A1 US 20140200169A1 US 201214119015 A US201214119015 A US 201214119015A US 2014200169 A1 US2014200169 A1 US 2014200169A1
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Prior art keywords
temperature oil
weight
oil
phloroglucinol
dialkyldithiophosphates
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US14/119,015
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Inventor
Thomas Kilthau
Karl Egersdorfer
Martin Schmidt-Amelunxen
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Klueber Lubrication Muenchen GmbH and Co KG
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Klueber Lubrication Muenchen SE and Co KG
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Assigned to KLUBER LUBRICATION MUNCHEN SE & Co. KG reassignment KLUBER LUBRICATION MUNCHEN SE & Co. KG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: Schmidt-Amelunxen, Martin, Dr., EGERSDORFER, KARL, KILTHAU, THOMAS, DR.
Publication of US20140200169A1 publication Critical patent/US20140200169A1/en
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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
    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic 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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—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
    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/06—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing butene
    • 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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds 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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular compounds
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
    • C10M2205/0265—Butene used as base material
    • 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
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • 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
    • C10M2207/28—Esters
    • C10M2207/285—Esters of aromatic polycarboxylic acids
    • C10M2207/2855—Esters of aromatic polycarboxylic acids used as base material
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/079—Liquid crystals
    • 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
    • C10N2030/02—Pour-point; Viscosity index
    • 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
    • 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
    • C10N2030/08—Resistance to extreme temperature
    • 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
    • C10N2030/74—Noack Volatility
    • 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
    • C10N2040/38—Conveyors or chain belts

Definitions

  • the invention relates to novel high-temperature oils based on aromatic esters such as trimellitic esters, pyromellitic esters, trimesic esters or a mixture, or derivatives of phloroglucinol such as phloroglucinol trioctanoate, phloroglucinol tridecanoate and phloroglucinol tridodecanoate thereof, and a fully hydrogenated or a hydrogenated polyisobutylene or a mixture thereof.
  • aromatic esters such as trimellitic esters, pyromellitic esters, trimesic esters or a mixture
  • derivatives of phloroglucinol such as phloroglucinol trioctanoate, phloroglucinol tridecanoate and phloroglucinol tridodecanoate thereof, and a fully hydrogenated or a hydrogenated polyisobutylene or a mixture thereof.
  • High-temperature oils which are used in the field of industrial chain lubrication, for example in conveying systems, painting lines, the textile industry, the insulating materials industry, the glass industry, etc., and belt lubrication in continuous wood pressing plants, typically consist of a three-component system.
  • This three-component system generally consists of an aromatic ester, a synthetic hydrocarbon and a polymer based on polyisobutylene.
  • the synthetic hydrocarbon is used as a solubilizer.
  • Also added to this lubricant system are commercial additives.
  • a disadvantage of these systems is that the use of the synthetic hydrocarbon limits the working temperature of the oil, since it vaporizes very rapidly at temperatures >200° C.
  • a three-component system is described, for example, in EP 1 154 011 B1.
  • a lubricant oil composition comprising an aromatic ester compound and, as a further base oil, an ⁇ -olefin oligomer, and also a polyisobutene, is provided.
  • the loss of performance for a three-component lubricant composition is high as a result of the vaporization of the solubilizer.
  • the vaporization results in formation of a deposit or a residue formed from the remaining constituents of the lubricant on the application surface or the application area, as a result of which full lubrication can no longer be ensured.
  • This deposit then has to be dissolved again.
  • operation has to be stopped and the residue has to be removed.
  • Such a high-temperature oil is especially required for chain and belt lubrication of wood presses, as present, for example, in ContipressenTM continuous presses for the production of laminate floors.
  • R1 is a linear or branched alkyl group having 6 to 16 carbon atoms and n is 3 or 4, or a compound of the general formula (II)
  • R is a linear or branched alkyl group having a chain length of 8 to 16 carbon atoms and n is equal to 3,
  • a hydrogenated polyisobutylene a fully hydrogenated polyisobutylene or a mixture of a fully hydrogenated and a hydrogenated polyisobutylene.
  • a fully hydrogenated polyisobutylene is included.
  • the high-temperature oil comprises 40 to 91.9% by weight of the aromatic ester of the general formula (I) or of the compound of the general formula (II) and 50 to 5% by weight of the hydrogenated, fully hydrogenated polyisobutylene or of a mixture of hydrogenated and fully hydrogenated polyisobutylene.
  • the high-temperature oil may comprise 0.1 to 6% by weight, especially 2 to 5% by weight, of an antioxidant.
  • the high-temperature oil may also comprise 0 to 4% by weight, especially 0.3 to 3.5% by weight, of an antiwear agent, 0.1 to 1.0% by weight of an anticorrosive, and 0 to 2% by weight, especially 0.1 to 1.5% by weight, of an ionic liquid.
  • the ester compound of formula (I) present in the high-temperature oil is preferably selected from the group consisting of esters of trimellitic acid, pyromellitic acid, trimesic acid or mixtures thereof.
  • the compound of the general formula (II) is a derivative of phloroglucinol (benzene-1,3,5-triol), preferably phloroglucinol trioctanoate, phloroglucinol tridecanoate and phloroglucinol tridodecanoate.
  • the antioxidant present in the high-temperature oil which may contain sulfur and/or nitrogen and/or phosphorus in the molecule, is selected from the group consisting of aromatic aminic antioxidants such as alkylated phenyl-alpha-naphthylamine, dialkyldiphenylamine, sterically hindered phenols such as butylhydroxytoluene (BHT), phenolic antioxidants having thioether groups, zinc dialkyldithiophosphates or molybdenum dialkyldithiophosphates or tungsten dialkyldithiophosphates, and phosphites.
  • aromatic aminic antioxidants such as alkylated phenyl-alpha-naphthylamine, dialkyldiphenylamine, sterically hindered phenols such as butylhydroxytoluene (BHT), phenolic antioxidants having thioether groups, zinc dialkyldithiophosphates or molybdenum dial
  • the antiwear agent present in the high-temperature oil is selected from the group consisting of antiwear additives based on diphenyl cresyl phosphate, amine-neutralized phosphates, alkylated and nonalkylated triaryl phosphates, alkylated and nonalkylated triaryl thiophosphates, zinc dialkyldithiophosphates or molybdenum dialkyldithiophosphates or tungsten dialkyldithiophosphates, carbamates, thiocarbamates, zinc dithiocarbamates or molybdenum dithiocarbamates or tungsten dithiocarbamates, dimercaptothiadiazole, calcium sulfonates and benzotriazole derivatives.
  • the anticorrosive present in the high-temperature oil is selected from the group consisting of additives based on “overbased” calcium sulfonates having a TBN of 100 to 300 mg KOH/g, amine-neutralized phosphates, alkylated calcium naphthalenesulfonates, oxazoline derivatives, imidazole derivatives, succinic monoesters, N-alkylated benzotriazoles.
  • the ionic liquid (IL) used in the high-temperature oil comprises what are called salt melts which, by definition, are liquid at temperatures below 100° C. Many ionic liquids are also liquid at room temperature or at lower temperatures. Suitable cations for ionic liquids have been found to be a quaternary ammonium cation, a phosphonium cation, an imidazolium cation, a pyridinium cation, a pyrazolium cation, an oxazolium cation, a pyrrolidinium cation, a guanidinium cation, a morpholinium cation or a triazolium cation, which may be combined with an anion selected from the group consisting of [PF 6 ] ⁇ , [BF 4 ] ⁇ , [CF 3 CO 2 ] ⁇ , [CF 3 SO 3 ] ⁇ .
  • R 4 and R 5 radicals are each independently selected from hydrogen; linear or branched, saturated or unsaturated, aliphatic or alicyclic alkyl groups having 1 to 20 carbon atoms; heteroaryl groups, heteroaryl-C 1 -C 6 -alkyl groups having 3 to 8 carbon atoms in the heteroaryl radical and at least one heteroatom from N, O and S which may be substituted by at
  • R 7 here represents partly or fully fluorinated radicals such as pentafluoroethyl or perfluorobutyl.
  • the ionic liquids In order to display positive action in oils, the ionic liquids should firstly show solubility in the oils, although complete miscibility is not absolutely necessary.
  • the ionic liquids should be thermally stable and not promote corrosion, for example by forming reaction products which are noncorrosive or corrosive only in a very delayed manner in the presence of water.
  • Particularly advantageous ionic liquids have been found to be those such as tetraalkylammonium bis(trifluoromethylsulfonyl)imides and tetraalkylphosphonium bis(trifluoromethylsulfonyl)imides, for example trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide (HPDimide) and methyltrioctylammonium bis(trifluoromethylsulfonyl)imide (Moimide).
  • HPDimide trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide
  • Moimide methyltrioctylammonium bis(trifluoromethylsulfonyl)imide
  • Ionic liquids which have likewise been found to be particularly advantageous are those such as tetraalkylammonium tris(perfluoroethyl)trifluorophosphate and tetraalkylphosphonium tris(perfluoroethyl)trifluorophosphate, for example tetrabutylphosphonium tris(perfluoroethyl)trifluorophosphate (BuPPFET), trihexyl(tetradecyl) tris(perfluoroethyl)trifluorophosphate (HDPPFET). It has likewise been found that pyrrolidinium tris(perfluoroethyl)trifluorophosphates are particularly advantageous.
  • tetraalkylammonium perfluorobutanesulfonates and tetraalkylphosphonium perfluorobutanesulfonates such as trihexyl(tetradecyl)phosphonium perfluorobutanesulfonate (HDPnonaflate).
  • the inventive two-component system has a much higher performance in terms of thermal stability and residue formation or residue characteristics.
  • the enormous rise in thermal stability is manifested particularly in a distinct increase in lubrication characteristics.
  • the relubrication intervals were extended and an energy saving of up to a 30% power saving was achieved.
  • FIG. 1 shows the friction values as a function of temperature at a load of 250 N for an inventive high-temperature oil based on two components from example 1 compared with a known oil based on three components from comparative example 1 at a kinematic viscosity at 40° C. of about 260 mm 2 /sec;
  • FIG. 2 shows the vaporization losses for an inventive high-temperature oil based on two components from example 1 compared with a known oil based on three components from comparative example 1 at a kinematic base oil viscosity at 40° C. of about 260 mm 2 /sec;
  • FIG. 3 shows the increase in the apparent dynamic viscosity of an inventive high-temperature oil based on two components from example 1 compared with a known oil based on three components from comparative example 1 at a kinematic base oil viscosity at 40° C. of about 260 mm 2 /sec;
  • FIG. 4 shows the friction values as a function of temperature at a load of 250 N for an inventive high-temperature oil based on two components from example 2 compared with a known oil based on three components from comparative example 2;
  • FIG. 5 shows the vaporization losses for an inventive high-temperature oil based on two components from example 2 compared with a known oil based on three components from comparative example 2 at a kinematic base oil viscosity at 40° C. of about 100 mm 2 /sec;
  • FIG. 6 shows the increase in the apparent viscosity of an inventive high-temperature oil based on two components from example 2 compared with a known oil based on three components from comparative example 2 at a kinematic base oil viscosity at 40° C. of about 100 mm 2 /sec;
  • FIG. 7 shows the friction values as a function of temperature at a load of 250 N for an inventive high-temperature oil based on two components from example 3 compared with a known oil based on three components from comparative example 3;
  • FIG. 8 shows the vaporization losses for an inventive high-temperature oil based on two components from example 3 compared with a known oil based on three components from comparative example 3 at a kinematic base oil viscosity at 40° C. of about 680 mm 2 /sec;
  • FIG. 9 shows the increase in the apparent dynamic viscosity of an inventive high-temperature oil based on two components from example 3 compared with a known oil based on three components from comparative example 3 at a kinematic base oil viscosity at 40° C. of about 680 mm 2 /sec;
  • FIG. 10 shows the vaporization losses for an inventive high-temperature oil based on two components with an ionic liquid from example 4 compared with comparative example 4, which corresponds to example 1 at a kinematic base oil viscosity of about 260 mm 2 /sec;
  • FIG. 11 shows the increase in the apparent dynamic viscosity of an inventive high-temperature oil based on two components with an ionic liquid from example 4 compared with comparative example 4, which corresponds to example 1 at a kinematic base oil viscosity of about 260 mm 2 /sec;
  • FIG. 12 shows the experimental setup for the high-performance chain test bed.
  • composition of the high-temperature oil is Composition of the high-temperature oil:
  • trimellitic ester is initially charged in a stirred tank. At 100° C., the polyisobutylene is added while stirring. Subsequently, the mixture is stirred for one 1 hour in order to obtain a homogeneous mixture. The antiwear agent and the antioxidant are added to the tank at 60° C. while stirring. After about 1 hour, the finished oil can be dispensed into the containers provided.
  • composition of the high-temperature oil is Composition of the high-temperature oil:
  • trimellitic ester is initially charged in a stirred tank together with the poly- ⁇ -olefin as the synthetic hydrocarbon.
  • the polyisobutylene is added while stirring.
  • the mixture is stirred for 1 hour in order to obtain a homogeneous mixture.
  • the antiwear agent and the antioxidant are added to the tank at 60° C. while stirring. After about 1 hour, the finished oil can be dispensed into the containers provided.
  • oils according to example 1 and comparative example 1 were compared with one another.
  • the oil to be tested is weighed to 5 g onto a steel sheet which has been bent to size and cleaned with solvent beforehand, and then vaporized off at 250° C. in an air circulation drying cabinet for min. 72 h.
  • the square sheet is bent manually on all four sides, so as to give a dish shape.
  • the inventive high-temperature oil forms a lower level of residue at 4.8% than the known oil, which has a residue of 6.0%.
  • the residue formed from the inventive high-temperature oil has very good surface dissolvability, which means that these residues are easy to dissolve with fresh oil.
  • the residue of the known oil has much poorer surface redissolvability with fresh oil.
  • FIG. 12 shows the high-performance chain test bed, which works under the following test conditions:
  • the chain Before the test, the chain is immersed into the lubricant oil to be tested. After the immersion, the chain is suspended, such that the excess lubricant can drip off. Subsequently, the chain is installed into the chain test bed (see FIG. 10 ) and the test is started under the conditions defined. It is possible to vary the temperature, the speed and the load.
  • the run time is fixed at a chain lengthening of 0.1%.
  • the lengthening of the chain arises through wear at the chain members during the test run.
  • composition of the inventive high-temperature oil is a composition of the inventive high-temperature oil
  • composition of the three-component high-temperature oil is Composition of the three-component high-temperature oil:
  • the production is effected as described in comparative example 1.
  • oils according to example 2 and comparative example 2 were compared with one another.
  • Both the inventive high-temperature oil and the known oil had a residue of 3.0%; the residue formed from the inventive high-temperature oil had very good surface dissolvability, which means that these residues can be dissolved easily with fresh oil. In contrast, the residue of the known oil has much poorer surface redissolvability with fresh oil.
  • the test on the high-performance chain test bed was conducted at 220° C., a speed of 2.0 m/sec and a load of 2600 N.
  • the run time after chain lengthening 0.1% is 19 h for example 2, and that for comparative example 2 is 17 h.
  • oils according to example 3 and comparative example 3 were compared with one another.
  • the inventive high-temperature oil forms a lower level of residues at 4.8% than the known oil, which has a residue of 11.8%.
  • the residue formed from the inventive high-temperature oil has very good surface dissolvability, which means that these residues can be dissolved easily with fresh oil.
  • the residue of the known oil has much poorer surface redissolvability with fresh oil.
  • the test on the high-performance chain test bed was conducted at 220° C., a speed of 2.0 m/sec and a load of 2600 N.
  • the run time after chain lengthening 0.1% was 17 h for example 3 and 15 h for comparative example 3.
  • the test was conducted as described in example 1.
  • composition of the inventive high-temperature oil is a composition of the inventive high-temperature oil
  • Example 4 Corresponds to example 1 Vaporization loss 19% 46% after 72 h/250° C. Increase in 2300 mPas 27 000 mPas apparent dynamic viscosity after 72 h/250° C.
  • the inventive two-component system has much higher performance with regard to thermal stability and residue formation or residue characteristics.
  • the enormous rise in thermal stability is manifested particularly in a distinct rise in lubrication characteristics.
  • the relubrication intervals were extended and an energy saving of up to a 30% power saving was achieved.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US14/119,015 2011-05-26 2012-05-22 High Temperature Oil Abandoned US20140200169A1 (en)

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US10711132B2 (en) 2015-09-25 2020-07-14 Compagnie Generale Des Etablissements Michelin Use of an esterified aromatic polyphenol derivative for the production of a phenol-aldehyde resin for reinforcement of a rubber composition
US10711131B2 (en) 2015-09-25 2020-07-14 Compagnie Generale Des Etablissements Michelin High-strength rubber composition comprising an aromatic polyphenol derivative

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US10590225B2 (en) 2015-09-25 2020-03-17 Compagnie Generale Des Etablissements Michelin Use of a silylated aromatic polyphenol derivative for the production of a phenol-aldehyde resin for reinforcement of a rubber composition
US10711132B2 (en) 2015-09-25 2020-07-14 Compagnie Generale Des Etablissements Michelin Use of an esterified aromatic polyphenol derivative for the production of a phenol-aldehyde resin for reinforcement of a rubber composition
US10711131B2 (en) 2015-09-25 2020-07-14 Compagnie Generale Des Etablissements Michelin High-strength rubber composition comprising an aromatic polyphenol derivative

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WO2012159738A1 (de) 2012-11-29
CN103764808A (zh) 2014-04-30
KR20140009499A (ko) 2014-01-22
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JP5752321B2 (ja) 2015-07-22
ES2601401T3 (es) 2017-02-15
KR101539218B1 (ko) 2015-07-29
EA201301331A1 (ru) 2014-05-30
EP2714872A1 (de) 2014-04-09
BR112013030286A2 (pt) 2016-11-29
CL2013003397A1 (es) 2014-07-11
BR112013030286B1 (pt) 2020-11-10
AU2012261221A1 (en) 2013-12-12
DE102011102540B4 (de) 2013-12-12
HUE029149T2 (hu) 2017-02-28
AU2012261221B2 (en) 2016-05-12
EP2714872B1 (de) 2016-08-03
DE102011102540A1 (de) 2012-11-29
MY164068A (en) 2017-11-15
JP2014515412A (ja) 2014-06-30

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