WO2021124807A1 - Composé siloxane à faible résidu et composition d'huile lubrifiante et lubrifiant l'utilisant - Google Patents

Composé siloxane à faible résidu et composition d'huile lubrifiante et lubrifiant l'utilisant Download PDF

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WO2021124807A1
WO2021124807A1 PCT/JP2020/043615 JP2020043615W WO2021124807A1 WO 2021124807 A1 WO2021124807 A1 WO 2021124807A1 JP 2020043615 W JP2020043615 W JP 2020043615W WO 2021124807 A1 WO2021124807 A1 WO 2021124807A1
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lubricating oil
silicone
group
siloxane compound
molecular weight
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PCT/JP2020/043615
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English (en)
Japanese (ja)
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真央 中垣
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株式会社Moresco
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/76—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing silicon
    • 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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/50—Lubricating compositions characterised by the base-material being a macromolecular compound containing silicon
    • 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
    • C10M111/02—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 non-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
    • 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
    • C10M175/00—Working-up used lubricants to recover useful products ; Cleaning
    • C10M175/04—Working-up used lubricants to recover useful products ; Cleaning aqueous emulsion based
    • 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
    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/02—Petroleum fractions
    • 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
    • C10M105/02—Well-defined hydrocarbons

Definitions

  • the present invention relates to a low-residue siloxane compound and a lubricating oil composition and a lubricant using the same.
  • Lubricating oils and lubricating oil compositions are used to reduce friction and wear between moving parts and moving surfaces of various mechanical devices.
  • a lubricating oil having a high viscosity index (VI) small change in viscosity with respect to temperature change
  • a lubricating oil having a high VI has a low viscosity at a low temperature, and the energy loss due to the viscous resistance of the lubricating oil itself is small, so that it is excellent in terms of energy saving (energy saving).
  • the viscosity does not become excessively low as compared with the lubricating oil having a low VI, so that the oil film necessary for lubrication can be retained on the lubricating surface, and the appropriate viscosity is maintained. Therefore, the scattering of lubricating oil is suppressed and the surroundings are less likely to be contaminated.
  • the siloxane compound has a problem that sludge (SiO 2 ) remains as a residue after oxidative deterioration, which causes pipe clogging and filter clogging. Therefore, existing lubricants containing a siloxane compound as a main component have restrictions on their uses. Therefore, in order to expand into a wider range of fields, it is required to further improve the lubricity and reduce the residue that becomes a bottleneck in the lubricant field.
  • polyalkylene glycol and ester oil are synthetic oils with less thickening and less sludge formation after deterioration, respectively. Therefore, it is considered that the lubricant composition also has a slight thickening and sludge formation after deterioration.
  • the VI of these mixed base oils is insufficient, and the VI improver (high molecular weight). Additives) need to be added.
  • the VI improver not only causes an increase in low-temperature viscosity, but also has a problem that it is affected by a shearing force in an environment in which the lubricating oil is used and impairs the initial lubricating oil characteristics (a decrease in viscosity occurs).
  • the object of the present invention is to solve the above-mentioned problems. That is, it is an object of the present invention to provide a siloxane compound having excellent lubricity and a high viscosity index (VI) and low residual property, and a lubricating oil composition using the same.
  • a siloxane compound having excellent lubricity and a high viscosity index (VI) and low residual property, and a lubricating oil composition using the same.
  • siloxane compound according to one aspect of the present invention is characterized by being represented by the following formula (1).
  • X 1 is the same or different, hydrogen, an alkyl group having 1 to 12 carbon atoms, or a polyoxyalkyl group represented by the following formula (2).
  • Y is an alkylene group having 2 to 12 carbon atoms.
  • Z 1 represents a divalent organic group bonded to an adjacent silicon atom by a carbon-silicon bond and to a polyoxyalkylene block by an oxygen atom.
  • p is an integer of 0 to 13
  • q and r are integers of 0 to 16, respectively
  • n is an integer of 2 to 4
  • a is an integer of 0 to 11.
  • Z 2 represents a divalent organic group bonded to an adjacent silicon atom by a carbon-silicon bond and to a polyoxyalkylene block by an oxygen atom.
  • X 2 is hydrogen or an alkyl group having 1 to 12 carbon atoms.
  • m is an integer of 2 to 4, and
  • b is an integer of 1 to 10.
  • FIG. 1 is NMR data of silicone A-2 synthesized in Examples.
  • FIG. 2 is the NMR data of the silicone A-4 synthesized in the example.
  • FIG. 3 is NMR data of the silicone A-5 synthesized in the examples.
  • FIG. 4 is the NMR data of the silicone A-9 synthesized in the example.
  • FIG. 5 is NMR data of the silicone A-10 synthesized in the example.
  • FIG. 6 is NMR data of the silicone molecule double-ended hydrodimethylsiloxy group-blocking dimethylsiloxane / hexylene copolymer synthesized in the examples.
  • FIG. 7 is the NMR data of the silicone A-13 synthesized in the example.
  • siloxane compound of the present embodiment is characterized by being represented by the following formula (1).
  • siloxane compound of the present embodiment has both a high viscosity index and low residue property, it can be used as a lubricant or the like in a wide range of fields.
  • X 1 is the same or different, hydrogen, an alkyl group having 1 to 12 carbon atoms, or a polyoxyalkyl group represented by the following formula (2).
  • X 2 represents hydrogen or an alkyl group having 1 to 12 carbon atoms.
  • the alkyl group having 1 to 12 carbon atoms in X 1 and X 2 may be cyclic or straight or branched. Specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an octyl group, a nonyl group and a dodecyl group. Alone or in these functional groups in the structure, it may contain a combination of two or more in X 1.
  • the carbon number of X 1 and X 2 is preferably 1 to 12, more preferably 1 to 10, and particularly preferably 1 to 8 from the viewpoint of maintaining a low viscosity at a low temperature. If the number of carbon atoms of X 1 and X 2 exceeds 12, the low temperature characteristics are significantly deteriorated, which makes it difficult to use the lubricating oil composition in a low temperature range.
  • Z 1 and Z 2 are divalent organic groups bonded to an adjacent silicon atom by a carbon-silicon bond and to a polyoxyalkylene block by an oxygen atom.
  • the structure of the divalent organic group in Z 1 and Z 2 is not particularly limited, and for example, -R-, -R-CO-, -R-NHCO-, -R-NHCONH-R 2- NHCO-,- R-OOCNH-R 2 -NHCO- (wherein R is, for example, ethylene, propylene, a divalent alkylene group such as butylene, R 2 is, for example -C 6 H 4 -, - C 6 H 4 -C 6 H 4 -, - C 6 H 4 -CH (CH 3) 2 -C 6 H 4 -. a divalent arylene group, such as suitably R 2 is a phenylene group). More preferably, Z 1 and Z 2 are divalent alkylene groups, especially
  • Y is an alkylene group having 2 to 12 carbon atoms.
  • the structure of Y is not particularly limited, and may be linear, branched, or cyclic.
  • an alkylene group such as an ethylene group, a propylene group, a butylene group, and a hexylene group can be mentioned.
  • These functional groups may be contained in the structure alone or in combination of two or more.
  • the number of carbon atoms of the alkylene group in Y is preferably 2 to 12, more preferably 2 to 10, and particularly preferably 2 to 8 from the viewpoint of maintaining a low viscosity at a low temperature. If the number of carbon atoms of the alkylene group in Y exceeds 12, the low temperature characteristics may be significantly deteriorated.
  • the number of repeating units of the polyoxyalkylene group is preferably 1 to 11 from the viewpoint of obtaining the viscosity required for the lubricating oil. If the number of repeating units exceeds 11, the proportion of the siloxane portion in the molecular structure may become small and the viscosity index may decrease.
  • p is an integer of 0 to 13. If the p exceeds 13, the amount of residue after thermal deterioration may increase.
  • q and r are the same or different integers of 0 to 16, respectively, but if these values exceed 16, the viscosity of the lubricating oil may become too high and energy saving may be lacking. ..
  • n is an integer of 2 to 4.
  • the polyoxyalkylene compound is polyoxyethylene, polyoxypropylene, polyoxybutylene, mixed polyoxyethylene-oxypropylene, etc.
  • m is an integer of 2 to 4.
  • b is an integer of 1 to 10. If b exceeds 10, the proportion of the siloxane portion in the molecular structure becomes small, and the viscosity index may decrease.
  • the mass average molecular weight of the siloxane compound of the present embodiment is not particularly limited, but is preferably 500 to 11000. If the mass average molecular weight is less than 500, the amount of evaporation may increase. Further, if the mass average molecular weight exceeds 11000, the viscosity of the lubricating oil becomes too high and energy saving is lacking, which is not preferable.
  • the mass average molecular weight of the siloxane compound in this embodiment is a value measured by 1 H-NMR as shown in Examples described later. In the following, the mass average molecular weight is also simply referred to as "average molecular weight”.
  • the siloxane compound of the present embodiment has a viscosity index of 200 or more, and the amount of residue after heating at 140 ° C. for 100 hours and then at 250 ° C. for 700 hours is 20% or less. Is preferable.
  • the viscosity index (VI) of the siloxane compound in this embodiment is preferably 200 or more in order to obtain a lubricating oil composition having a high VI. More preferably, it is 240 or more.
  • VI is a value measured and calculated based on JIS K 2283 (2000).
  • the method for synthesizing the siloxane compound as described above is not particularly limited, but some production examples show, for example, the presence of a platinum catalyst in a hydrodimethylsiloxy group-blocking dimethylsiloxane at both ends of the molecular chain and a divinyl ether of polyalkylene glycol.
  • the siloxane compound (silicone oil) of the present embodiment can be obtained by hydrosilylation reaction underneath.
  • a siloxane is obtained by hydrosilylating a hydrodimethylsiloxy group-blocking dimethylsiloxane at both ends of the molecular chain and a divinyl ether of a polyalkylene glycol in the presence of a platinum catalyst, and then hydrosilylating the olefin compound in the presence of a platinum catalyst.
  • a compound (silicone oil) can be obtained.
  • the siloxane compound of the present embodiment can be used as it is alone as various lubricants, but it is lubricated by combining a hydrocarbon-based lubricating oil as described later with at least one of an antioxidant and an extreme pressure agent. It may be used as an oil composition.
  • the lubricating oil composition of the present embodiment contains (A) the above-mentioned siloxane compound, (B) a hydrocarbon-based lubricating oil, (C) an extreme pressure agent, and (D) at least one of an antioxidant. Is characterized by containing at least.
  • the viscosity index (VI) of the lubricating oil composition of this embodiment is preferably 180 or more. More preferably, it is 200 or more, and further preferably 250 or more.
  • the content of the siloxane compound (A) with respect to the entire composition is 30 to 95% by mass from the viewpoint of viscosity index and lubricity. In particular, it is preferably 50 to 90% by mass, and more preferably 60 to 90% by mass. Even if the content of the component (A) is less than 30% by mass, it is possible to improve the viscosity index when the lubricating oil composition is used, but the effect of improving the viscosity index is poor, and the upper limit is set. There is no particular limitation, and as described above, 100% by mass may be a siloxane compound.
  • the lubricating oil composition of the present embodiment has a hydrocarbon-based lubricating oil.
  • the hydrocarbon-based lubricating oil that can be used is not particularly limited as long as it is compatible with the above-mentioned (A) siloxane compound (silicone oil), but specifically, for example, ester oil, ether oil, and the like. Examples thereof include poly ⁇ -olefin (PAO) oil and mineral oil.
  • ester oil examples include esters of monohydric alcohols or polyhydric alcohols with monobasic acids or polybasic acids.
  • Examples of the monohydric alcohol or polyhydric alcohol include monohydric alcohols or polyhydric alcohols having a hydrocarbon group having 1 to 30 carbon atoms, preferably 4 to 20 carbon atoms, and more preferably 6 to 18 carbon atoms. ..
  • Specific examples of the multivalent alcohols include trimethylolpropane, pentaerythritol, and dipentaerythritol.
  • Examples of the monobasic acid or polybasic acid include monobasic acids or polybasic acids having a hydrocarbon group having 1 to 30 carbon atoms, preferably 4 to 20 carbon atoms, and more preferably 6 to 18 carbon atoms. Be done.
  • the hydrocarbon group referred to here may be a straight chain or a branched chain, and for example, an alkyl group, an alkenyl group, a cycloalkyl group, an alkylcycloalkyl group, an aryl group, an alkylaryl group, or an arylalkyl group.
  • an alkyl group an alkenyl group
  • a cycloalkyl group an alkylcycloalkyl group
  • an alkylcycloalkyl group an alkylcycloalkyl group
  • an aryl group an alkylaryl group
  • arylalkyl group such as hydrocarbon groups.
  • ester oil when used as the component (B) in the present embodiment, the above-mentioned ester oil may be used alone or in combination of two or more.
  • ester oil a dibasic acid ester or a polyhydric alcohol fatty acid ester having a flash point of 200 ° C. or higher and a pour point of ⁇ 40 ° C. or lower can be used.
  • a polyhydric alcohol fatty acid ester such as a fatty acid ester of trimethylolpropane or a fatty acid ester of pentaerythritol is more preferable.
  • ether oil examples include polyoxy ether, dialkyl ether, aromatic ether and the like.
  • poly- ⁇ -olefin oil examples include polymers of ⁇ -olefins having 2 to 15 carbon atoms such as polybutene, 1-octene oligomer, and 1-decene oligomer, or hydrides thereof.
  • the mineral oil is an atmospheric residual oil obtained by atmospheric distillation of crude oils such as paraffinic, naphthenic and intermediate base oils; a distillate obtained by vacuum distillation of the atmospheric residual oil; the distillate.
  • Mineral oil refined by performing one or more treatments such as solvent removal, solvent extraction, hydrocracking, solvent dewaxing, catalytic dewaxing, hydrorefining, etc., for example, light neutral oil, medium neutral.
  • the above-mentioned hydrocarbon-based lubricating oil can be used alone, or two or more kinds can be used in combination.
  • the content of the (B) hydrocarbon-based lubricating oil in the lubricating oil composition of the present embodiment is 0 to 70% by mass with respect to the entire composition from the viewpoint of lubricity and viscosity index. In particular, it is preferably 10 to 50% by mass, and even more preferably 10 to 20% by mass. If the content of the hydrocarbon-based lubricating oil is less than 10% by mass, it becomes difficult to obtain sufficient lubricity, and if it exceeds 70% by mass, the content of the (A) siloxane compound in the lubricating oil composition is contained. This is not preferable because the amount is small and the viscosity index of the lubricating oil composition is low.
  • the lubricating oil composition of the present embodiment further improves the lubricity of the lubricating oil composition by containing 10% by mass or more of ester oil as the (B) hydrocarbon-based lubricating oil. That is, as a preferred embodiment, it is desirable that the (B) hydrocarbon-based lubricating oil contains 10 to 50% by mass of an ester oil.
  • the lubricating oil composition of the present embodiment contains at least one of (C) an extreme pressure agent and (D) an antioxidant described later.
  • the lubricating oil composition of the present embodiment contains (C) an extreme pressure agent
  • the lubricating oil composition of the present embodiment has an advantage that the lubricity and wear resistance can be further improved.
  • Examples of the (C) extreme pressure agent that can be used in the present embodiment include thiaxazole compounds, polysulfides, thiocarbamate compounds, sulfide fats and oils, sulfide olefins, sulfide esters, sulfide fatty acids, thiophosphate esters, thiophosphate, thiophosphite, and di.
  • Sulfur-based extreme pressure agents such as molybdenum alkylthiocarbamate, molybdenum dialkyldithiophosphate, zinc dialkylthiocarbamate, and zinc dialkylthiophosphate can be preferably used. These may be used alone or in combination of two or more.
  • At least one selected from thiophosphate ester, dithiocarbamate, olefin sulfide, and dimercaptothiadiazole-based compound is preferable to use at least one selected from thiophosphate ester, dithiocarbamate, olefin sulfide, and dimercaptothiadiazole-based compound as the (C) extreme pressure agent.
  • the content thereof is 0.5 to 10.0% by mass with respect to the entire composition from the viewpoint of obtaining sufficient wear resistance. Degree.
  • an antioxidant generally used for lubricating oil can be used without particular limitation.
  • phenolic compounds, amine compounds, phosphorus compounds and the like can be mentioned.
  • alkylphenols such as 2,6-di-tert-butyl-4-methylphenol, methylene-4,4-bisphenol (2,6-di-tert-butyl-4-methylphenol).
  • alkylphenols such as 2,6-di-tert-butyl-4-methylphenol, methylene-4,4-bisphenol (2,6-di-tert-butyl-4-methylphenol).
  • alkylphenols such as 2,6-di-tert-butyl-4-methylphenol, methylene-4,4-bisphenol (2,6-di-tert-butyl-4-methylphenol).
  • naphthylamines such as phenyl- ⁇ -naphthylamine, dialkyldiphenylamines, phosphite esters and the like.
  • phosphorus-based compounds such as phosphoric acid esters, phosphite esters, acidic phosphoric acid esters, and phosphonic acid esters.
  • the lubricating oil composition of the present embodiment uses two or more kinds of (D) antioxidants in combination.
  • D a phenol-based compound or an amine-based compound that functions as a primary antioxidant in combination with a secondary antioxidant such as a phosphorus-based compound.
  • the content of the (D) antioxidant in the entire composition is 0.5 to 10 from the viewpoint of suppressing oxidation and reducing evaporation. It is set to 0.0% by mass. More preferably, it is 2.0 to 7.0% by mass.
  • the lubricating oil composition of the present embodiment contains the metal inactivating agent, as long as the effects of the present invention are not impaired, in order to further improve its performance or, if necessary, to impart further performance.
  • Various additives such as defoaming agents, thickeners, and colorants may be blended alone or in combination of two or more.
  • metal inactivating agent examples include benzotriazole-based, tolyltriazole-based, and imidazole-based compounds.
  • defoaming agent examples include polysiloxane, polyacrylate, styrene ester polymer and the like.
  • thickener examples include metal soap (for example, lithium soap), silica, expanded graphite, polyurea, clay (for example, hectorite or bentonite) and the like.
  • the amount of the additives added is 0.0 to 10.0% by mass or 0 with respect to the entire lubricating oil composition (total mass). It can be used in an amount of about 1 to 5% by mass.
  • the thickener for producing grease using the lubricating oil composition of the present embodiment can be used in an amount of 5 to 25% by mass with respect to the entire lubricating grease composition (total mass).
  • the method for preparing the lubricating oil composition of the present embodiment is not particularly limited, and for example, (A) a siloxane compound, (B) a hydrocarbon-based oil, (C) an extreme pressure agent, and (D) an antioxidant. It can be adjusted by heating at least one of them or other additives to 100 ° C. and mixing them.
  • the lubricating oil composition of the present embodiment is stable for a long period of time and can be used at a wide range of temperatures, it can be used as various lubricants.
  • it is suitably used as a lubricant for turbo machines, a lubricant for compressors, a lubricant for hydraulic equipment, a lubricant for machine tools, a grease base oil, a refrigerating machine oil, a plasticizer and the like.
  • the amount of residue when heated and burned is smaller than before, it is less likely that pipe blockage or filter clogging due to the residue occurs, and it is suitable for applications in which a lubricant is used in a circulation system.
  • the siloxane compound according to one aspect of the present invention is characterized by being represented by the following formula (1).
  • X 1 is the same or different, hydrogen, an alkyl group having 1 to 12 carbon atoms, or a polyoxyalkyl group represented by the following formula (2).
  • Y is an alkylene group having 2 to 12 carbon atoms.
  • Z 1 represents a divalent organic group bonded to an adjacent silicon atom by a carbon-silicon bond and to a polyoxyalkylene block by an oxygen atom.
  • p is an integer of 0 to 13
  • q and r are integers of 0 to 16, respectively
  • n is an integer of 2 to 4
  • a is an integer of 0 to 11.
  • Z 2 represents a divalent organic group bonded to an adjacent silicon atom by a carbon-silicon bond and to a polyoxyalkylene block by an oxygen atom.
  • X 2 is hydrogen or an alkyl group having 1 to 12 carbon atoms.
  • m is an integer of 2 to 4, and
  • b is an integer of 1 to 10.
  • the siloxane compound has a viscosity index of 200 or more, and the amount of residue after heating at 140 ° C. for 100 hours and then at 250 ° C. for 700 hours is 20% or less. Thereby, it is considered that the above-mentioned effect can be obtained more reliably.
  • the lubricating oil composition according to another aspect of the present invention includes (A) the siloxane compound according to claim 1 or 2, (B) a hydrocarbon-based lubricating oil, (C) an extreme pressure agent, and (D). ) It is characterized by containing at least one of the antioxidants. With such a configuration, it is possible to provide a lubricating oil composition having very excellent lubricity and low residue property.
  • the lubricant according to still another aspect of the present invention is characterized by using the above-mentioned siloxane compound or lubricating oil composition. Further, the present invention includes the above-mentioned siloxane compound, a lubricating composition or lubricant using the same, greases and emulsions using them, and a lubrication method using them.
  • Silicone A-1 is 1,1,3,3-tetramethyldisiloxane manufactured by Tokyo Chemical Industry Co., Ltd. (average molecular weight 134, average number of dimethyl units (p in the above formula (1) is 0)). ..
  • the silicone A-2 has an average molecular weight of 529 and an average number of dimethyl units (p in the above formula (1)) of 5. It was found that the number of silicones A-3 was 1154, and the average number of dimethyl units (p in the above formula (1)) was 13.8.
  • FIG. 1 shows the NMR data of silicone A-2.
  • the 1 H-NMR analysis method for the hydrodimethylsiloxy group-blocked dimethylsiloxane at both ends of the molecular chain shown in Silicones A-2 to A-3 is as follows. a (chemical shift 0.05 to 0.10 ppm) indicates the peak of hydrogen derived from the methyl group of the repeating unit of dimethylsiloxane. b (chemical shift 0.17 to 0.22 ppm) indicates the peak of hydrogen derived from the methyl group of the hydrodimethylsiloxy group at both ends of the molecular chain.
  • the average molecular weight and the average number of dimethyl units were calculated from the following formulas based on the integrated values (ratio) of the peaks of the above a and b, respectively.
  • Average number of dimethyl units 2a ⁇ b
  • Average molecular weight average number of dimethyl units x molecular weight of dimethyl units + molecular weight of hydrodimethylsiloxy groups at both ends of the molecular chain
  • the filtrate was placed in a 200 mL separable flask, heated and depressurized to remove the residual hydrodimethylsiloxy group-blocked dimethylsiloxane at both ends of the molecular chain from the reaction product, and the hydrodimethylsiloxy group-blocked dimethylsiloxane at both ends of the molecule.
  • 51 g of a polyether copolymer (silicone A-4) was obtained.
  • the silicone A-4 has an average molecular weight of 3546, an average number of dimethyl units (p in the above formula (1)) of 4.6, and dimethyl. It was found that the number of repeating units of siloxane / polyether (r in the above formula (1)) was 3.1, and the number of repeating units of oxyethylene (a in the above formula (1)) was 10.1.
  • FIG. 2 shows the NMR data of silicone A-4.
  • the 1 H-NMR analysis method for silicone A-4 and the hydrodimethylsiloxy group-blocking dimethylsiloxane / polyether copolymer at both ends of the molecule shown in silicones A-7, A-8, and A-12, which will be described later, is as follows. It's a street. a (chemical shift 0.01 to 0.10 ppm) indicates a peak of hydrogen derived from the methyl group of the repeating unit of dimethylsiloxane and the methyl group of the dimethylsiloxane unit bonded to the polyether. b (chemical shift 0.16 to 0.21 ppm) indicates the peak of hydrogen derived from the methyl group of the hydrodimethylsiloxy group at both ends of the molecular chain.
  • c (chemical shift 0.40 to 1.10 ppm) indicates the peak of hydrogen derived from CH 2 next to silicon in the polyether portion bonded to silicon.
  • d (chemical shift 3.30 to 3.70 ppm) indicates the peak of hydrogen derived from CH 2 that binds to oxygen in the repeating portion of oxyethylene in the polyether portion, the repeating portion of oxyethylene, and the hydrocarbon portion connecting silicon.
  • the average molecular weight, the average number of dimethyl units, the average number of repeating units of dimethylsiloxane / polyether, and the average number of repeating units of oxyethylene are based on the integrated values (ratio) of the peaks of a, b, c, and d. In addition, it was calculated from the following formulas.
  • Average molecular weight (repeated number of oxyethylene x molecular weight of oxyethylene + average number of dimethyl units x molecular weight of dimethyl units + molecular weight of hydrocarbon part connecting polyether part and silicon + connecting via polyether part and hydrocarbon part (Molecular weight of silicon part) x average number of repeating units of dimethylsiloxane / polyether + average number of dimethyl units x molecular weight of dimethyl units + molecular weight of hydrocarbon siloxy groups at both ends of the molecular chain
  • the silicone A-5 has an average molecular weight of 739 and an average number of dimethyl units (p in the above formula (1)) of 5.1. I understood it.
  • FIG. 3 shows the NMR data of Silicone A-5.
  • the 1 H-NMR analysis method for silicone A-5 and the molecular double-ended alkyldimethylsiloki group-blocking dimethylsiloxane shown in silicone A-6 described later is as follows.
  • a (chemical shift 0.06 to 0.12 ppm) indicates the peak of hydrogen derived from the methyl group of the repeating unit of dimethylsiloxane.
  • b (chemical shift 0.45 to 0.72 ppm) indicates the peak of hydrogen derived from CH 2 next to the silicon of the alkyl group bonded to silicon.
  • the average molecular weight and the average number of dimethyl units were calculated from the following formulas based on the integrated values (ratio) of the peaks a and b.
  • Average number of dimethyl units 2a ⁇ 3b
  • Average molecular weight average number of dimethyl units x molecular weight of dimethyl units + molecular weight of alkyldimethylsiloxy groups at both ends of the molecular chain
  • the silicone A-6 has an average molecular weight of 677 and an average number of dimethyl units (p in the above formula (1)) of 5.1. I understood it.
  • the mixed solution was heated and aged at 60 ° C. for 5 hours. After completion of aging, 1 H-NMR was used to confirm the disappearance of the unsaturated double bond peak. Subsequently, after cooling to room temperature, the platinum catalyst was removed by filtration.
  • the silicone A-7 has an average molecular weight of 1470, an average number of dimethyl units (p in the above formula (1)) of 4.9, and dimethyl. It was found that the number of repeating units of siloxane / polyether (r in the above formula (1)) was 1.4, and the number of repeating units of oxyethylene (a in the above formula (1)) was 3.1.
  • the silicone A-8 has an average molecular weight of 2760, an average number of dimethyl units (p in the above formula (1)) of 4.6, and dimethyl. It was found that the number of repeating units of siloxane / polyether (r in the above formula (1)) was 3.5, and the number of repeating units of oxyethylene (a in the above formula (1)) was 3.0.
  • the dropping speed was adjusted so as to keep the liquid temperature at 65 to 75 ° C.
  • the mixed solution of 1-hexene and platinum catalyst it was aged at 65 ° C. for 5.5 hours. After completion of aging, 1 H-NMR was used to confirm the disappearance of the SiH group peak. Subsequently, the mixture was heated and depressurized to remove residual 1-hexene and toluene from the reaction product to obtain 52 g of a dimethylsiloxane-polyether copolymer (silicone A-9) having both ends of the molecule sealed with a hexyldimethylsiloki group.
  • the silicone A-9 has an average molecular weight of 2772, an average number of dimethyl units (p in the above formula (1)) of 4.4, and dimethyl. It was found that the number of repeating units of siloxane / polyether (r in the above formula (1)) was 3.3, and the number of repeating units of oxyethylene (a in the above formula (1)) was 3.1.
  • FIG. 4 shows the NMR data of Silicone A-9.
  • the 1 H-NMR analysis method for silicone A-9 and the molecular double-ended alkyldimethylsiloki group-blocking dimethylsiloxane / polyether copolymer shown in silicone A-11, which will be described later, is as follows.
  • a (chemical shift 0.01 to 0.15 ppm) is a peak of hydrogen derived from the methyl group of the dimethylsiloxane repeating unit, the methyl group of the dimethylsiloxane unit bonded to the polyether, and the methyl group of the dimethylsiloxane unit bonded to the alkyl group.
  • b (chemical shift 0.80 to 0.95 ppm) indicates the peak of hydrogen derived from CH 3 at the terminal of the alkyl group bonded to silicon.
  • c shows a peak of hydrogen from CH 2 next to the CH 2 next to the silicon polyether portion bonded to silicon.
  • d (chemical shift 3.30 to 3.75 ppm) indicates the peak of hydrogen derived from CH 2 that binds to oxygen in the repeating portion of oxyethylene in the polyether portion, the repeating portion of oxyethylene, and the hydrocarbon portion connecting silicon.
  • the average molecular weight, the average number of dimethyl units, the average number of repeating units of dimethylsiloxane / polyether, and the average number of repeating units of oxyethylene are also the integrated values (ratio) of the peaks of a, b, c, and d. And, each was calculated from the following formulas.
  • Silicone A-8 was heated, and after the liquid temperature reached 30 ° C., dropping of the mixed solution of the dropping funnel was started. After dropping all the mixed solution of the dropping funnel, it was aged at 80 ° C. for 22 hours. After completion of aging, 1 H-NMR was used to confirm the disappearance of the SiH group peak. Subsequently, the mixture was heated and depressurized to remove residual alphamethylstyrene (AMS) and toluene used as a solvent from the reaction product, and a 2-phenylpropyldimethylsiloki group-blocking dimethylsiloxane-polyether copolymer (silicone) at both ends of the molecule. A-10) 24 g was obtained.
  • AMS alphamethylstyrene
  • silicone 2-phenylpropyldimethylsiloki group-blocking dimethylsiloxane-polyether copolymer
  • the silicone A-10 has an average molecular weight of 3933, an average number of dimethyl units (p in the above formula (1)) of 4.7, and dimethyl. It was found that the number of repeating units of siloxane / polyether (r in the above formula (1)) was 4.8, and the number of repeating units of oxyethylene (a in the above formula (1)) was 2.9.
  • FIG. 5 shows the NMR data of Silicone A-10.
  • the 1 H-NMR analysis method of the 2-phenylpropyldimethylsiloki group-blocking dimethylsiloxane / polyether copolymer shown at both ends of the molecule shown in Silicone A-10 is as follows. a (chemical shift 0.01 to 0.15 ppm) indicates a peak of hydrogen derived from the methyl group of the repeating unit of dimethylsiloxane and the methyl group of the dimethylsiloxane unit bonded to the polyether. b (chemical shift 0.99 to 1.05 ppm) shows the peak of hydrogen derived from CH 2 next to silicon in the polyether portion bonded to silicon.
  • c (chemical shift 2.85 to 3.00 ppm) indicates the peak of hydrogen derived from CH of the aralkyl group bonded to silicon.
  • d (chemical shift 3.30 to 3.75 ppm) indicates the peak of hydrogen derived from CH 2 that binds to oxygen in the repeating portion of oxyethylene in the polyether portion, the repeating portion of oxyethylene, and the hydrocarbon portion connecting silicon.
  • the average molecular weight, the average number of dimethyl units, the average number of repeating units of dimethylsiloxane / polyether, and the average number of repeating units of oxyethylene are the integrated values (ratio) of the peaks of a, b, c, and d. Based on this, each was calculated from the following formulas.
  • the mixed solution was heated, and after the liquid temperature reached 30 ° C., dropping of the mixed solution of the dropping funnel was started. After dropping all the mixed solution of the dropping funnel, it was aged at 85 ° C. for 16 hours. After completion of aging, 1 H-NMR was used to confirm the disappearance of the SiH group peak. Subsequently, the mixture was heated and depressurized to remove residual 1-dodecene and toluene used as a solvent from the reaction product, and 27 g of a dimethylsiloxane-polyether copolymer (silicone A-11) with both ends of the molecule dodecene dimethylshiroki group-blocked Obtained.
  • a dimethylsiloxane-polyether copolymer silicone A-11
  • the silicone A-11 has an average molecular weight of 2865, an average number of dimethyl units (p in the above formula (1)) of 4.4, and dimethyl. It was found that the number of repeating units of siloxane / polyether (r in the above formula (1)) was 3.2, and the number of repeating units of oxyethylene (a in the above formula (1)) was 3.0.
  • the silicone A-12 has an average molecular weight of 10572, an average number of dimethyl units (p in the above formula (1)) of 4.1, and dimethyl. It was found that the number of repeating units of siloxane / polyether (r in the above formula (1)) was 16.2, and the number of repeating units of oxyethylene (a in the above formula (1)) was 3.0.
  • the mixed solution was heated and aged at 80 ° C. for 5 hours. After completion of aging, 1 H-NMR was used to confirm the disappearance of the unsaturated double bond peak. Subsequently, after cooling to room temperature, the platinum catalyst was removed by filtration.
  • the filtrate was placed in a 100 mL eggplant flask, heated and depressurized to remove the residual hydrodimethylsiloxy group-blocking dimethylsiloxane at both ends of the molecular chain and toluene used as a solvent, and the hydrodimethylsiloxy at both ends of the molecule. 14 g of a base-sealed dimethylsiloxane / hexylene copolymer was obtained. 1 As a result of analyzing the copolymer obtained by using H-NMR, the copolymer had an average molecular weight of 1201, an average number of dimethyl units (p in the above formula (1)) of 5.3, and dimethylsiloxane. It was found that the number of repeating units of hexylene (q in the above formula (1)) was 1.1.
  • FIG. 6 shows NMR data of the hydrodimethylsiloxy group-blocking dimethylsiloxane / hexylene copolymer at both ends of the molecule.
  • the 1 H-NMR analysis method of the hydrodimethylsiloxy group-blocked dimethylsiloxane / hexylene copolymer at both ends of the molecule is as follows.
  • a (chemical shift 0.01 to 0.11 ppm) indicates the peak of hydrogen derived from the methyl group of the dimethylsiloxane unit bonded to the hexylene group and the methyl group of the repeating unit of dimethylsiloxane.
  • b (chemical shift 0.17 to 0.21 ppm) indicates the peak of hydrogen derived from the methyl group of the hydrodimethylsiloxy group at both ends of the molecular chain.
  • c (chemical shift 0.45 to 0.60 ppm) indicates the peak of hydrogen derived from CH 2 next to the silicon of the hexylene group bonded to silicon.
  • the average molecular weight, the average number of dimethyl units, and the average number of repeating units of dimethylsiloxane / hexylene were calculated by the following formulas based on the integrated values (ratio) of the peaks a, b, and c above. ..
  • the mixed solution was heated, and after the liquid temperature reached 35 ° C., dropping of the mixed solution of the dropping funnel was started. After dropping all the mixed solution of the dropping funnel, it was aged at 75 ° C. for 23 hours. After completion of aging, 1 H-NMR was used to confirm the disappearance of the SiH group peak. Subsequently, distilled water and hexane were added to the obtained reaction solution, the hexane layer was recovered, hexane and toluene used as solvents were removed, and both ends of the molecule were polyoxyalkyldimethylsiloki group-blocked dimethylsiloxane / hexylene co-weight. 4 g of coalesced (silicone A-13) was obtained.
  • the silicone A-13 has an average molecular weight of 1897, an average number of dimethyl units (p in the above formula (1)) of 4.6, and dimethyl. It was found that the number of repeating units of siloxane / hexylene (q in the above formula (1)) was 1.4, and the number of repeating units of oxyethylene at the molecular terminal (b in the above formula (2)) was 6.0. ..
  • FIG. 7 shows the NMR data of Silicone A-13.
  • the 1 H-NMR analysis method of the molecular double-ended polyoxyalkyldimethylsiloxy group-blocking dimethylsiloxane / alkylene copolymer shown in Silicone A-13 is as follows.
  • a (chemical shift 0.01 to 0.15 ppm) is the peak of hydrogen derived from the methyl group of the dimethylsiloxane unit bonded to the methyl group of the dimethylsiloxane repeating unit and the methyl group of the dimethylsiloxane unit bonded to the polyether group.
  • b (chemical shift 1.20 to 1.40 ppm) shows the peak of hydrogen derived from CH 2 of the hexylene group not bonded to silicon.
  • c shows a peak of hydrogen from CH 2 next to the CH 2 next to the silicon polyoxyethylene alkyl group attached to silicon.
  • d shows the peak of hydrogen derived from the repeating portion of ethylene in the polyoxyalkyl moiety.
  • the average molecular weight, the average number of dimethyl units, the average number of repeating units of dimethylsiloxane / polyether, and the average number of repeating units of oxyethylene are the integrated values (ratio) of the peaks of a, b, c, and d. Based on this, each was calculated from the following formulas.
  • Average number of dimethyl units (4a-6b-18c) ⁇ 3b
  • Average number of repeating units of dimethylsiloxane / hexylene b / 2c
  • Number of repetitions of oxyethylene d ⁇ 2c
  • Average molecular weight (average number of dimethyl units x molecular weight of dimethyl units + molecular weight of hexylene + molecular weight of silicon part connected to hexylene part) x average number of repeating units of dimethylsiloxane / hexylene + average number of dimethyl units x dimethyl units
  • the amount of residue (% by weight) in the table was measured by the method described later.
  • silicone oils shown in Table 1 for silicone A-3, the value of p in the formula (1) exceeds 13, so it is considered that the amount of residue has increased.
  • -PAO oil poly- ⁇ -olefin manufactured by Chevron Phillips, product name: Synfluid PAO 6 cSt (40 ° C. kinematic viscosity: 30.5 mm 2 / s, 100 ° C. kinematic viscosity: 5.9 mm 2 / s, VI: 137)
  • -Ether oil Alkyl diphenyl ether "Moresco High Lube LB-100" manufactured by MORESCO Co., Ltd.
  • kinematic viscosity 12.6mm 2 / s, 100 °C kinematic viscosity: 2.9mm 2 / s, VI: 56) -PAG (Polyalkylene Glycol): "New Pole HB50-660" manufactured by Sanyo Chemical Industries, Ltd. (40 ° C. kinematic viscosity: 130.1 mm 2 / s, 100 ° C. kinematic viscosity: 20.1 mm 2 / s, VI: 178)
  • ((C) Extreme pressure agent) Sulfur-based extreme pressure agent: isobutylene sulfide, manufactured by Rhein Chemie, "RC 2545” -Sulfur-phosphorus extreme pressure agent: Thiophosphate ester, made by LUBRIZOL "LUBRIZOL IC9AW31” -Phosphorus-based extreme pressure agent: Amin salt of fatty acid phosphate, "NA-LUBE AW-6400FG” manufactured by Kingindustries
  • (D) Antioxidant) -Primary antioxidant BASF's aromatic amine compound, "IRGANOX L-57” -Primary antioxidant: BASF's phenolic compound, "IRGANOX L-135" -Secondary antioxidant: Johoku Chemical Industry "JP-310", a phosphite ester compound manufactured by Co., Ltd.
  • (Other) -Metal inactivating agent Vanderbilt's benzotriazole compound "CUVAN303" -Silicone used in the comparative test 1: Methylphenyl silicone, "SH-550” manufactured by Toray Dow Corning Co., Ltd. (40 ° C kinematic viscosity: 75.3 mm 2 / s, 100 ° C kinematic viscosity: 20.1 mm 2 / s , VI: 291) -Silicone used in the comparative test: Alkylic silicone, "KF-4917” manufactured by Shin-Etsu Chemical Co., Ltd. (40 ° C kinematic viscosity: 13.8 mm 2 / s, 100 ° C kinematic viscosity: 4.6 mm 2 / s, VI : 292)
  • Examples 1 to 22 and Comparative Examples 1 to 6 For Examples 1 to 10, various siloxane compounds (silicone oils) obtained in the above synthesis examples shown in Table 2 were used as they were. In Examples 11 to 22 and Comparative Examples 1 to 6, the respective components were blended in proportions (% by mass) shown in Tables 2 and 3 below, and (A) silicone oil and (B) hydrocarbons were blended. Each lubricating oil composition was prepared by heating the system oil, (C) extreme pressure agent, (D) antioxidant, and other additives to 100 ° C. and mixing them.
  • Viscosity index The viscosity index (VI) was measured and calculated according to JIS K 2283 (2000). The evaluation criteria are as follows.
  • Residue ratio (% by weight) is 10% or less ⁇ Residue ratio (% by weight) is more than 10% to 20% or less ⁇ Residue ratio (% by weight) exceeds 20% ⁇
  • the above results are shown in Tables 2 and 3.
  • Examples 11 to 22 it was shown that even if the siloxane compound of the present invention is used as a composition together with other components, a high viscosity index and a low residual property can be achieved at the same time.
  • the larger the amount of the siloxane compound blended the smaller the residue after heating.
  • the larger the amount of the siloxane compound blended the better the viscosity index.
  • the siloxane compound and the lubricating oil composition of the present invention can be used as a lubricating oil having excellent lubricity, they can be used as lubricants for various purposes, for example, lubricants for turbo machinery, lubricants for compressors, and hydraulic equipment. It can be suitably used as a lubricant, a lubricant for machine tools, a grease base oil, a refrigerating machine oil, a plasticizer and the like. Especially suitable for high load applications.

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Abstract

La présente invention concerne le composé siloxane représenté par la formule (1).　
PCT/JP2020/043615 2019-12-20 2020-11-24 Composé siloxane à faible résidu et composition d'huile lubrifiante et lubrifiant l'utilisant WO2021124807A1 (fr)

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