WO2016181726A1 - ケイ素含有イオン液体を含む潤滑剤 - Google Patents
ケイ素含有イオン液体を含む潤滑剤 Download PDFInfo
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- UJZJLHQWWPJNKA-UHFFFAOYSA-O CCCC(N)[PH+](C(CCC)N)C(CCC)N Chemical compound CCCC(N)[PH+](C(CCC)N)C(CCC)N UJZJLHQWWPJNKA-UHFFFAOYSA-O 0.000 description 1
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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
- 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
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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 System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
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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
- C10M111/02—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
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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
- 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
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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
- 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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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—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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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/083—Dibenzyl sulfide
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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
- 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
- C10M2223/0603—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds used as base material
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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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
- C10M2227/045—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes used as base material
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- 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
- C10N2020/077—Ionic Liquids
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- 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
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- 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
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- 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
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
Definitions
- the present invention relates to a lubricant containing a silicon-containing ionic liquid.
- An ionic liquid is a salt composed only of ions and generally has a melting point of 100 ° C. or lower.
- Various application studies have been made on ionic liquids due to their characteristics, and in particular, application studies as lubricants have also been made in terms of non-volatility, flame retardancy, high heat resistance, etc. (Patent Documents 1, 2, Non-patent documents 1, 2, etc.).
- Ionic liquids have the necessary physicochemical properties as lubricants.
- ionic liquids containing fluorine-containing ions such as tetrafluoroborate, hexafluorophosphate, and bis (trifluoromethanesulfonyl) imide salts have improved wear resistance. It is said to be excellent.
- the mixing of moisture is a problem, and even if a very small amount of moisture is mixed, it reacts with hydrogen fluoride derived from a fluorine-based anion decomposed by a chemical reaction (tribochemical reaction) activated by friction, and metal There was a fatal defect that the material was corroded or the polymer material was deteriorated.
- fluorine-containing ionic liquids are generally evaluated as lubricants that can only be used in space where moisture is not present, or ceramics that do not have a metal interface. It has not been converted.
- the present invention has been made in view of such circumstances, and provides a lubricant containing a silicon-containing ionic liquid that does not generate hydrogen fluoride by decomposition and does not deteriorate metal materials, polymer materials, and the like. With the goal.
- an ionic liquid containing no anion containing a silicon atom and no fluorine atom comprising a phosphonium cation has a small friction coefficient and is useful as a lubricant. As a result, the present invention has been completed.
- a lubricant containing a silicon-containing ionic liquid represented by the following formula (1) (Wherein R 1 represents an alkyl group having 1 to 10 carbon atoms, R 2 represents an alkyl group having 8 to 20 carbon atoms, and R 3 represents an alkyl group having 1 to 8 carbon atoms, provided that , R 2 has more carbon atoms than R 1. ) 2.
- R 1 represents an alkyl group having 1 to 10 carbon atoms
- R 2 represents an alkyl group having 8 to 20 carbon atoms
- R 3 represents an alkyl group having 1 to 8 carbon atoms, provided that , R 2 has more carbon atoms than R 1.
- the lubricant according to 1 or 2 wherein R 1 is all n-butyl group or n-hexyl group. 4).
- the lubricant according to any one of 1 to 4 comprising only the silicon-containing ionic liquid represented by the formula (1). 6).
- the additive is a friction modifier or an antiwear agent. 8).
- the ionic liquid has a low coefficient of friction and is halogen-free, so it has a low environmental impact and does not produce a toxic substance such as hydrogen fluoride. Can also be used, and is useful as a general-purpose lubricant.
- FIG. 3 is a 1 H-NMR spectrum of ionic liquid 2 synthesized in Synthesis Example 2.
- FIG. 3 is a 1 H-NMR spectrum of ionic liquid 4 synthesized in Synthesis Example 4.
- FIG. 6 is a 1 H-NMR spectrum of ionic liquid 5 synthesized in Synthesis Example 5. It is a figure which shows the time-dependent change of the friction coefficient measured in Example 2 and Comparative Example 2. It is a figure which shows the time-dependent change of the friction coefficient measured in Example 3 and Comparative Example 3. It is a figure which shows the abrasion volume of the test ball
- FIG. FIG. 6 is a graph showing changes with time in the friction coefficient measured in Examples 4-1 to 4-3 and Comparative Example 4-1.
- FIG. 6 is a graph showing the wear volume of test balls measured in Examples 5-1 to 5-3.
- the lubricant of the present invention contains a silicon-containing ionic liquid represented by the following formula (1).
- R 1 represents an alkyl group having 1 to 10 carbon atoms
- R 2 represents an alkyl group having 8 to 20 carbon atoms
- R 3 represents an alkyl group having 1 to 8 carbon atoms.
- the carbon number of R 2 is larger than the carbon number of R 1 .
- the alkyl group having 1 to 10 carbon atoms may be linear, branched or cyclic, for example, methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl.
- the alkyl group having 8 to 20 carbon atoms may be linear, branched or cyclic, for example, n-octyl group, 2-ethylhexyl group, n-nonyl group, n-decyl group, n-undecyl group. N-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-eicosyl group and the like.
- the alkyl group having 1 to 8 carbon atoms may be linear, branched or cyclic, and among the groups exemplified as the alkyl group having 1 to 10 carbon atoms, the same groups as those having 1 to 8 carbon atoms can be used. Can be mentioned.
- R 1 is particularly preferably a linear alkyl group having 2 to 8 carbon atoms, more preferably a linear alkyl group having 3 to 8 carbon atoms, and even more preferably a linear alkyl group having 4 to 8 carbon atoms.
- n-butyl group or n-hexyl group is more preferable in consideration of characteristics (hydrophobicity, heat resistance) and production cost of the ionic liquid.
- R 2 is preferably a straight-chain alkyl group having 10 to 20 carbon atoms, more preferably a straight-chain alkyl group having 12 to 20 carbon atoms, in consideration of the characteristics of the ionic liquid (hydrophobicity and heat resistance).
- R 3 is preferably an alkyl group having 1 to 4 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and most preferably a methyl group.
- the ionic liquid can be synthesized, for example, according to the method described in JP2013-14536A.
- the ionic liquid is hydrophobic, has a small friction coefficient, and its fluctuation is small, it can be suitably used as a lubricant. Further, since the ionic liquid does not generate a toxic substance such as hydrogen fluoride, there is no possibility of deteriorating a metal material, a polymer material, or the like. Therefore, the ionic liquid can be applied to various uses as a general-purpose lubricant.
- the lubricant of the present invention may be composed only of the ionic liquid, but may further contain an additive.
- the additive is not particularly limited as long as it is generally used as an additive for lubricating oil and can be dissolved in the ionic liquid described above.
- Conventional ionic liquids containing fluorine-containing anions such as NTf 2 ⁇ , BF 4 ⁇ , and PF 6 ⁇ have a small ability to dissolve such additives, and it is difficult to improve tribological properties.
- the silicon-containing ionic liquid can dissolve such additives, and thus the tribological properties of the ionic liquid can be improved cost-effectively.
- additive examples include surfactants, dispersants, antioxidants, antiwear agents, rust inhibitors, corrosion inhibitors, friction modifiers, extreme pressure additives, antifoaming agents, viscosity modifiers, and pour points. Depressant and the like.
- the surfactant examples include sulfonate surfactants such as alkyl sulfonate and alkyl benzene sulfonate, salicylate surfactants, phosphate surfactants, phenate surfactants, and the like.
- the content thereof is preferably 0.1 to 10% by mass in the lubricant.
- dispersant examples include polyalkenyl succinimide, polyalkenyl succinate, Mannich base, and organic phosphates.
- the content thereof is preferably 0.1 to 10% by mass in the lubricant.
- antioxidants examples include zinc dithiophosphate, phenolic antioxidants, aromatic amine antioxidants, organic sulfur compound antioxidants, hindered phenols, phosphite antioxidants, and the like.
- the content thereof is preferably 0.1 to 10% by mass in the lubricant.
- antiwear agent examples include phosphorus antiwear agents, sulfur antiwear agents, boric acid derivatives, chlorine antiwear agents, and zinc dithiophosphate.
- an antiwear agent When an antiwear agent is included, its content is preferably 0.1 to 10% by mass in the lubricant.
- rust preventive examples include sulfonate, polyhydric alcohol ester, alkylamine and the like.
- the content thereof is preferably 0.1 to 10% by mass in the lubricant.
- the corrosion inhibitor examples include nitrogen-containing compounds such as benzotriazole compounds.
- nitrogen-containing compounds such as benzotriazole compounds.
- its content is preferably 0.1 to 10% by mass in the lubricant.
- the friction modifier examples include glycerin fatty acid esters such as glycerol monooleate and alkylamines such as oleylamine.
- the content thereof is preferably 0.1 to 10% by mass in the lubricant.
- extreme pressure additive examples include sulfur-based extreme pressure additives such as sulfurized fats and oils, sulfurized olefins, dibenzyl disulfide and dialkyl disulfide, and phosphorus-based extreme pressure additives.
- sulfur-based extreme pressure additives such as sulfurized fats and oils, sulfurized olefins, dibenzyl disulfide and dialkyl disulfide, and phosphorus-based extreme pressure additives.
- the content thereof is preferably 0.1 to 10% by mass in the lubricant.
- antifoaming agent examples include silicon-based antifoaming agents such as polymethylsiloxane.
- the antifoaming agent When the antifoaming agent is included, its content is preferably 0.1 to 10% by mass in the lubricant.
- viscosity modifier examples include hydrocarbon viscosity modifiers such as polyisobutylene, olefin copolymer, styrene / isoprene copolymer, and ester viscosity modifiers such as styrene ester and polymethacrylate.
- hydrocarbon viscosity modifiers such as polyisobutylene, olefin copolymer, styrene / isoprene copolymer, and ester viscosity modifiers such as styrene ester and polymethacrylate.
- pour point depressant examples include alkylated aromatic compounds, styrene / maleic acid ester copolymers, and polymethacrylates.
- the content thereof is preferably 0.1 to 10% by mass in the lubricant.
- a friction modifier or an antiwear agent is included from the viewpoint that the tribological characteristics can be highly controlled.
- Ionic liquid 2 was synthesized in the same manner as in Synthesis Example 1, except that sodium 2- (trimethylsilyl) -1-ethanesulfonate was used instead of sodium 3- (trimethylsilyl) -1-propanesulfonate.
- Sodium 2- (trimethylsilyl) -1-ethanesulfonate was synthesized according to the method described in US Pat. No. 3,141,898.
- a 1 H-NMR spectrum of ionic liquid 2 (apparatus: AL-400 manufactured by JEOL Ltd., solvent: deuterated chloroform) is shown in FIG. When this ionic liquid 2 was mixed with an equal volume of water, it was completely separated into two layers and confirmed to be hydrophobic.
- the ionic liquid 3 was synthesized in the same manner as in Synthesis Example 1 except that tributyl dodecyl phosphonium bromide (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of tributyl hexadecyl phosphonium bromide. When this ionic liquid 3 was mixed with an equal volume of water, it was completely separated into two layers and confirmed to be hydrophobic.
- the ionic liquid 4 was synthesized in the same manner as in Synthesis Example 2 except that tributyl dodecyl phosphonium bromide (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of tributyl hexadecyl phosphonium bromide.
- the 1 H-NMR spectrum of ionic liquid 4 (apparatus: AL-400 manufactured by JEOL Ltd., solvent: deuterated chloroform) is shown in FIG. When this ionic liquid 4 was mixed with an equal volume of water, it was completely separated into two layers and confirmed to be hydrophobic.
- Ionic liquid 5 was synthesized in the same manner as in Synthesis Example 2, except that trihexyltetradecylphosphonium bromide (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of tributylhexadecylphosphonium bromide.
- the 1 H-NMR spectrum of ionic liquid 5 (apparatus: AL-400 manufactured by JEOL Ltd., solvent: deuterated chloroform) is shown in FIG. When this ionic liquid 5 was mixed with an equal volume of water, it was completely separated into two layers and confirmed to be hydrophobic.
- Lubricant B A lubricant consisting only of ionic liquid 2 was used as Lubricant B.
- Lubricant C A lubricant consisting only of ionic liquid 3 was designated as Lubricant C.
- Example 1-2 Preparation of Lubricant D A lubricant consisting only of ionic liquid 4 was designated as lubricant D.
- Lubricant E A lubricant consisting only of ionic liquid 5 was used as Lubricant E.
- Example 1-4 Preparation of Lubricant F To ionic liquid 2, glycerol monooleate (GMO) as an additive was added to 5% by mass and gently stirred at room temperature (20 to 25 ° C.). A homogeneous solution was obtained and Lubricant F was prepared.
- GMO glycerol monooleate
- Lubricant G Lubricant was lubricated in the same manner as in Example 1-4, except that dibenzyl disulfide (DBDS) was used instead of GMO, and the temperature during stirring was set to 35 to 40 ° C. Agent G was prepared.
- DBDS dibenzyl disulfide
- Lubricant H was prepared in the same manner as in Example 1-4, except that oleylamine (OleAm) was used instead of GMO.
- OleAm oleylamine
- Friction test [Example 2, Comparative Example 2] A friction test was performed using the lubricants A (Comparative Example 2) and B (Example 2). The friction test was performed by a steel ball-steel plate (steel ball-steel plate) contact using an SRV tester (manufactured by Optimol) specified in ASTM D 6425. Specifically, after setting the test piece on the testing machine, the change in friction coefficient with time was traced according to the conditions shown in Table 2. The results are shown in FIG.
- Lubricant B (Example 2) was stable immediately after the start of the test and was stable at a coefficient of friction of 0.1 or less, whereas Lubricant A (Comparative Example 2) had a coefficient of friction immediately after the start of the test. It was 0.1 or more, and it took time to reach a steady state (until a stable state with little fluctuation). Therefore, the lubricant B was superior in performance as a lubricant.
- Example 3 A friction test was performed using Lubricant B (Example 3) and commercially available lubricating oil for hydraulic equipment 1 (mineral oil, API Group I) (Comparative Example 3). The friction test was performed under the conditions shown in Table 3 using the same SRV test machine and sphere-plate as in Example 2. Specifically, after setting the test piece on the testing machine, the temperature was changed every 30 minutes to track the change in the coefficient of friction over time. In addition, about the lubrication agent B, each sample was measured twice and the repeatability was confirmed. The results are shown in FIG.
- Lubricating oil 1 had a friction coefficient of 0.11 or more at 25 ° C., and a tendency for the friction coefficient to increase with increasing temperature was observed.
- the lubricant B showed a smaller coefficient of friction than the lubricant 1. The performance tended to improve rather than inferior even in the range of 75 to 100 ° C. That is, the lubricant B showed an excellent lubricating performance as compared with the lubricating oil 1 under more severe conditions. Regarding the lubricant B, the repeatability was also good.
- the ionic liquid used in the present invention has a performance comparable to that of commercially available lubricating oil for hydraulic equipment, has a small friction coefficient, and is a particularly useful lubricant under heating conditions of 50 to 100 ° C. It was shown that.
- Lubricants B, D, and E are all ionic liquids having NTf 2 ⁇ as an anion, which has a small coefficient of friction of 0.1 or less, and is known to have good performance as a lubricant with existing ionic liquids.
- the coefficient of friction was about 10 to 20% smaller.
- the friction coefficients of the lubricants B, D, and E were all stable and small immediately after the start of the test, and the fluctuation was small.
- [BMIM] [NTf 2 ] had a large coefficient of friction immediately after the start of the test, and it took time to reach a steady state.
- Examples 5-1 to 5-3 A friction test was performed using the lubricants F, G, and H (Examples 5-1 to 5-3). The friction test was performed by a steel ball-steel plate (steel ball-steel plate) contact using an SRV tester (manufactured by Optimol) specified in ASTM D 6425. Specifically, after setting the test piece on the testing machine, the change in friction coefficient with time was traced according to the conditions shown in Table 5.
- the lubricant of the present invention has excellent performance.
Abstract
Description
1.下記式(1)で表されるケイ素含有イオン液体を含む潤滑剤。
2.前記R2が、炭素数10~20の直鎖アルキル基である1の潤滑剤。
3.前記R1が、全てn-ブチル基又はn-ヘキシル基である1又は2の潤滑剤。
4.前記R3が、全てメチル基である1~3のいずれかの潤滑剤。
5.式(1)で表されるケイ素含有イオン液体のみからなる1~4のいずれかの潤滑剤。
6.更に、界面活性剤、分散剤、酸化防止剤、耐摩耗剤、防錆剤、腐食防止剤、摩擦調整剤、極圧添加剤、消泡剤、粘度調整剤及び流動点降下剤から選ばれる添加剤を少なくとも1種含む1~4のいずれかの潤滑剤。
7.前記添加剤が、摩擦調整剤又は耐摩耗剤である6の潤滑剤。
8.下記式(1)で表されるケイ素含有イオン液体。
9.下記式(2)~(4)で表される8のケイ素含有イオン液体。
イオン液体1~5の融点(Tm)、分解点(Td)、粘度(η)及び電気伝導率(χ)を測定した。融点は、セイコーインスツルメンツ(株)製DSC6200を用いて、20~60℃まで毎分10℃昇温、60℃で1分間保持後、60~-90℃まで毎分1℃降温、-90℃で1分間保持後、-90℃~60℃まで毎分1℃昇温の条件で測定した。分解点は、空気雰囲気下、30~500℃まで毎分10℃昇温の条件で測定し、10%重量減少した温度を分解点とした。粘度は、BROOKFIELD社製プログラマブルレオメーターを用いて、25℃及び60℃における粘度(イオン液体5は25℃における粘度のみ)を測定した。電気伝導率は、東亜ディーケーケー(株)製電気伝導率計CM-30Rを用いて、25℃及び60℃における電気伝導率(イオン液体5は25℃における電気伝導率のみ)を測定した。結果を表1に示す。
[比較例1-1]潤滑剤Aの調製
イオン液体1のみからなる潤滑剤を潤滑剤Aとした。
イオン液体2のみからなる潤滑剤を潤滑剤Bとした。
イオン液体3のみからなる潤滑剤を潤滑剤Cとした。
イオン液体4のみからなる潤滑剤を潤滑剤Dとした。
イオン液体5のみからなる潤滑剤を潤滑剤Eとした。
イオン液体2に、添加剤としてグリセロールモノオレエート(GMO)を5質量%となるように加え、室温(20~25℃)で穏やかに攪拌して均一溶液を得、潤滑剤Fを調製した。
GMOのかわりにジベンジルジスルフィド(DBDS)を用い、攪拌時の温度を35~40℃とした以外は、実施例1-4と同様の方法で潤滑剤Gを調製した。
GMOのかわりにオレイルアミン(OleAm)を用いた以外は、実施例1-4と同様の方法で潤滑剤Hを調製した。
[実施例2、比較例2]
潤滑剤A(比較例2)及びB(実施例2)を用いて、摩擦試験を行った。摩擦試験は、ASTM D 6425で規定された、SRV試験機(オプチモール社製)を用いたスチール球-スチール平板(鋼玉-鋼板)接触で実施した。具体的には、試験片を試験機にセットした後、表2の条件に従って摩擦係数の経時変化を追跡した。結果を図4に示す。
潤滑剤B(実施例3)及び市販の油圧機器用潤滑油1(鉱油、API Group I)(比較例3)を用いて、摩擦試験を行った。摩擦試験は、実施例2と同じSRV試験機と球-平板を使用して、表3の条件で行った。具体的には、試験片を試験機にセットした後、30分ごとに温度を変化させて摩擦係数の経時変化を追跡した。なお、潤滑剤Bについては、各試料2回の測定を行って繰り返し性を確認した。結果を図5に示す。
市販のイオン液体であるブチルメチルイミダゾリウムビス(トリフルオロメタンスルホニル)イミド(関東化学(株)製、以下、[BMIM][NTf2]と略す)(比較例4-1)及び潤滑剤B、D、E(実施例4-1~4-3)について、摩擦係数を比較した。摩擦係数の測定は、実施例1と同じSRV試験機と球-平板を使用して表4の条件で行った。結果を図7に示す。
市販のフッ素系合成潤滑剤(ソルベイ社製Fomblin-317926)について、表4と同じ条件で摩擦係数を測定した。結果を図8に示す。なお、測定は2回(Run 1、Run 2)行った。
市販のフッ素系合成潤滑剤(ソルベイ社製Fomblin-317950)について、表4と同じ条件で摩擦係数を測定した。結果を図9に示す。なお、測定は2回(Run 1、Run 2)行った。
潤滑剤F、G、H(実施例5-1~5-3)を用いて、摩擦試験を行った。摩擦試験は、ASTM D 6425で規定された、SRV試験機(オプチモール社製)を用いたスチール球-スチール平板(鋼玉-鋼板)接触で実施した。具体的には、試験片を試験機にセットした後、表5の条件に従って摩擦係数の経時変化を追跡した。
Claims (9)
- 前記R2が、炭素数10~20の直鎖アルキル基である請求項1記載の潤滑剤。
- 前記R1が、全てn-ブチル基又はn-ヘキシル基である請求項1又は2記載の潤滑剤。
- 前記R3が、全てメチル基である請求項1~3のいずれか1項記載の潤滑剤。
- 式(1)で表されるケイ素含有イオン液体のみからなる請求項1~4のいずれか1項記載の潤滑剤。
- 更に、界面活性剤、分散剤、酸化防止剤、耐摩耗剤、防錆剤、腐食防止剤、摩擦調整剤、極圧添加剤、消泡剤、粘度調整剤及び流動点降下剤から選ばれる添加剤を少なくとも1種含む請求項1~4のいずれか1項記載の潤滑剤。
- 前記添加剤が、摩擦調整剤又は耐摩耗剤である請求項6記載の潤滑剤。
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WO2021199911A1 (ja) * | 2020-04-01 | 2021-10-07 | 日清紡ホールディングス株式会社 | 潤滑油組成物及びイオン液体 |
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