Classifications

• • 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
  • C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
  • C10M105/58—Amines, e.g. polyalkylene polyamines, quaternary amines
• • 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
  • C10M105/72—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing sulfur, selenium or tellurium
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
  • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
  • C10M133/38—Heterocyclic nitrogen compounds
  • C10M133/44—Five-membered ring containing nitrogen and carbon only
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
  • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
  • C10M133/38—Heterocyclic nitrogen compounds
  • C10M133/48—Heterocyclic nitrogen compounds the ring containing both nitrogen and oxygen
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
  • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
  • C10M137/04—Phosphate esters
  • C10M137/08—Ammonium or amine salts

Definitions

• the present invention relates to an anti-wear agent.
• Ionic liquids such as pyrrolidinium type ionic liquids are known as base materials that have low viscosity and excellent low volatility and thermal stability compared to MAC oils (cyclopentane oils such as tris(2-octyldodecyl)cyclopentane) that are generally used as base materials for space lubricants. Therefore, taking advantage of the characteristics of low volatility and thermal stability, it is particularly desirable for ionic liquids to be used as base materials for long-life lubricants. In order to be used for a long period of time in lubricants, they need to have excellent wear resistance and rust prevention properties.
• ionic liquids since the properties of ionic liquids are significantly different from those of mineral oils and synthetic oils that are generally used as lubricant base materials, the types of additives that can be used are limited. Therefore, in lubricant compositions based on ionic liquids, it is desirable for the additives to have multiple properties.
• additives to be blended with ionic liquids imidazolium phosphate compounds in which the cation has an imidazolium structure are known (see, for example, Patent Documents 1 and 2).
• the present invention was made in consideration of the above problems, and aims to provide an anti-wear agent that is excellent in maintaining abrasion resistance and rust prevention properties.
• An anti-wear agent comprising one or more compounds selected from the group consisting of compounds represented by the following general formula (B1):
• R B1 represents an alkyl group having 1 to 9 carbon atoms.
• R B2 represents an alkyl group having 1 to 9 carbon atoms.
• R B3 represents an alkyl group having 1 to 9 carbon atoms.
• R B4 represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms.
• R represents an alkyl group having 1 to 3 carbon atoms.
• Y represents a methylene group or an oxygen atom.
• n1 is 1 or 2. When n1 is 1, m is an integer from 0 to 8. When n1 is 2, m is an integer from 0 to 10.
• the present invention makes it possible to provide an anti-wear agent that is excellent in maintaining wear resistance and rust prevention properties.
• the anti-wear agent of the present embodiment is an anti-wear agent containing one or more compounds selected from the compounds represented by the following general formula (B1).
• each symbol represents the following.
• R B1 represents an alkyl group having 1 to 9 carbon atoms.
• R B2 represents an alkyl group having 1 to 9 carbon atoms.
• R B3 represents an alkyl group having 1 to 9 carbon atoms.
• R B4 represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms.
• R represents an alkyl group having 1 to 3 carbon atoms.
• Y represents a methylene group or an oxygen atom.
• n1 is 1 or 2. When n1 is 1, m is an integer from 0 to 8. When n1 is 2, m is an integer from 0 to 10.
• the present inventors have conducted extensive research to solve the above problems. As a result, it was found that when a pyrrolidinium-type ionic liquid is used, the deterioration of rust prevention properties after a long time can be suppressed by using an anti-wear agent containing a pyrrolidinium-type phosphate compound whose cationic portion has a similar structure to the ionic liquid. It was also found that excellent anti-wear properties can be obtained by optimizing the carbon chain length of the alkyl group of the phosphoric acid, which is the anionic portion. Based on these findings, the present invention has been completed.
• R B1 in the general formula (B1) represents an alkyl group having 1 to 9 carbon atoms, preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, and still more preferably 1 to 4 carbon atoms.
• the alkyl group may be linear or branched.
• R B2 in the general formula (B1) represents an alkyl group having 1 to 9 carbon atoms, preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, and still more preferably 1 to 4 carbon atoms.
• the alkyl group may be linear or branched.
• R B2 is an alkyl group having 1 to 9 carbon atoms, the rust prevention properties, thermal stability, and solubility in the ionic liquid are improved.
• R B2 may be the same alkyl group as R B1 .
• R B3 in the general formula (B1) represents an alkyl group having 1 to 9 carbon atoms, preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, and still more preferably 1 to 4 carbon atoms.
• the alkyl group may be linear or branched.
• R B3 is an alkyl group having 1 to 9 carbon atoms
• the rust prevention properties, thermal stability, wear resistance, and solubility in ionic liquids are improved. If the alkyl group of R B3 has 10 or more carbon atoms, the abrasion resistance and solubility in the ionic liquid become insufficient.
• R B4 represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms.
• the alkyl group preferably has 1 to 8 carbon atoms, more preferably has 1 to 6 carbon atoms, and further preferably has 1 to 4 carbon atoms.
• R B4 represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms
• the alkyl group may be linear or branched. If the alkyl group of R B4 has 10 or more carbon atoms, the abrasion resistance and thermal stability become insufficient.
• R B2 , R B3 , and R B4 may be the same alkyl group or different alkyl groups, but from the viewpoint of synthesis, they are preferably the same alkyl group.
• R B1 , R B2 , R B3 and R B4 preferably have 1 to 8 carbon atoms, more preferably have 1 to 6 carbon atoms, and further preferably have 1 to 4 carbon atoms.
• R in the general formula (B1) represents an alkyl group having 1 to 3 carbon atoms, and preferably has 1 carbon atom.
• the alkyl group may be linear or branched.
• Y represents a methylene group or an oxygen atom, and is preferably a methylene group.
• n1 is 1 or 2, and preferably 1.
• n1 in the general formula (B1) is 1, m is an integer of 0 to 8, and preferably 0.
• n1 is 2, m is an integer of 0 to 10, and preferably 0.
• the total number of carbon atoms in the alkyl group of R B1 and the number of carbon atoms in the alkyl group of R B2 is not particularly limited, but is preferably 6 or less.
• the total number of carbon atoms in the alkyl group of R B1 and the alkyl group of R B2 is 6 or less, the abrasion resistance is easily improved and the thermal stability is also excellent.
• the antiwear agent of the present embodiment is excellent not only in terms of wear resistance but also in terms of maintaining the rust prevention properties.
• rust means "a product generated as a result of the progression of the corrosion phenomenon in a metal in contact with an ionic liquid.”
• the present inventors have found that rust tends to form on the surface of a metal in contact with an ionic liquid (the interface between the ionic liquid and the metal). This is presumably because the ionic liquid contains cations and anions, and the ionic conductivity of the ionic liquid accelerates the generation of rust.
• the inventors surmise that by using an anti-wear agent containing a pyrrolidinium-type phosphate compound in which the cationic portion has a similar structure to an ionic liquid, the deterioration of rust prevention properties over a long period of time can be suppressed.
• the antiwear agent of this embodiment can maintain the rust prevention properties that suppress the occurrence of rust for a long period of time.
• the rust-preventing properties of the anti-wear agent of this embodiment are evaluated as being desirable when "no rust occurs.”
• the compound represented by the general formula (B1) can be obtained, for example, by ionizing an alkylpyrrolidine and a trialkylphosphate to synthesize the compound represented by the general formula (B1).
• R , R , and R in the general formula (B1) are the same alkyl group, the alkyl group can be rearranged from a triester in the phosphate, which is an anion, to generate an alkyl group of a pyrrolidinium, which is a cation, and thus the synthesis is easy.
• the anti-wear agent of the present embodiment may consist of only one or more compounds selected from the compounds represented by general formula (B1), but may or may not contain components other than the compounds.
• the content of one or more compounds selected from the compounds represented by general formula (B1) in the anti-wear agent of this embodiment is, based on the total amount of the anti-wear agent, preferably 50% by mass to 100% by mass, more preferably 60% by mass to 100% by mass, even more preferably 70% by mass to 100% by mass, still more preferably 80% by mass to 100% by mass, even more preferably 90% by mass to 100% by mass, still more preferably 95% by mass to 100% by mass, and even more preferably 98% by mass to 100% by mass.
• the anti-wear agent of the present embodiment is preferably used together with an ionic liquid.
• the anti-wear agent may be used in conjunction with an ionic liquid, for example, in an ionic liquid-based lubricant composition.
• the ionic liquid is a liquid compound composed of cations and anions, and various compounds that do not contain metals can be used.
• the compound represented by the general formula (B1) is not included in the ionic liquid.
• the anion of the ionic liquid preferably contains bis(trifluoromethanesulfonyl)imide.
• the cation of the ionic liquid preferably contains a cation represented by the following general formula (A1).
• A1 each symbol represents the following.
• n2 is 1 or 2.
• X represents a methylene group or an oxygen atom.
• R A11 and R A12 each independently represent an alkyl group having 1 to 12 carbon atoms which may have one or more groups selected from an ether group, an ester group, a nitrile group, and a silyl group.
• the alkyl groups of R A11 and R A12 in general formula (A1) preferably have 1 to 6 carbon atoms, and more preferably 1 to 4 carbon atoms, from the viewpoint of reducing the viscosity of the ionic liquid and improving the thermal stability.
• R A11 is preferably a methyl group
• R A12 is preferably an n-butyl group or a methoxyethyl group.
• Examples of the cation represented by the general formula (A1) include 1-butyl-1-methylpyrrolidinium, 1-pentyl-1-methylpyrrolidinium, 1-hexyl-1-methylpyrrolidinium, 1-heptyl-1-methylpyrrolidinium, 1-octyl-1-methylpyrrolidinium, 1-nonyl-1-methylpyrrolidinium, 1-decyl-1-methylpyrrolidinium, 1-undecyl-1-methylpyrrolidinium, 1-dodecyl-1-methylpyrrolidinium, 1-methoxymethyl-1-methylpyrrolidinium, 1-(2-methoxyethyl)- 1-methylpyrrolidinium, 1-(2-methoxy-2-oxoethyl)-1-methylpyrrolidinium, 1-cyanomethyl-1-methylpyrrolidinium, 1-trimethylsilylmethyl-1-methylpyrrolidinium, 1-butyl-1-methylpiperidinium, 1-pentyl-1-methylpiperid
• the ionic liquid preferably contains at least one selected from the compounds represented by the following general formula (A2) and the compounds represented by the following general formula (A3).
• n3 is 1 or 2.
• X represents a methylene group or an oxygen atom.
• R A21 represents an alkyl group having 2 to 12 carbon atoms.
• n4 is 1 or 2.
• X represents a methylene group or an oxygen atom.
• R A31 represents an alkylene group having 1 to 5 carbon atoms.
• R A32 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
• the number of carbon atoms in R A21 is preferably 2 to 8, more preferably 3 to 6.
• the side chain can move freely and the symmetry is low, so that crystallization can be suppressed and the function as an ionic liquid can be improved.
• the number of carbon atoms in R A21 is 12 or less, the side chain does not become too large and the ionicity of the entire compound is high, so that oxidative deterioration can be easily suppressed.
• the carbon number of R A31 is preferably 1 to 3, more preferably 1 to 2.
• the carbon number of R A32 is preferably 1 to 2.
• the carbon number of R A31 is 1 or more, the side chain can move freely and the symmetry is low, so that crystallization can be suppressed and the function as an ionic liquid can be improved.
• the carbon number of R A31 is 5 or less, or the carbon number of R A32 is 3 or less, the side chain does not become too large and the ionicity of the entire compound is high, so that oxidative deterioration is easily suppressed.
• the content of the compound represented by general formula (A2) in the ionic liquid is preferably 60% by mass to 100% by mass, more preferably 70% by mass to 100% by mass, and even more preferably 80% by mass to 100% by mass, based on the total amount of the ionic liquid.
• the content of the compound represented by general formula (A3) in the ionic liquid is preferably 60% by mass to 100% by mass, more preferably 70% by mass to 100% by mass, and even more preferably 80% by mass to 100% by mass, based on the total amount of the ionic liquid.
• one or more types selected from the compounds represented by the above general formula (A2) may be used, one or more types selected from the compounds represented by the above general formula (A3) may be used, or one or more types selected from the compounds represented by the above general formula (A2) and one or more types selected from the compounds represented by the above general formula (A3) may be used in combination.
• the content of the ionic liquid is not particularly limited, but from the viewpoint of improving the effects of the present invention, the content is preferably 50 mass % or more, more preferably 60 mass % or more, even more preferably 70 mass % or more, still more preferably 80 mass % or more, and even more preferably 85 mass % or more, based on the total amount (100 mass %) of the lubricant composition.
• the upper limit of the ionic liquid content is appropriately set depending on the amount of components other than the ionic liquid, and is preferably 99.8% by mass or less, more preferably 99.7% by mass or less, preferably 99.5% by mass or less, more preferably 99.0% by mass or less, and even more preferably 98.5% by mass or less.
• the upper and lower limits of these numerical ranges can be arbitrarily combined. Specifically, the range is preferably 50% by mass to 100% by mass, more preferably 60% by mass to 100% by mass, even more preferably 70% by mass to 100% by mass, still more preferably 90% by mass to 100% by mass, and even more preferably 95% by mass to 100% by mass.
• the lubricant composition may contain a base material component other than the above-mentioned ionic liquid (for example, a base material component that does not fall under the category of an ionic liquid, such as ethyl acetate) as the base material.
• a base material component other than the above-mentioned ionic liquid for example, a base material component that does not fall under the category of an ionic liquid, such as ethyl acetate
• the content of the above-mentioned ionic liquid is preferably 50 mass% or more, more preferably 70 mass% or more, even more preferably 90 mass% or more, and even more preferably 100 mass% based on the total amount of the base material.
• the ratio (B/A) of the content B of the compound represented by the above general formula (B1) to the content A of the ionic liquid is preferably 0.0005 or more and 0.15 or less, more preferably 0.001 or more and 0.111 or less, and even more preferably 0.003 or more and 0.08 or less, in mass ratio.
• (B/A) is 0.0005 or more, sufficient rust prevention properties are easily obtained.
• (B/A) is 0.15 or less, the solubility of the compound represented by the above general formula (B1) in the ionic liquid is easily sufficient.
• the lubricant composition may contain other components, as necessary, in addition to the anti-wear agent of this embodiment, within the scope of not impairing the effects of the present invention.
• the other components include by-products generated in the synthesis process of the compound represented by the general formula (B1), unreacted raw materials remaining in the synthesis process of the compound represented by the general formula (B1), diluents, etc.
• examples of other components other than the anti-wear agent of this embodiment include additives such as viscosity index improvers, thickeners, etc. These may be used alone or in combination of two or more.
• the abrasion resistance of the compound represented by the general formula (B1) is preferably such that the abrasion width is 250 ⁇ m or less, more preferably 230 ⁇ m or less, and even more preferably 200 ⁇ m or less, when evaluated by the method described in the Examples.
• the rust-preventive properties of the compound represented by the general formula (B1) are preferably such that no reddish-brown or black discoloration (rust) is observed on the surface when evaluated by the method described in the examples below.
• the antiwear agent of the present embodiment is excellent not only in terms of wear resistance but also in terms of maintaining rust prevention properties, and can therefore be blended in lubricant compositions that require high rust prevention properties.
• the lubricant composition include lubricant compositions for lubricating devices mounted on devices used in space, semiconductors, liquid crystal or organic EL flat panel displays, manufacturing equipment for solar cell panels, etc., but the lubricant composition may also be used for other purposes. Therefore, the anti-wear agent according to the present embodiment provides the following (1) and (2). (1) A method of suppressing wear by using the anti-wear agent according to this embodiment. (2) Use of the anti-wear agent according to this embodiment for lubricating at least one of equipment mounted on devices used in space, semiconductors, liquid crystal or organic electroluminescence flat panel displays, and solar panels.
• An anti-wear agent comprising one or more compounds selected from the group consisting of compounds represented by the following general formula (B1):
• R B1 represents an alkyl group having 1 to 9 carbon atoms.
• R B2 represents an alkyl group having 1 to 9 carbon atoms.
• R B3 represents an alkyl group having 1 to 9 carbon atoms.
• R B4 represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms.
• R represents an alkyl group having 1 to 3 carbon atoms.
• Y represents a methylene group or an oxygen atom.
• n1 is 1 or 2.
• n1 When n1 is 1, m is an integer from 0 to 8. When n1 is 2, m is an integer from 0 to 10.
• the ionic liquid contains a cation represented by the following general formula (A1): In the general formula (A1), each symbol represents the following. n2 is 1 or 2.
• X represents a methylene group or an oxygen atom.
• R A11 and R A12 each independently represent an alkyl group having 1 to 12 carbon atoms which may have one or more groups selected from an ether group, an ester group, a nitrile group, and a silyl group.
• X represents a methylene group or an oxygen atom.
• R A21 represents an alkyl group having 2 to 12 carbon atoms.
• n4 is 1 or 2.
• X represents a methylene group or an oxygen atom.
• R A31 represents an alkylene group having 1 to 5 carbon atoms.
• R A32 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
• Compound 1 is a compound in which the symbols in the general formula (B1) are as follows.
• R B1 is a methyl group having one carbon atom.
• R B2 , R B3 , and R B4 are each an ethyl group having 2 carbon atoms.
• Y is a methylene group.
• n is 1.
• m is 0.
• Compound 2 is a compound in which the symbols in general formula (B1) are as follows.
• R B1 , R B2 , R B3 and R B4 are each a methyl group having one carbon atom.
• Y is a methylene group.
• n is 1.
• m is 0.
• Compound 3 is a compound in which the symbols in general formula (B1) are as follows.
• R B1 is an n-butyl group having 4 carbon atoms.
• R B2 , R B3 , and R B4 are each an ethyl group having 2 carbon atoms.
• Y is a methylene group.
• n is 1.
• m is 0.
• Compound 4 is a compound in which the symbols in general formula (B1) are as follows.
• R B1 is an n-butyl group having 4 carbon atoms.
• R B2 , R B3 , and R B4 are each a methyl group having one carbon atom.
• Y is a methylene group.
• n is 1.
• m is 0.
• Comparative Compound 1 As comparative compound 1, 1-butyl-3-methylimidazolium dibutyl phosphate (manufactured by Tokyo Chemical Industry Co., Ltd.) was prepared.
• Comparative Compound 2 1,3-dimethylimidazolium dimethyl phosphate (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) was prepared.
• Comparative Production Example 1 Synthesis of Comparative Compound 3 First, 2.0 g (5.0 mmol) of didecyl phosphate sodium salt, 1.1 g (5.0 mmol) of N,N-butylmethylpyrrolidinium bromide, 10 mL of ion-exchanged water, and 10 mL of methanol were added to a recovery flask and stirred at room temperature for 1 hour. After adding 20 mL of dichloromethane, the mixture was washed three times with 10 mL of ion-exchanged water to obtain 0.21 g (0.4 mmol) of Comparative Compound 3.
• Comparative Production Example 2 Synthesis of Comparative Compound 4 First, 5.0 g (7.2 mmol) of a 40% aqueous solution of tetrabutylphosphonium hydroxide and 1.5 g (7.2 mmol) of dibutyl phosphate were added to a recovery flask and stirred at room temperature for 1 hour. Next, moisture was removed using an evaporator to obtain 3.2 g (6.8 mmol) of Comparative Compound 4.
• Example 1 to 5 As the ionic liquid, N-(2-methoxyethyl)-N-methylpyrrolidinium-bis(trifluoromethanesulfonyl)imide was used. As shown in Table 1, in Examples 1 to 5, compounds 1 to 4 were blended as anti-wear agents, and in Comparative Examples 1 to 6, comparative compounds 1 to 5 were blended as anti-wear agents to prepare lubricant compositions, and the following evaluations were performed. The results are shown in Table 1.
• ⁇ Evaluation of maintenance of rust prevention properties 5 g of distilled water and 5 g of each lubricant composition were added to a 10 mL sample bottle.
• a SUS440C plate cut into a strip (length: 51 mm, width: 13 mm, thickness: 3.0 mm) was placed in the bottle and allowed to stand at room temperature for 14 days. After that, the appearance of the SUS440C plate was observed, and the rust prevention properties were judged as follows. A: No reddish brown or black discoloration (rust) was observed on the surface. B: Reddish brown or black discoloration (rust) was observed on the surface.
• Example 1 which contain Compounds 1 to 4 as anti-wear agents, the wear width is 250 ⁇ m or less, which shows that the wear resistance is excellent. In addition, Examples 1 to 5 also show excellent results in maintaining the rust prevention properties.
• Comparative Examples 1 to 5 which contain Comparative Compounds 1 to 4 as anti-wear agents, were inferior in at least one of the wear resistance and the maintenance of rust prevention. Specifically, Comparative Example 4 had an abrasion width far exceeding 250 ⁇ m, and the wear resistance was very insufficient. Comparative Examples 1 to 3 and Comparative Example 5 were inferior in the maintenance of rust prevention. And, Comparative Example 6 could not evaluate the maintenance of wear resistance and rust prevention because Comparative Compound 5 was not dissolved in the ionic liquid.

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• 2022
  • 2022-11-16 JP JP2022183350A patent/JP2024072503A/ja active Pending
• 2023
  • 2023-11-13 WO PCT/JP2023/040805 patent/WO2024106393A1/ja active Application Filing
  • 2023-11-13 CN CN202380078445.9A patent/CN120112619A/zh active Pending

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