Compound, rust inhibitor, and lubricant composition

Abstract

To provide compounds excellent in thermal stability and rust prevention and free of metal content.SOLUTION: A compound represented by the general formula (B1) in the figure is provided. [L1 is a C1-10 divalent saturated aliphatic hydrocarbon group; L2 and L3 are each independently a C1-6 alkylene group; and Y1 and Y2 are each independently a methylene group or O.]SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a compound, a rust inhibitor, and a lubricant composition. More specifically, the present invention relates to a compound, a rust inhibitor containing the compound, and a lubricant composition containing the compound. [Background technology]

[0002] Ionic liquids are known as base materials for lubricant compositions that have low viscosity yet excellent lubricating properties and thermal stability. However, compared with mineral oils and synthetic oils, which are commonly used base materials in lubricant compositions, ionic liquids have the disadvantage of being highly corrosive and having poor rust prevention properties. To overcome these disadvantages, a method is known in which one or more selected from sodium nitrite, sodium molybdate, and sodium sebacate are blended with the ionic liquid (see Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2009-249585 Summary of the Invention [Problem to be solved by the invention]

[0004] In recent years, due to the above advantages of ionic liquids, it has been expected that lubricant compositions based on ionic liquids will be used in high-vacuum, high-temperature environments such as vacuum chambers in semiconductor manufacturing equipment. However, in the semiconductor manufacturing process, it is necessary to avoid contamination of semiconductors with metals such as alkali metals and heavy metals, and therefore it is not possible to improve the rust prevention properties of a lubricant composition by blending sodium nitrite, sodium molybdate, and sodium sebacate with an ionic liquid, as described in Patent Document 1.

[0005] Therefore, an object of the present invention is to provide a compound that has excellent thermal stability and rust prevention properties and does not contain metal components, a rust inhibitor containing the compound, and a lubricant composition containing the compound. [Means for solving the problem]

[0006] The present inventors have conducted extensive research to solve the above problems, and as a result have found that a compound having a specific structure can solve the above problems, thereby completing the present invention.

[0007] That is, the present invention relates to the following [1] to [5]. [1] A compound represented by the following general formula (B1): [ka] [In the general formula (B1), each symbol represents the following.] L 1 represents a divalent saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms. L 2 and L 3 each independently represents an alkylene group having 1 to 6 carbon atoms. Y 1 and Y 2 each independently represents a methylene group or an oxygen atom. n1 and n2 each independently represent 1 or 2. When n1 is 1, m1 is an integer of 0 to 8. When n1 is 2, m1 is an integer of 0 to 10. When n2 is 1, m2 is an integer of 0 to 8. When n2 is 2, m2 is an integer of 0 to 10. R 1 and R 2 each independently represents an alkyl group having 1 to 3 carbon atoms. [2] A method of using the compound according to [1] above as a rust inhibitor. [3] A rust inhibitor containing the compound described in [1] above. [4] A lubricant composition containing an ionic liquid and the compound described in [1] above. [5] A method for producing a lubricant composition, comprising the step of mixing an ionic liquid with the compound described in [1] above. [Effects of the Invention]

[0008] According to the present invention, it is possible to provide a compound that is excellent in thermal stability and rust prevention properties and does not contain any metal components, a rust inhibitor containing said compound, and a lubricant composition containing said compound. DETAILED DESCRIPTION OF THE INVENTION

[0009] The upper and lower limits of the ranges described herein can be combined in any way. For example, when the ranges are "A to B" and "C to D," the ranges "A to D" and "C to B" are also included in the scope of the present invention. Furthermore, unless otherwise specified, the numerical range "lower limit to upper limit" described in this specification means that the range is equal to or greater than the lower limit and equal to or less than the upper limit. In this specification, the numerical values ​​in the examples are numerical values ​​that can be used as upper or lower limit values.

[0010] [Compound Aspects] The compound of this embodiment is represented by the following general formula (B1). [ka] [In the general formula (B1), each symbol represents the following.] L 1 represents a divalent saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms. L 2 and L 3 each independently represents an alkylene group having 1 to 6 carbon atoms. Y 1 and Y 2 each independently represents a methylene group or an oxygen atom. n1 and n2 each independently represent 1 or 2. When n1 is 1, m1 is an integer of 0 to 8. When n1 is 2, m1 is an integer of 0 to 10. When n2 is 1, m2 is an integer of 0 to 8. When n2 is 2, m2 is an integer of 0 to 10. R 1 and R 2 each independently represents an alkyl group having 1 to 3 carbon atoms.

[0011] The present inventors have conducted various studies to solve the above problems. As a result, the present inventors have found that compounds having a specific structure, among compounds having a structure in which two betaine structures are present on the left and right sides via a linker, and in which the betaine structure is composed of a cation and a carboxy anion of an intramolecular heterocycle having one nitrogen atom as a heteroatom, can solve the above-mentioned problems. The mechanism by which the compound of this embodiment exhibits the effects of the present invention is not clear, but is presumed to be, for example, as follows. That is, (i) the structure in which two betaine structures are present approximately on the left and right sides via a linker contributes to improving the thermal stability of the compound, (ii) the heterocyclic structure constituting the betaine structure contributes to further improving the thermal stability of the compound, (iii) the two carboxy anions at the end of the compound also contribute to further improving the thermal stability and also contributing to rust prevention, and (iv) the appropriate lengths of the linker connecting the two hetero rings and the linker connecting the hetero ring and the carboxy anion contribute to thermal stability and rust prevention.These contributions are presumed to combine comprehensively to form a compound with excellent thermal stability and excellent rust prevention.In other words, the compound of this embodiment can be said to be a compound in which the structures for achieving the effects of the present invention are efficiently and efficiently integrated into one molecule. Furthermore, the following points are worth noting. That is, compounds containing metal components such as alkali metals, such as sodium sebacate, generally tend to have excellent thermal stability. In contrast, the compound of the present embodiment does not contain any metal components, but has excellent thermal stability due to the structural features (i) to (iv) above. The compound of this embodiment will be described in detail below.

[0012] <L 1 > In the above general formula (B1), L 1 represents a divalent saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms. L 1 When the carbon number of the divalent saturated aliphatic hydrocarbon group that can be selected as L is less than 1, 1 Since L does not exist, the structure of the compound of this embodiment cannot be obtained. 1 If the number of carbon atoms in the divalent saturated aliphatic hydrocarbon group that can be selected for exceeds 10, it becomes difficult to ensure sufficient thermal stability of the compound represented by the above general formula (B1). In addition, L 1 If is a group other than a divalent saturated aliphatic hydrocarbon group, it becomes difficult to synthesize the compound represented by the general formula (B1) above, and the effects of the present invention are also difficult to achieve.

[0013] Here, from the viewpoint of easily ensuring sufficient rust prevention properties of the compound represented by the general formula (B1), L 1 The number of carbon atoms in the divalent saturated aliphatic hydrocarbon group that can be selected as L is preferably 2 or more, more preferably 3 or more, and even more preferably 4 or more. In addition, from the viewpoint of easily ensuring sufficient thermal stability of the compound represented by the general formula (B1), L 1 The number of carbon atoms of the divalent saturated aliphatic hydrocarbon group that can be selected as is preferably 8 or less, more preferably 7 or less, and even more preferably 6 or less. The upper and lower limits of these numerical ranges can be arbitrarily combined. Specifically, the range is preferably 2 to 8, more preferably 3 to 7, and even more preferably 4 to 6.

[0014] L 1Divalent saturated aliphatic hydrocarbon groups that can be selected as include acyclic saturated hydrocarbons and cyclic saturated hydrocarbons. Specific examples include alkylene groups having 1 to 10 carbon atoms, cycloalkylene groups having 5 to 10 carbon atoms, alkylcycloalkylene groups having 6 to 10 carbon atoms, alkylene-cycloalkylene groups having 6 to 10 carbon atoms, alkylene-cycloalkylene-alkylene groups having 7 to 10 carbon atoms, alkylene-alkylcycloalkylene groups having 7 to 10 carbon atoms, and alkylene-alkylcycloalkylene-alkylene groups having 8 to 10 carbon atoms.

[0015] The term "alkylene group" refers to a divalent group formed by removing two hydrogen atoms from an alkane. The alkylene group may be linear or branched, but is preferably linear from the viewpoint of improving the rust prevention properties of the compound represented by the general formula (B1).

[0016] A "cycloalkylene group" is a divalent group formed by removing two hydrogen atoms from a cycloalkane.

[0017] The term "alkylcycloalkylene group" refers to a group in which at least one hydrogen atom constituting a cycloalkylene group is substituted with an alkyl group, and examples thereof include a methylcyclohexylene group. The number of carbon atoms in an "alkylcycloalkylene group" is the total number of carbon atoms in the alkyl group and cycloalkylene group that constitute the alkylcycloalkylene group.

[0018] The term "alkylene-cycloalkylene group" refers to a group in which one of two bonds of an alkylene group is bonded to one of two bonds of a cycloalkylene group, and examples thereof include a methylene-cyclohexylene group. The number of carbon atoms in an "alkylene-cycloalkylene group" is the total number of carbon atoms in the alkylene group and the cycloalkylene group that constitute the alkylene-cycloalkylene group.

[0019] The term "alkylene-cycloalkylene-alkylene group" refers to a group in which one of two bonds of a first alkylene group is bonded to one of two bonds of a cycloalkylene group, and one of two bonds of a second alkylene group is bonded to the other of two bonds of the cycloalkylene group, and examples thereof include a methylene-cyclohexylene-methylene group. The number of carbon atoms in an "alkylene-cycloalkylene-alkylene group" is the total number of carbon atoms in the two alkylene groups and the cycloalkylene group that constitute the alkylene-cycloalkylene-alkylene group.

[0020] The term "alkylene-alkylcycloalkylene group" refers to a group in which one of two bonds of an alkylene group is bonded to one of two bonds of an alkylcycloalkylene group, and examples thereof include a methylene-methylcyclohexylene group. The number of carbon atoms in an "alkylene-alkylcycloalkylene group" is the total number of carbon atoms in the alkylene group and alkylcycloalkylene group (alkyl group and cycloalkylene group) that constitute the alkylene-alkylcycloalkylene group.

[0021] The term "alkylene-alkylcycloalkylene-alkylene group" refers to a group in which one of two bonds of a first alkylene group is bonded to one of two bonds of an alkylcycloalkylene group, and one of two bonds of a second alkylene group is bonded to the other of two bonds of the alkylcycloalkylene group, and examples thereof include a methylene-methylcyclohexylene-methylene group. The number of carbon atoms in an "alkylene-alkylcycloalkylene-alkylene group" is the total number of carbon atoms in the two alkylene groups and the alkylcycloalkylene group (the alkyl group and the cycloalkylene group) that constitute the alkylene-alkylcycloalkylene-alkylene group.

[0022] The "alkylene groups" constituting the "alkylene-cycloalkylene group," "alkylene-cycloalkylene-alkylene group," "alkylene-alkylcycloalkylene group," and "alkylene-alkylcycloalkylene-alkylene group" may be linear or branched, but are preferably linear from the viewpoint of improving the rust prevention properties of the compound represented by the above general formula (B1).

[0023] Here, from the viewpoint of improving the effects of the present invention and from the viewpoint of ease of synthesis of the compound represented by the general formula (B1), L 1 is preferably a linear or branched alkylene group having 1 to 10 carbon atoms, more preferably a linear or branched alkylene group having 2 to 8 carbon atoms, even more preferably a linear or branched alkylene group having 3 to 7 carbon atoms, and even more preferably a linear or branched alkylene group having 4 to 6 carbon atoms. From the same viewpoint, the alkylene group is preferably linear.

[0024] <L 2 and L 3 > In the above general formula (B1), L 2 and L 3 each independently represents an alkylene group having 1 to 6 carbon atoms. L 2 and L 3 When the number of carbon atoms in the alkylene group that can be selected as L is less than 1 (in other words, 2 and L 3 is not present), the betaine structure of the compound represented by general formula (B1) cannot be stably maintained, and the effects of the present invention cannot be achieved. Also, L 2 and L 3 If the alkylene group that can be selected for has more than 6 carbon atoms, it becomes difficult to ensure the thermal stability of the compound represented by the above general formula (B1). Here, from the viewpoint of improving the effect of the present invention, L 2 and L 3 The alkylene group that can be selected as the alkylene group preferably has 1 to 3 carbon atoms, more preferably 1 to 2 carbon atoms, and even more preferably 1 carbon atom.

[0025] <L 1 The number of carbon atoms and L 2 The number of carbon atoms and L 3 The total number of carbon atoms In this embodiment, L in the general formula (B1) 1 The number of carbon atoms and L 2 The number of carbon atoms and L 3 The total number of carbon atoms is preferably 3 to 16, more preferably 4 to 16, even more preferably 5 to 14, and still more preferably 6 to 12, from the viewpoint of improving thermal stability and rust prevention.

[0026] <Y 1 and Y 2 and n1 and n2> In the above general formula (B1), Y 1 and Y 2 are each independently a methylene group or an oxygen atom. In the above general formula (B1), n1 and n2 each independently represent 1 or 2. Y 1 and Y 2 is a group other than a methylene group or an oxygen atom, and n1 and n2 are 0 or an integer of 3 or more, the heterocyclic structure in the general formula (B1) becomes unstable, the stability of the compound represented by the general formula (B1) decreases, and it becomes difficult to ensure thermal stability. Examples of the heterocyclic structure in the general formula (B1) include a pyrrolidinium ring, a piperidinium ring, an oxazolidine ring, and a morpholinium ring. Here, from the viewpoint of improving the effect of the present invention, Y 1 and Y 2 are preferably methylene groups. That is, the heterocyclic structure in the general formula (B1) is preferably a pyrrolidinium ring or a piperidinium ring. 1 and Y 2 are preferably both methylene groups, and n1 and n2 are preferably both 1. That is, it is more preferable that the heterocyclic structures in the above general formula (B1) are all pyrrolidinium rings.

[0027] <m1 and m2, R 1 and R 2 > In the general formula (B1), when n1 is 1, m1 is an integer from 0 to 8. When n1 is 2, m1 is an integer from 0 to 10. In the general formula (B1), when n2 is 1, m2 is an integer from 0 to 8. When n2 is 2, m2 is an integer from 0 to 10. Also, in the general formula (B1), R 1 and R 2 each independently represents an alkyl group having 1 to 3 carbon atoms. When m1 is 2 or more, multiple R 1 may be the same or different. Also, when m2 is 2 or more, multiple R 2 may be the same or different. Here, the definitions of m1 and m2 and R 1 and R 2 in this embodiment mean that the hydrogen atoms constituting the heterocyclic structure in the general formula (B1) may be substituted with an alkyl group having 1 to 3 carbon atoms. From the viewpoint of improving the effects of the present invention, m1 and m2 are preferably 0. That is, the heterocyclic structure in the general formula (B1) is preferably unsubstituted.

[0028] <Preferred embodiments of the compound> From the viewpoint of more easily improving the effects of the present invention, the compound of this embodiment is preferably in the following embodiments. L 1 is a linear or branched alkylene group having 1 to 10 carbon atoms (the alkylene group is linear or branched, preferably linear). L 2 and L 3 each independently represents an alkylene group having 1 to 3 carbon atoms (the number of carbon atoms of the alkylene group is preferably 1 to 2, more preferably 1). Y 1 and Y 2 are methylene groups. n1 and n2 are 1. m1 and m2 are 0. Furthermore, the compound of this embodiment preferably has the following features. L 1 is an alkylene group having 2 to 8 carbon atoms (the alkylene group is linear or branched, and is preferably linear). L 2 and L 3 are each independently an alkylene group having 1 to 3 carbon atoms (the number of carbon atoms in the alkylene group is preferably 1 to 2, and more preferably 1). Y 1 and Y 2 is a methylene group. n1 and n2 are 1. m1 and m2 are 0. Furthermore, the compound of this embodiment preferably has the following aspects. L 1 is an alkylene group having 3 to 7 carbon atoms (the alkylene group is linear or branched, and is preferably linear). L 2 and L 3 are each independently an alkylene group having 1 to 3 carbon atoms (the number of carbon atoms in the alkylene group is preferably 1 to 2, and more preferably 1). Y 1 and Y 2 is a methylene group. n1 and n2 are 1. m1 and m2 are 0. Furthermore, the compound of this embodiment is more preferably in the following form. L 1 is an alkylene group having 4 to 6 carbon atoms (the alkylene group is linear or branched, and is preferably linear). L 2 and L 3 are each independently an alkylene group having 1 to 3 carbon atoms (the number of carbon atoms in the alkylene group is preferably 1 to 2, and more preferably 1). Y 1 and Y2 is a methylene group. n1 and n2 are 1. m1 and m2 are 0.

[0029] <Method for synthesizing compounds> The method for synthesizing the compound of this embodiment is not particularly limited, but examples thereof include the following synthesis methods. First, starting compounds represented by the following general formula (B1-1) and general formula (B1-2) are reacted with a starting compound represented by the following general formula (B1-3) to produce intermediate 1 represented by the following general formula (B1-4). When the starting compounds represented by the following general formula (B1-1) and general formula (B1-2) are different from each other, it is preferable to synthesize intermediate 1 by, for example, reacting one of the starting compounds represented by the following general formula (B1-1) and general formula (B1-2) with a starting compound represented by the following general formula (B1-3) in a solvent to produce a mono-substituted compound, and then reacting the mono-substituted compound with the other starting compound represented by the following general formula (B1-1) and general formula (B1-2). [ka] [ka] [ka] [ka] [In the general formula (B1-1), the general formula (B1-2), the general formula (B1-3), and the general formula (B1-4), each symbol has the same meaning as in the general formula (B1). In the above general formula (B1-3), A 1 and A 2 are each independently a halogen atom (fluorine, chlorine, bromine, iodine), preferably bromine.

[0030] Next, intermediate 1 is reacted with raw material compounds represented by the following general formula (B1-5) and the following general formula (B1-6) to produce intermediate 2 represented by the following general formula (B1-7). When the starting compounds represented by the following general formula (B1-5) and the following general formula (B1-6) are different compounds, it is preferable to synthesize intermediate 2 by reacting one of the starting compounds represented by the following general formula (B1-5) and the following general formula (B1-6) with intermediate 1 in a solvent to produce a mono-substituted product, and then reacting the mono-substituted product with the other of the starting compounds represented by the following general formula (B1-5) and the following general formula (B1-6). [ka] [ka]

[0031] [ka] [In the general formula (B1-5), the general formula (B1-6) and the general formula (B1-7), each symbol has the same meaning as in the general formula (B1). In the above general formula (B1-5), the above general formula (B1-6), and the above general formula (B1-7), A 3 and A 4 are each independently a halogen atom (fluorine, chlorine, bromine, iodine), preferably bromine. 11 and R 12 are each independently an alkyl group having 1 to 3 carbon atoms.]

[0032] Next, intermediate 2 is dissolved in various solvents such as acetonitrile, and then brought into contact with an ion exchange resin (anion exchange resin) to carry out hydrolysis and ion exchange. The solvent is then removed to obtain the compound of this embodiment.

[0033] In each reaction step, a solvent or the like may be used as appropriate. Intermediate 1, Intermediate 2, and the final product may be washed with a solvent or the like as appropriate.

[0034] <Uses of the compound> The compound of this embodiment has excellent thermal stability. Moreover, it can also exhibit excellent rust prevention properties, thereby improving the rust prevention properties of lubricant compositions based on ionic liquids. Furthermore, the compound of this embodiment does not contain any metal components. Therefore, the compound of this embodiment is suitable for use as a rust inhibitor.In addition, the compound of this embodiment is suitable for use as a rust inhibitor for ionic liquids, which is mixed with the compound and used in ionic liquids.Furthermore, the compound of this embodiment is suitable for use as a rust inhibitor for lubricant compositions used in semiconductor manufacturing equipment. Therefore, according to this embodiment, the following aspects are provided. (1) The compound of the present embodiment is used as a rust inhibitor. (2) The compound of the present embodiment is used as a rust inhibitor for ionic liquids. (3) The compound of the present embodiment is used as a rust inhibitor for a lubricant composition used in semiconductor manufacturing equipment. Furthermore, the compound of this embodiment provides the following methods of use. (4) A method of using the compound of the present embodiment as a rust inhibitor. (5) A method of using the compound of the present embodiment, which comprises blending the compound with an ionic liquid and using the resulting mixture as a rust inhibitor. (6) A method of using the compound of this embodiment, which comprises blending the compound of this embodiment into a lubricant composition used in semiconductor manufacturing equipment and using the compound as a rust inhibitor. In this embodiment, the term "ionic liquid" refers to an ionic liquid used as a base material for a lubricant composition, and is a concept used to distinguish it from the compound of this embodiment.

[0035] <Physical properties of compounds> The compound of this embodiment preferably has the following physical properties.

[0036] (Thermal decomposition start temperature) The compound of this embodiment has a thermal decomposition initiation temperature of preferably 200°C or higher, more preferably 210°C or higher, and even more preferably 220°C or higher. The thermal decomposition starting temperature means a value measured by the method described in the examples below.

[0037] (Rust prevention properties of compounds) When the compound of this embodiment is evaluated by the method described in the examples below, it is preferable that no reddish-brown or black discoloration (rust) is observed on the surface.

[0038] [Rust inhibitor] The compound represented by the above general formula (B1) has excellent rust prevention properties. Therefore, according to this embodiment, there is provided a rust inhibitor containing one or more compounds selected from the compounds represented by the above general formula (B1). The rust inhibitor may consist of only one or more compounds selected from the compounds represented by the general formula (B1) above, but may or may not contain other components in addition to the compounds. The content of one or more compounds selected from the compounds represented by the general formula (B1) in the rust inhibitor is, based on the total amount of the rust inhibitor, 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, and even more preferably 95% by mass to 100% by mass. The other components include by-products generated in the synthesis process of the compound of this embodiment, unreacted raw materials remaining in the synthesis process of the compound, diluents, and the like. The rust inhibitor is preferably used together with an ionic liquid.

[0039] [Lubricant composition] The lubricant composition of this embodiment contains an ionic liquid and a compound represented by the above general formula (B1).

[0040] In the following description, the "ionic liquid" and the "compound represented by the above general formula (B1)" will also be referred to as "component (A)" and "component (B)", respectively.

[0041] In the lubricant composition of this embodiment, the total content of component (A) and component (B) is preferably 70 mass % or more, more preferably 80 mass % or more, even more preferably 90 mass % or more, and still more preferably 95 mass % or more, based on the total amount of the lubricant composition. In the lubricant composition of this embodiment, the upper limit of the total content of components (A) and (B) may be 100% by mass. However, when the lubricant composition contains components other than components (A) and (B), the upper limit of the total content of components (A) and (B) may be adjusted in relation to the other components, and may be, for example, less than 100% by mass, 99% by mass or less, or 98% by mass or less.

[0042] In the lubricant composition of this embodiment, the content of the compound represented by general formula (B1) is preferably 0.01% by mass to 10% by mass, more preferably 0.1% by mass to 10% by mass, even more preferably 0.1% by mass to 5.0% by mass, still more preferably 1.0% by mass to 3.0% by mass, and even more preferably 1.5% by mass to 2.5% by mass, based on the total amount of the lubricant composition, from the viewpoint of the solubility of the compound in the ionic liquid and the viewpoint of improving rust prevention properties. The compound represented by the general formula (B1) may be used alone or in combination of two or more. When two or more compounds are used, the preferred total content is the same as the content described above.

[0043] Each component contained in the lubricant composition of this embodiment will be described below.

[0044] <Ionic liquid> The lubricant composition of the present embodiment contains an ionic liquid. The ionic liquid is a liquid compound composed of cations and anions, and various compounds that do not contain metals can be used.

[0045] Here, the anion of the ionic liquid preferably contains bis(trifluoromethanesulfonyl)amide.

[0046] The cation of the ionic liquid preferably contains a cation represented by the following general formula (A1). [ka] [In the general formula (A1), each symbol represents the following.] n3 is 1 or 2. X represents a methylene group or an oxygen atom. R A11 and R A12 each independently represents 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.

[0047] R in the above general formula (A1) A11 and R A12 The number of carbon atoms in the alkyl group is preferably 1 to 6, and more preferably 1 to 4, from the viewpoint of reducing the viscosity of the ionic liquid and improving its thermal stability. R A11 A methyl group is preferred as R A12 As the alkyl group, an n-butyl group and a methoxyethyl group are preferred.

[0048] 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-methylpiperidinium, 1-hexyl-1-methylpiperidinium, 1-heptyl-1-methylpiperidinium, 1-octyl-1-methylpiperidinium, 1-nonyl-1-methylpiperidinium, 1-decyl-1-methylpiperidinium, 1-undecyl-1 -methylpiperidinium, 1-dodecyl-1-methylpiperidinium, 1-methoxymethyl-1-methylpiperidinium, 1-(2-methoxyethyl)-1-methylpiperidinium, 1-(2-methoxy-2-oxoethyl)-1-methylpiperidinium, 1-cyanomethyl-1-methylpiperidinium, 1-trimethylsilylmethyl-1-methylpiperidinium, 1-butyl-1-methylmorpholinium, 1-pentyl-1-methylmorpholinium, 1-hexyl-1-methylmorpholinium, 1-heptyl-1-methylmorpholinium morpholinium, 1-octyl-1-methylmorpholinium, 1-nonyl-1-methylmorpholinium, 1-decyl-1-methylmorpholinium, 1-undecyl-1-methylmorpholinium, 1-dodecyl-1-methylmorpholinium, 1-(2-methoxyethyl)-1-methylmorpholinium, 1-methoxymethyl-1-methylmorpholinium, 1-(2-methoxy-2-oxoethyl)-1-methylmorpholinium, 1-cyanomethyl-1-methylmorpholinium, 1-trimethylsilylmethyl-1-methylmorpholinium, and the like. Among these, from the viewpoint of reducing the viscosity and improving the thermal stability of the ionic liquid, preferred are 1-butyl-1-methylpyrrolidinium, 1-pentyl-1-methylpyrrolidinium, 1-hexyl-1-methylpyrrolidinium, 1-(2-methoxyethyl)-1-methylpyrrolidinium, 1-butyl-1-methylpiperidinium, 1-(2-methoxyethyl)-1-methylpiperidinium, and 1-(2-methoxyethyl)-1-methylmorpholinium, more preferred are 1-butyl-1-methylpyrrolidinium, 1-(2-methoxyethyl)-1-methylpyrrolidinium, and 1-(2-methoxyethyl)-1-methylpiperidinium, and even more preferred are 1-butyl-1-methylpyrrolidinium and 1-(2-methoxyethyl)-1-methylpyrrolidinium.

[0049] Here, 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).

[0050] [ka] [In the general formula (A2), each symbol represents the following.] n4 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.]

[0051] [ka] [In the general formula (A3), n5 is 1 or 2, X is a methylene group or oxygen, and R A31 represents an alkylene group having 1 to 5 carbon atoms, and R A32 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.]

[0052] In the general formula (A2), R A21 The number of carbon atoms in R is preferably 2 to 8, and more preferably 3 to 6.A21 When the carbon number of R is 2 or more, the side chain can move freely and the symmetry is low, which suppresses crystallization and improves the function as an ionic liquid. A21 When the number of carbon atoms is 12 or less, the side chain does not become too large and the ionic character of the compound as a whole is high, so that oxidative degradation is easily suppressed.

[0053] In the general formula (A3), R A31 The number of carbon atoms in R is preferably 1 to 3, more preferably 1 to 2. A32 The number of carbon atoms in R is preferably 1 to 2. A31 When the carbon number of R is 1 or more, the side chain can move freely and the symmetry is low, which suppresses crystallization and improves the function as an ionic liquid. A31 or R A32 When the number of carbon atoms is 3 or less, the side chain does not become too large and the ionic character of the compound as a whole is high, so that oxidative degradation is easily suppressed.

[0054] 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. As the ionic liquid, one or more types selected from the compounds represented by the general formula (A2) above may be used, or one or more types selected from the compounds represented by the general formula (A3) above may be used, or one or more types selected from the compounds represented by the general formula (A2) above may be used in combination with one or more types selected from the compounds represented by the general formula (A3) above.

[0055] (Physical properties of ionic liquids) The kinematic viscosity of the ionic liquid at 40°C is preferably 2.0 mm from the viewpoint of low evaporation and suppressing power loss due to viscous resistance. 2 / s~100.0mm 2 / s, more preferably 10.0 mm 2 / s~70.0mm 2 / s, more preferably 20.0 mm 2 / s~40.0mm 2 / s. The kinematic viscosity of the ionic liquid at 100°C is preferably 1.0 mm from the viewpoint of low volatility and suppressing power loss due to viscous resistance. 2 / s~20.0mm 2 / s, more preferably 2.0 mm 2 / s~10.0mm 2 / s, more preferably 3.0 mm 2 / s~7.0mm 2 / s. The viscosity index of the ionic liquid is preferably 100 or more, more preferably 120 or more, and even more preferably 140 or more, from the viewpoint of minimizing viscosity changes even when used in a space environment where the temperature range changes greatly between low and high temperatures. The 40°C kinematic viscosity, the 100°C kinematic viscosity, and the viscosity index can be measured or calculated in accordance with JIS K 2283:2000. Furthermore, when the ionic liquid is a mixture of two or more types of ionic liquids, the kinematic viscosity and viscosity index of the mixture preferably fall within the above ranges.

[0056] The pour point of the ionic liquid is preferably 0°C or lower, more preferably -10°C or lower, and even more preferably -20°C or lower, from the viewpoint of suppressing an increase in viscous resistance at low temperatures. The pour point of the ionic liquid can be measured in accordance with JIS K 2269:1987.

[0057] From the viewpoint of rust prevention, the acid value of the ionic liquid is preferably 1 mgKOH / g or less, more preferably 0.5 mgKOH / g or less, and even more preferably 0.3 mgKOH / g or less.

[0058] From the viewpoint of low volatility, the flash point of the ionic liquid is preferably 200°C or higher, more preferably 250°C or higher, and even more preferably 300°C or higher.

[0059] The ion concentration of the ionic liquid measured at 15°C is preferably 1.0 mol / dm 3 More preferably, 1.5 mol / dm 3 More preferably, 2.0 mol / dm 3 That's all. Here, the ion concentration is the density (g / cm) measured at 15°C in the ionic liquid. 3 ) / molecular weight Mw (g / mol)] × 1000. When the ion concentration of the ionic liquid is 1.0 mol / dm 3 If the content is above this, low volatility and thermal stability can be further improved.

[0060] The molecular weight of the ionic liquid is preferably 410 or more and 570 or less, more preferably 410 or more and 470 or less, and even more preferably 420 or more and 440 or less. When the molecular weight of the ionic liquid is within this range, the charge density and the alkyl chain length of the cation fall within appropriate ranges, and the viscosity of the ionic liquid can be reduced and the thermal stability can be improved.

[0061] In the lubricant composition of this embodiment, the content of the ionic liquid is not particularly limited, but from the viewpoint of improving the effects of the present invention, it is preferably 50 mass % or more, more preferably 60 mass % or more, and even more preferably 70 mass % or more based on the total amount (100 mass %) of the lubricant composition. The upper limit of the ionic liquid content is set appropriately depending on the amount of components other than the ionic liquid added, and is preferably 99.5 mass % or less, more preferably 99.0 mass % or less, and even more preferably 98.5 mass % or less. The upper and lower limits of these numerical ranges can be combined arbitrarily. Specifically, the content is preferably 50% by mass to 99.5% by mass, more preferably 60% by mass to 99.0% by mass, and even more preferably 70% by mass to 98.5% by mass.

[0062] The lubricant composition of this embodiment may contain a base component other than the ionic liquid (component (A)) described above (for example, a base component that does not fall under the category of an ionic liquid, such as ethyl acetate). From the viewpoint of improving the effects of the present invention, the content of the ionic liquid (component (A)) described above is preferably 50 mass % or more, more preferably 70 mass % or more, even more preferably 90 mass % or more, and still more preferably 100 mass % based on the total amount of the base.

[0063] The ratio (B / A) of the content of the compound represented by the general formula (B1) (component (B)) to the content of the ionic liquid (component (A)) 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 0.005 or more and 0.08 or less, by mass. When (B / A) is 0.0005 or more, sufficient rust prevention properties are likely to be achieved. When (B / A) is 0.15 or less, the solubility of the compound represented by the general formula (B1) in the ionic liquid is likely to be sufficient.

[0064] <Other ingredients> The lubricant composition of the present embodiment may contain other components in addition to the above components, as needed, within the range that does not impair the effects of the present invention. Examples of the other components include a viscosity index improver and a thickener. These may be used alone or in combination of two or more.

[0065] (viscosity index improver) By including a viscosity index improver in the lubricant composition of this embodiment, the viscosity index of the lubricant composition can be improved, thereby minimizing viscosity changes even when used in a space environment where the temperature range varies greatly between low and high temperatures.

[0066] Examples of viscosity index improvers include polymers such as non-dispersant poly(meth)acrylate and dispersant poly(meth)acrylate, which are soluble in the ionic liquid. These may be used alone or in combination of two or more. The mass average molecular weight (Mw) of these viscosity index improvers is usually 5,000 to 1,000,000, preferably 6,000 to 100,000, and more preferably 10,000 to 50,000, but is set appropriately depending on the type of polymer. In this specification, the weight average molecular weight (Mw) of each component is a value calculated as a standard polystyrene as measured by gel permeation chromatography (GPC). The content of the viscosity index improver, calculated as the resin content, can be adjusted as appropriate within a range that does not impair the effects of the present invention, but is typically 0.001 to 15 mass%, preferably 0.005 to 10 mass%, more preferably 0.01 to 7 mass%, and even more preferably 0.03 to 5 mass%, based on the total amount of the lubricant composition.

[0067] (thickener) The lubricant composition of the present embodiment may be in the form of a grease composition by containing a thickener. Examples of thickeners include urea compounds such as diurea compounds and polyurea compounds, fluorine-based resins such as tetrafluoroethylene (PTFE) resin, tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer (PFA) resin, and tetrafluoroethylene-hexafluoropropylene copolymer (FEP) resin, and non-metallic thickeners such as non-fluorine-based resins such as polyester and polyamide. These may be used alone or in combination of two or more. When the lubricant composition of the present embodiment contains a thickener (in other words, when the lubricant composition of the present embodiment is a grease composition), the content of the thickener is preferably 5% by mass to 50% by mass, more preferably 5% by mass to 40% by mass, and even more preferably 5% by mass to 35% by mass, based on the total amount of the lubricant composition. When the lubricant composition of this embodiment contains a thickener (in other words, when the lubricant composition of this embodiment is a grease composition), the content of the ionic liquid is preferably 50% by mass or more, more preferably 60% by mass or more, and even more preferably 70% by mass or more, based on the total amount of the lubricant composition, and is preferably 95% by mass or less, more preferably 90% by mass or less, and even more preferably 85% by mass or less. The upper and lower limits of these numerical ranges can be arbitrarily combined. Specifically, the content is preferably 50% by mass to 95% by mass, more preferably 60% by mass to 90% by mass, and even more preferably 70% by mass to 85% by mass.

[0068] In this specification, the additives as the other components may be diluted and dissolved in a part of the ionic liquid and blended with other components in the form of a solution, taking into consideration ease of handling, solubility in the ionic liquid, etc. In such a case, in this specification, the content of the additives as the other components refers to the content calculated as the active ingredient (resin content) excluding the diluent.

[0069] [Physical properties of lubricant composition] <40°C kinematic viscosity, 100°C kinematic viscosity, and viscosity index> The kinematic viscosity at 40°C of the lubricant composition of this embodiment is preferably 2.0 mmHg from the viewpoint of low volatility and suppressing power loss due to viscous resistance. 2 / s~200.0mm 2 / s, more preferably 10.0 mm 2 / s~150.0mm 2 / s, more preferably 20.0 mm 2 / s~100.0mm 2 / s. The kinematic viscosity at 100°C of the lubricant composition of this embodiment is preferably 1.0 mmHg from the viewpoint of low volatility and suppression of power loss due to viscous resistance. 2 / s~40.0mm 2 / s, more preferably 2.0 mm 2 / s~30.0mm 2 / s, more preferably 3.0 mm 2 / s~20.0mm2 / s. The viscosity index of the lubricant composition of this embodiment is preferably 100 or more, more preferably 120 or more, and even more preferably 140 or more, from the viewpoint of minimizing viscosity changes due to temperature changes in the usage environment. The 40°C kinematic viscosity, the 100°C kinematic viscosity, and the viscosity index of the lubricant composition are values ​​measured or calculated in accordance with JIS K 2283:2000.

[0070] <Metal content> The lubricant composition of this embodiment preferably contains substantially no metal components. Specifically, the lubricant composition of this embodiment preferably has a metal content (metal element) of less than 0.1 mass %, more preferably less than 0.01 mass %, based on the total amount of the lubricant composition, and even more preferably contains no metal content (metal element).

[0071] <Rust prevention> When the lubricant composition of this embodiment is evaluated by the method described in the examples below, it is preferred that no reddish-brown or black discoloration (rust) is observed on the surface.

[0072] [Method of manufacturing lubricant composition] The method for producing the lubricant composition of this embodiment is not particularly limited, but for example, the lubricant composition is produced by a production method including a step of mixing an ionic liquid with a compound represented by the following general formula (B1). [ka] [In the general formula (B1), each symbol represents the following.] L 1 represents a divalent saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms. L 2 and L 3 each independently represents an alkylene group having 1 to 6 carbon atoms. Y 1 and Y 2 each independently represents a methylene group or an oxygen atom. n1 and n2 each independently represent 1 or 2. When n1 is 1, m1 is an integer of 0 to 8. When n1 is 2, m1 is an integer of 0 to 10. When n2 is 1, m2 is an integer of 0 to 8. When n2 is 2, m2 is an integer of 0 to 10. R 1 and R 2 each independently represents an alkyl group having 1 to 3 carbon atoms. The method for mixing the above components is not particularly limited, but examples include a method in which the compound represented by the general formula (B1) is blended with the ionic liquid and then mixed. The manufacturing method of this embodiment may further include the step of adding the other components described above.

[0073] [Uses of lubricant composition] The lubricant composition of the present embodiment has excellent thermal stability and rust prevention properties, and does not contain any metal components. Therefore, the lubricant composition of this embodiment can be suitably used in semiconductor manufacturing equipment. Specifically, the lubricant composition of this embodiment can be suitably used to lubricate moving parts in a high-vacuum, high-temperature environment, such as a vacuum chamber in a semiconductor manufacturing equipment. Examples of such moving parts include, but are not limited to, speed reducers and speed increasers. Examples of semiconductor manufacturing equipment include equipment that performs physical vapor deposition (PVD) and equipment that performs chemical vapor deposition (CVD). Examples of physical vapor deposition include vacuum deposition, sputtering, ion plating, and ion bombardment using various ion guns. Examples of vacuum vapor deposition include general resistance heating vapor deposition, electron beam vapor deposition, ion-assisted electron beam vapor deposition, and arc vapor deposition. These physical vapor deposition methods may be used in appropriate combination. Examples of chemical vapor deposition include thermal CVD, plasma CVD, photo CVD, epitaxial CVD, and atomic layer CVD. These chemical vapor deposition methods may be used in combination as appropriate, or may be used in combination with physical vapor deposition as appropriate.

[0074] [One aspect of the present invention provided] In one aspect of the present invention, the following [1] to

[11] are provided. [1] A compound represented by the following general formula (B1): [ka] [In the general formula (B1), each symbol represents the following.] L 1 represents a divalent saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms. L 2 and L 3 each independently represents an alkylene group having 1 to 6 carbon atoms. Y 1 and Y 2 each independently represents a methylene group or an oxygen atom. n1 and n2 each independently represent 1 or 2. When n1 is 1, m1 is an integer of 0 to 8. When n1 is 2, m1 is an integer of 0 to 10. When n2 is 1, m2 is an integer of 0 to 8. When n2 is 2, m2 is an integer of 0 to 10. R 1 and R 2 each independently represents an alkyl group having 1 to 3 carbon atoms. [2] L 1 The number of carbon atoms and L 2 The number of carbon atoms and L 3 and the total number of carbon atoms is 3 to 16. [3] The compound according to [1] or [2] above, which is used as a rust inhibitor. [4] A method of using the compound according to [1] or [2] above as a rust inhibitor. [5] A rust inhibitor containing the compound according to [1] or [2] above. [6] The rust inhibitor according to [5] above, which is used together with an ionic liquid. [7] A lubricant composition containing an ionic liquid and the compound according to [1] or [2] above. [8] The lubricant composition according to the above [7], wherein the ionic liquid contains a cation represented by the following general formula (A1): [ka] [In the general formula (A1), each symbol represents the following.] n3 is 1 or 2. X represents a methylene group or an oxygen atom. R A11 and R A12 each independently represents 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. [9] The lubricant composition according to [7] or [8] above, wherein the ionic liquid comprises at least one compound selected from the group consisting of a compound represented by the following general formula (A2) and a compound represented by the following general formula (A3): [ka] [In the general formula (A2), each symbol represents the following.] n4 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.] [ka] [In the general formula (A3), each symbol represents the following.] n5 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.]

[10] The lubricant composition according to any one of the above [7] to [9], which is used in semiconductor manufacturing equipment.

[11] A method for producing a lubricant composition, comprising the step of mixing an ionic liquid with the compound according to [1] or [2] above. [Example]

[0075] The present invention will be specifically described with reference to the following examples, although the present invention is not limited to the following examples.

[0076] [Production Examples 1-2, Comparative Production Examples 1-3, Comparative Compound 4] Various compounds were synthesized by the methods shown in Production Examples 1-2 and Comparative Production Examples 1-3. Furthermore, comparative compound 4 was prepared.

[0077] <Production Example 1: Synthesis of Compound 1> A four-neck flask purged with nitrogen was equipped with a stirrer, thermometer, condenser, and dropping funnel, and 11 g (150 mmol) of pyrrolidine was added. While stirring, 4.9 g (20 mmol) of 1,6-dibromohexane was added dropwise. The reaction was terminated by heating at an internal temperature of 60°C for 2 hours using an oil bath, and then the excess pyrrolidine was removed using an evaporator. 30 mL of ethyl acetate was added to the resulting reaction product, which was then washed three times with 30 mL of ion-exchanged water, yielding 4.0 g (18 mmol) of 1,1'-hexamethylenedipyrrolidine as a clear liquid. The obtained 1,1'-hexamethylenedipyrrolidine was added to a four-necked flask purged with nitrogen, and a stirrer, thermometer, condenser, and dropping funnel were attached. 20 mL of tetrahydrofuran was added as a solvent. 6.4 g (37 mmol) of ethyl bromoacetate was added while stirring, and the mixture was heated in an oil bath at an internal temperature of 60°C for 2 hours to terminate the reaction. The obtained hexamethylene N,N'-ethyl diethyl pyrrolidinium bromide was washed with a mixture of acetonitrile and ethyl acetate to obtain a white solid. The obtained hexamethylene N,N'-ethyl diethyl pyrrolidinium bromide was placed in a recovery flask equipped with a stirrer and dissolved in 20 mL of acetonitrile. After complete dissolution, the mixture was washed with an ion-exchange resin (Organo Corporation, Amberlite (registered trademark) 400 OH). - After stirring for 2 hours, the ion exchange resin was removed by filtration, and the solvent was removed by an evaporator to obtain 5.1 g (15 mmol) of Compound 1.

[0078] The structural formula of Compound 1 is shown below. [ka] Compound 1 is a compound in which the symbols in the above general formula (B1) represent the following. L 1 represents a linear alkylene group having 6 carbon atoms (n-hexylene group). L 2 and L 3 represents an alkylene group (methylene group) having one carbon atom. Y 1 and Y 2 represents a methylene group. n1 and n2 are 1. m1 and m2 are 0. In addition, L 1 The number of carbon atoms and L 2 The number of carbon atoms and L 3 The total number of carbon atoms is 8.

[0079] <Production Example 2: Synthesis of Compound 2> The synthesis was carried out in the same manner as in Production Example 1, except that 4.3 g (20 mmol) of 1,4-dibromobutane was used instead of 1,6-dibromohexane. 4.7 g (15 mmol) of the final compound 2 was obtained.

[0080] The structural formula of Compound 2 is shown below. [ka] Compound 2 is a compound in which the symbols in the above general formula (B1) represent the following. L 1 represents a linear alkylene group having 4 carbon atoms (n-butylene group). L 2 and L 3 represents an alkylene group (methylene group) having one carbon atom. Y 1 and Y 2 represents a methylene group. n1 and n2 are 1. m1 and m2 are 0. In addition, L 1 The number of carbon atoms and L 2 The number of carbon atoms and L 3 The total number of carbon atoms is 6.

[0081] <Comparative Production Example 1: Synthesis of Comparative Compound 1> 20 g of a 10 wt% aqueous solution of tetramethylammonium hydroxide (tetramethylammonium hydroxide: 2.0 g, 22 mmol) and 4.4 g (22 mmol) of sebacic acid were added to a recovery flask and stirred at room temperature for 1 hour. After removing the water, the resulting white solid was collected, and 5.4 g (2.1 mmol) of comparative compound 2 was obtained as a white solid.

[0082] The structural formula of comparative compound 1 is shown below. [ka]

[0083] <Comparative Production Example 2: Synthesis of Comparative Compound 2> 3.4 g (20 mmol) of N,N,N',N'-tetramethyl-1,6-diaminohexane was added to a four-neck flask purged with nitrogen, and a stirrer, thermometer, condenser, and dropping funnel were attached. 20 mL of tetrahydrofuran was added as a solvent. 8.6 g (44 mmol) of ethyl bromoacetate was added while stirring, and the mixture was heated in an oil bath at an internal temperature of 60°C for 2 hours to terminate the reaction. The resulting hexamethylene-N,N,N',N'-tetramethylene-N,N'-ethyl diaminopyrrolidinium bromide was washed with a mixture of acetonitrile and ethyl acetate to obtain a white solid. The resulting hexamethylene-N,N'-ethyl diaminopyrrolidinium bromide was placed in a recovery flask equipped with a stirrer and dissolved in 20 mL of acetonitrile. After complete dissolution, the mixture was washed with an ion-exchange resin (Organo Corporation, Amberlite (registered trademark) 400 OH). - After stirring for 2 hours, the ion exchange resin was removed by filtration, and the solvent was removed by an evaporator to obtain 4.4 g (15 mmol) of comparative compound 1.

[0084] The structural formula of comparative compound 2 is shown below. [ka]

[0085] <Comparative Production Example 3: Synthesis of Comparative Compound 3> 10 g of a 25 wt % aqueous solution of hexamethonium (hexamethonium: 2.5 g, 11 mmol) and 2.1 g (11 mmol) of sebacic acid were stirred in a recovery flask at room temperature for 1 hour. After removing the water, the resulting white solid was collected, and 3.8 g (9.5 mmol) of comparative compound 3 was obtained.

[0086] The structural formula of comparative compound 3 is shown below. [ka]

[0087] <Preparation of Comparative Compound 4> A reagent sold by Wako Pure Chemical Industries was used as comparative compound 4.

[0088] The structural formula of comparative compound 4 is shown below. [ka]

[0089] [evaluation] Compounds 1 and 2 and comparative compounds 1 to 4 were evaluated as described below.

[0090] <Evaluation 1: Evaluation of thermal decomposition onset temperature (evaluation of single compound)> The thermal decomposition onset temperatures of compounds 1 to 2 and comparative compounds 1 to 4 were measured at a heating rate of 10°C / min using a simultaneous thermogravimetry and differential thermal analyzer (product name: TG / DTA6200, manufactured by SII Nano Technology Co., Ltd. (now Hitachi High-Tech Science Corporation)). The results are shown in Table 1.

[0091] [Table 1]

[0092] The results shown in Table 1 show that both Compounds 1 and 2 have thermal decomposition starting temperatures of 200° C. or higher, and are excellent in thermal stability. On the other hand, the comparative compounds 1 to 3 all have thermal decomposition starting temperatures of less than 200° C., which indicates that they have poor thermal stability. Although Comparative Compound 4 has a thermal decomposition starting temperature of 200°C or higher and is excellent in thermal stability, it cannot be used for semiconductor manufacturing equipment applications because it contains sodium, an alkali metal.

[0093] [Examples 1 to 2, Comparative Examples 1 to 4] The ionic liquid used was N-butyl-N-methylpyrrolidinium-bis(trifluoromethane)sulfonylimide. Lubricant compositions were prepared according to the formulations shown in Table 2 and subjected to Evaluation 2 below. In addition, N-butyl-N-methylpyrrolidinium-bis(trifluoromethane)sulfonylimide is a compound represented by the general formula (A2) above, where n4=1, X is a methylene group, and R A21 is a butyl group.

[0094] <Evaluation 2: Evaluation of rust prevention> A SUS440C plate cut into a strip shape was immersed in a solution prepared by mixing 10 g of distilled water and 10 g of each lubricant composition. The temperature of the solution was set to 60°C, and the SUS440C plate was immersed for 7 days. The appearance of the SUS440C plate was then observed. The rust prevention properties were evaluated 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.

[0095] [Table 2]

[0096] From Table 2, we can see the following: The results shown in Examples 1 and 2 show that the lubricant compositions containing Compounds 1 and 2 have excellent rust prevention properties. As mentioned above, Compounds 1 and 2 have high thermal decomposition starting temperatures and are excellent in thermal stability. Furthermore, Compounds 1 and 2 do not contain metal components. In contrast, the results shown in Comparative Examples 1 to 4 indicate that although the lubricating oil compositions containing Comparative Compounds 1 to 4 all have excellent rust prevention properties, as previously mentioned, Comparative Compounds 1 to 3 have low thermal decomposition onset temperatures and poor thermal stability. Furthermore, Comparative Compound 4 has a high thermal decomposition onset temperature and excellent thermal stability, but because it contains metal components, it cannot be used in semiconductor manufacturing equipment applications.

Claims

1. A compound represented by the following general formula (B1): 【Chemistry 1】 [In the general formula (B1), each symbol represents the following.] L １ represents a divalent saturated aliphatic hydrocarbon group having 1 to 10 carbon atoms. L ２ and L ３ each independently represents an alkylene group having 1 to 6 carbon atoms. Y １ and Y ２ each independently represents a methylene group or an oxygen atom. n1 and n2 each independently represent 1 or 2. When n1 is 1, m1 is an integer of 0 to 8. When n1 is 2, m1 is an integer of 0 to 10. When n2 is 1, m2 is an integer from 0 to 8. When n2 is 2, m2 is an integer from 0 to 10. R １ and R ２ each independently represents an alkyl group having 1 to 3 carbon atoms.

2. L １ The number of carbon atoms and L ２ The number of carbon atoms and L ３ and the total number of carbon atoms is 3 to 16.

3. 3. The compound according to claim 1 or 2, which is used as a rust inhibitor.

4. 3. A method of using the compound according to claim 1 or 2 as a rust inhibitor.

5. A rust inhibitor comprising the compound according to claim 1 or 2.

6. The rust inhibitor according to claim 5 , which is used together with an ionic liquid.

7. A lubricant composition comprising an ionic liquid and the compound according to claim 1 or 2.

8. The lubricant composition according to claim 7, wherein the ionic liquid contains a cation represented by the following general formula (A1): 【Chemistry 2】 [In the general formula (A1), each symbol represents the following.] n3 is 1 or 2. X represents a methylene group or an oxygen atom. R Ａ１１ and R Ａ１２ each independently represents 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.

9. The lubricant composition according to claim 7, wherein the ionic liquid comprises at least one selected from the group consisting of a compound represented by the following general formula (A2) and a compound represented by the following general formula (A3): 【Transformation 3】 [In the general formula (A2), each symbol represents the following.] n4 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. 【Chemistry 4】 [In the general formula (A3), each symbol represents the following.] n5 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.

10. The lubricant composition according to claim 7, which is used in semiconductor manufacturing equipment.

11. A method for producing a lubricant composition, comprising the step of mixing an ionic liquid with the compound according to claim 1 or 2.

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