Novel borate compound-containing composition

Abstract

The purpose of the present invention is to provide a composition containing a borate compound which is useful as a cocatalyst for the solution polymerization of olefin or diene and is soluble in a hydrocarbon solvent.　According to the present invention, provided are a composition which is useful as a cocatalyst for the solution polymerization of olefin or diene and contains a compound represented by formula (1) and a compound represented by formula (4) (the definitions of the symbols in the formulae are as described in the specification); and a method for producing the same.

Description

[Technical field]

[0001] The present invention relates to a borate compound-containing composition useful as a cocatalyst in the solution polymerization system of olefins or dienes, and a method for producing the same. [Background technology]

[0002] There have been many reports of the use of non-metallocene metal complex catalysts such as metallocene compounds, diimine complexes, and phenoxy complexes as polymerization catalysts for olefins and dienes. In many of the catalyst systems using these metal complex catalysts, methylaluminoxane and tetrakis(pentafluorophenyl)borate compounds are used as cocatalysts to stabilize the active species. Tetrakis(pentafluorophenyl)borate compounds are widely used as cocatalysts in solution polymerization systems because they have better thermal stability than methylaluminoxane and can be used in a smaller stoichiometric ratio to the metal complex than methylaluminoxane.

[0003] In addition, non-polar hydrocarbon solvents are generally used as solvents for the polymerization of olefins and dienes using metal complex catalysts. In particular, from the viewpoint of odor and toxicity, there has been a shift from aromatic hydrocarbon solvents such as toluene to aliphatic hydrocarbon solvents such as hexane.

[0004] However, it is known that ordinary tetrakis(pentafluorophenyl)borate compounds are poorly soluble in aromatic hydrocarbon solvents such as toluene, and even if they dissolve, they separate into two liquid-liquid phases: a concentrated phase in which the borate compound is dissolved and a dilute phase in which the borate compound is not dissolved (Patent Document 1).

[0005] In addition, because normal tetrakis(pentafluorophenyl)borate compounds are poorly soluble in aliphatic hydrocarbon solvents such as hexane and heptane, tetrakis(pentafluorophenyl)borate compounds that are soluble in aliphatic hydrocarbon solvents are desired and have been proposed (Patent Document 2). Di(octadecyl)methylammonium tetrakis(pentafluorophenyl)borate and bis(hydrogenated tallow alkyl)methylammonium tetrakis(pentafluorophenyl)borate described in Patent Document 2 are useful as compounds that are easily soluble in hydrocarbon solvents.

[0006] However, in the manufacturing method described in Patent Document 2, lithium tetrakis(pentafluorophenyl)borate is prepared by reacting with a hydrochloride of a dialkylmethylamine prepared separately, and in this method, the raw material lithium tetrakis(pentafluorophenyl)borate or hydrochloride of a long-chain aliphatic amine, which is poorly soluble in water, remains in the product, and there is a concern that these act as catalyst poisons and do not show sufficient activity when used as a polymerization cocatalyst. In fact, in Example 2 of Patent Document 2, diethyl ether remains in the product, and it is presumed that a diethyl ether complex of lithium tetrakis(pentafluorophenyl)borate, which is poorly soluble in water, remains.

[0007] Patent Document 3 discloses a method for producing an ammonium tetrakis(pentafluorophenyl)borate derivative, which comprises mixing an alkali metal salt of tetrakis(pentafluorophenyl)borate with an amine and then treating the mixture with a protonic acid. However, even with this method, there is concern that an ether complex of an alkali metal salt of tetrakis(pentafluorophenyl)borate or a protonic acid salt of a long-chain aliphatic amine remains in the product and acts as a catalyst poison.

[0008] Patent Document 4 discloses a composition containing a trialkylammonium tetrakis(pentafluorophenyl)borate compound and an amine compound, and a method for producing the composition, and discloses that the composition is soluble in a hydrocarbon solvent. However, trialkylamine, which is an amine compound described in Patent Document 4, is highly basic and nucleophilic, and therefore there is concern that it may be a catalyst poison for the polymerization reaction of olefins or dienes. [Prior art documents] [Patent documents]

[0009] [Patent Document 1] JP 2018-104335 A [Patent Document 2] Special Publication No. 2000-507157 [Patent Document 3] Special Publication No. 2007-530673 [Patent Document 4] JP 2019-59795 A Summary of the Invention [Problem to be solved by the invention]

[0010] In view of these conventional techniques, the present invention aims to provide a borate compound-containing composition which is soluble in hydrocarbon solvents, particularly aliphatic hydrocarbon solvents, and which does not act as a catalyst poison in the polymerization reaction of olefins or dienes, and an industrial process for producing the same. [Means for solving the problem]

[0011] As a result of extensive investigation, the present inventors have discovered a composition comprising a compound represented by the following formula (1) and a compound represented by the following formula (4):

[0012] [ka]

[0013] [ka]

[0014] [In the formula, R 1 , R 2 , R 3 and R 4 Each independently represents one or more fluorine atoms or one or more fluoro C 1-4 C substituted with alkyl groups 6-14 represents an aryl group, A + is a hydrogen ion (H + ), formula (2):

[0015] [ka]

[0016] (In the formula, R 5 , R 6 and R 7 each independently represents an optionally substituted C 1-30 An alkyl group or an optionally substituted C 6-14 A cation having a total of 25 or more carbon atoms represented by formula (3):

[0017] [ka]

[0018] (In the formula, Ar 1 , Ar 2 and Ar 3 are each independently one or more C 1-30 Alkyl group or C 1-30 C optionally substituted with an alkoxy group 6-14 represents an aryl group; and R and R′ are each independently an optionally substituted C 1-30 Alkyl groups, optionally substituted C 3-15 Cycloalkyl group or optionally substituted C 6-14 Represents an aryl group. However, A + But hydrogen ions (H + ), the total number of carbon atoms in R and R′ is 20 or more, and the content of the compound represented by the formula (4) is 2 moles or more relative to 1 mole of the compound represented by the formula (1), A + is a cation represented by formula (2) or a cation represented by formula (3), the total number of carbon atoms in R and R' is 8 or more.] (hereinafter also referred to as "the composition of the present invention") is soluble in hydrocarbon solvents, particularly aliphatic hydrocarbon solvents, does not generate compounds that are catalyst poisons in the polymerization reaction of olefins or dienes, and is useful as a co-catalyst, which has led to the completion of the present invention.

[0019] That is, the present invention is as follows. [1] A composition containing a compound represented by the following formula (1) and a compound represented by the following formula (4):

[0020] [ka]

[0021] [ka]

[0022] [In the formula, R 1 , R 2 , R 3 and R 4 Each independently represents one or more fluorine atoms or one or more fluoro C 1-4 C substituted with alkyl groups 6-14 represents an aryl group, A + is a hydrogen ion (H + ), formula (2):

[0023] [ka]

[0024] (In the formula, R 5 , R 6 and R 7 each independently represents an optionally substituted C 1-30 Alkyl group or optionally substituted C 6-14 A cation having a total of 25 or more carbon atoms represented by formula (3):

[0025] [ka]

[0026] (In the formula, Ar 1 , Ar 2 and Ar 3 are each independently one or more C 1-30 Alkyl group or C 1-30 C optionally substituted with an alkoxy group 6-14 represents an aryl group; and R and R′ are each independently an optionally substituted C 1-30 Alkyl groups, optionally substituted C 3-15 Cycloalkyl group or optionally substituted C 6-14 Represents an aryl group. However, A + But hydrogen ions (H + ), the total number of carbon atoms in R and R′ is 20 or more, and the content of the compound represented by the formula (4) is 2 moles or more relative to 1 mole of the compound represented by the formula (1), A + is a cation represented by formula (2) or a cation represented by formula (3), the total number of carbon atoms in R and R′ is 8 or more. [2] R and R' are each independently C 1-30 Alkyl group or optionally substituted C 6-14 is an aryl group, and The total number of carbon atoms in R and R' is A + But hydrogen ions (H + ), is 25 or more, A +is 8 or more when it is a cation represented by formula (2) or a cation represented by formula (3). [3] R 1 , R 2 , R 3 and R 4 are each independently substituted with one or more fluorine atoms or trifluoromethyl groups, and are a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 9-phenanthryl group, or a 3-phenanthryl group. [4]R 1 , R 2 , R 3 and R 4 are all pentafluorophenyl groups, 2,2',3,3',4',5,5',6,6'-nonafluoro-4-(1,1'-biphenylyl) groups, 2,3,4,5,6,7,8-heptafluoro-1-naphthyl groups, or 1,3,4,5,6,7,8-heptafluoro-2-naphthyl groups. [5]A + is a hydrogen ion. [6]A + is a cation having a total of 35 or more carbon atoms and represented by the formula (2), R 5 , R 6 and R 7 However, each independently, C 1-30 an alkyl group, or (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups and (4) HaroC 1-30 Alkyl group C, which may be substituted with a substituent selected from the group consisting of 6-14 Aryl Group The composition according to any one of the above [1] to [4], [7]A +is a cation having a total carbon number of 35 or more and represented by the formula (2), R 5 but, (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups and (4) HaroC 1-6 Alkyl group C, which may be substituted with a substituent selected from the group consisting of 6-14 is an aryl group, and R 6 and R 7 each independently represents an optionally substituted C 1-30 The composition according to any one of the above [1] to [4], wherein the group is an alkyl group. [8]A + is a cation having a total carbon number of 35 or more and represented by the formula (2), R 5 is substituted with one or more fluorine atoms 6-14 Aryl-substituted C 1-30 C substituted with one or more alkyl or fluorine atoms 1-30 is an alkyl group, and R 6 and R 7 However, each independently, (1) C optionally substituted with a halogen atom 6-14 Aryl groups, (2) Halogen atoms and (3) C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 1-30 Alkyl group The composition according to any one of the above [1] to [4], [9]A + is a cation having a total carbon number of 35 or more and represented by the formula (2), R 5 But Fluoro C 1-6 is an alkyl group, and R 6 and R 7 However, each independently, (1) C optionally substituted with a halogen atom 6-14 Aryl groups, (2) Halogen atoms and (3) C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 1-30 Alkyl group The composition according to any one of the above [1] to [4],

[10] A + is a cation having a total of 35 or more carbon atoms and represented by the formula (3), Ar 1 , Ar 2 and Ar 3 are each independently 1-30 Alkyl group or C 1-30 The composition according to any one of the above [1] to [4], wherein the phenyl group may be substituted with an alkoxy group.

[11] A + is a hydrogen ion, and R and R' are each independently (1) a halogen atom, (2) C 1-30 Alkoxy groups and (3) Haro C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 1-30 Alkyl groups; (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups, (4) HaroC 1-30 Alkyl groups and (5) Haro C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 3-15 a cycloalkyl group; or (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups, (4) HaroC 1-30 Alkyl groups and (5) Haro C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 6-14 Aryl Group The composition according to any one of the above [1] to [4],

[12] A + is a hydrogen ion, and R and R' are each independently C 1-30 The composition according to any one of the above [1] to [4], wherein the group is an alkyl group.

[13] A + is a hydrogen ion, R and R' are each independently C 14-30 is an alkyl group, and The composition according to any one of the above [1] to [4], wherein the total number of carbon atoms in R and R' is 28 or more.

[14] A + is a hydrogen ion, and The composition according to any one of the above [1] to [4], wherein R and R' are the same group.

[15] A + is a cation represented by the formula (2) or (3), and R and R′ are each independently C 1-30 The composition according to any one of the above [1] to [4] and [6] to

[10] , wherein R is an alkyl group, and the total number of carbon atoms in R and R' is 8 or more.

[16] The formula (1) (wherein A + is a cation represented by the formula (2) or (3). The content of the compound represented by the formula (4) is in the range of 0.01 to 10 mol per 1 mol of the compound represented by the formula (4).

[17] The formula (1) (wherein A + is a cation represented by the formula (2) or (3). The content of the compound represented by the formula (4) is in the range of 0.01 to 3 mol relative to 1 mol of the compound represented by the formula (4).

[18] The composition according to any one of the above [1] to

[17] , which has a solubility of 5% by weight or more at 25°C in n-hexane, isohexane, n-heptane, n-octane, cyclohexane, methylcyclohexane, or a mixed solvent thereof.

[19] The composition according to any one of the above [1] to

[18] , which is substantially free of ethers having a total carbon number of 7 or less.

[20] A co-catalyst for polymerization of at least one monomer selected from the group consisting of olefins and dienes, comprising the composition according to any one of [1] to

[19] above.

[21] A method for producing a polymer, comprising polymerizing at least one monomer selected from the group consisting of olefins and dienes by using the composition according to any one of the above [1] to

[19] as a co-catalyst.

[22] A composition containing a compound represented by the following formula (1) and a compound represented by the following formula (4):

[0027] [ka]

[0028] [ka]

[0029] [In the formula, R 1 , R 2 , R 3 and R 4 Each independently represents one or more fluorine atoms or one or more fluoro C 1-4 C substituted with alkyl groups 6-14 represents an aryl group, A + is a hydrogen ion (H + ), R and R′ are each independently an optionally substituted C 1-30 Alkyl groups, optionally substituted C 3-15 Cycloalkyl group or optionally substituted C 6-14represents an aryl group, and the total number of carbon atoms in R and R' is 20 or more; and The content of the compound represented by the formula (4) is 2 moles or more relative to 1 mole of the compound represented by the formula (1).

[0030] [ka]

[0031] [In the formula, R 1 , R 2 , R 3 and R 4 has the same meaning as above, R 8 and R 9 are each independently 1-6 represents an alkyl group, and R 8 OR 9 The total number of carbon atoms is 7 or less. The compound represented by the following formula (4):

[0032] [ka]

[0033] [In the formula, R and R′ are as defined above.] A production method comprising the step of reacting a compound represented by the formula:

[23] R 8 and R 9 and are both ethyl groups. Effect of the Invention

[0034] According to the present invention, there can be provided a composition containing a borate compound which is soluble in a hydrocarbon solvent, particularly an aliphatic hydrocarbon solvent, and is useful as a co-catalyst for the polymerization reaction of olefins or dienes, and a method for producing the same. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0035] The definitions of the terms and symbols used in this specification are explained below.

[0036] In this specification, the term "halogen atom" means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0037] In this specification, the term "alkyl (group)" refers to a straight-chain or branched-chain alkyl group having one or more carbon atoms.

[0038] In this specification, "C 1-30 The term "alkyl (group)" refers to a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, and examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, 1-ethylpropyl, hexyl, isohexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl, octadecyl, nonadecyl, eicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, and triacontyl.

[0039] In this specification, "C 4-30 The term "alkyl (group)" refers to a linear or branched alkyl group having 4 to 30 carbon atoms, and examples thereof include butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, 1-ethylpropyl, hexyl, isohexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl, octadecyl, nonadecyl, eicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, and triacontyl.

[0040] In this specification, "C 14-30The term "alkyl (group)" means a straight-chain or branched-chain alkyl group having 14 to 30 carbon atoms, and examples thereof include tetradecyl, hexadecyl, octadecyl, nonadecyl, eicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, and triacontyl.

[0041] In this specification, "C 1-6 The term "alkyl (group)" refers to a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, and examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, 1-ethylpropyl, hexyl, isohexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, and 2-ethylbutyl. Among these, C 1-4 Alkyl groups are preferred.

[0042] As used herein, "haloC 1-30 The alkyl group is defined as "C 1-30 It means a group in which one or more hydrogen atoms in the "alkyl" group are substituted with a halogen atom. Specific examples include difluoromethyl, trifluoromethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 2,2-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2-difluorobutyl, 4,4,4-trifluorobutyl, 2,2-difluoropentyl, 5,5,5-trifluoropentyl, 2,2-difluorohexyl, and 6,6,6-trifluorohexyl. Among them, the above-mentioned "C 1-6 "HaloC" in which one or more hydrogen atoms in the "alkyl" group are replaced with halogen atoms 1-6 Alkyl is preferred.

[0043] As used herein, "fluoro C 1-6 The term "alkyl (group)" refers to the above-mentioned "haloC 1-6"alkyl" means a group in which the halogen atom in the group is a fluorine atom. Specific examples include difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 2,2-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2-difluorobutyl, 4,4,4-trifluorobutyl, 2,2-difluoropentyl, 5,5,5-trifluoropentyl, 2,2-difluorohexyl, 6,6,6-trifluorohexyl, and the like. Among these, "fluoro-C" such as difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 2,2-difluoropropyl, 2,2,3,3-tetrafluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2-difluorobutyl, and 4,4,4-trifluorobutyl are preferred. 1-4 Alkyl (group) is preferred, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, 2,2-difluoropropyl is more preferred, and trifluoromethyl, 2,2,2-trifluoroethyl is particularly preferred.

[0044] In the present specification, the term "cycloalkyl (group)" refers to a cyclic alkyl group, and when there is no particular limitation on the carbon number range, it is preferably C 3-15 is a cycloalkyl group, more preferably C 3-8 It is a cycloalkyl group.

[0045] In this specification, "C 3-15 The term "cycloalkyl (group)" refers to a cyclic alkyl group having 3 to 15 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl, and cyclopentadecyl. 3-8The term "cycloalkyl (group)" refers to a cyclic alkyl group having 3 to 8 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. 3-6 Cycloalkyl groups are preferred.

[0046] As used herein, the term "alkoxy (group)" refers to a group in which a straight-chain or branched-chain alkyl group is bonded to an oxygen atom.

[0047] In this specification, "C 1-30 The term "alkoxy (group)" means a straight-chain or branched-chain alkoxy group having 1 to 30 carbon atoms, and examples thereof include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, neopentyloxy, hexyloxy, isohexyloxy, 1,1-dimethylbutoxy, 2,2-dimethylbutoxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, hexadecyloxy, octadecyloxy, eicosyloxy, docosyloxy, tricosyloxy, tetracosyloxy, pentacosyloxy, hexacosyloxy, heptacosyloxy, octacosyloxy, nonacosyloxy, and triacontyloxy.

[0048] In this specification, "C 4-30The term "alkoxy (group)" means a straight-chain or branched-chain alkoxy group having 4 to 30 carbon atoms, and examples thereof include butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, neopentyloxy, hexyloxy, isohexyloxy, 1,1-dimethylbutoxy, 2,2-dimethylbutoxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, hexadecyloxy, octadecyloxy, eicosyloxy, docosyloxy, tricosyloxy, tetracosyloxy, pentacosyloxy, hexacosyloxy, heptacosyloxy, octacosyloxy, nonacosyloxy, and triacontyloxy.

[0049] In this specification, "C 14-30 The term "alkoxy (group)" means a straight-chain or branched-chain alkoxy group having 14 to 30 carbon atoms, and examples thereof include tetradecyloxy, hexadecyloxy, octadecyloxy, eicosyloxy, docosyloxy, tricosyloxy, tetracosyloxy, pentacosyloxy, hexacosyloxy, heptacosyloxy, octacosyloxy, nonacosyloxy, triacontyloxy, and the like.

[0050] In this specification, "C 1-6 The term "alkoxy (group)" refers to a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms, and examples thereof include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, neopentyloxy, and hexyloxy. 1-4 Alkoxy groups are preferred.

[0051] As used herein, "haloC 1-30 The alkoxy group is defined as the above-mentioned "C 1-30It means a group in which one or more hydrogen atoms in the "alkoxy" group are substituted with a halogen atom. Specific examples include difluoromethoxy, trifluoromethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, 2,2-difluoropropoxy, 2,2,3,3-tetrafluoropropoxy, 3,3,3-trifluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, 2,2-difluorobutoxy, 4,4,4-trifluorobutoxy, 2,2-difluoropentyloxy, 5,5,5-trifluoropentyloxy, 2,2-difluorohexyloxy, and 6,6,6-trifluorohexyloxy. Among them, the above-mentioned "C 1-6 "HaloC" in which one or more hydrogen atoms in the "alkoxy" group are replaced with halogen atoms 1-6 Alkoxy is preferred.

[0052] As used herein, "fluoro C 1-6 The term "alkoxy (group)" refers to the above-mentioned "halo C 1-6"Alkoxy" means a group in which the halogen atom in the group is a fluorine atom. Specific examples include difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, 2,2-difluoropropoxy, 2,2,3,3-tetrafluoropropoxy, 3,3,3-trifluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, 2,2-difluorobutoxy, 4,4,4-trifluorobutoxy, 2,2-difluoropentyloxy, 5,5,5-trifluoropentyloxy, 2,2-difluorohexyloxy, and 6,6,6-trifluorohexyloxy. Among these, “fluoro-C” such as difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, pentafluoroethoxy, 2,2-difluoropropoxy, 2,2,3,3-tetrafluoropropoxy, 3,3,3-trifluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, 2,2-difluorobutoxy, and 4,4,4-trifluorobutoxy are preferred. 1-4 Alkoxy (group) is preferred, with difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, and 2,2-difluoropropoxy being more preferred, and trifluoromethoxy and 2,2,2-trifluoroethoxy being particularly preferred.

[0053] In the present specification, the term "aryl (group)" refers to a monocyclic or polycyclic (condensed) hydrocarbon group exhibiting aromaticity, and specifically includes, for example, C aryl groups such as phenyl, 1-naphthyl, 2-naphthyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 1-anthryl, 2-anthryl, 9-anthryl, 3-phenanthryl, and 9-phenanthryl. 6-14 Among them, phenyl, 4-biphenylyl, 1-naphthyl, and 2-naphthyl are preferred.

[0054] In the present specification, the term "nitrogen-containing aromatic heterocyclic compound" refers to a monocyclic or condensed polycyclic aromatic heterocyclic compound containing, as ring-constituting atoms other than carbon atoms, 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom, and an oxygen atom, and containing at least one nitrogen atom as a ring-constituting atom. Preferable examples of the "nitrogen-containing aromatic heterocyclic compound" include 5- or 6-membered monocyclic nitrogen-containing aromatic heterocyclic compounds such as pyrrole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, triazole, tetrazole, and triazine; benzimidazole, benzoxazole, benzisoxazole, benzothiazole, benzisothiazole, benzotriazole, imidazopyridine, thienopyridine, furopyridine, pyrrolidone ... Examples of the nitrogen-containing aromatic heterocyclic compounds include 8-14 membered condensed polycyclic (preferably bicyclic or tricyclic) nitrogen-containing aromatic heterocyclic compounds such as 1H-indazole, ...

[0055] In the present specification, the term "optionally substituted" means unsubstituted or having one or more substituents, and unless otherwise specified, the "substituents" include (1) a halogen atom, (2) a nitro group, (3) a cyano group, (4) a C 1-30 Alkyl group, (5) haloC 1-30 Alkyl group, (6) C 3-8 Cycloalkyl groups, (7) C 1-30Alkoxy group, (8) haloC 1-30 Alkoxy group, (9) C 6-14 Among them, halogen atoms, cyano groups, C 1-6 Alkyl group, haloC 1-6 Alkyl group, C 1-6 Alkoxy group, haloC 1-6 An alkoxy group or a phenyl group is preferred, a halogen atom (e.g., a fluorine atom), C 1-6 Alkyl groups (e.g., methyl, ethyl), C 1-6 Alkoxy group (e.g., methoxy, ethoxy) or haloC 1-6 More preferred are alkyl groups (e.g., trifluoromethyl). When multiple substituents are present, each of the substituents may be the same or different. The above substituents may each further comprise one or more of C 1-6 Alkyl group, C 1-6 It may be substituted with an alkoxy group, a halogen atom, a phenyl group, or the like.

[0056] In the present specification, the term "hydrocarbon solvent" refers to solvents including aromatic hydrocarbon solvents and / or aliphatic hydrocarbon solvents. Among them, aliphatic hydrocarbon solvents are preferred from the viewpoints of odor and toxicity.

[0057] In the present specification, examples of the "aromatic hydrocarbon solvent" include benzene, toluene, xylene, etc.

[0058] In the present specification, examples of the "aliphatic hydrocarbon solvent" include n-hexane, isohexane, n-heptane, n-octane, cyclohexane, methylcyclohexane, and mixed solvents thereof.

[0059] In this specification, "soluble in a hydrocarbon solvent (or an aliphatic hydrocarbon solvent)" means that in a solution of the composition of the present invention and a hydrocarbon solvent (or an aliphatic hydrocarbon solvent) at 25° C., the composition of the present invention dissolves at a concentration of 5% by weight or more to form a transparent homogeneous solution. In addition, "easily soluble in a hydrocarbon solvent (or an aliphatic hydrocarbon solvent)" means that in a solution of the composition of the present invention and a hydrocarbon solvent (or an aliphatic hydrocarbon solvent) at 25° C., the composition of the present invention dissolves at a concentration of 20% by weight or more (preferably 30% by weight or more) to form a transparent homogeneous solution.

[0060] (Composition of the present invention) The composition of the present invention will now be described.

[0061] The composition of the present invention is a composition containing a compound represented by the following formula (1) and a compound represented by the following formula (4):

[0062] [ka]

[0063] [ka]

[0064] [In the formula, R 1 , R 2 , R 3 and R 4 Each independently represents one or more fluorine atoms or one or more fluoro C 1-4 Alkyl-substituted C 6-14 represents an aryl group, A + is a hydrogen ion (H + ), formula (2):

[0065] [ka]

[0066] (In the formula, R5 , R 6 and R 7 each independently represents an optionally substituted C 1-30 An alkyl group or an optionally substituted C 6-14 A cation having a total of 25 or more carbon atoms represented by formula (3):

[0067] [ka]

[0068] (In the formula, Ar 1 , Ar 2 and Ar 3 are each independently one or more C 1-30 Alkyl group or C 1-30 C optionally substituted with an alkoxy group 6-14 represents an aryl group; and R and R′ are each independently an optionally substituted C 1-30 Alkyl groups, optionally substituted C 3-15 Cycloalkyl group or optionally substituted C 6-14 Represents an aryl group. However, A + But hydrogen ions (H + ), the total number of carbon atoms in R and R′ is 20 or more, and the content of the compound represented by the formula (4) is 2 moles or more relative to 1 mole of the compound represented by the formula (1), A + is a cation represented by formula (2) or a cation represented by formula (3), the total number of carbon atoms in R and R′ is 8 or more.

[0069] The composition containing the compound represented by formula (1) and the compound represented by formula (4) is not particularly limited as long as it contains both compounds, and may contain a compound in which the compound represented by formula (4) is coordinated to the compound represented by formula (1) to form a complex. The composition of the present invention is preferably a composition containing a complex formed by the compound represented by formula (1) and the compound represented by formula (4).

[0070] Preferred embodiments of the compound represented by formula (1) (hereinafter also referred to as "compound (1)") will be described below.

[0071] Each group in compound (1) will be explained below.

[0072] R 1 , R 2 , R 3 and R 4 are preferably each independently one or more fluorine atoms or one or more fluoro C 1-4 R is a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 3-phenanthryl group, or a 9-phenanthryl group, each of which is substituted with an alkyl group (e.g., a trifluoromethyl group), more preferably a phenyl group, a 1-naphthyl group, a 2-naphthyl group, or a 4-biphenylyl group, each of which is independently substituted with one or more fluorine atoms or one or more trifluoromethyl groups, particularly preferably 1 , R 2 , R 3 and R 4 are all identical to each other, a pentafluorophenyl group, a 2,2',3,3',4',5,5',6,6'-nonafluoro-4-(1,1'-biphenylyl) group, a 2,3,4,5,6,7,8-heptafluoro-1-naphthyl group, or a 1,3,4,5,6,7,8-heptafluoro-2-naphthyl group.

[0073] A + is preferably a hydrogen ion (H + ).

[0074] A + Another preferred embodiment of the cation is represented by the above formula (2) and has a total of 25 or more carbon atoms, and preferably has a total of 35 or more carbon atoms. R in Equation (2) 5 , R 6 and R 7 are preferably each independently 1-30 an alkyl group, or (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups and (4) HaroC 1-30 Alkyl group C, which may be substituted with a substituent selected from the group consisting of 6-14 Aryl Group and more preferably, R 5 but, (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups and (4) HaroC 1-30 Alkyl group C, which may be substituted with a substituent selected from the group consisting of 6-14 is an aryl group, R 6 and R 7 each independently represents an optionally substituted C 1-30 It is an alkyl group.

[0075] A + In another preferred embodiment, the cation has a total carbon number of 35 or more and is represented by the formula (2), and R 5 is substituted with one or more fluorine atoms 6-14 Aryl-substituted C 1-30 C substituted with one or more alkyl or fluorine atoms 1-30 is an alkyl group, and R 6 and R 7 However, each independently, (1) C optionally substituted with a halogen atom 6-14 Aryl groups, (2) Halogen atoms and (3) C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 1-30 More preferably, R 5 But Fluoro C 1-6 is an alkyl group, and R 6 and R 7 However, each independently, (1) C optionally substituted with a halogen atom 6-14 Aryl groups, (2) Halogen atoms and (3) C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 1-30 Alkyl group It is.

[0076] A + Another preferred embodiment of the cation is represented by the formula (3) and has a total carbon number of 35 or more, Among these, Ar in formula (3) is preferable. 1 , Ar 2 and Ar 3 However, each independently, C 1-30 Alkyl group or C 1-30 A phenyl group which may be substituted with an alkoxy group is more preferred, and Ar 1 , Ar 2 and Ar 3 However, each independently, C 4-30 It is a phenyl group which may be substituted with an alkyl group.

[0077] Suitable compounds (1) include the following compounds:

[0078] [Compound (1-1)] In the formula (1), R 1 , R 2 , R 3 and R4 each independently represents one or more fluorine atoms or fluoro C 1-4 a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 3-phenanthryl group, or a 9-phenanthryl group substituted with an alkyl group (e.g., a trifluoromethyl group), and A + But hydrogen ions (H + ), compound (1).

[0079] [Compound (1-2-A)] In the formula (1), R 1 , R 2 , R 3 and R 4 each independently represents one or more fluorine atoms or one or more fluoro C 1-4 a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 3-phenanthryl group, or a 9-phenanthryl group substituted with an alkyl group (e.g., a trifluoromethyl group), and A + is a cation having a total carbon number of 25 or more represented by the formula (2), and R 5 , R 6 and R 7 However, each independently, C 1-30 (1) an alkyl group, or (2) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups and (4) HaroC 1-30 Alkyl group C, which may be substituted with a substituent selected from the group consisting of 6-14 Aryl Group Compound (1).

[0080] [Compound (1-2)] In the formula (1), R1 , R 2 , R 3 and R 4 each independently represents one or more fluorine atoms or one or more fluoro C 1-4 a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 3-phenanthryl group, or a 9-phenanthryl group substituted with an alkyl group (e.g., a trifluoromethyl group), and A + is a cation having a total carbon number of 35 or more represented by the formula (2), and R 5 , R 6 and R 7 However, each independently, C 1-30 (1) an alkyl group, or (2) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups and (4) HaroC 1-30 Alkyl group C, which may be substituted with a substituent selected from the group consisting of 6-14 Aryl Group Compound (1).

[0081] [Compound (1-2-B)] In the formula (1), R 1 , R 2 , R 3 and R 4 each independently represents one or more fluorine atoms or one or more fluoro C 1-4 a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 3-phenanthryl group or a 9-phenanthryl group (preferably a phenyl group, a 1-naphthyl group, a 2-naphthyl group or a 4-biphenylyl group) substituted by an alkyl group (e.g., a trifluoromethyl group), and A +is a cation having a total carbon number of 25 or more (preferably 35 or more) represented by the above formula (2), and R 5 but, (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups and (4) HaroC 1-30 Alkyl group C, which may be substituted with a substituent selected from the group consisting of 6-14 Aryl Group and R 6 and R 7 each independently represents an optionally substituted C 1-30 Compound (1), which is an alkyl group.

[0082] [Compound (1-2-C)] In the formula (1), R 1 , R 2 , R 3 and R 4 each independently represents one or more fluorine atoms or one or more fluoro C 1-4 a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 3-phenanthryl group or a 9-phenanthryl group (preferably a phenyl group, a 1-naphthyl group, a 2-naphthyl group or a 4-biphenylyl group) substituted by an alkyl group (e.g., a trifluoromethyl group), and A + is a cation having a total carbon number of 25 or more (preferably 35 or more) represented by the above formula (2), and R 5 is substituted with one or more fluorine atoms 6-14 Aryl-substituted C 1-30 C substituted with one or more alkyl or fluorine atoms 1-30 is an alkyl group, and R 6 and R 7 However, each independently, (1) C optionally substituted with a halogen atom 6-14Aryl groups, (2) Halogen atoms and (3) C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 1-30 Alkyl group Compound (1).

[0083] [Compound (1-2-D)] In the formula (1), R 1 , R 2 , R 3 and R 4 each independently represents one or more fluorine atoms or one or more fluoro C 1-4 a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 3-phenanthryl group or a 9-phenanthryl group (preferably a phenyl group, a 1-naphthyl group, a 2-naphthyl group or a 4-biphenylyl group) substituted by an alkyl group (e.g., a trifluoromethyl group), and A + is a cation having a total carbon number of 25 or more (preferably 35 or more) represented by the above formula (2), and R 5 But Fluoro C 1-6 is an alkyl group, and R 6 and R 7 However, each independently, (1) C optionally substituted with a halogen atom 6-14 Aryl groups, (2) Halogen atoms and (3) C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 1-30 Alkyl group Compound (1).

[0084] [Compound (1-3)] In the formula (1), R 1 , R 2 , R 3 and R4 each independently represents one or more fluorine atoms or one or more fluoro C 1-4 a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 3-phenanthryl group, or a 9-phenanthryl group substituted with an alkyl group (e.g., a trifluoromethyl group), and A + is a cation having a total carbon number of 35 or more represented by the formula (3), 1 , Ar 2 and Ar 3 However, each independently, C 1-30 Alkyl group or C 1-30 Compound (1), which is a cation which is a phenyl group which may be substituted with an alkoxy group.

[0085] [Compound (1-4)] In the formula (1), R 1 , R 2 , R 3 and R 4 are each independently a phenyl group, a 1-naphthyl group, a 2-naphthyl group, or a 4-biphenylyl group substituted with one or more fluorine atoms or one or more trifluoromethyl groups, and A + But hydrogen ions (H + ), compound (1).

[0086] [Compound (1-5)] In the formula (1), R 1 , R 2 , R 3 and R 4 are each independently a phenyl group, a 1-naphthyl group, a 2-naphthyl group, or a 4-biphenylyl group substituted with one or more fluorine atoms or one or more trifluoromethyl groups, and A + is a cation having a total carbon number of 35 or more represented by the formula (2), and R 5 , R 6 and R7 One of the following: (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups and (4) HaroC 1-30 Alkyl group A phenyl group which may be substituted with a substituent selected from the group consisting of The other two are C 1-30 Alkyl groups (preferably C 14-30 Compound (1), wherein the alkyl group is a cyclic alkyl group.

[0087] [Compound (1-6)] In the formula (1), R 1 , R 2 , R 3 and R 4 are each independently a phenyl group, a 1-naphthyl group, a 2-naphthyl group, or a 4-biphenylyl group substituted with one or more fluorine atoms or one or more trifluoromethyl groups, and A + is a cation having a total carbon number of 35 or more represented by the formula (3), 1 , Ar 2 and Ar 3 However, each independently, C 4-30 Compound (1), which is a phenyl group optionally substituted with an alkyl group.

[0088] [Compound (1-7)] In the formula (1), R 1 , R 2 , R 3 and R 4 are all identical to each other and are a pentafluorophenyl group, a 2,2',3,3',4',5,5',6,6'-nonafluoro-4-(1,1'-biphenylyl) group, a 2,3,4,5,6,7,8-heptafluoro-1-naphthyl group, or a 1,3,4,5,6,7,8-heptafluoro-2-naphthyl group, and A + But hydrogen ions (H +), compound (1).

[0089] [Compound (1-8)] In the formula (1), R 1 , R 2 , R 3 and R 4 are all identical to each other and are a pentafluorophenyl group, a 2,2',3,3',4',5,5',6,6'-nonafluoro-4-(1,1'-biphenylyl) group, a 2,3,4,5,6,7,8-heptafluoro-1-naphthyl group, or a 1,3,4,5,6,7,8-heptafluoro-2-naphthyl group, and A + is a cation having a total carbon number of 35 or more represented by the formula (2), and R 5 , R 6 and R 7 One of the following: (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups and (4) HaroC 1-30 Alkyl group A phenyl group which may be substituted with a substituent selected from the group consisting of The other two are C 1-30 Alkyl groups (preferably C 14-30 Compound (1), wherein the alkyl group is a cyclic alkyl group.

[0090] [Compound (1-9)] In the formula (1), R 1 , R 2 , R 3 and R 4 are all identical to each other and are a pentafluorophenyl group, a 2,2',3,3',4',5,5',6,6'-nonafluoro-4-(1,1'-biphenylyl) group, a 2,3,4,5,6,7,8-heptafluoro-1-naphthyl group, or a 1,3,4,5,6,7,8-heptafluoro-2-naphthyl group, and A +is a cation having a total carbon number of 35 or more represented by the formula (3), 1 , Ar 2 and Ar 3 However, each independently, C 4-30 Compound (1), which is a phenyl group optionally substituted with an alkyl group.

[0091] Preferred specific examples of compound (1) include, for example, hydrogenated tetrakis(pentafluorophenyl)borate, hydrogenated tetrakis(heptafluoronaphthyl)borate, hydrogenated tetrakis(nonafluorobiphenyl)borate, N,N-dioctadecylmethylammonium tetrakis(pentafluorophenyl)borate, N,N-dioctadecylanilinium tetrakis(pentafluorophenyl)borate, N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate, N,N-dioctadecyl-(2,3,4,5,6-pentafluorophenyl)methylammonium tetrakis(pentafluorophenyl)borate, N,N-dioctadecyl-2,2,3,3,3-pentafluoropropylammonium tetrakis(pentafluorophenyl)borate, and N,N-didodecyl-2,2,2-trifluoroethylammonium. Tetrakis(pentafluorophenyl)borate, N,N-dioctadecyl-2,2-difluoroethylammonium Tetrakis(pentafluorophenyl)borate, N,N-dioctadecyl-3,3,3-trifluoropropylammonium Tetrakis(pentafluorophenyl)borate, N,N-dioctadecyl-2-fluoroethylammonium Tetrakis(pentafluorophenyl)borate, N,N-didococosyl-2,2,2-trifluoroethylammonium Tetrakis(pentafluorophenyl)borate, N,N-bis(3,7,11,15-tetramethylhexadecyl)-2,2,2-trifluoroethylammonium Tetrakis(pentafluorophenyl)borate, N,N-bis(3,7,11-trimethyldodecyl)-2,2,2-trifluoroethylammonium Tetrakis(pentafluorophenyl)borate, N,N-ditetradecyl-2,2,2-trifluoroethylammonium Tetrakis(pentafluorophenyl)borate, N,N-dihexadecyl-2,2,2-trifluoroethylammonium Tetrakis(pentafluorophenyl)borate, N,N-dioctadecyl-2,2,2-trifluoroethylammonium Tetrakis(heptafluoronaphthyl)borate, N,N-dioctadecyl-2,2,2-Trifluoroethylammonium tetrakis(nonafluorobiphenyl)borate, etc.

[0092] A preferred embodiment of the compound represented by formula (4) (hereinafter also referred to as "compound (4)") will be described below.

[0093] Each group in compound (4) will be explained below.

[0094] A preferred embodiment of compound (4) is A in compound (1). + Varies depending on the type.

[0095] A in compound (1) + But hydrogen ions (H + ), then The total number of carbon atoms in R and R' is 20 or more, preferably 25 or more, more preferably 28 or more, and even more preferably 30 or more. R and R′ are each independently an optionally substituted C 1-30 Alkyl groups, optionally substituted C 3-15 Cycloalkyl group or optionally substituted C 6-14 are each independently an aryl group, (1) a halogen atom, (2) C 1-30 Alkoxy groups and (3) Haro C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 1-30 Alkyl groups; (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups, (4) HaroC 1-30 Alkyl groups and (5) Haro C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 3-15 a cycloalkyl group; or (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups, (4) HaroC 1-30 Alkyl groups and (5) Haro C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 6-14 Aryl Group and more preferably, each independently is C 1-30 an alkyl group, or (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups, (4) HaroC 1-30 Alkyl groups and (5) Haro C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 6-14 Aryl Group and more preferably, each independently represents C 14-30 It is an alkyl group.

[0096] A in compound (1) + is a cation represented by formula (2) or a cation represented by formula (3), the total number of carbon atoms in R and R' is preferably 8 or more, and more preferably 10 or more. R and R' are preferably each independently C 1-30 It is an alkyl group.

[0097] A in compound (1) + But hydrogen ions (H + ) Suitable compounds (4) include the following compounds:

[0098] [Compound (4-1-A)] In the formula (4), R and R' are each independently (1) a halogen atom, (2) C 1-30 Alkoxy groups and (3) Haro C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 1-30 Alkyl groups; (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups, (4) HaroC 1-30 Alkyl groups and (5) Haro C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 3-15 a cycloalkyl group; or (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups, (4) HaroC 1-30 Alkyl groups and (5) Haro C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 6-14 Aryl Group and Compound (4), wherein the total number of carbon atoms in R and R′ is 20 or more (preferably, 25 or more).

[0099] [Compound (4-1-B)] In the formula (4), R and R' are each independently C 1-30 an alkyl group, or (1) a halogen atom, (2) C 1-30 Alkyl groups, (3) C 1-30 Alkoxy groups, (4) HaroC 1-30 Alkyl groups and (5) Haro C 1-30 Alkoxy group C, which may be substituted with a substituent selected from the group consisting of 6-14 Aryl Group and Compound (4), wherein the total number of carbon atoms in R and R′ is 20 or more (preferably, 25 or more).

[0100] [Compound (4-1-C)] In the formula (4), R and R' are each independently C 1-30 is an alkyl group, and Compound (4), wherein the total number of carbon atoms in R and R′ is 20 or more (preferably, 25 or more).

[0101] [Compound (4-1)] In the formula (4), R and R' are each independently C 14-30 is an alkyl group, and Compound (4), wherein the total number of carbon atoms in R and R′ is 28 or more.

[0102] A in compound (1) + But hydrogen ions (H + ) Preferred specific examples of compound (4) include didecyl ether, didodecyl ether, ditetradecyl ether, dihexadecyl ether, dioctadecyl ether, docosylethyl ether, tetradecyloxyethyl tetradecyl ether, and the like.

[0103] A in compound (1) + When is a cation represented by formula (2) or a cation represented by formula (3), suitable compounds (4) include the following compounds.

[0104] [Compound (4-2)] In the formula (4), R and R' are each independently C 1-30 is an alkyl group, and Compound (4), wherein the total number of carbon atoms in R and R′ is 8 or more.

[0105] [Compound (4-3)] In the formula (4), R and R' are each independently C 1-30 is an alkyl group, and Compound (4), wherein the total number of carbon atoms in R and R′ is 10 or more.

[0106] A in compound (1) + is a cation represented by formula (2) or a cation represented by formula (3), preferred specific examples of compound (4) include dibutyl ether, dihexyl ether, dioctyl ether, didecyl ether, didodecyl ether, ditetradecyl ether, dihexadecyl ether, dioctadecyl ether, cyclopentyl methyl ether, diphenyl ether, and octadecyl phenyl ether. Among these, didodecyl ether, ditetradecyl ether, dihexadecyl ether, and dioctadecyl ether are preferred.

[0107] When the total number of carbon atoms of the groups R and R' in the compound (4) is 7 or less, there is a concern that it may be difficult to industrially control the content thereof due to the low boiling point.

[0108] Specific examples of suitable combinations of compound (1) and compound (4) contained in the composition of the present invention include a combination of compound (1-1) and compound (4-1), a combination of compound (1-2) and compound (4-2), a combination of compound (1-3) and compound (4-2), a combination of compound (1-4) and compound (4-1), a combination of compound (1-5) and compound (4-3), a combination of compound (1-6) and compound (4-3), and a combination of compound (1-7) and compound (4-1). In addition, examples of the combination include a combination of compound (1-8) and compound (4-3), a combination of compound (1-9) and compound (4-3), a combination of compound (1-2-A) and compound (4-2), a combination of compound (1-2-B) and compound (4-2), a combination of compound (1-2-C) and compound (4-2), a combination of compound (1-2-D) and compound (4-1), a combination of compound (1-2-D) and compound (4-2), and a combination of compound (1-2-D) and compound (4-1-C).

[0109] In the composition of the present invention, a suitable range of the content of compound (4) relative to 1 mole of compound (1) is + Varies depending on the type.

[0110] A in compound (1) + But hydrogen ions (H + ), the content of compound (4) is 2 mol or more, preferably 2 to 3 mol, per mol of compound (1).

[0111] A in compound (1) + is a cation represented by formula (2) or a cation represented by formula (3), the content of compound (4) is usually 0.01 to 10 mol, preferably 0.01 to 3 mol, per 1 mol of compound (1). Here, the content of compound (4) per mole of compound (1) is A + But hydrogen ions (H + ), the cation represented by formula (2) or the cation represented by formula (3), corresponds to the amount of each compound charged during production.

[0112] The composition of the present invention is soluble in a hydrocarbon solvent at room temperature (15 to 30° C.). Conventionally known borate compounds (e.g., hydrogenated tetrakis(pentafluorophenyl)borate, hydrogenated tetrakis(pentafluorophenyl)borate diethyl ether complex, lithium tetrakis(pentafluorophenyl)borate, etc.) are insoluble in aliphatic hydrocarbon solvents such as hexane and can be a catalyst poison for metal catalysts used in homogeneous olefin or diene polymerization reactions, whereas the composition of the present invention exhibits good solubility in aliphatic hydrocarbon solvents and does not become a catalyst poison, and is therefore useful as a co-catalyst for homogeneous olefin or diene polymerization reactions.

[0113] (Method of producing the composition of the present invention) The method for producing the composition of the present invention will now be described.

[0114] The composition of the present invention is substantially free of ether compounds (e.g., diethyl ether, etc.) having a total carbon number of 7 or less that can be a catalyst poison. The term "substantially free of ether compounds having a total carbon number of 7 or less" means that 1 This means that no ether compounds with a total carbon number of 7 or less were detected as a result of H-NMR analysis.

[0115] The method for producing the composition of the present invention is not particularly limited, but the composition of the present invention can be produced, for example, according to the following Production Methods 1 to 4.

[0116] (Method 1) (A + But hydrogen ions (H + A method for producing the composition of the present invention containing compound (1a) Preparation method 1 is a method for obtaining the composition of the present invention containing compound (1a) and compound (4) (or a complex of compound (1a) and compound (4)) by reacting compound (5) with a protonic acid in the presence of compound (4) in a solvent that does not influence the reaction.

[0117] [ka]

[0118] (In the formula, M + represents a metal ion (e.g., lithium ion, potassium ion, sodium ion, etc.), n represents a number of 2 or more, and the definitions of the other symbols are the same as those defined above.

[0119] The reaction solvent for this reaction is not particularly limited, but examples thereof include aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chloroform, dichloromethane and 1,2-dichloroethane, aliphatic hydrocarbons such as hexane, isohexane, heptane, octane and methylcyclohexane, and mixtures thereof. Among them, dichloromethane or 1,2-dichloroethane, hexane, isohexane, heptane, octane and methylcyclohexane are preferred.

[0120] In this production method, the compound (5) used as a raw material is A in the above formula (1). + M + Examples of the metal salts include those in which the tetrakis(pentafluorophenyl)borate is replaced by the tetrakis(pentafluorophenyl)borate. Compound (5) may be a commercially available product or a purified product, or may be prepared by a method known per se. Specific examples of compound (5) include lithium tetrakis(pentafluorophenyl)borate, potassium tetrakis(pentafluorophenyl)borate, lithium tetrakis(heptafluoronaphthyl)borate, potassium tetrakis(heptafluoronaphthyl)borate, chloromagnesium tetrakis(pentafluorophenyl)borate, chloromagnesium tetrakis(heptafluoronaphthyl)borate, bromomagnesium tetrakis(pentafluorophenyl)borate, bromomagnesium tetrakis(heptafluoronaphthyl)borate, lithium tetrakis(nonafluorobiphenyl)borate, potassium tetrakis(nonafluorobiphenyl)borate, chloromagnesium tetrakis(nonafluorobiphenylyl)borate, and bromomagnesium tetrakis(nonafluorobiphenyl)borate.

[0121] Examples of the compound (4) used in this production method include the above-mentioned compound (4-1) and compound (4-2). The amount of compound (4) used is 2 moles or more, preferably 2 to 3 moles, per mole of compound (5).

[0122] The protonic acid used in the present production method includes hydrogen chloride, hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, hydroiodic acid, etc. Among them, hydrochloric acid and a hydrogen chloride-diethyl ether solution are preferred. The amount of protonic acid used is not particularly problematic as long as it is an equivalent amount or more per mole of compound (5), but in order to prevent the protonic acid used from remaining in the organic phase after treatment, it is preferable to wash the organic phase with water until the pH of the aqueous phase after washing is 3 or more. If the pH of the aqueous phase is less than 3, there is a concern that the protonic acid salt used in the organic phase will remain in the composition of the present invention and act as a catalyst poison during polymerization.

[0123] The reaction temperature is usually 0° C. to 40° C., preferably 10° C. to 35° C., more preferably room temperature (15° C. to 30° C.), and the reaction time is usually about 10 minutes to 10 hours, preferably about 1 to 3 hours.

[0124] (Method 2) (A + But hydrogen ions (H + A method for producing the composition of the present invention containing compound (1a) Preparation method 2 is a method for obtaining the composition of the present invention containing compound (1a) and compound (4) (or a complex of compound (1a) and compound (4)) by reacting compound (6) with compound (4) in a solvent that does not affect the reaction.

[0125] [ka]

[0126] (The definition of each symbol in the formula is the same as above.)

[0127] The reaction solvent for this reaction is not particularly limited, but examples thereof include aromatic hydrocarbon solvents such as toluene and xylene, halogenated hydrocarbon solvents such as chloroform, dichloromethane and 1,2-dichloroethane, aliphatic hydrocarbon solvents such as hexane, isohexane, heptane, octane and methylcyclohexane, and mixtures thereof. Among these, dichloromethane or 1,2-dichloroethane, hexane, isohexane, heptane, octane and methylcyclohexane are preferred.

[0128] In this production method, the compound (6) used as a starting material may be a commercially available product, or a product produced according to a method known per se (see, for example, Organometallics, 2000, 19, 1442-1444) or a method analogous thereto.

[0129] Examples of the compound (4) used in this production method include the above-mentioned compound (4-1) and compound (4-2). The amount of compound (4) used is usually 2 mol or more, preferably 2 to 3 mol, per mol of compound (6).

[0130] The reaction temperature is usually 0° C. to 40° C., preferably 10° C. to 35° C., more preferably room temperature (15° C. to 30° C.), and the reaction time is usually about 10 minutes to 10 hours, preferably about 1 to 3 hours.

[0131] (Method 3) (A + But hydrogen ions (H + (1b) is a cation other than the compound (1b) of the present invention. Preparation method 3 is a method for obtaining a composition of the present invention containing compound (1b) and compound (4) by subjecting the steps to a step (step 1) of adding compound (6) and compound (7) (e.g., an amine deprotonated from a cation represented by formula (2)) in a solvent that does not influence the reaction, suspending the mixture, adding a protonic acid dropwise to the suspension, stirring the mixture, filtering the mixture, and concentrating the filtrate under reduced pressure, and then mixing and stirring compound (1b) and compound (4) in a solvent that does not influence the reaction.

[0132] [ka]

[0133] (The definition of each symbol in the formula is the same as above.)

[0134] (Process 1) Examples of the solvent used in this step include hydrocarbon solvents such as toluene, n-hexane, isohexane, n-heptane, n-octane, cyclohexane, and methylcyclohexane, and mixtures thereof. Among these, aliphatic hydrocarbon solvents such as n-hexane, isohexane, n-heptane, n-octane, cyclohexane, and methylcyclohexane are preferred.

[0135] Examples of the compound (7) used in this step include tertiary amines deprotonated from the cation represented by the formula (2). Among these, preferred are dihydrogenated beef tallow alkylmethylamine, N,N-dioctadecylmethylamine, N,N-dioctadecylaniline, N,N-dioctadecyl-2,2,2-trifluoroethylamine, N,N-dioctadecyl-(2,3,4,5,6-pentafluorophenyl)methylamine, N,N-dioctadecyl-2,2,3,3,3-pentafluoropropylamine, N,N-didodecyl-2,2,2-trifluoroethylamine, N,N-dioctadecyl-2,2-difluoroethylamine, and N,N-dioctadecyl-3 ,3,3-trifluoropropylamine, N,N-dioctadecyl-2-fluoroethylamine, N,N-didococosyl-2,2,2-trifluoroethylamine, N,N-bis(3,7,11,15-tetramethylhexadecyl)-2,2,2-trifluoroethylamine, N,N-bis(3,7,11-trimethyldodecyl)-2,2,2-trifluoroethylamine, N,N-ditetradecyl-2,2,2-trifluoroethylamine, and N,N-dihexadecyl-2,2,2-trifluoroethylamine. The amount of compound (7) used is usually 1 to 10 mol, and preferably 1 to 2 mol, per 1 mol of compound (6).

[0136] Examples of the protonic acid used in this step include hydrogen chloride, sulfuric acid, nitric acid, hydrogen bromide, hydrogen iodide, etc. Among these, hydrogen chloride (more preferably, a hydrogen chloride-diethyl ether solution) is preferred. The amount of protonic acid used is not particularly problematic as long as it is an equivalent amount or more per mole of compound (7), but in order to prevent the protonic acid used from remaining in the organic phase after treatment, it is preferable to wash the organic phase with water until the pH of the aqueous phase after washing is 3 or more. If the pH of the aqueous phase is less than 3, there is a concern that the protonic acid salt used in the organic phase will remain in the composition of the present invention and act as a catalyst poison during polymerization.

[0137] In the preparation method 3, the compound (1b) prepared as above can be used in the step 2 as it is.

[0138] (Process 2) The solvent used in this step is not particularly limited, but examples thereof include aliphatic hydrocarbon solvents such as n-hexane, isohexane, n-heptane, n-octane, cyclohexane, and methylcyclohexane, and among these, n-hexane is preferred.

[0139] Examples of the compound (4) used in this step include the aforementioned compound (4-3) and compound (4-4). The amount of compound (4) used is usually 0.01 to 10 mol, and preferably 0.01 to 3 mol, per 1 mol of compound (1b).

[0140] The reaction temperature is usually 0° C. to 40° C., preferably 10° C. to 35° C., more preferably room temperature (15° C. to 30° C.), and the reaction time is usually about 10 minutes to 10 hours, preferably about 1 to 3 hours.

[0141] (Method 4) (A + But hydrogen ions (H + (1b) is a cation other than the compound (1b) of the present invention. Preparation method 4 is a method for obtaining a composition of the present invention containing compound (1b) and compound (4) by subjecting the process to a step (step 1) of adding compound (8) and compound (5) in a solvent that does not influence the reaction, stirring the mixture, filtering the reaction mixture, and concentrating the filtrate under reduced pressure, and then subjecting the process to a step (step 2) of mixing and stirring compound (1b) and compound (4) in a solvent that does not influence the reaction.

[0142] [ka]

[0143] (In the formula, X represents a halogen atom, and the other symbols are the same as defined above.)

[0144] (Process 1) Examples of the solvent used in this step include hydrocarbon solvents such as toluene, n-hexane, isohexane, n-heptane, n-octane, cyclohexane, methylcyclohexane, and n-heptane, halogenated solvents such as dichloromethane and chloroform, and mixtures thereof. Among these, aliphatic hydrocarbon solvents such as n-hexane, isohexane, n-heptane, n-octane, cyclohexane, and methylcyclohexane are preferred.

[0145] The compound (8) used in this step is, for example, preferably, N,N-dioctadecylmethylamine hydrochloride, dihydrogenated beef tallow alkylmethylamine hydrochloride, N,N-dioctadecylaniline hydrochloride, N,N-dioctadecyl-2,2,2-trifluoroethylamine hydrochloride, N,N-dioctadecyl-(2,3,4,5,6-pentafluorophenyl)methylamine hydrochloride, N,N-dioctadecyl-2,2,3,3,3-pentafluoropropylamine hydrochloride, N,N-didodecyl-2,2,2-trifluoroethylamine hydrochloride, N,N-dioctadecyl-2,2-di ... Decyl-3,3,3-trifluoropropylamine hydrochloride, N,N-dioctadecyl-2-fluoroethylamine hydrochloride, N,N-didococosyl-2,2,2-trifluoroethylamine hydrochloride, N,N-bis(3,7,11,15-tetramethylhexadecyl)-2,2,2-trifluoroethylamine hydrochloride, N,N-bis(3,7,11-trimethyldodecyl)-2,2,2-trifluoroethylamine hydrochloride, N,N-ditetradecyl-2,2,2-trifluoroethylamine hydrochloride, N,N-dihexadecyl-2,2,2-trifluoroethylamine hydrochloride, and tri(p-octylphenyl)chloromethane. The amount of compound (8) used is usually 1 to 2 mol, and preferably 1 to 1.1 mol, per 1 mol of compound (5).

[0146] In the preparation method 4, the compound (1b) prepared as above can be used in the step 2 as it is.

[0147] (Process 2) The solvent used in this step is not particularly limited, but examples thereof include aliphatic hydrocarbon solvents such as n-hexane, isohexane, n-heptane, n-octane, cyclohexane, and methylcyclohexane, and among these, n-hexane is preferred.

[0148] Examples of the compound (4) used in this step include the aforementioned compound (4-3) and compound (4-4). The amount of compound (4) used is usually 0.01 to 10 mol, and preferably 0.01 to 3 mol, per 1 mol of compound (1b).

[0149] The reaction temperature is usually 0° C. to 40° C., preferably 10° C. to 35° C., more preferably room temperature (15° C. to 30° C.), and the reaction time is usually about 10 minutes to 10 hours, preferably about 1 to 3 hours.

[0150] The composition of the present invention contains compound (1) and compound (4), is soluble (or easily soluble) in hydrocarbon solvents, particularly aliphatic hydrocarbon solvents, and is substantially free of compounds that can act as catalyst poisons, such as highly basic and nucleophilic amine compounds and ether compounds having a total carbon number of 7 or less, and is therefore useful as a polymerization cocatalyst for olefins and dienes.

[0151] The present invention includes a method for producing a polymer comprising polymerizing at least one monomer selected from the group consisting of olefins and dienes using the composition of the present invention as a cocatalyst.

[0152] The production of a polymer using the compound (compound (1)) (or composition) of the present invention as a cocatalyst can be specifically carried out, for example, in accordance with the method described in the Test Examples described below. EXAMPLES

[0153] The present invention will be specifically described below with reference to Examples, Production Examples, and Test Examples, but the present invention is not limited to these Examples, etc. Percentages indicate mol / mol% for yields, and percent by weight for other items unless otherwise specified. Room temperature indicates a temperature of 15°C to 30°C unless otherwise specified.

[0154] The following instruments were used for the analysis: 1 H-NMR and 19 F-NMR: 400YH manufactured by JEOL Ltd. (JEOL)

[0155] [Example 1] Dihexadecyl ether (Tokyo Chemical Industry Co., Ltd.) (0.92 g, 1.93 mmol) and lithium tetrakis(pentafluorophenyl)borate triethyl ether complex (AGC Corporation) (1.00 g, 0.97 mmol) were added to dichloromethane (10 ml), and then 6M hydrochloric acid (15 ml) was added and stirred at room temperature for 1 hour. The reaction solution was separated, and the organic phase was concentrated. n-Hexane (15 ml) was added to the concentrated solution, which was stirred and then concentrated. This operation was repeated to obtain an oily hydrogenated tetrakis(pentafluorophenyl)borate bis(dihexadecyl ether) complex (1.67 g). 1 H NMR(CDCl3) δ: 0.88 (t, 12H), 1.25 (m, 104H), 1.59 (m, 8H), 3.60 (t, 8H); 19 F NMR(CDCl3) δ: -132.9 (d, 8F), -162.2 (t, 4F), -166.3 (t, 8F).

[0156] It was confirmed that the complex (composition) obtained in Example 1 was dissolved in n-hexane at a concentration of 20% by weight.

[0157] [Example 2] Dihexadecyl ether (0.56g, 1.21mmol) and hydrogenated tetrakis(pentafluorophenyl)borate diethyl ether complex (0.50g, 0.60mmol) obtained by a method known per se (see, for example, Organometallics, 2000, 19, 1442-1444) were dissolved in 1,2-dichloroethane (10ml) and then concentrated. The concentrated solution was added with 1,2-dichloroethane (10ml), stirred, and then concentrated twice, and then n-hexane (10ml) was added to the concentrated solution, stirred, and then concentrated three times. An oily hydrogenated tetrakis(pentafluorophenyl)borate bis(dihexadecyl ether) complex (0.97g) was obtained.

[0158] [Example 3] Ditetradecyl ether (Tokyo Chemical Industry Co., Ltd.) (0.50g, 1.21mmol) and hydrogenated tetrakis(pentafluorophenyl)borate diethyl ether complex (0.50g, 0.60mmol) were dissolved in 1,2-dichloroethane (10ml) and then concentrated. The concentrated solution was added with 1,2-dichloroethane (10ml), stirred, and then concentrated twice, and then hexane (10ml) was added to the concentrated solution, stirred, and then concentrated three times. An oily hydrogenated tetrakis(pentafluorophenyl)borate bis(ditetradecyl ether) complex (0.94g) was obtained. 1 H NMR(CDCl3) δ: 0.88 (t, 12H), 1.25 (m, 88H), 1.65 (m, 8H), 3.79 (t, 8H); 19 F NMR(CDCl3) δ: -132.9 (d, 8F), -162.2 (t, 4F), -166.3 (t, 8F).

[0159] It was confirmed that the complex (composition) obtained in Example 3 was dissolved in n-hexane at a concentration of 20% by weight.

[0160] [Example 4] (1) N,N-dioctadecylaniline (3.3g, 5.5mmol) prepared by a method known per se (see, for example, Huaxue Xuebao, 2008, 66(14), 1687-1692) and lithium tetrakis(perfluorophenyl)borate triethyl ether complex (5.0g, 5.5mmol) were suspended in n-hexane (50mL), and then 1.0M hydrogen chloride-diethyl ether solution (5.5mL) was added dropwise and stirred at room temperature for 3 hours. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure at 50°C to obtain N,N-dioctadecylanilinium tetrakis(pentafluorophenyl)borate (7.0g, 90%). 1 H NMR (CDCl3) δ: 0.86-0.89 (6H, m), 1.15-1.50 (27H, m), 3.40-3.50 (4H, m),7.26-7.28 (2H, m), 7.58-7.63 (3H, m); 19 F NMR (CDCl3) δ: -133.8 (8F, t), -163.3(4F, t), -167.4 (8F, t). (2) N,N-dioctadecylanilinium tetrakis(pentafluorophenyl)borate (127.8 mg, 0.1 mmol) obtained in (1) above was added to n-hexane (474 ​​mg) to prepare a two-phase separation solution (concentration: 20 wt%). Ditetradecyl ether (21 mg, 0.05 mmol) was added to the solution and stirred to obtain a uniform n-hexane solution.

[0161] [Example 5] N,N-dioctadecylanilinium tetrakis(pentafluorophenyl)borate (127.8 mg, 0.1 mmol) obtained in Example 4(1) was added to n-hexane (474 ​​mg) to prepare a two-phase separation solution (concentration: 20 wt%). Didodecyl ether (Tokyo Chemical Industry Co., Ltd.) (17.7 mg, 0.05 mmol) was then added and stirred to obtain a uniform n-hexane solution.

[0162] [Example 6] N,N-dioctadecylanilinium tetrakis(pentafluorophenyl)borate (127.8 mg, 0.1 mmol) obtained in Example 4(1) was added to n-hexane (474 ​​mg) to prepare a two-phase separation solution (concentration: 20 wt%). Dibutyl ether (manufactured by Junsei Chemical Co., Ltd.) (6.5 mg, 0.2 mmol) was then added and stirred to obtain a uniform n-hexane solution.

[0163] [Example 7] Dioctadecyl ether (Tokyo Chemical Industry Co., Ltd.) (0.66 g, 1.21 mmol) and hydrogenated tetrakis(pentafluorophenyl)borate diethyl ether complex (0.50 g, 0.60 mmol) were dissolved in dichloromethane (15 ml) and then concentrated. Dichloromethane (15 ml) was added to the concentrated solution, and the mixture was stirred and concentrated four times. Then, n-hexane (10 ml) was added to the concentrated solution, and the mixture was stirred and concentrated three times. Solid hydrogenated tetrakis(pentafluorophenyl)borate bis(dioctadecyl ether) complex (1.05 g) was obtained. 1 H NMR(CDCl3) δ: 0.88 (t, 12H), 1.25 (m, 120H), 1.65 (m, 8H), 3.79 (t, 8H); 19 F NMR(CDCl3) δ: -132.9 (d, 8F), -162.2 (t, 4F), -166.3 (t, 8F).

[0164] It was confirmed that the complex (composition) obtained in Example 7 was dissolved in n-hexane at a concentration of 20% by weight.

[0165] [Example 8] Didodecyl ether (Tokyo Chemical Industry Co., Ltd.) (0.45g, 1.21mmol) and hydrogenated tetrakis(pentafluorophenyl)borate diethyl ether complex (0.50g, 0.60mmol) were dissolved in 1,2-dichloroethane (10ml) and then concentrated. The concentrated solution was added with 1,2-dichloroethane (10ml), stirred, and then concentrated twice, and then methylcyclohexane (10ml) was added to the concentrated solution, stirred, and then concentrated three times. An oily hydrogenated tetrakis(pentafluorophenyl)borate bis(didodecyl ether) complex (0.90g) was obtained. 1 H NMR(CDCl3) δ: 0.88 (t, 12H), 1.25 (m, 72H), 1.65 (m, 8H), 3.60 (t, 8H); 19 F NMR(CDCl3) δ: -132.9 (d, 8F), -162.2 (t, 4F), -166.3 (t, 8F).

[0166] It was confirmed that the complex (composition) obtained in Example 8 was dissolved in methylcyclohexane at a concentration of 20% by weight.

[0167] [Example 9] Didecyl ether (Tokyo Chemical Industry Co., Ltd.) (0.38g, 1.21mmol) and hydrogenated tetrakis(pentafluorophenyl)borate diethyl ether complex (0.50g, 0.60mmol) were dissolved in 1,2-dichloroethane (10ml) and then concentrated. The concentrated solution was added with 1,2-dichloroethane (10ml), stirred, and then concentrated twice, after which methylcyclohexane (10ml) was added to the concentrated solution, stirred, and then concentrated three times. An oily hydrogenated tetrakis(pentafluorophenyl)borate bis(didecyl ether) complex (0.81g) was obtained. 1 H NMR(CDCl3) δ: 0.88 (t, 12H), 1.25 (m, 56H), 1.65 (m, 8H), 3.60 (t, 8H); 19F NMR(CDCl3) δ: -132.9 (d, 8F), -162.2 (t, 4F), -166.3 (t, 8F).

[0168] It was confirmed that the complex (composition) obtained in Example 9 was dissolved in methylcyclohexane at a concentration of 20% by weight.

[0169] [Example 10] A diethyl ether solution (47 wt%, 5.00 g, 2.28 mmol) of lithium tetrakis(heptafluoronaphthyl)borate produced by a method known per se (see, for example, International Publication No. 2007 / 070770) was added to 1,2-dichloroethane (10 ml), and then 6 M hydrochloric acid (7.6 ml) was added and stirred at room temperature for 1 hour. The reaction solution was separated, and the organic phase was concentrated. Ditetradecyl ether (Tokyo Chemical Industry Co., Ltd.) (1.88 g, 4.55 mmol) and 30 ml of 1,2-dichloroethane were added to the concentrated solution, dissolved, and then concentrated. The concentrated solution was added with 1,2-dichloroethane (30 ml), stirred, and then concentrated twice, and then n-hexane (30 ml) was added to the concentrated solution, stirred, and then concentrated three times. An oily hydrogenated tetrakis(heptafluoronaphthyl)borate bis(ditetradecyl ether) complex (4.21 g) was obtained. 1 H NMR(CDCl3) δ: 0.87 (t, 12H), 1.22 (m, 88H), 1.58 (m, 8H), 3.66 (t, 8H); 19 F NMR(CDCl3) δ: -108.3 (m, 4F), -125.1 (m, 4F), -145.1 (m, 4F), -149.0 (m, 4F), -154.5 (m, 4F), -158.3 (m, 4F), -159.8 (m, 4F).

[0170] It was confirmed that the complex (composition) obtained in Example 10 was dissolved in n-hexane at a concentration of 20% by weight.

[0171] [Production Example 1] Docosyl bromide (Tokyo Chemical Industry Co., Ltd.) (1.00 g, 2.57 mmol) and cesium carbonate (1.26 g, 3.85 mmol) were added to 20 ml of ethanol and reacted at 150°C for 30 minutes using a microwave synthesis device (Biotage). After the reaction was completed, water and methylcyclohexane were added and the organic phase was concentrated after separation. The concentrated liquid was purified by column chromatography to obtain docosyl ethyl ether (0.60 g) as a white solid. 1 H NMR(CDCl3) δ: 0.89 (t, 3H), 1.21 (t, 3H), 1.26 (m, 38H), 1.57 (m, 2H), 3.41 (t, 2H), 3.47 (q, 2H).

[0172] [Example 11] The docosyl ethyl ether (0.21 g, 0.60 mmol) and hydrogenated tetrakis(pentafluorophenyl)borate diethyl ether complex (0.25 g, 0.30 mmol) obtained in Production Example 1 were dissolved in 1,2-dichloroethane (5 ml) and then concentrated. The concentrated solution was added with 1,2-dichloroethane (5 ml), stirred, and then concentrated twice, and then methylcyclohexane (5 ml) was added to the concentrated solution, stirred, and then concentrated three times. A solid hydrogenated tetrakis(pentafluorophenyl)borate bis(docosyl ethyl ether) complex (0.46 g) was obtained. 1 H NMR(CDCl3) δ: 0.87 (m, 12H), 1.27 (m, 82H), 1.65 (m, 4H), 3.76 (t, 4H), 3.85(q, 4H); 19 F NMR(CDCl3) δ: -132.9 (d, 8F), -162.2 (t, 4F), -166.3 (t, 8F).

[0173] It was confirmed that the complex (composition) obtained in Example 11 was dissolved in methylcyclohexane at a concentration of 20% by weight.

[0174] [Production Example 2] Tetradecyl bromide (Tokyo Chemical Industry Co., Ltd.) (1.79 g, 6.44 mmol), ethylene glycol (0.20 g, 3.22 mmol), tetrabutylammonium bromide (Tokyo Chemical Industry Co., Ltd.) (0.10 g, 0.32 mmol) and potassium hydroxide (0.64 g, 9.67 mmol) were added to dioxane (10 ml) and heated at 100°C for 3 hours. After cooling, water and diethyl ether were added and the mixture was separated. The organic phase was dried over sodium sulfate and then concentrated. The concentrate was purified by column chromatography to obtain ethylene glycol ditetradecyl ether (0.32 g) as a white solid. 1 H NMR(CDCl3) δ: 0.88 (t, 6H), 1.25 (m, 44H), 1.58 (m, 4H), 3.46 (t, 4H), 3.57 (s, 4H).

[0175] [Example 12] The ethylene glycol ditetradecyl ether (0.22 g, 0.48 mmol) and hydrogenated tetrakis(pentafluorophenyl)borate diethyl ether complex (0.20 g, 0.24 mmol) obtained in Production Example 2 were dissolved in 1,2-dichloroethane (5 ml) and then concentrated. The concentrated solution was added with 1,2-dichloroethane (5 ml), stirred, and then concentrated twice, and then n-hexane (5 ml) was added to the concentrated solution, stirred, and then concentrated three times. An oily hydrogenated tetrakis(pentafluorophenyl)borate bis(ethylene glycol ditetradecyl ether) complex (0.41 g) was obtained. 1 H NMR(CDCl3) δ: 0.87 (t, 12H), 1.27 (m, 88H), 1.58 (m, 8H), 3.58 (t, 8H), 3.70 (s, 8H); 19 F NMR(CDCl3) δ: -132.9 (d, 8F), -162.2 (t, 4F), -166.3 (t, 8F).

[0176] It was confirmed that the complex (composition) obtained in Example 12 was dissolved in n-hexane at a concentration of 20% by weight.

[0177] [Production Example 3] N,N-dioctadecylamine (2.0g, 3.8mmol) and triethylamine (0.5g, 5.0mmol) were dissolved in tetrahydrofuran (10mL), and trifluoroacetic anhydride (1.0g, 4.8mmol) was added thereto at room temperature. The mixture was stirred at room temperature for 1 hour, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1M hydrochloric acid and saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (n-hexane / ethyl acetate = 100 / 0-95 / 5) to obtain N,N-dioctadecyl-2,2,2-trifluoroacetamide (1.87g, 79%). 1 H NMR (CDCl3) δ: 0.89 (6H, t), 1.26-1.43 (62H, m), 1.56-1.59 (4H, m), 3.30-3.37 (4H, m); 19 F NMR (CDCl3) δ: -68.1 (3F, s).

[0178] [Production Example 4] The N,N-dioctadecyl-2,2,2-trifluoroacetamide (1.0 g, 1.6 mmol) obtained in Production Example 3 was dissolved in tetrahydrofuran (10 mL), and 1M borane-tetrahydrofuran complex in tetrahydrofuran (5 mL) was added and refluxed for 3 hours. After cooling the mixture with ice, water was carefully added dropwise and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain N,N-dioctadecyl-2,2,2-trifluoroethylamine (0.87 g, 88%). 1 H NMR (CDCl3) δ: 0.88 (6H, t), 1.25-1.40 (60H, m), 1.42-1.44 (4H, m), 2.56 (4H, t), 3.00 (2H, q); 19F NMR (CDCl3) δ: -69.2 (3F, t).

[0179] [Production Example 5] N,N-dioctadecyl-2,2,2-trifluoroethylamine (1.0 g, 1.7 mmol) obtained in Production Example 4 was dissolved in n-hexane (10 mL), 1.0 M hydrogen chloride-diethyl ether solution (10 mL) was added, and the mixture was stirred at room temperature for 3 hours. The precipitate was collected by filtration, washed with n-hexane, and then dried under reduced pressure to obtain N,N-dioctadecyl-2,2,2-trifluoroethylamine hydrochloride (0.987 g, 93%). 1 H NMR (CDCl3) δ: 0.88 (6H, t), 1.19-1.40 (60H, m), 1.93 (4H, br s), 3.15 (4H, br s), 3.77 (2H, q); 19 F NMR (CDCl3) δ: -61.4 (3F, t).

[0180] [Production Example 6] N,N-Dioctadecyl-2,2,2-trifluoroethylamine obtained in Production Example 5 The hydrochloride (0.32 g, 0.50 mmol) was dissolved in chloroform (30 mL), and lithium tetrakis(pentafluorophenyl)borate triethyl ether complex (0.45 g, 0.5 mmol) was added and stirred at room temperature for 1 hour. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was dried at 45°C under reduced pressure to obtain N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (0.62 g, 97%). 1 H NMR (CDCl3) δ: 0.88 (6H, t), 1.19-1.40 (60H, m), 1.94 (4H, br s), 3.15 (4H, br s), 3.77 (2H, q); 19F NMR (CDCl3) δ: -64.7 (3F, t), -132.1 (8H, m), -161.1 (4H, m), -165.5 (8H, m).

[0181] [Example 13] The N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (0.30 g, 0.22 mmol) obtained in Production Example 6 and ditetradecyl ether (0.09 g, 0.22 mmol) were mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and ditetradecyl ether. 1 H NMR (CDCl3) δ: 0.85-0.90 (12H, m), 1.20-1.33 (104H, m), 1.52-1.68 (8H, m), 3.14-3.18 (4H, m), 3.40 (4H, t), 3.62 (2H, q); 19 F NMR (CDCl3) δ: -66.8 (3F, br s), -134.0 (8F, m), -163.2 (4F, t), -167.5 (8F, m).

[0182] N-hexane was added to the composition obtained in Example 13 to prepare a 20 wt % n-hexane solution, which was confirmed to be a homogeneous solution.

[0183] Isohexane was added to the composition obtained in Example 13 to prepare a 20 wt % isohexane solution, which was confirmed to be a homogeneous solution.

[0184] A 20 wt % n-heptane solution was prepared by adding n-heptane to the composition obtained in Example 13, and it was confirmed that the solution was homogeneous.

[0185] The composition obtained in Example 13 was added with ISOPAR E (R) Add 20% by weight of ISOPAR E (R)A solution was prepared and confirmed to be a homogeneous solution.

[0186] Cyclohexane was added to the composition obtained in Example 13 to prepare a 20 wt % cyclohexane solution, which was confirmed to be a homogeneous solution.

[0187] Methylcyclohexane was added to the composition obtained in Example 13 to prepare a 20 wt % methylcyclohexane solution, which was confirmed to be a homogeneous solution.

[0188] [Example 14] The N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (300 mg, 0.23 mmol) obtained in Production Example 6 and dibutyl ether (62 mg, 0.46 mmol) were mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and dibutyl ether. 1 H NMR (CDCl3) δ: 0.87 (6H, t), 0.92 (12H, t), 1.20-1.68 (78H, m), 3.14-3.18 (4H, m), 3.41 (8H, t), 3.62 (2H, q); 19 F NMR (CDCl3) δ: -66.7 (3F, s), -134.0 (8F, s), -163.3 (4F, t), -167.5 (8H, m).

[0189] It was confirmed that the composition obtained in Example 14 was soluble in n-hexane at a concentration of 30% by weight.

[0190] [Example 15] N,N-ditetradecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (58 mg, 0.05 mmol) and didodecyl ether (40 mg, 0.10 mmol) were added and mixed to obtain a composition containing N,N-ditetradecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and didodecyl ether. 1 H NMR (CDCl3) δ: 0.85-0.88 (18H, m), 1.24-1.35 (116H, m), 1.51-1.58 (8H, m), 1.64-1.70 (4H, m), 3.11-3.15 (4H, m), 3.38 (8H, t), 3.60 (2H, q); 19 F NMR (CDCl3) δ: -66.6 (3F, s), -134.0 (8F, s), -163.5 (4F, t), -167.6 (8F, t).

[0191] N-hexane was added to the composition obtained in Example 15 to prepare a 20 wt % n-hexane solution, which was confirmed to be a homogeneous solution.

[0192] [Example 16] N,N-dihexadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (60 mg, 0.05 mmol) and dihexadecyl ether (23 mg, 0.05 mmol) were added and mixed to obtain a composition containing N,N-dihexadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and dihexadecyl ether. 1 H NMR (CDCl3) δ: 0.86-0.90 (12H, m), 1.20-1.36 (104H, m), 1.52-1.58 (4H, m), 1.63-1.70 (4H, m), 3.15-3.19 (4H, m), 3.39 (4H, t), 3.64 (2H, q); 19 F NMR (CDCl3) δ: -66.7 (3F, s), -134.1 (8F, s), -163.5 (4F, t), -167.6 (8F, t).

[0193] N-hexane was added to the composition obtained in Example 16 to prepare a 20 wt % n-hexane solution, which was confirmed to be a homogeneous solution.

[0194] [Example 17] The N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (64 mg, 0.05 mmol) obtained in Production Example 6 and dioctyl ether (12 mg, 0.05 mmol) were added and mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and dioctyl ether. 1 H NMR (CDCl3) δ: 0.88 (12H, t), 1.20-1.37 (80H, m), 1.52-1.58 (4H, m), 1.65-1.70 (4H, m), 3.14-3.19 (4H, m), 3.39 (4H, t), 3.63 (2H, q); 19 F NMR (CDCl3) δ: -66.6 (3F, br s), -134.0 (8F, br s), -163.4 (4F, t), -167.6 (8F, t).

[0195] N-hexane was added to the composition obtained in Example 17 to prepare a 20 wt % n-hexane solution, which was confirmed to be a homogeneous solution.

[0196] [Example 18] The N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (64 mg, 0.05 mmol) obtained in Production Example 6 and didodecyl ether (15 mg, 0.05 mmol) were added and mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and didodecyl ether. 1 H NMR (CDCl3) δ: 0.86-0.90 (12H, m), 1.20-1.38 (96H, m), 1.53-1.60 (4H, m), 1.65-1.72 (4H, m), 3.15-3.20 (4H, m), 3.39 (4H, t), 3.65 (2H, q); 19 F NMR (CDCl3) δ: -66.4 (3F, br s), -134.0 (8F, br s), -163.4 (4F, t), -167.5 (8F, m).

[0197] N-hexane was added to the composition obtained in Example 18 to prepare a 20 wt % n-hexane solution, which was confirmed to be a homogeneous solution.

[0198] [Example 19] The N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (64 mg, 0.05 mmol) obtained in Production Example 6 and dihexadecyl ether (23 mg, 0.05 mmol) were added and mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and dihexadecyl ether. 1 H NMR (CDCl3) δ:0.86-0.98, (12H, m), 1.20-1.35 (112H, m), 1.52-1.75 (8H, m), 3.15-3.20 (4H, m), 3.39 (4H, t), 3.65 (2H, q); 19 F NMR (CDCl3) δ: -66.5 (3F, br s), -134.2 (8F, br s), -163.6 (4F, t), -167.7 (8F, m).

[0199] N-hexane was added to the composition obtained in Example 19 to prepare a 20 wt % n-hexane solution, which was confirmed to be a homogeneous solution.

[0200] [Example 20] The N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (64 mg, 0.05 mmol) obtained in Production Example 6 and diphenyl ether (8.5 mg, 0.05 mmol) were added and mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and diphenyl ether. 1 H NMR (CDCl3) δ: 0.86-0.90, (6H, m), 1.20-1.40 (58H, m), 1.62-1.68 (4H, m), 3.12-3.16 (4H, m), 3.61 (4H, q), 6.99-7.03 (4H, m), 7.08-7.12 (2H, m), 7.31-7.36 (4H, m); 19 F NMR (CDCl3) δ: -66.9 (3F, br s), -134.1 (8F, br s), -163.4 (4F, t), -167.6 (8F, m).

[0201] N-hexane was added to the composition obtained in Example 20 to prepare a 20 wt % n-hexane solution, which was confirmed to be a homogeneous solution.

[0202] [Example 21] The N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (64 mg, 0.05 mmol) obtained in Production Example 6 and octadecyl phenyl ether (18 mg, 0.05 mmol) were added and mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and octadecyl phenyl ether. 1 H NMR (CDCl3) δ: 0.84-0.98 (12H, m), 1.20-1.44 (85H, m), 1.62-1.81 (6H, m), 3.13-3.18 (4H, m), 3.61 (4H,q), 3.95 (2H, t),6.88-6.94 (2H, m), 7.25-7.30 (3H, m); 19 F NMR (CDCl3) δ: -66.8 (3F, br s), -134.1 (8F, br s), -163.4 (4F, t), -167.6 (8F, m).

[0203] N-hexane was added to the composition obtained in Example 21 to prepare a 20 wt % n-hexane solution, which was confirmed to be a homogeneous solution.

[0204] [Example 22] The N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (64 mg, 0.05 mmol) obtained in Production Example 6 and cyclopentyl methyl ether (10 mg, 0.10 mmol) were added and mixed to obtain a composition containing N,N-dioctadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and cyclopentyl methyl ether. 1H NMR (CDCl3) δ: 0.88 (6H, t), 1.20-1.35 (60H, m), 1.53-1.56 (4H, m), 1.61-1.76 (16H, m), 3.12-3.17 (4H, m), 3.28 (6H,s), 3.61 (2H, q), 3.79-3.83 (2H, m); 19 F NMR (CDCl3) δ: -66.6 (3F, br s), -133.9 (8F, br s), -163.5 (4F, t), -167.6 (8F, m).

[0205] N-hexane was added to the composition obtained in Example 22 to prepare a 20 wt % n-hexane solution, which was confirmed to be a homogeneous solution.

[0206] [Production Example 7] Synthesis of N,N-ditetradecyl-2,2,2-trifluoroethylamine 1-Tetradecanal (4.0g, 18.8mmol), 2,2,2-trifluoroethylamine (0.90g, 9.1mmol) and acetic acid (0.3mL) were dissolved in tetrahydrofuran (30mL), sodium triacetoxyborohydride (4.0g, 18.9mmol) was added and stirred at room temperature for 15 hours. The reaction mixture was made basic by adding saturated aqueous sodium bicarbonate solution and extracted with n-hexane. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 100 / 0-95 / 5) to obtain the title compound (4.0g, 89%). 1 H NMR (CDCl3) δ: 0.88 (6H, t), 1.26-1.43 (48H, m), 2.55 (4H, t), 3.00 (2H, q); 19 F NMR (CDCl3) δ: -71.3 (3F, t).

[0207] [Production Example 8] Synthesis of N,N-ditetradecyl-2,2,2-trifluoroethylamine hydrochloride N,N-ditetradecyl-2,2,2-trifluoroethylamine (1.50 g, 3.05 mmol) obtained in Production Example 7 was dissolved in n-hexane (30 mL), and 1.0 M hydrogen chloride-diethyl ether solution (20 mL) was added and stirred for 1 hour. The reaction mixture was concentrated under reduced pressure to obtain the title compound (1.45 g, 90%). 1 H NMR (CDCl3) δ: 0.88 (6H, t), 1.20-1.40 (44H, m), 1.96 (4H, br s), 3.15 (4H, br s), 3.78 (2H, q); 19 F NMR (CDCl3) δ: -63.4 (3F, t).

[0208] [Production Example 9] Synthesis of N,N-ditetradecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate The N,N-ditetradecyl-2,2,2-trifluoroethylamine hydrochloride (0.60 g, 1.14 mmol) obtained in Production Example 8 was dissolved in chloroform (30 mL), and lithium tetrakis(pentafluorophenyl)borate triethyl ether complex (1.04 g, 1.14 mmol) was added and stirred at room temperature for 1 hour. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was dried at 70°C under reduced pressure to obtain the title compound (1.34 g, 100%). 1 H NMR (CDCl3) δ: 0.88 (6H, t), 1.19-1.36 (44H, m), 1.65-1.70 (4H, m), 3.14-3.18 (4H, m), 3.62 (2H, q); 19 F NMR (CDCl3) δ: -66.4 (3F, t), -134.0 (8F, m), -163.4 (4F, t), -167.6 (8F, t).

[0209] [Production Example 10] Synthesis of N,N-dihexadecyl-2,2,2-trifluoroethylamine 1-Hexadecanal (4.0g, 16.6mmol), 2,2,2-trifluoroethylamine (0.84g, 8.5mmol) and acetic acid (0.5mL) were dissolved in tetrahydrofuran (50mL), sodium triacetoxyborohydride (4.0g, 18.9mmol) was added and stirred at room temperature for 15 hours. The reaction mixture was made basic by adding a saturated aqueous solution of sodium bicarbonate and extracted with n-hexane. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 100 / 0-95 / 5) to obtain the title compound (4.56g, 98%). 1 H NMR (CDCl3) δ: 0.88 (6H, t), 1.26-1.43 (56H, m), 2.56 (4H, t), 3.00 (2H, q); 19 F NMR (CDCl3) δ: -71.3 (3F, t).

[0210] [Production Example 11] Synthesis of N,N-dihexadecyl-2,2,2-trifluoroethylamine hydrochloride N,N-dihexadecyl-2,2,2-trifluoroethylamine (1.50 g, 2.74 mmol) obtained in Production Example 10 was dissolved in n-hexane (30 mL), and 1.0 M hydrogen chloride-diethyl ether solution (20 mL) was added and stirred for 1 hour. The reaction mixture was concentrated under reduced pressure to obtain the title compound (1.55 g, 97%). 1 H NMR (CDCl3) δ: 0.88 (6H, t), 1.19-1.40 (52H, m), 1.93 (4H, br s), 3.15 (4H, br s), 3.77 (2H, q); 19 F NMR (CDCl3) δ: -63.4 (3F, t).

[0211] [Production Example 12] Synthesis of N,N-dihexadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate N,N-dihexadecyl-2,2,2-trifluoroethylamine hydrochloride (0.60 g, 1.03 mmol) obtained in Preparation Example 11 was dissolved in chloroform (30 mL), and lithium tetrakis(pentafluorophenyl)borate triethyl ether complex (0.95 g, 1.05 mmol) was added and stirred at room temperature for 1 hour. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was dried at 70°C under reduced pressure to obtain the title compound (1.51 g). 1 H NMR (CDCl3) δ: 0.88 (6H, t), 1.19-1.36 (54H, m), 1.65-1.70 (4H, m), 3.14-3.18 (4H, m), 3.62 (2H, q); 19 F NMR (CDCl3) δ: -66.4 (3F, t), -134.0 (8F, m), -163.4 (4F, t), -167.6 (8F, t).

[0212] [Example 23] The N,N-dihexadecyl-2,2,2-trifluoroethylamine hydrochloride (8.10 g, 13.9 mmol) obtained in Production Example 11 was dissolved in dichloromethane (80 mL), and ditetradecyl ether (8.10 g, 13.9 mmol) and lithium tetrakis(pentafluorophenyl)borate tri-diethyl ether complex (14.2 g, 13.7 mmol) were added and stirred at room temperature for 1 hour. Water was added to the reaction mixture and stirred at room temperature for 1 hour. The aqueous layer was separated and the organic layer was washed with water. The organic layer was dried over anhydrous sodium sulfate, followed by filtration and the filtrate was concentrated under reduced pressure. The residue was dried at 80° C. under reduced pressure to obtain a composition (22.5 g) containing N,N-dihexadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and ditetradecyl ether. 1 H NMR (CDCl3) δ: 0.87-0.89 (12H, m), 1.20-1.80 (104H, m), 3.21-3.24 (4H, m), 3.38-3.41 (4H, m), 3.69 (2H, q); 19 F NMR (CDCl3) δ: -66.7 (3F, brs), -134.0 (8F, m), -163.4 (4F, t), -167.5 (8F, t).

[0213] N-hexane was added to the composition obtained in Example 23 to prepare a 20 wt % n-hexane solution, which was confirmed to be a homogeneous solution.

[0214] [Example 24] The N,N-dihexadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate (439.2 mg, 0.36 mmol) and didodecyl ether (254 mg, 0.72 mmol) obtained in Production Example 12 were mixed, and n-hexane (1.756 g) was added to prepare a uniform n-hexane solution of a composition containing N,N-dihexadecyl-2,2,2-trifluoroethylammonium tetrakis(pentafluorophenyl)borate and didodecyl ether. It was confirmed that the solution was a uniform solution. This solution was concentrated under reduced pressure and analyzed by NMR. 1 H NMR (CDCl3) δ: 0.87-0.91 (12H, m), 1.20-1.42 (100H, m), 1.53-1.69 (12H, m), 3.20-3.24 (4H, m), 3.40 (8H, t), 3.67 (2H, q); 19 F NMR (CDCl3) δ: -66.9 (3F, t), -134.0 (8F, m), -163.8 (4F, t), -167.4 (8F, t).

[0215] [Example 25] Ditetradecyl ether (5.96 g, 14.3 mmol) and lithium tetrakis(pentafluorophenyl)borate bis(ditetradecyl ether) complex (5.00 g, 4.81 mmol) were suspended in dichloroethane (25 mL), 6 M hydrochloric acid (5.5 mL, 30.0 mmol) was added, and the mixture was stirred at room temperature for 2 hours. The organic layer was separated and washed with water (10 mL). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The mixture was dried under reduced pressure at room temperature for 16 hours to obtain a composition (10.4 g) containing hydrogenated tetrakis(pentafluorophenyl)borate bis(ditetradecyl ether) complex and ditetradecyl ether. 1 H NMR (CDCl3) δ: 0.88 (18H, t), 1.20-1.30 (94H, m), 1.56-1.60 (12H, m), 3.57 (12H, t); 19 F NMR (CDCl3) δ: -134.0 (8F, m), -163.8 (4F, t), -167.8 (8F, t).

[0216] N-hexane was added to the composition obtained in Example 25 to prepare a 20 wt % n-hexane solution, which was confirmed to be a homogeneous solution.

[0217] [Comparative Example 1] It was confirmed that the hydrogenated tetrakis(pentafluorophenyl)borate diethyl ether complex obtained by a method known per se (for example, see Organometallics, 2000, 19, 1442-1444) is poorly soluble in aliphatic hydrocarbon solvents such as hexane and cyclohexane. In the test examples described later, the hydrogenated tetrakis(pentafluorophenyl)borate diethyl ether complex was used as the co-catalyst in Comparative Example 1.

[0218] [Comparative Example 2] An attempt was made to prepare a 10 wt% n-hexane solution of N,N-dioctadecylmethylammonium tetrakis(pentafluorophenyl)borate obtained by a method known per se (see, for example, U.S. Patent No. 6,121,185), but no homogeneous solution was obtained. In the test examples described below, N,N-dioctadecylmethylammonium tetrakis(pentafluorophenyl)borate was used as the cocatalyst of Comparative Example 2.

[0219] [Test Example] (Polymerization Performance Evaluation) A typical polymerization method using the composition (complex) of the present invention as a cocatalyst is shown below.

[0220] In a glove box, 1-octene, triisobutylaluminum (TIBA, 0.55M n-hexane solution), and a solvent (methylcyclohexane (MCH) or toluene) were added to a 100 mL autoclave to prepare a comonomer solution. The polymerization catalyst dimethylsilylene(tert-butylamido)-(tetramethylcyclopentadienyl)-titanium(IV)-dichloride (CGC), triisobutylaluminum (0.55M n-hexane solution), and a solvent were added to prepare a catalyst solution of a predetermined concentration, which was then transferred to a Schlenk flask. The composition of the present invention (cocatalyst) was dissolved in a solvent to prepare a cocatalyst solution of a predetermined concentration, which was then transferred to a Schlenk flask. After mixing the comonomer solution, catalyst solution, and cocatalyst solution, the total amount of the solvent and the total amount of triisobutylaluminum were adjusted to be constant. After purging the autoclave with ethylene gas, the catalyst solution and the cocatalyst solution were added to the autoclave in sequence, and the ethylene gas pressure was immediately adjusted to a predetermined pressure and stirred at a predetermined temperature (25°C or 100°C) for a predetermined time. After cooling the reaction mixture on ice and venting the ethylene gas, the mixture was poured into methanol (100mL) containing 3mL of hydrochloric acid and stirred at room temperature for 30 minutes. The precipitate was collected by filtration and dried under reduced pressure at 60°C to obtain an ethylene-octene copolymer.

[0221] Melting Point Determination Differential scanning calorimetry (DSC) measurements were performed using a DSC6220 instrument (Seiko Instruments Inc.) and the sample (polymer) was heated from 40° C. to 150° C. at a rate of 10° C. / min to measure the melting point.

[0222] The results of the polymerization reaction at 25° C. and 100° C. are shown in Tables 1 and 2, respectively.

[0223] [Table 1]

[0224] [Table 2]

[0225] According to Tables 1 and 2, the compositions (or complexes) of the present invention (Examples 2, 3, 5, 10, and 13) were more active than the compound of Comparative Example 2 in the polymerization reaction in methylcyclohexane (MCH), regardless of the polymerization temperature. Also, in the polymerization reaction in toluene, the compositions (or complexes) of the present invention (Examples 3 and 10) were more active than the compound of Comparative Example 1 (Table 1). Furthermore, as shown in Table 1, the compositions (or complexes) of the present invention (Examples 2, 3, 5, 10, and 13) gave polymers with lower melting points than the comparative examples depending on the polymerization conditions, and it is considered that the amount of comonomer incorporated is increased. [Industrial Applicability]

[0226] The composition of the present invention is useful as a cocatalyst for the polymerization of olefins and dienes since it is soluble (or easily soluble) in hydrocarbon solvents, particularly aliphatic hydrocarbon solvents, and does not poison the catalyst.

[0227] This application is based on Japanese Patent Application No. 2020-043244 filed on March 12, 2020, Japanese Patent Application No. 2020-144176 filed on August 28, 2020, and Japanese Patent Application No. 2020-196703 filed on November 27, 2020, the contents of which are incorporated in their entirety herein.

Claims

1. A composition containing a compound represented by the following formula (1) and a compound represented by the following formula (4): 【Chemistry 1】 【Chemistry 2】 [In the formula, R １ , R ２ , R ３ and R ４ all represent a pentafluorophenyl group, a 2,3,4,5,6,7,8-heptafluoro-1-naphthyl group, or a 1,3,4,5,6,7,8-heptafluoro-2-naphthyl group, A ＋ is a hydrogen ion (H ＋ ), or formula (2): 【Chemistry 3】 (In the formula, R ５ teeth, (1) a halogen atom, (2) a C 1-30 alkyl group, (3) a C 1-30 alkoxy group, and (4) haloC 1-30 alkyl group represents a C 6-14 aryl group optionally substituted with a substituent selected from the group consisting of R ６ and R ７ are each independently １－３０ represents an alkyl group, or R 5 is a C 1-30 alkyl group substituted with a C 6-14 aryl group substituted with one or more fluorine atoms, or a C 1-30 alkyl group substituted with one or more fluorine atoms; and R 6 and R 7 are each independently (1) a C 6-14 aryl group optionally substituted by a halogen atom, (2) a halogen atom, and (3) C 1-30 alkoxy group represents a C 1-30 alkyl group which may be substituted with a substituent selected from the group consisting of: R and R′ are each independently (1) a halogen atom, (2) a C 1-30 alkoxy group, and (3) haloC 1-30 alkoxy group C optionally substituted with a substituent selected from the group consisting of １－３０ Alkyl groups; (1) a halogen atom, (2) a C 1-30 alkyl group, (3) a C alkoxy group, (4) haloC 1-30 alkyl groups, and (5) haloC 1-30 alkoxy group C optionally substituted with a substituent selected from the group consisting of ３－１５ a cycloalkyl group; or (1) a halogen atom, (2) a C 1-30 alkyl group, (3) a C alkoxy group, (4) haloC 1-30 alkyl groups, and (5) haloC 1-30 alkoxy group C optionally substituted with a substituent selected from the group consisting of ６－１４ Aryl Group Represents. However, A ＋ is hydrogen ion (H ＋ ), the total number of carbon atoms in R and R′ is 20 or more, and the content of the compound represented by the formula (4) is 2 moles or more relative to 1 mole of the compound represented by the formula (1); A ＋ is a cation represented by formula (2), the total number of carbon atoms in R and R′ is 8 or more.

2. R and R′ are each independently C １－３０ an alkyl group; or (1) a halogen atom, (2) a C 1-30 alkyl group, (3) a C alkoxy group, (4) haloC 1-30 alkyl groups, and (5) haloC 1-30 alkoxy group C optionally substituted with a substituent selected from the group consisting of ６－１４ Aryl Group and The total number of carbon atoms of R and R′ is A ＋ is hydrogen ion (H ＋ ), is 25 or more, A ＋ The composition according to claim 1 , wherein when is a cation represented by formula (2), is 8 or more.

3. A ＋ The composition according to claim 1 or 2, wherein is a hydrogen ion.

4. A ＋ is a cation having a total carbon number of 35 or more and represented by the formula (2), R ５ is substituted with one or more fluorine atoms ６－１４ C substituted with an aryl group １－３０ C substituted with one or more alkyl groups or fluorine atoms １－３０ is an alkyl group, and R ６ and R ７ However, each independently, (1) C optionally substituted with a halogen atom ６－１４ Aryl groups, (2) Halogen atoms and (3) C １－３０ Alkoxy group C optionally substituted with a substituent selected from the group consisting of １－３０ Alkyl group The composition according to claim 1 or 2,

5. A ＋ is a cation having a total carbon number of 35 or more and represented by the formula (2), R ５ But Fluoro C １－６ is an alkyl group, and R ６ and R ７ However, each independently, (1) C optionally substituted with a halogen atom ６－１４ Aryl groups, (2) Halogen atoms and (3) C １－３０ Alkoxy group C optionally substituted with a substituent selected from the group consisting of １－３０ Alkyl group The composition according to claim 1 or 2,

6. R and R' are each independently C 1－３０ The composition of claim 3, wherein the group is an alkyl group.

7. R and R' are each independently C １４－３０ is an alkyl group, and The composition of claim 3, wherein the total number of carbon atoms in R and R' is 28 or more.

8. The composition of claim 3, wherein R and R' are the same group.

9. A ＋ is a cation represented by the formula (2), and R and R′ are each independently C １－３０ The composition according to any one of claims 1, 2, 4, and 5, wherein R and R' are alkyl groups and the total number of carbon atoms in R and R' is 8 or more.

10. The formula (1) (wherein A ＋ is a cation represented by formula (2). The composition according to any one of claims 1, 2, 4, 5, and 9, wherein the content of the compound represented by formula (4) is in the range of 0.01 to 10 moles relative to 1 mole of the compound represented by formula (3).

11. The formula (1) (wherein A ＋ is a cation represented by formula (2). The content of the compound represented by formula (4) is in the range of 0.01 to 3 moles per mole of the compound represented by formula (2).

12. The composition according to any one of claims 1 to 11, having a solubility of 5% by weight or more at 25°C in n-hexane, isohexane, n-heptane, n-octane, cyclohexane, methylcyclohexane, or a mixed solvent thereof.

13. The composition according to any one of claims 1 to 12, which does not contain any ether having a total carbon number of 7 or less.

14. A cocatalyst for the polymerization of at least one monomer selected from the group consisting of olefins and dienes, comprising the composition according to any one of claims 1 to 13.

15. A method for producing a polymer, comprising polymerizing at least one monomer selected from the group consisting of olefins and dienes by using the composition according to any one of claims 1 to 13 as a cocatalyst.

16. A composition containing a compound represented by the following formula (1) and a compound represented by the following formula (4): 【Chemistry 4】 【Chemistry 5】 [In the formula, R １ , R ２ , R ３ and R ４ all represent a pentafluorophenyl group, a 2,3,4,5,6,7,8-heptafluoro-1-naphthyl group, or a 1,3,4,5,6,7,8-heptafluoro-2-naphthyl group, A ＋ is a hydrogen ion (H ＋ ) R and R′ are each independently (1) a halogen atom, (2) a C 1-30 alkoxy group, and (3) haloC 1-30 alkoxy group C optionally substituted with a substituent selected from the group consisting of １－３０ Alkyl groups; (1) a halogen atom, (2) a C 1-30 alkyl group, (3) a C alkoxy group, (4) haloC 1-30 alkyl groups, and (5) haloC 1-30 alkoxy group C optionally substituted with a substituent selected from the group consisting of ３－１５ a cycloalkyl group; or (1) a halogen atom, (2) a C 1-30 alkyl group, (3) a C alkoxy group, (4) haloC 1-30 alkyl groups, and (5) haloC 1-30 alkoxy group C optionally substituted with a substituent selected from the group consisting of ６－１４ Aryl Group and the total number of carbon atoms in R and R′ is 20 or more; and The content of the compound represented by the formula (4) relative to 1 mole of the compound represented by the formula (1) is 2 moles or more. 【Chemistry 6】 [In the formula, R １ , R ２ , R ３ and R ４ has the same meaning as above, R ８ and R ９ are each independently １－６ represents an alkyl group, and R ８ OR ９ The total number of carbon atoms is 7 or less. The compound represented by the following formula (4): 【Chemistry 7】 [In the formula, R and R′ are as defined above.] A production method comprising the step of reacting a compound represented by the formula:

17. R ８ and R ９ The method according to claim 16, wherein both are ethyl groups.

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