New compositions containing borate compounds

Abstract

The present invention aims to provide a composition containing a borate compound that is useful as a co-catalyst for the polymerization of olefins and dienes and is soluble in a hydrocarbon solvent, and a method for producing the same. The present invention relates to a composition comprising: a base A or a compound having a total carbon number of 8 or more represented by the following formula (5) [wherein the symbols are defined as described in the specification]; and a borate compound represented by the following formula (1) [wherein the symbols are defined as described in the specification]. The present invention also relates to a method for producing the aforementioned composition.

Description

Technical Field

[0001] The present invention relates to a composition containing a borate compound and a base, which is useful as a co-catalyst for the polymerization of olefins and dienes, and a method for producing the composition. Background Art

[0002] Conventionally, non-metallocene metal complex catalysts such as metallocene compounds, diimine complexes, and phenoxy complexes have been reported as catalysts for the polymerization of olefins and dienes. In most catalytic 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 superior thermal stability compared to methylaluminoxane and can be used in a smaller stoichiometric ratio relative to the metal complex than methylaluminoxane.

[0003] Furthermore, as solvents used in the polymerization of olefins and dienes using metal complex catalysts, non-polar hydrocarbon solvents are used. In particular, from the perspectives of odor and toxicity, aliphatic hydrocarbon solvents such as hexane are being switched over to aromatic hydrocarbon solvents such as toluene.

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

[0005] In addition, since conventional tetrakis(pentafluorophenyl)borate compounds are poorly soluble in aliphatic hydrocarbon solvents such as hexane and heptane, tetrakis(pentafluorophenyl)borate compounds soluble in aliphatic hydrocarbon solvents have been desired and proposed (Patent Document 2). Dioctadecylmethylammoniumtetrakis(pentafluorophenyl)borate and bis(hydrogenated tallow alkyl)methylammoniumtetrakis(pentafluorophenyl)borate described in Patent Document 2 are useful as compounds readily soluble in hydrocarbon solvents.

[0006] However, the production method described in Patent Document 2 involves reacting lithium tetrakis(pentafluorophenyl)borate with a separately prepared dialkylmethylamine hydrochloride. This method raises concerns that the poorly water-soluble starting materials, lithium tetrakis(pentafluorophenyl)borate or the hydrochloride of a long-chain aliphatic amine, may remain in the product, acting as catalyst poisons and thus failing to exhibit sufficient activity when used as a polymerization co-catalyst. In Example 2 of Patent Document 2, diethyl ether remains in the product, suggesting that a poorly water-soluble diethyl ether complex of lithium tetrakis(pentafluorophenyl)borate may remain.

[0007] Patent Document 3 discloses a method for producing an ammonium tetrakis(pentafluorophenyl)borate derivative by mixing an alkali metal salt of tetrakis(pentafluorophenyl)borate with an amine and then treating the mixture with a protonic acid. However, this method also raises concerns that ether complexes of alkali metal tetrakis(pentafluorophenyl)borate or protonic acid salts of long-chain aliphatic amines may remain in the product and act as catalyst poisons.

[0008] Patent Document 4 discloses a composition containing a trialkylammonium tetrakis(pentafluorophenyl)borate compound and an amine compound, and a method for producing the same. The composition is also disclosed as being soluble in a hydrocarbon solvent. However, the trialkylamine, the amine compound described in Patent Document 4, is highly basic and nucleophilic, leading to concerns that it may act as a catalyst poison in polymerization reactions of olefins and dienes.

[0009] Prior art literature

[0010] Patent Literature

[0011] Patent Document 1: Japanese Patent Application Publication No. 2018-104335

[0012] Patent Document 2: Japanese Patent Application No. 2000-507157

[0013] Patent Document 3: Japanese Patent Application No. 2007-530673

[0014] Patent Document 4: Japanese Patent Application Publication No. 2019-59795 Summary of the Invention

[0015] Problems to be solved by the invention

[0016] In view of these prior arts, the present invention provides a composition containing a borate compound which is soluble in hydrocarbon solvents, particularly aliphatic hydrocarbon solvents, and does not serve as a catalyst poison in the polymerization reaction of olefins and dienes, and a method for its industrial production.

[0017] Solutions for solving problems

[0018] The present inventors have conducted intensive studies and, as a result, have discovered for the first time that a composition (hereinafter also referred to as the "composition of the present invention") is soluble in hydrocarbon solvents, particularly aliphatic hydrocarbon solvents, does not generate a compound that acts as a catalyst poison in the polymerization reaction of olefins and dienes, and is useful as a co-catalyst, thereby completing the present invention. The composition comprises:

[0019] (I) a base A or a compound having a total carbon number of 8 or more represented by the following formula (5); and (II) a compound represented by the following formula (1),

[0020]

[0021] [wherein, R and R' each independently represent an optionally substituted C 1-30 Alkyl, optionally substituted C 3-15 Cycloalkyl or optionally substituted C 6-14 Aryl.]

[0022]

[0023] [Where R 1 、R 2 、R 3 and R 4 Each independently represents one or more fluorine atoms or fluorinated C 1-4 Alkyl substituted C 6-14 Aryl, and

[0024] [AH] + represents a cation derived from base A.

[0025] Here, the aforementioned base A represents:

[0026] (i) Two or more identical or different C 1-30 Alkyl or C 1-30 Alkyloxy-substituted nitrogen-containing aromatic heterocyclic compounds with a total carbon number of 25 or more; or

[0027] (ii) An aromatic amine compound having a total carbon number of 25 or more and represented by the following formula (2).

[0028]

[0029] (wherein Ar represents an optionally substituted C 6-14 Aryl, and

[0030] R 5 and R 6 Each independently represents an optionally substituted C 1-30 alkyl.)]

[0031] That is, the present invention is as follows.

[0032] [1] A composition comprising (I) a base A or a compound having a total carbon number of 8 or more represented by the following formula (5); and (II) a compound represented by the following formula (1),

[0033]

[0034] [wherein, R and R' each independently represent an optionally substituted C 1-30 Alkyl, optionally substituted C 3-15 Cycloalkyl or optionally substituted C 6-14 Aryl.]

[0035]

[0036] [Where R 1 、R 2 、R 3 and R 4 Each independently represents one or more fluorine atoms or fluorinated C 1-4 Alkyl substituted C 6-14 Aryl, and

[0037] [AH] + represents a cation derived from base A.

[0038] Wherein, the aforementioned base A represents:

[0039] (i) Two or more identical or different C 1-30 Alkyl or C 1-30 Alkyloxy-substituted nitrogen-containing aromatic heterocyclic compounds with a total carbon number of 25 or more; or

[0040] (ii) an aromatic amine compound having a total carbon number of 25 or more represented by the following formula (2),

[0041]

[0042] (wherein Ar represents an optionally substituted C 6-14 Aryl, and

[0043] R 5 and R 6 Each independently represents an optionally substituted C 1-30 alkyl.).]

[0044] [2] A composition comprising a base A and a compound represented by the following formula (1),

[0045]

[0046] [Where R 1 、R 2 、R 3 and R 4 Each independently represents one or more fluorine atoms or fluorinated C 1-4 Alkyl substituted C 6-14 Aryl, and

[0047] [AH] + represents a cation derived from base A.

[0048] Here, the aforementioned base A represents:

[0049] (i) Two or more identical or different C 1-30 Alkyl or C 1-30Alkyloxy-substituted nitrogen-containing aromatic heterocyclic compounds with a total carbon number of 25 or more; or

[0050] (ii) an aromatic amine compound having a total carbon number of 25 or more represented by the following formula (2),

[0051]

[0052] (wherein Ar represents an optionally substituted C 6-14 Aryl, and

[0053] R 5 and R 6 Each independently represents an optionally substituted C 1-30 alkyl.).].

[0054] [2'] The composition according to [1] above, wherein component (I) is base A.

[0055] [3] The composition according to [1], wherein the component (I) is a compound represented by the above formula (5).

[0056] [4] The composition according to any one of [1] to [3], wherein R 1 、R 2 、R 3 and R 4 Each is independently substituted by one or more fluorine atoms or trifluoromethyl groups: phenyl, 1-naphthyl, 2-naphthyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 1-anthryl, 2-anthryl, 9-anthryl, 9-phenanthrenyl or 3-phenanthrenyl.

[0057] [5] The composition according to any one of [1] to [3], wherein R 1 、R 2 、R 3 and R 4 All are pentafluorophenyl, 2,2',3,3',4',5,5',6,6'-nonafluoro-4-(1,1'-biphenyl)yl, 2,3,4,5,6,7,8-heptafluoro-1-naphthyl or 1,3,4,5,6,7,8-heptafluoro-2-naphthyl.

[0058] [6] The composition according to any one of [1], [2], [2'], [4] and [5], wherein the base A is 9-30 Alkyl or C 9-30 Alkyloxy-substituted, 5- or 6-membered monocyclic nitrogen-containing aromatic heterocyclic compound having a total carbon number of 35 or more.

[0059] [7] The composition according to [6] above, wherein the 5- or 6-membered monocyclic nitrogen-containing aromatic heterocyclic compound is pyridine or imidazole.

[0060] [8] The composition according to any one of [1], [2], [2'], [4] and [5], wherein the base A is 9-30 Alkyl or C 9-30 Alkyloxy-substituted, bicyclic nitrogen-containing aromatic heterocyclic compound having a total carbon number of 25 or more.

[0061] [9] The composition according to [8] above, wherein the bicyclic nitrogen-containing aromatic heterocyclic compound is benzimidazole.

[0062]

[10] The composition according to any one of [1], [2], [2'], [4] and [5], wherein the base A is an aromatic amine compound having a total carbon number of 25 or more represented by the above formula (2),

[0063] Ar is optionally selected from halogen atoms, C 1-30 Alkyl, C 1-30 Alkoxy and halogenated C 1-6 phenyl substituted with a substituent in the group consisting of an alkyl group, and

[0064] R 5 and R 6 Each independently is C 1-30 alkyl.

[0065]

[11] The composition according to any one of [1], [2], [2′], and [4] to

[10] , wherein the content of the base A is in the range of 0.01 to 10 mol per 1 mol of the compound represented by the formula (1).

[0066]

[12] The composition according to any one of [1] and [3] to [5], wherein R and R' are each independently C 1-30 The total number of carbon atoms in R and R' is 8 or more.

[0067]

[13] The composition according to any one of [1] and [3] to [5], wherein R and R' are each independently C 1-30 The total number of carbon atoms in R and R' is 16 or more.

[0068]

[14] The composition according to any one of [1], [3] to [5],

[12] and

[13] , wherein the content of the compound represented by the formula (5) is in the range of 0.1 to 10 mol per 1 mol of the compound represented by the formula (1).

[0069]

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

[14] above.

[0070]

[16] A method for producing a composition according to any one of [1], [2], [2'] and [4] to

[11] , characterized in that it includes a step of reacting a compound represented by formula (3) with the base A, and using the base A in an amount exceeding 1 mole relative to 1 mole of the compound represented by formula (3).

[0071]

[0072] [Where R 1 、R 2 、R 3 and R 4 Each independently represents one or more fluorine atoms or fluorinated C 1-4 Alkyl substituted C 6-14 Aryl.]

[0073]

[17] The production method according to

[16] , wherein the amount of the base A used is in the range of 1.01 to 3 mol relative to 1 mol of the compound represented by formula (3).

[0074]

[18] A method for producing the composition described in any one of [1], [2], [2'], and [4] to

[11] , comprising the step of reacting a compound represented by formula (4), the base A, and a protonic acid, wherein the base A is used in an amount exceeding 1 mol relative to 1 mol of the compound represented by formula (4).

[0075]

[0076] [Where R 1 、R 2 、R 3 and R 4 Each independently represents one or more fluorine atoms or fluorinated C 1-4 Alkyl substituted C 6-14 Aryl,

[0077] M represents an alkali metal or an alkaline earth metal, and

[0078] n represents 1 or 2. ].

[0079]

[19] A method for producing the composition according to any one of [1], [3] to [5], and

[12] to

[14] , comprising: reacting a compound represented by formula (4), 1 mol of the base A, and a protonic acid relative to 1 mol of the compound represented by formula (4), and then adding a compound represented by formula (5) having 8 or more carbon atoms in an amount of 0.1 mol or more relative to 1 mol of the compound represented by formula (4).

[0080]

[0081] [Where R 1 、R 2 、R 3 and R 4 Each independently represents one or more fluorine atoms or fluorinated C 1-4 Alkyl substituted C 6-14 Aryl,

[0082] M represents an alkali metal or an alkaline earth metal, and

[0083] n represents 1 or 2.]

[0084]

[0085] [wherein, R and R' each independently represent an optionally substituted C 1-30 Alkyl, optionally substituted C 3-15 Cycloalkyl or optionally substituted C 6-14 Aryl. ].

[0086]

[20] A method for producing a polymer, comprising: using the composition described in any one of [1] to

[14] as a co-catalyst to polymerize at least one monomer selected from the group consisting of olefins and dienes.

[0087] Effects of the Invention

[0088] According to the present invention, there can be provided a composition containing the 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 and dienes, and a method for producing the same. DETAILED DESCRIPTION

[0089] The following describes the definitions of terms and symbols used in this specification.

[0090] In this specification, a "halogen atom" means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0091] In this specification, the "alkyl group" refers to a linear or branched alkyl group having 1 or more carbon atoms.

[0092] In this manual, "C 1-30 The term "alkyl (group)" refers to a linear or branched 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.

[0093] In this manual, "C 9-30 The term "alkyl group" refers to a linear or branched alkyl group having 9 to 30 carbon atoms, and examples thereof include nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl, octadecyl, nonadecyl, eicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, and triacontyl.

[0094] In this manual, “C 1-6 The term "alkyl (group)" refers to a linear or branched alkyl group having 1 to 6 carbon atoms, and includes, for example, 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.

[0095] In this specification, "halogenated C 1-6 Alkyl (group)" refers to the aforementioned "C 1-6 "alkyl" group in which one or more hydrogen atoms are substituted by halogen. Specifically, for example, difluoromethyl, trifluoromethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 2,2,3,3-tetrafluoropropyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, 5,5,5-trifluoropentyl, 6,6,6-trifluorohexyl, etc. are mentioned. Among them, "halogenated C 1-4 alkyl".

[0096] In this specification, "fluorinated C 1-6 Alkyl (group)" refers to the aforementioned "halogenated C 1-6The halogen atom in the "alkyl" group is a fluorine atom. Specifically, for example, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 2,2,3,3-tetrafluoropropyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, 5,5,5-trifluoropentyl, 6,6,6-trifluorohexyl, etc. are mentioned. Among them, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 2,2,3,3,3-pentafluoropropyl, 2,2,3,3-tetrafluoropropyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, etc. are preferred. 1-4 The alkyl group is more preferably difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl or pentafluoroethyl, and particularly preferably trifluoromethyl.

[0097] In this specification, "cycloalkyl (group)" refers to a cyclic alkyl group, and when the carbon number range is not particularly limited, it is preferably C 3-8 Cycloalkyl.

[0098] In this manual, “C 3-8 The 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. Among them, C 3-6 Cycloalkyl.

[0099] In the present specification, an "alkoxy (group)" refers to a group in which a linear or branched alkyl group is bonded to an oxygen atom.

[0100] In this manual, “C 1-30 The term "alkoxy (group)" refers to a linear or branched alkoxy group having 1 to 30 carbon atoms, and examples thereof include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, isopentoxy, neopentoxy, hexoxy, isohexoxy, 1,1-dimethylbutoxy, 2,2-dimethylbutoxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, heptoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, hexadecyloxy, octadecyloxy, nonadecyloxy, eicosyloxy, docosyloxy, tricosyloxy, tetracosyloxy, pentacosyloxy, hexacosyloxy, heptacosyloxy, octacosyloxy, nonacosyloxy, and triacosyloxy.

[0101] In this manual, “C 9-30The term "alkoxy (group)" refers to a linear or branched alkoxy group having 9 to 30 carbon atoms, and examples thereof include nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, hexadecyloxy, octadecyloxy, nonadecyloxy, eicosyloxy, docosyloxy, tricosyloxy, tetracosyloxy, pentacosyloxy, hexacosyloxy, heptacosyloxy, octacosyloxy, nonacosyloxy, and triacosyloxy.

[0102] In this manual, “C 1-6 The term "alkoxy (group)" refers to a linear or branched 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. Among these, C 1-4 Alkoxy.

[0103] In this specification, "halogenated C 1-6 Alkoxy (group)" refers to the aforementioned "C 1-6 "alkoxy" group in which one or more hydrogen atoms are substituted by a halogen atom. Specifically, for example, difluoromethoxy, trifluoromethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, 2,2,3,3,3-pentafluoropropoxy, 2,2,3,3-tetrafluoropropoxy, 3,3,3-trifluoropropoxy, 4,4,4-trifluorobutoxy, 5,5,5-trifluoropentyloxy, 6,6,6-trifluorohexyloxy, etc. are mentioned. Among them, "halogenated C 1-4 Alkoxy".

[0104] In this specification, "fluorinated C 1-6 Alkoxy (group)" refers to the aforementioned "halogenated C 1-6 The halogen atom in the "alkoxy" group is a fluorine atom. Specifically, for example, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, 2,2,3,3-tetrafluoropropoxy, 3,3,3-trifluoropropoxy, 4,4,4-trifluorobutoxy, 5,5,5-trifluoropentyloxy, 6,6,6-trifluorohexyloxy, etc. are mentioned. Among them, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, 2,2,3,3,3-pentafluoropropoxy, 2,2,3,3-tetrafluoropropoxy, 3,3,3-trifluoropropoxy, 4,4,4-trifluorobutoxy, etc. are preferred. 1-4 The alkoxy (group)" is more preferably a difluoromethoxy, a trifluoromethoxy, a 2,2,2-trifluoroethoxy, a pentafluoroethoxy or a pentafluoroethoxy, and particularly preferably a trifluoromethoxy.

[0105] In this specification, the term "aryl" refers to a monocyclic or polycyclic (condensed) hydrocarbon group exhibiting aromaticity, and specific examples thereof include phenyl, 1-naphthyl, 2-naphthyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 1-anthracene, 2-anthracene, 9-anthracene, 3-phenanthrene, 9-phenanthrene, and the like. 6-14 Among them, phenyl, 1-naphthyl or 2-naphthyl is preferred.

[0106] In this specification, a "nitrogen-containing aromatic heterocyclic compound" is a monocyclic or condensed polycyclic aromatic heterocyclic compound containing, as ring-constituting atoms, 1 to 4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms in addition to carbon atoms, and refers to a compound containing at least one nitrogen atom as a ring-constituting atom.

[0107] Suitable examples of the "nitrogen-containing aromatic heterocyclic compound" include, for example, 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, triazine, etc.; benzimidazole, benzoxazole, benzisoxazole, benzothiazole, benzisothiazole, benzotriazole, imidazopyridine, thienopyridine, furopyridine, pyrrolopyridine, pyrazolopyridine, oxazole; The present invention also includes 8-14 membered fused polycyclic (preferably 2- or 3-ring) nitrogen-containing aromatic heterocyclic compounds such as pyridine, thiazolopyridine, imidazopyrazine, imidazopyrimidine, thienopyrimidine, furopyrimidine, pyrrolopyrimidine, pyrazolopyrimidine, oxazolopyrimidine, thiazolopyrimidine, pyrazolotriazine, indole, isoindole, 1H-indazole, purine, isoquinoline, quinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, carbazole, β-carboline, phenanthridine, acridine, phenolazine, phenothiazine, and phenoxazine, and preferably 5- or 6-membered monocyclic nitrogen-containing aromatic heterocyclic compounds or 2-ring nitrogen-containing aromatic heterocyclic compounds. As the 5- or 6-membered monocyclic nitrogen-containing aromatic heterocyclic compound, pyridine or imidazole is more preferred, and as the 2-ring nitrogen-containing aromatic heterocyclic compound, benzimidazole is more preferred. Among them, pyridine or imidazole is particularly preferred.

[0108] In the present specification, "optionally substituted" means unsubstituted or having one or more substituents. Examples of the "substituent" include (1) a halogen atom, (2) a nitro group, (3) a cyano group, (4) a C 1-30 Alkyl, (5) halogenated C 1-6 Alkyl, (6)C 3-8 Cycloalkyl, (7)C 1-30 Alkoxy, (8) halogenated C 1-6 Alkoxy, (9)C 6-14 Among them, halogen atoms, cyano groups, C1-6 Alkyl, halogenated C 1-6 Alkyl, C 1-6 Alkoxy, halogenated C 1-6 Alkoxy or phenyl, more preferably a halogen atom (such as a fluorine atom), C 1-6 Alkyl (such as methyl, ethyl), C 1-6 Alkoxy (e.g. methoxy, ethoxy) or halogenated C 1-6 Alkyl (e.g. trifluoromethyl). In addition, when there are multiple substituents, each substituent may be the same or different. In addition, the above substituents may be replaced by one or more C 1-6 Alkyl, C 1-6 It may be substituted by an alkoxy group, a halogen atom, a phenyl group or the like.

[0109] In this specification, the term "hydrocarbon solvent" refers to a solvent including an aromatic hydrocarbon solvent and / or an aliphatic hydrocarbon solvent. Among them, aliphatic hydrocarbon solvents are preferred from the viewpoint of odor and toxicity.

[0110] In this specification, examples of the “aromatic hydrocarbon solvent” include benzene, toluene, and xylene.

[0111] In the present specification, examples of the "aliphatic hydrocarbon solvent" include n-hexane, isohexane, n-heptane, n-octane, cyclohexane, methylcyclohexane, and mixed solvents thereof.

[0112] In this specification, the phrase "soluble in a hydrocarbon solvent (or aliphatic hydrocarbon solvent)" means that the composition of the present invention dissolves at a concentration of 5% by weight or greater in a solution of a hydrocarbon solvent (or aliphatic hydrocarbon solvent) and the composition of the present invention at 25°C, forming a transparent, uniform solution. Furthermore, the phrase "readily soluble in a hydrocarbon solvent (or aliphatic hydrocarbon solvent)" means that the composition of the present invention dissolves at a concentration of 20% by weight or greater (preferably 30% by weight or greater) in a solution of a hydrocarbon solvent (or aliphatic hydrocarbon solvent) and the composition of the present invention at 25°C, forming a transparent, uniform solution.

[0113] (Composition of the present invention)

[0114] Hereinafter, the composition of the present invention will be described.

[0115] The composition of the present invention is a composition comprising: (I) a base A or a compound having a total carbon number of 8 or more represented by the following formula (5); and (II) a compound represented by the following formula (1).

[0116]

[0117] [wherein, R and R' each independently represent an optionally substituted C 1-30 Alkyl, optionally substituted C 3-15 Cycloalkyl or optionally substituted C6-14 Aryl.]

[0118]

[0119] [Where R 1 、R 2 、R 3 and R 4 Each independently represents one or more fluorine atoms or fluorinated C 1-4 Alkyl substituted C 6-14 Aryl, and

[0120] [AH] + represents a cation derived from base A.

[0121] Here, the aforementioned base A represents:

[0122] (i) Two or more identical or different C 1-30 Alkyl or C 1-30 Alkyloxy-substituted nitrogen-containing aromatic heterocyclic compounds with a total carbon number of 25 or more; or

[0123] (ii) An aromatic amine compound having a total carbon number of 25 or more and represented by the following formula (2).

[0124]

[0125] (wherein Ar represents an optionally substituted C 6-14 Aryl, and

[0126] R 5 and R 6 Each independently represents an optionally substituted C 1-30 alkyl.)].

[0127] Preferred embodiments of the base A are described below.

[0128] The nitrogen-containing aromatic heterocyclic compound (i) as the base A is preferably a compound having two identical or different C 9-30 Alkyl or C 9-30 Alkyloxy-substituted, 5- or 6-membered monocyclic nitrogen-containing aromatic heterocyclic compounds (e.g., 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, triazine, etc.), more preferably substituted with the same or different two C 14-30 Alkyl or C 14-30 Alkoxy substituted, pyridine or imidazole.

[0129] The nitrogen-containing aromatic heterocyclic compound preferably has a total carbon number of 25 or more, more preferably a total carbon number of 30 or more, and even more preferably a total carbon number of 35 or more.

[0130] Preferred specific examples of the nitrogen-containing aromatic heterocyclic compound as the base A include 2,5-dionadecylpyridine, 2,6-dionadecylpyridine, 2-nonadecyl-5-octadecylpyridine, 2-nonadecyl-4-octadecyloxypyridine, 2-nonadecyl-6-octadecyloxypyridine, 4-nonadecyl-1-octadecylimidazole, 5-nonadecyl-1-octadecylimidazole, and 2-nonadecyl-1-octadecylimidazole.

[0131] Another preferred nitrogen-containing aromatic heterocyclic compound as the base A (i) includes: 9-30 Alkyl or C 9-30 Alkyloxy-substituted, bicyclic nitrogen-containing aromatic heterocyclic compounds (e.g., benzimidazole, benzoxazole, benzisoxazole, benzothiazole, benzisothiazole, benzotriazole, imidazopyridine, thienopyridine, furopyridine, pyrrolopyridine, pyrazolopyridine, oxazolopyridine, thiazolopyridine, imidazopyrazine, imidazopyrimidine, thienopyrimidine, furopyrimidine, pyrrolopyrimidine, pyrazolopyrimidine, oxazolopyrimidine, thiazolopyrimidine, pyrazolotriazine, indole, isoindole, 1H-indazole, purine, isoquinoline, quinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, etc.), wherein the alkyl group is preferably replaced by two identical or different C 9-30 Alkyl or C 9-30 Alkoxy (more preferably C 14-30 Alkyl or C 14-30 alkoxy) substituted benzimidazole.

[0132] The nitrogen-containing aromatic heterocyclic compound preferably has a total carbon number of 25 or more, more preferably a total carbon number of 30 or more, and even more preferably a total carbon number of 35 or more.

[0133] Specific examples of another preferred nitrogen-containing aromatic heterocyclic compound as the base A include 2,6-dinonadecylbenzimidazole, 1,2-dioctadecylbenzimidazole, 1,2-diheptadecylbenzimidazole, 2-heptadecyl-1-octadecylbenzimidazole, and 1-heptadecyl-2-octadecylbenzimidazole.

[0134] (ii) an aromatic amine compound represented by formula (2) (hereinafter also referred to as "compound (2)") as base A,

[0135] Ar in the above formula (2) is preferably optionally selected from halogen atoms, cyano groups, C 1-30 Alkyl, halogenated C 1-6 Alkyl, C 1-30Alkoxy and halogenated C 1-6 The substituents in the group consisting of alkoxy groups are substituted with C 6-14 Aryl, more preferably optionally selected from halogen atoms, C 1-30 Alkyl, C 1-30 Alkoxy and halogenated C 1-6 substituted with a substituent selected from the group consisting of alkyl, phenyl, 1-naphthyl or 2-naphthyl (particularly preferably phenyl). In addition, another preferred embodiment of Ar is optionally selected from halogen atoms, C 1-6 Alkyl, C 1-6 Alkoxy and halogenated C 1-6 The substituents in the group consisting of alkyl are substituted with phenyl.

[0136] The total carbon number of compound (2) is preferably 30 or more, more preferably 35 or more.

[0137] R in the above formula (2) 5 and R 6 Preferably, each independently is C optionally substituted by a halogen atom (such as a fluorine atom). 1-30 Alkyl, more preferably each independently C 1-30 Alkyl, more preferably C 9-30 Alkyl, particularly preferably the same C 14-30 alkyl.

[0138] Examples of suitable compounds (2) include the following compounds.

[0139] [Compound (2-1)]

[0140] A compound (2), wherein the

[0141] Ar is optionally selected from halogen atoms, cyano groups, C 1-30 Alkyl, halogenated C 1-6 Alkyl, C 1-30 Alkoxy and halogenated C 1-6 The substituents in the group consisting of alkoxy groups are substituted with C 6-14 Aryl,

[0142] R 5 and R 6 are each independently C optionally substituted by a halogen atom (such as a fluorine atom) 1-30 alkyl, and

[0143] The total carbon number is 25 or more (preferably 30 or more).

[0144] [Compound (2-2)]

[0145] A compound (2), wherein the

[0146] Ar is optionally selected from halogen atoms, C 1-30 Alkyl, C 1-30 Alkoxy and halogenated C 1-6 The following groups substituted by substituents in the group consisting of alkyl: phenyl, 1-naphthyl or 2-naphthyl (preferably phenyl),

[0147] R 5 and R 6 Each independently is C 1-30 alkyl, and

[0148] The total carbon number is 35 or more.

[0149] [Compound (2-3)]

[0150] A compound (2), wherein the

[0151] Ar is phenyl,

[0152] R 5 and R 6 For the same C 14-30 alkyl, and

[0153] The total carbon number is 35 or more.

[0154] Preferred specific examples of the compound (2) include N,N-dihexadecylaniline, N,N-dioctadecylaniline, and N,N-dibehenylaniline.

[0155] As the base A, a commercially available product may be used as it is, or a compound obtained by the production method shown below may be used.

[0156] (Method for producing base A (compound (2)))

[0157] Compound (2) can be prepared as shown in the following formula by reacting an aniline derivative (a1) with a haloalkyl group (R 5 -X and R 6 -X) are produced by sequential reactions.

[0158]

[0159] (In the formula, X represents a halogen atom, and the definitions of other symbols are the same as above.)

[0160] R 5 With R 6 When they are the same group, compound (2) can be produced from aniline derivative (a1) in one step.

[0161] Haloalkyl (R 5 -X or R6 -X) is used in an amount of 1 to 2 mol (preferably 1 to 1.2 mol) based on 1 mol of the aniline derivative ((a1) or (a2)).

[0162] R 5 With R 6 When they are the same group, the amount of the haloalkyl group used is 2 to 4 moles (preferably 2 to 3 moles) based on 1 mole of the aniline derivative (a1).

[0163] The reaction solvent is not particularly limited, but examples thereof include ether solvents such as tetrahydrofuran and diethoxyethane, toluene, dimethylformamide, and dimethyl sulfoxide.

[0164] Examples of the base include sodium hydride, potassium carbonate, potassium tert-butoxide, etc. The amount of the base used is 1 to 2 mol (preferably 1 to 1.2 mol) per 1 mol of the aniline derivative ((a1) or (a2)).

[0165] The reaction temperature is preferably room temperature to 180°C.

[0166] The reaction time is usually 1 to 48 hours.

[0167] (base A(with two or more C 1-30 Alkyl or C 1-30 Method for producing an alkoxy-substituted nitrogen-containing aromatic heterocyclic compound having a total carbon number of 25 or more

[0168] The nitrogen-containing aromatic heterocyclic compound having a total carbon number of 25 or more can be prepared as shown in the following formula by reacting a phosphonium salt (R 7 -CH2PPh3X') is reacted with compound (a3) ​​to obtain compound (a4) (step 1), and then reacted with a reducing agent (step 2) to produce base (A2).

[0169]

[0170] (Where, formula: The group shown represents a nitrogen-containing aromatic heterocyclic group, X' represents a halogen atom, R 7 represents an optionally substituted C 1-30 alkyl, n1 represents an integer greater than 2.)

[0171] In the above-mentioned step 1, examples of the base used include sodium hydride, potassium carbonate, potassium tert-butoxide, and the like.

[0172] The amount of the base to be used is 1 to 2 mol (preferably 1 to 1.2 mol) relative to the equivalent amount (1 mol) of the formyl group of compound (a3).

[0173] The phosphonium salt (R 7 -CH2PPh3X') is also used in an amount of 1 to 2 moles (preferably 1 to 1.2 moles).

[0174] The reaction solvent in step 1 is not particularly limited, and examples thereof include ether solvents such as tetrahydrofuran and diethoxyethane, aromatic hydrocarbon solvents such as toluene, aliphatic hydrocarbon solvents such as hexane, dimethylformamide, and dimethyl sulfoxide.

[0175] The reaction temperature in step 1 is preferably room temperature to 180°C.

[0176] The reaction time of step 1 is usually 0.5 to 48 hours.

[0177] In the above step 2, as the reducing agent, for example, hydrogen, ammonium formate, ammonium chloride, etc. can be used in the presence of a metal catalyst. As the metal catalyst, a transition metal catalyst such as Pd / C or Pt / C is preferred.

[0178] The amount of the metal catalyst used is 0.001 to 1.0 mol (preferably 0.01 to 0.5 mol) per 1 mol of the double bonds in the compound (a4).

[0179] The reaction solvent in step 2 is not particularly limited, and for example, hexane, toluene, tetrahydrofuran, ethanol, etc. are preferred, and a mixed solvent thereof can be used.

[0180] The reduction reaction in step 2 can be carried out under conditions such as normal pressure or medium pressure, as appropriate depending on the progress of the reaction.

[0181] The reaction temperature in step 2 is preferably room temperature to 180°C.

[0182] The reaction time of step 2 is usually 1 to 72 hours.

[0183] Preferred embodiments of the compound represented by the above formula (5) (hereinafter also referred to as "compound (5)") will be described below.

[0184] Hereinafter, each group of compound (5) will be described.

[0185] The total number of carbon atoms in R and R' is 8 or more, preferably 16 or more. The total number of carbon atoms in R and R' may be 20 or more, 25 or more, or 28 or more. The total number of carbon atoms in R and R' is preferably 32 or less.

[0186] R and R' are each independently an optionally substituted C 1-30 Alkyl, optionally substituted C 3-15 Cycloalkyl or optionally substituted C 6-14Aryl, preferably each independently a C 1-30 alkyl:

[0187] (1) Halogen atoms,

[0188] (2)C 1-30 Alkoxy, and

[0189] (3) Halogenated C 1-30 alkoxy;

[0190] C optionally substituted by a substituent selected from the group consisting of 3-15 Cycloalkyl:

[0191] (1) Halogen atoms,

[0192] (2)C 1-30 alkyl,

[0193] (3)C 1-30 Alkoxy,

[0194] (4) Halogenated C 1-30 Alkyl, and

[0195] (5) Halogenated C 1-30 alkoxy;

[0196] or C optionally substituted by a substituent selected from the group consisting of 6-14 Aryl,

[0197] (1) Halogen atoms,

[0198] (2)C 1-30 alkyl,

[0199] (3)C 1-30 Alkoxy,

[0200] (4) Halogenated C 1-30 Alkyl, and

[0201] (5) Halogenated C 1-30 Alkoxy,

[0202] More preferably, each independently is C 1-30 Alkyl; C 3-8 cycloalkyl (e.g., cyclopentyl, cyclohexyl, etc.); or phenyl optionally substituted by a substituent selected from the group consisting of:

[0203] (1) Halogen atoms,

[0204] (2)C 1-6 alkyl,

[0205] (3)C 1-6 Alkoxy,

[0206] (4) Halogenated C 1-6 Alkyl, and

[0207] (5) Halogenated C 1-6 Alkoxy

[0208] More preferably, each independently is C 1-30 Alkyl (preferably methyl, butyl, hexyl, octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, etc.) 1-18 alkyl), particularly preferably each independently C 14-30 alkyl.

[0209] Suitable compounds (5) include the following compounds.

[0210] [Compound (5-1)]

[0211] A compound (5), wherein the

[0212] R and R' are each independently C 1-30 alkyl, and

[0213] The total number of carbon atoms in R and R' is 8 or more.

[0214] [Compound (5-2)]

[0215] A compound (5), wherein the

[0216] R and R' are each independently C 1-30 alkyl, and

[0217] The total number of carbon atoms in R and R' is 10 or more.

[0218] [Compound (5-3)]

[0219] A compound (5), wherein the

[0220] R and R' are each independently C optionally substituted with a substituent selected from the group consisting of the following groups 1-30 alkyl:

[0221] (1) Halogen atoms,

[0222] (2)C 1-30 Alkoxy, and

[0223] (3) Halogenated C 1-30 alkoxy;

[0224] C optionally substituted by a substituent selected from the group consisting of 3-15 Cycloalkyl:

[0225] (1) Halogen atoms,

[0226] (2)C 1-30 alkyl,

[0227] (3)C 1-30 Alkoxy,

[0228] (4) Halogenated C 1-30 Alkyl, and

[0229] (5) Halogenated C 1-30 alkoxy;

[0230] or C optionally substituted by a substituent selected from the group consisting of 6-14 Aryl:

[0231] (1) Halogen atoms,

[0232] (2)C 1-30 alkyl,

[0233] (3)C 1-30 Alkoxy,

[0234] (4) Halogenated C 1-30 Alkyl, and

[0235] (5) Halogenated C 1-30 alkoxy, and

[0236] The total number of carbon atoms in R and R' is 16 or more.

[0237] [Compound (5-4)]

[0238] A compound (5), wherein the

[0239] R and R' are each independently C 1-30 an alkyl group, or a C 6-14 Aryl:

[0240] (1) Halogen atoms,

[0241] (2)C 1-30 alkyl,

[0242] (3)C 1-30 Alkoxy,

[0243] (4) Halogenated C 1-30 Alkyl, and

[0244] (5) Halogenated C 1-30 alkoxy, and

[0245] The total number of carbon atoms in R and R' is 16 or more.

[0246] [Compound (5-5)]

[0247] A compound (5), wherein the

[0248] R and R' are each independently C 1-30 Alkyl, C 3-8 Cycloalkyl (e.g., cyclopentyl, cyclohexyl, etc.), or phenyl optionally substituted by a substituent selected from the group consisting of:

[0249] (1) Halogen atoms,

[0250] (2)C 1-6 alkyl,

[0251] (3)C 1-6 Alkoxy,

[0252] (4) Halogenated C 1-6 Alkyl, and

[0253] (5) Halogenated C 1-6 alkoxy, and

[0254] The total number of carbon atoms in R and R' is 16 or more.

[0255] [Compound (5-6)]

[0256] A compound (5), wherein the

[0257] R and R' are each independently C 1-30 alkyl, and

[0258] The total number of carbon atoms in R and R' is 16 or more.

[0259] Preferred specific examples of compound (5) include dibutyl ether, dihexyl ether, dioctyl ether, didecyl ether, didodecyl ether, ditetradecyl ether, dihexadecyl ether, distearyl ether, behenyl ethyl ether, tetradecyloxyethyltetradecyl ether, cyclopentyl methyl ether, diphenyl ether, and octadecylphenyl ether. Among them, dibutyl ether, dihexyl ether, dioctyl ether, didecyl ether, didodecyl ether, ditetradecyl ether, dihexadecyl ether, distearyl ether, and dinonadecyl ether are more preferred. R and R' are each independently C 1-30 The compound (5) wherein the total carbon number of R and R' is 8 or more is more preferably ditetradecyl ether, dihexadecyl ether, dioctadecyl ether, dinonadecyl ether, etc., wherein R and R' are each independently C 14-30 A compound (5) in which the total carbon number of R and R' is 16 or more and 32 or less.

[0260] The compound (5) in which the total carbon number of R and R' is 7 or less has a low boiling point, and therefore, there is a concern that it may be difficult to control its content industrially and may become a catalyst poison, and therefore is not preferred.

[0261] Preferred embodiments of the compound represented by formula (1) (hereinafter also referred to as "compound (1)") are described below.

[0262] Hereinafter, each group of compound (1) will be described.

[0263] R 1 、R 2 、R 3 and R 4 Preferably, each independently is substituted with one or more fluorine atoms or fluorinated C 1-4 The following groups substituted with an alkyl group (e.g., trifluoromethyl): phenyl, 1-naphthyl, 2-naphthyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 1-anthryl, 2-anthryl, 9-anthryl, 3-phenanthrenyl or 9-phenanthrenyl, more preferably each independently substituted with one or more fluorine atoms or trifluoromethyl groups: phenyl, 1-naphthyl or 2-naphthyl, particularly preferably R 1 、R 2 、R 3 and R 4 All are the same and are pentafluorophenyl, 2,2',3,3',4',5,5',6,6'-nonafluoro-4-(1,1'-biphenyl)yl, 2,3,4,5,6,7,8-heptafluoro-1-naphthyl or 1,3,4,5,6,7,8-heptafluoro-2-naphthyl.

[0264] [AH] as a cation derived from base A + Preferred aspects of A in are the same as those described above.

[0265] Examples of suitable compounds (1) include the following compounds.

[0266] [Compound (1-1)]

[0267] A compound (1), wherein the

[0268] R 1 、R 2 、R 3 and R 4 Each independently is substituted with one or more fluorine atoms or fluorinated C 1-4 the following groups substituted with alkyl groups (e.g. trifluoromethyl): phenyl, 1-naphthyl, 2-naphthyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 1-anthryl, 2-anthryl, 9-anthryl, 3-phenanthrenyl or 9-phenanthrenyl,

[0269] A is represented by the above formula (2), where

[0270] Ar is optionally selected from halogen atoms, cyano groups, C 1-30 Alkyl, halogenated C 1-6 Alkyl, C 1-30 Alkoxy and halogenated C 1-6 The substituents in the group consisting of alkoxy groups are substituted with C 6-14 Aryl,

[0271] R 5 and R 6 are each independently C optionally substituted by a halogen atom (such as a fluorine atom) 1-30 alkyl, and

[0272] The total carbon number is 25 or more (preferably 30 or more).

[0273] [Compound (1-2)]

[0274] A compound (1), wherein the

[0275] R 1 、R 2 、R 3 and R 4 Each independently represents the following groups substituted by one or more fluorine atoms or trifluoromethyl groups: phenyl, 1-naphthyl or 2-naphthyl,

[0276] A is represented by the above formula (2), where

[0277] Ar is optionally selected from halogen atoms, C 1-30 Alkyl, C 1-30 Alkoxy and halogenated C 1-6 The following groups substituted by substituents in the group consisting of alkyl: phenyl, 1-naphthyl or 2-naphthyl (preferably phenyl), R 5 and R 6 Each independently is C 1-30 alkyl, and

[0278] The total carbon number is 35 or more.

[0279] [Compound (1-3)]

[0280] A compound (1), wherein R in the above formula (1) 1 、R 2 、R 3 and R 4 All are the same, pentafluorophenyl, 2,2',3,3',4',5,5',6,6'-nonafluoro-4-(1,1'-biphenyl)yl, 2,3,4,5,6,7,8-heptafluoro-1-naphthyl or 1,3,4,5,6,7,8-heptafluoro-2-naphthyl,

[0281] A is represented by the above formula (2), where

[0282] Ar is phenyl,

[0283] R 5 and R 6 For the same C 14-30 alkyl, and

[0284] The total carbon number is 35 or more.

[0285] [Compound (1-4)]

[0286] A compound (1), wherein the

[0287] R 1 、R 2 、R 3 and R 4 Each independently is substituted with one or more fluorine atoms or fluorinated C 1-4 the following groups substituted with an alkyl group (e.g., trifluoromethyl): phenyl, 1-naphthyl, 2-naphthyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 1-anthryl, 2-anthryl, 9-anthryl, 3-phenanthrenyl, or 9-phenanthrenyl,

[0288] A is replaced by two or more identical or different C 9-30 Alkyl or C 9-30 Alkyloxy-substituted, 5- or 6-membered monocyclic nitrogen-containing aromatic heterocyclic compounds (e.g., 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, triazine, etc.), and

[0289] The total carbon number is 25 or more (preferably 30 or more).

[0290] [Compound (1-5)]

[0291] A compound (1), wherein the

[0292] R 1 、R 2 、R 3 and R 4 Each is independently the following group substituted with one or more fluorine atoms or trifluoromethyl groups: phenyl, 1-naphthyl or 2-naphthyl,

[0293] A is the same or different 2 C 14-30 Alkyl or C 14-30Alkoxy-substituted, pyridine or imidazole (preferably 2,5-dionadecylpyridine, 2,6-dionadecylpyridine, 2-nonadecyl-5-octadecylpyridine, 2-nonadecyl-4-octadecyloxypyridine, 2-nonadecyl-6-octadecyloxypyridine, 4-nonadecyl-1-octadecylimidazole, 5-nonadecyl-1-octadecylimidazole, or 2-nonadecyl-1-octadecylimidazole), and

[0294] The total carbon number is 35 or more.

[0295] [Compound (1-6)]

[0296] A compound (1), wherein R in the above formula (1) 1 、R 2 、R 3 and R 4 All are the same, pentafluorophenyl, 2,2',3,3',4',5,5',6,6'-nonafluoro-4-(1,1'-biphenyl)yl, 2,3,4,5,6,7,8-heptafluoro-1-naphthyl or 1,3,4,5,6,7,8-heptafluoro-2-naphthyl (preferably pentafluorophenyl),

[0297] A is the same or different 2 C 14-30 Alkyl or C 14-30 an alkoxy-substituted pyridine (preferably 2,5-dionadecylpyridine, 2,6-dionadecylpyridine, 2-nonadecyl-5-octadecylpyridine, 2-nonadecyl-4-octadecyloxypyridine or 2-nonadecyl-6-octadecyloxypyridine), and

[0298] The total carbon number is 35 or more.

[0299] [Compound (1-7)]

[0300] A compound (1), wherein the

[0301] R 1 、R 2 、R 3 and R 4 Each independently is substituted with one or more fluorine atoms or fluorinated C 1-4 the following groups substituted with an alkyl group (e.g., trifluoromethyl): phenyl, 1-naphthyl, 2-naphthyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 1-anthryl, 2-anthryl, 9-anthryl, 3-phenanthrenyl, or 9-phenanthrenyl,

[0302] A is replaced by two or more identical or different C 9-30 Alkyl or C 9-30Alkyloxy-substituted, bicyclic nitrogen-containing aromatic heterocyclic compounds (e.g., benzimidazole, benzoxazole, benzisoxazole, benzothiazole, benzisothiazole, benzotriazole, imidazopyridine, thienopyridine, furopyridine, pyrrolopyridine, pyrazolopyridine, oxazolopyridine, thiazolopyridine, imidazopyrazine, imidazopyrimidine, thienopyrimidine, furopyrimidine, pyrrolopyrimidine, pyrazolopyrimidine, oxazolopyrimidine, thiazolopyrimidine, pyrazolotriazine, indole, isoindole, 1H-indazole, purine, isoquinoline, quinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, etc.), and

[0303] The total carbon number is 25 or more (preferably 30 or more).

[0304] [Compound (1-8)]

[0305] A compound (1), wherein the

[0306] R 1 、R 2 、R 3 and R 4 Each is independently the following group substituted with one or more fluorine atoms or trifluoromethyl groups: phenyl, 1-naphthyl or 2-naphthyl,

[0307] A is the same or different 2 C 14-30 Alkyl or C 14-30 Alkoxy-substituted benzimidazole (preferably 2,6-dinonadecylbenzimidazole, 1,2-dioctadecylbenzimidazole, 1,2-diheptadecylbenzimidazole, 2-heptadecyl-1-octadecylbenzimidazole or 1-heptadecyl-2-octadecylbenzimidazole), and

[0308] The total carbon number is 35 or more.

[0309] [Compound (1-9)]

[0310] A compound (1), wherein R in the above formula (1) 1 、R 2 、R 3 and R 4 All are the same, pentafluorophenyl, 2,2',3,3',4',5,5',6,6'-nonafluoro-4-(1,1'-biphenyl)yl, 2,3,4,5,6,7,8-heptafluoro-1-naphthyl or 1,3,4,5,6,7,8-heptafluoro-2-naphthyl (preferably pentafluorophenyl),

[0311] A is the same or different 2 C 14-30 Alkyl or C 14-30Alkoxy-substituted benzimidazole (preferably 2,6-dinonadecylbenzimidazole, 1,2-dioctadecylbenzimidazole, 1,2-diheptadecylbenzimidazole, 2-heptadecyl-1-octadecylbenzimidazole or 1-heptadecyl-2-octadecylbenzimidazole), and

[0312] The total carbon number is 35 or more.

[0313] Preferred specific examples of compound (1) include N,N-dioctadecylanilinium tetrakis(pentafluorophenyl)borate, 2,6-dinonadecypyridinium tetrakis(pentafluorophenyl)borate, 2-nonadecy-5-octadecyloxypyridinium tetrakis(pentafluorophenyl)borate, 4-nonadecy-1-octadecylimidazolium tetrakis(pentafluorophenyl)borate, 5-nonadecy-1-octadecylimidazolium tetrakis(pentafluorophenyl)borate, 2-nonadecy-1-octadecylimidazolium tetrakis(pentafluorophenyl)borate, 1-heptadecy-2-octadecylbenzimidazolium tetrakis(pentafluorophenyl)borate, and 2-heptadecy-1-octadecylbenzimidazolium tetrakis(pentafluorophenyl)borate.

[0314] Another preferred specific example of compound (1) includes, for example, 2,6-dinonadecylbenzimidazolium tetrakis(pentafluorophenyl)borate, 1,2-dioctadecylbenzimidazolium tetrakis(pentafluorophenyl)borate, 1,2-diheptadecylbenzimidazolium tetrakis(pentafluorophenyl)borate, 2-heptadecyl-1-octadecylbenzimidazolium tetrakis(pentafluorophenyl)borate, 1-heptadecyl-2-octadecylbenzimidazolium tetrakis(pentafluorophenyl)borate, and 2-heptadecyl-1-octadecylbenzimidazolium tetrakis(pentafluorophenyl)borate.

[0315] In the composition of the present invention, it is preferred that the base A and [AH] + The same as A. In addition, [AH] + A preferred embodiment of the present invention includes cations obtained by adding protons to the preferred embodiments of the above-mentioned base A.

[0316] In the composition of the present invention, the content of the base A is usually 0.01 to 10 mol, preferably 0.01 to 2 mol, more preferably 0.01 to 1 mol, particularly preferably 0.01 to 0.5 mol, based on 1 mol of compound (1).

[0317] In the composition of the present invention, the blending ratio of compound (5) to compound (1) is not particularly limited. However, from the viewpoint of improving solubility in aliphatic hydrocarbon solvents, the content of compound (5) is 0.1 mol or more, preferably in the range of 0.1 to 10 mol, and more preferably in the range of 0.1 to 3 mol, relative to 1 mol of compound (1).

[0318] The composition of the present invention is soluble in hydrocarbon solvents at room temperature (15-30°C). Furthermore, while conventional borate-type cocatalysts are insoluble in aliphatic hydrocarbon solvents such as n-hexane, the composition of the present invention exhibits good solubility in aliphatic hydrocarbon solvents, making it useful as a cocatalyst for the polymerization of homogeneous olefins and dienes.

[0319] (Method for producing the composition of the present invention)

[0320] Hereinafter, the method for producing the composition of the present invention (hereinafter also referred to as "the production method of the present invention") will be described.

[0321] The composition of the present invention preferably does not contain a hydroborate compound represented by formula (3) described later (e.g., hydrotetrakis(pentafluorophenyl)borate) which forms a complex with an ether compound having a total carbon number of 7 or less and thus becomes a catalyst poison, or a metal salt of a tetrasubstituted borate compound described later (e.g., lithium tetrakis(pentafluorophenyl)borate). In addition, the composition of the present invention preferably does not contain an ether compound having a total carbon number of 7 or less which may become a catalyst poison. Not containing an ether compound having a total carbon number of 7 or less means 1 As a result of H-NMR analysis, no ether compound having a total carbon number of 7 or less was detected.

[0322] The production method of the present invention (hereinafter also referred to as "production method 1 of the present invention") is characterized in that it includes a step of reacting a hydroborate compound represented by the following formula (3) (hereinafter also referred to as "compound (3)") with the aforementioned base A, and the base A is used in an amount exceeding 1 mol relative to 1 mol of compound (3).

[0323]

[0324] [R in the formula 1 、R 2 、R 3 and R 4 has the same meaning as above.]

[0325] In the above-mentioned production method, examples of the compound (3) used as a raw material include known compounds such as hydrogenated tetrakis(pentafluorophenyl)borate, hydrogenated tetrakis(nonafluoro[1,1'-biphenyl]-4-yl)borate, hydrogenated tetrakis(heptafluoro-2-naphthyl)borate, and hydrogenated [3,5-bis(trifluoromethyl)phenyl]borate.

[0326] The method for producing compound (3) is not particularly limited, and examples thereof include a method of treating a compound represented by formula (4) (hereinafter also referred to as "compound (4)") with a protonic acid.

[0327]

[0328] [Where R 1 、R 2 、R 3 and R 4 Each independently represents one or more fluorine atoms or fluorinated C 1-4 Alkyl substituted C 6-14 Aryl,

[0329] M represents an alkali metal such as lithium, potassium, or sodium, or an alkaline earth metal such as calcium, magnesium, or barium, and

[0330] n represents 1 or 2. ].

[0331] The compound (4) used in the production of compound (3) may be a commercially available product, a purified product, or one prepared by a known method (e.g., see Angew. Chem. Int. Ed., 2009, 48(40), 7444-7447).

[0332] The solvent used in the production of compound (3) is not particularly limited, but preferably used are ether solvents such as diethyl ether, tert-butyl methyl ether, cyclopentyl methyl ether, diisopropyl ether, halogen solvents such as dichloromethane and chloroform, aromatic hydrocarbon solvents such as toluene and benzene, and aliphatic hydrocarbon solvents such as n-hexane, isohexane, n-heptane, octane, cyclohexane, and methylcyclohexane. These solvents may be used alone or in combination.

[0333] The protonic acid used when treating compound (4) is not particularly limited, and examples thereof include hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, and hydroiodic acid.

[0334] The amount of the protonic acid used in the production of compound (3) is preferably 1 mol relative to 1 mol of compound (4). When 1 mol or more of the protonic acid is used, the organic phase is preferably washed with water until the pH of the aqueous phase after washing is 3 or higher, so that the protonic acid does not remain in the treated organic phase. If the pH of the aqueous phase is less than 3, there is a concern that the protonic acid salt used may remain in the organic phase, and in the reaction with base A, a protonic acid salt of base A may be generated and remain in the composition of the present invention, thereby becoming a catalyst poison during polymerization.

[0335] In the production method 1 of the present invention, the solution of compound (3) prepared as described above can be used directly for the reaction with base A.

[0336] Examples of the base A used in the production method 1 of the present invention include the aforementioned compounds having a total carbon number of 25 or more (preferably 30 or more, more preferably 35 or more). Specific examples of the base A include nitrogen-containing aromatic heterocyclic compounds such as 2,5-dionadecylpyridine, 2,6-dionadecylpyridine, 2-nonadecyl-5-octadecylpyridine, 2-nonadecyl-4-octadecyloxypyridine, 2-nonadecyl-6-octadecyloxypyridine, 4-nonadecyl-1-octadecylimidazole, 5-nonadecyl-1-octadecylimidazole, and 2-nonadecyl-1-octadecylimidazole; and aromatic amine compounds such as N,N-dihexadecylaniline, N,N-dioctadecylaniline, N,N-dinonadecylaniline, and N,N-didocosylaniline.

[0337] wherein, by combining compound (3) with a C 9-30 Alkyl (preferably C 14-30 Alkyl) or C 9-30 Alkoxy (preferably C 14-30 The composition containing the base A and the compound (1) obtained by the reaction of the base A with an alkoxy group is also soluble in an aliphatic hydrocarbon solvent.

[0338] In the production method 1 of the present invention, the base A is used in an amount exceeding 1 mol relative to 1 mol of the compound (3). This can suppress the unreacted compound (3) from remaining in the composition as the product. The amount of the base A used relative to 1 mol of the compound (3) is in the range of 1.01 to 5.0 mol, preferably in the range of 1.01 to 2.0 mol, and particularly preferably in the range of 1.01 to 1.5 mol. When the amount of the base A is 1.0 mol or less, an ether solvent having a total carbon number of 7 or less (i.e., an ether compound) or compound (3) with added water may remain in the composition as the product. When used as a polymerization co-catalyst, there is a concern that the ether compound having a total carbon number of 7 or less or compound (3) with added water may act as a catalyst poison. In addition, when the amount of the base A used is 1 mol relative to the compound (3), the solubility of the composition of the present invention in an aliphatic hydrocarbon solvent is reduced.

[0339] The reaction temperature and time in the production method 1 of the present invention are not particularly limited. The reaction temperature is usually 10°C to 40°C, preferably 10°C to 35°C, more preferably room temperature (15°C to 30°C), and the reaction time is 10 minutes or longer.

[0340] After the reaction of compound (3) and base A is completed, the reaction solution is dehydrated with a drying agent such as anhydrous sodium sulfate or anhydrous magnesium sulfate, and the solvent is removed to obtain a composition containing base A and compound (1).

[0341] Alternatively, as another method, after the reaction of compound (3) and base A is completed, a solution of a composition containing base A and compound (1) can be obtained by distilling off a portion of the reaction solvent, or by performing solvent dilution and solvent distillation (solvent replacement) in one or more steps.

[0342] Preferred embodiments of the aforementioned compound (3) are based on preferred embodiments of the anion portion of the aforementioned compound (1) (the anion portions of compounds (1-1) to (1-9)).

[0343] Suitable examples of compound (4) include the following compounds.

[0344] [Compound (4-1)]

[0345] A compound (4), wherein the

[0346] R 1 、R 2 、R 3 and R 4 Each independently is substituted with one or more fluorine atoms or fluorinated C 1-4 the following groups substituted with alkyl groups (e.g. trifluoromethyl): phenyl, 1-naphthyl, 2-naphthyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 1-anthryl, 2-anthryl, 9-anthryl, 3-phenanthrenyl or 9-phenanthrenyl,

[0347] M is lithium, sodium, potassium, calcium, magnesium or barium, and

[0348] n is 1 or 2.

[0349] [Compound (4-2)]

[0350] A compound (4), wherein the

[0351] R 1 、R 2 、R 3 and R 4 Each is independently the following group substituted with one or more fluorine atoms or trifluoromethyl groups: phenyl, 1-naphthyl or 2-naphthyl,

[0352] M is lithium, sodium or potassium, and

[0353] n is 1.

[0354] [Compound (4-3)]

[0355] A compound (4), wherein the

[0356] R 1 、R 2 、R3 and R 4 All are the same, pentafluorophenyl, 2,2',3,3',4',5,5',6,6'-nonafluoro-4-(1,1'-biphenyl)yl, 2,3,4,5,6,7,8-heptafluoro-1-naphthyl or 1,3,4,5,6,7,8-heptafluoro-2-naphthyl,

[0357] M is lithium or sodium, and

[0358] n is 1.

[0359] Preferred specific examples of compound (4) include, for example, lithium tetrakis(pentafluorophenyl)borate, sodium tetrakis(pentafluorophenyl)borate, lithium tetrakis(nonafluoro[1,1'-biphenyl]-4-yl)borate, lithium tetrakis(heptafluoro-2-naphthyl)borate, lithium [3,5-bis(trifluoromethyl)phenyl]borate, sodium [3,5-bis(trifluoromethyl)phenyl]borate, lithium tetrakis(2,3,4,5,6,7,8-heptafluoro-1-naphthyl)borate, lithium tetrakis(1,3,4,5,6,7,8-heptafluoro-2-naphthyl)borate, sodium tetrakis(2,3,4,5,6,7,8-heptafluoro-1-naphthyl)borate, and sodium tetrakis(1,3,4,5,6,7,8-heptafluoro-2-naphthyl)borate.

[0360] As another preferred embodiment of the production method of the present invention, the following production methods (Production Method 2 and Production Method 3 of the present invention) can be mentioned.

[0361] (Manufacturing method 2 of the present invention)

[0362] The composition of the present invention can be produced as shown in the following formula by mixing the base A, the protonic acid, and the aforementioned compound (4) in a solvent that does not affect the reaction, either sequentially or simultaneously, without limiting the order, and stirring.

[0363]

[0364] (The symbols in the formula have the same meanings as above.)

[0365] The amounts of base A, protonic acid and compound (4), reaction solvent, reaction temperature, reaction time, etc. used in the production method 2 of the present invention are the same as those in the above-mentioned production method 1 of the present invention.

[0366] (Manufacturing method 3 of the present invention)

[0367] The composition of the present invention can be produced as shown in the following formula by mixing 1 mol of base A and 1 mol of a protonic acid with the compound (4) in a solvent that does not affect the reaction, in any order or simultaneously, stirring, and then mixing the compound (5).

[0368]

[0369] (The symbols in the formula have the same meanings as above.)

[0370] The amount of compound (5) used in the production method 3 of the present invention is 0.1 mol or more, preferably 0.1 to 10 mol, and more preferably 0.1 to 3 mol, relative to 1 mol of compound (1) (compound (4)). If the amount of compound (5) is less than 0.1 mol, the solubility of the composition of the present invention is reduced. In addition, the types, amounts, reaction solvents, reaction temperatures, reaction times, etc. of the base A, protonic acid, and compound (4) used in the production method 3 of the present invention are the same as those of the production method 1 of the present invention described above.

[0371] The composition of the present invention comprises a base A or compound (5) and compound (1), is soluble (or easily soluble) in a hydrocarbon solvent, particularly an aliphatic hydrocarbon solvent, and does not contain compounds that would act as catalyst poisons, such as a basic and highly nucleophilic amine compound, a protonate salt of the base A, or an ether compound having a total carbon number of 7 or less. Therefore, the composition is useful as a cocatalyst for the polymerization of olefins and dienes.

[0372] The present invention includes a method for producing a polymer, comprising: using the composition of the present invention as a co-catalyst to polymerize at least one monomer selected from the group consisting of olefins and dienes. The use of a borate compound similar to compound (1) of the present invention as a co-catalyst to polymerize at least one monomer selected from the group consisting of olefins and dienes is known, for example, as described in Patent Document 2. Therefore, the method for producing a polymer of the present invention can be carried out by referring to the method for producing a polymer described in Patent Document 2, except that the composition of the present invention is used as a co-catalyst.

[0373] Example

[0374] The present invention is described in detail by the following preparation examples and examples, but the present invention is not limited to these preparation examples and examples. % refers to mol / mol% for yield, and other terms refer to weight% unless otherwise specified. In addition, room temperature refers to a temperature of 15°C to 30°C unless otherwise specified.

[0375] The following equipment was used for analysis.

[0376] 1 H-NMR and 19 F-NMR: 400YH manufactured by JEOL Ltd.

[0377] Unless otherwise specified, solvents and reagents used in the following examples were purchased from distributors such as Sigma-Aldrich, Tokyo Chemical Industry Co., Ltd., Fujifilm Wako Pure Chemical Corporation, Junsei Chemical Co., Ltd., Kanto Chemical Co., Ltd., and Combi-Blocks, Inc. Deuterated solvents used in NMR measurements were purchased from Kenbrich Instruments Research Institute.

[0378] [Example 1]

[0379] Composition containing N,N-dioctadecylaniline tetrakis(pentafluorophenyl)borate and N,N-dioctadecylaniline

[0380] N,N-Dioctadecylaniline (4.3 g, 7.2 mmol) and a triethyl ether complex of lithium tetrakis(pentafluorophenyl)borate (manufactured by AGC Wakasa Chemical Co., Ltd.) (5.0 g, 5.5 mmol) were suspended in n-hexane (50 mL). A 1.0 M hydrogen chloride-ether solution (5.5 mL) was then added dropwise, and the mixture was 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 the title composition (7.31 g).

[0381] 1 H NMR(CDCl3)δ:0.86-0.89(6H,m),1.17-1.48(27H,m),3.41(4H,t),7.23-7.26(2H,m),7.45-7.46(3H,m);

[0382] 19 F NMR(CDCl3)δ:-133.8(8F,t),-163.4(4F,t),-167.4(8F,t).

[0383] It was confirmed that the composition obtained in Example 1 was soluble in n-hexane and cyclohexane at a concentration of 20% by weight.

[0384] [Example 2]

[0385] Composition containing N,N-dioctadecylaniline tetrakis(pentafluorophenyl)borate and N,N-dioctadecylaniline

[0386] N,N-dioctadecylanilinium tetrakis(pentafluorophenyl)borate (128 mg, 0.1 mmol) was added with n-hexane (512 mg) and stirred (concentration 20 wt%). N,N-dioctadecylaniline (24 mg, 0.04 mmol) was added to the resulting two-layer separated solution and stirred to obtain a uniform n-hexane solution containing a composition of N,N-dioctadecylanilinium tetrakis(pentafluorophenyl)borate and N,N-dioctadecylaniline. The n-hexane was distilled off under reduced pressure, and the mixture was dried under reduced pressure at 50°C to obtain the title composition.

[0387] 1 H NMR(CDCl3)δ:0.8(6H,t),1.10-1.50(64H,m),3.36-3.40(4H,m),7.10-7.12(2H,m),7.33-7.51(3H,m);

[0388] 19 F NMR(CDCl3)δ:-133.8(8F,t),-163.4(4F,t),-167.5(8F,t).

[0389] It was confirmed that the composition obtained in Example 2 was dissolved in n-hexane at a concentration of 20% by weight.

[0390] [Production Example 1]

[0391] Synthesis of 2,6-bis(nonadecen-1-yl)pyridine

[0392] To a mixture of pyridine-2,6-dicarbaldehyde (1.0 g, 7.4 mmol), octadecyltriphenylphosphonium bromide (10 g, 17 mmol) and tetrahydrofuran (100 mL) was added potassium tert-butoxide (2.0 g, 18 mmol) at room temperature. The mixture was stirred at 60°C for 2 hours and then cooled to room temperature. The reaction mixture was carefully added to water and extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was suspended in diethyl ether, the insoluble matter was filtered out, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 98 / 2 to 90 / 10) to obtain 2,6-bis(nonadecen-1-yl)pyridine (E / Z mixture; 3.9 g, 86%).

[0393] 1H NMR(CDCl3)δ:0.88(6H,t),1.20-1.48(60H,m),2.56-2.62(4H,m),5.82-5.89 (1H,m),6.42-6.49(2H,m),7.04(2H,d),7.26-7.35(1H,m),7.53-7.57(1H,m).

[0394] [Production Example 2]

[0395] Synthesis of 2,6-di(nonadecyl)pyridine

[0396] A mixture of 2,6-bis(nonadecen-1-yl)pyridine (E / Z mixture; 3.5 g, 5.8 mmol) obtained in Preparation Example 1, 10% Pd / C (50% aqueous; 0.70 g), and tetrahydrofuran (100 mL) was stirred under a hydrogen atmosphere at room temperature and atmospheric pressure for 15 hours. The mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 95 / 5) to obtain 2,6-bis(nonadecyl)pyridine (3.0 g, 85%).

[0397] 1 H NMR(CDCl3)δ:0.88(6H,t),1.17-1.40(64H,m),1.65-1.70(4H,m),2.72-2.76(4H,m),6.93(2H,d),7.48(1H,t).

[0398] [Production Example 3]

[0399] Synthesis of 2,6-di(nonadecyl)pyridine hydrochloride

[0400] A 1 M hydrogen chloride-ether solution (10 mL) was added to a n-hexane solution (30 mL) of 2,6-dinonadecylpyridine (3.0 g, 4.9 mmol) obtained in Preparation Example 2 at room temperature, and the mixture was stirred for 1 hour. The resulting precipitate was collected by filtration, washed with n-hexane, and dried under reduced pressure to obtain 2,6-dinonadecylpyridine hydrochloride (3.0 g, 94%).

[0401] 1 H NMR(CDCl3)δ:0.88(6H,t),1.24-1.45(64H,m),1.79-1.87(4H,m),3.32(4H,br),7.41(2H,d),8.08(1H,br).

[0402] [Production Example 4]

[0403] Synthesis of 2,6-di(nonadecyl)pyridinium tetrakis(pentafluorophenyl)borate

[0404] 2,6-Dinonadecylpyridinium hydrochloride (0.50 g, 0.77 mmol) obtained in Preparation Example 3 and lithium tetrakis(pentafluorophenyl)borate monoethyl ether complex (0.59 g, 0.78 mmol) were suspended in dichloromethane (20 mL) and stirred at room temperature for 1 hour. The resulting suspension was filtered, and the filtrate was concentrated under reduced pressure at 50°C to obtain 2,6-dinonadecylpyridinium tetrakis(pentafluorophenyl)borate (0.99 g, 99%).

[0405] 1 H NMR(CDCl3)δ:0.85-0.89(6H,m),1.23-1.35(64H,m),1.72-1.76(4H,m),2.94-2.98(4H,t),7.57(2H,d),8.27(1H,dd);

[0406] 19 F NMR(CDCl3)δ:-133.3(8F,t),-163.2(4F,t),-167.7(8F,t).

[0407] [Example 3]

[0408] Composition containing 2,6-di(nonadecyl)pyridinium tetrakis(pentafluorophenyl)borate and 2,6-di(nonadecyl)pyridine

[0409] To 2,6-di(nonadecyl)pyridinium tetrakis(pentafluorophenyl)borate (129 mg, 0.1 mmol) obtained in Preparation Example 4 was added 2,6-di(nonadecyl)pyridinium tetrakis(pentafluorophenyl)borate (129 mg, 0.1 mmol), followed by n-hexane (0.52 g). The mixture was stirred for 1 hour to obtain a uniform n-hexane solution. The solvent was distilled off under reduced pressure to obtain the title composition.

[0410] 1 H NMR(CDCl3)δ:0.88(6H,t),1.20-1.50(64H,m),1.67-1.73(4H,m),2.88(4H,t),7.38(2H,d),8.03(1H,dd);

[0411] 19 F NMR(CDCl3)δ:-133.9(8F,t),-163.6(4F,t),-167.7(8F,t).

[0412] It was confirmed that the composition obtained in Example 3 was dissolved in n-hexane at a concentration of 20% by weight.

[0413] [Production Example 5]

[0414] Synthesis of 2-(Nodecen-1-yl)-5-octadecyloxypyridine

[0415] Potassium tert-butoxide (1.4 g, 12 mmol) was added to a mixture of 5-octadecyloxypyridine-2-carboxaldehyde (2.0 g, 5.3 mmol), octadecyltriphenylphosphonium bromide (7.0 g, 12 mmol), and tetrahydrofuran (100 mL) at room temperature. The mixture was stirred at 60°C for 2 hours and then cooled to room temperature. The reaction mixture was carefully added to water and extracted with ethyl acetate. The organic phase was washed with saturated saline solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was suspended in diethyl ether, the insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 98 / 2 to 90 / 10) to obtain 2-(nonadecen-1-yl)-5-octadecyloxypyridine (E / Z mixture; 3.1 g, 95%).

[0416] 1 H NMR(CDCl3)δ:0.87(6H,t),1.24-1.50(60H,m),1.76-1.80(2H,m),2.48-2.54(2H,m),3.9 5-4.00(2H,m),7.71-7.78(1H,m),6.36-6.40(1H,m),7.13-7.18(2H,m),8.2-8.27(1H,m).

[0417] [Production Example 6]

[0418] Synthesis of 2-nonadecanyl-5-octadecyloxypyridine

[0419] A mixture of 2-(nonadecen-1-yl)-5-octadecyloxypyridine (E / Z mixture; 2.5 g, 4.1 mmol) obtained in Preparation Example 5, 10% Pd / C (50% aqueous; 0.70 g), n-hexane (100 mL), and tetrahydrofuran (100 mL) was stirred under a hydrogen atmosphere at room temperature and atmospheric pressure for 15 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 95 / 5) to obtain 2-nonadecanyl-5-octadecyloxypyridine (1.0 g, 40%).

[0420] 1H NMR(CDCl3)δ:0.87(6H,t),1.17-1.40(64H,m),1.42-1.76(4H,m),2.67-2.72(2H,m),3.95(1H,t),7.02(2H,d),7.10(2H,dd),8.19(1H,d).

[0421] [Example 4]

[0422] Composition containing 2-nonadecyl-5-octadecyloxypyridinium tetrakis(pentafluorophenyl)borate and 2-nonadecyl-5-octadecyloxypyridine

[0423] 2-Nonadecyl-5-octadecyloxypyridine (0.65 g, 1.1 mmol) obtained in Preparation Example 6 and lithium tetrakis(pentafluorophenyl)borate triethyl ether complex (0.80 g, 0.88 mmol) were suspended in cyclohexane (20 mL). 1 M hydrogen chloride-diethyl ether solution (0.88 mL, 0.88 mmol) was added, and the mixture was stirred at room temperature for 3 hours. Insoluble matter was removed by filtration, and the filtrate was dried under reduced pressure at 45°C to obtain the title composition.

[0424] 1 H NMR(CDCl3)δ:0.88(3H,t),1.22-1.44(64H,m),1.69-1.86(4H,m),2.93(2H,t),4.02(2H,t),7.60(1H,d),7.84(1H,dd),7.90(1H,d).

[0425] It was confirmed that the composition obtained in Example 4 was dissolved in n-hexane at a concentration of 20% by weight.

[0426] [Production Example 7]

[0427] Synthesis of 1-octadecyl imidazole-2-carboxaldehyde

[0428] A mixture of 1H-imidazole-2-carboxaldehyde (2.0 g, 21 mmol), 1-bromooctadecane (7.5 g, 22 mmol), potassium carbonate (4.5 g, 33 mmol), and N,N-dimethylformamide was stirred at room temperature for 15 hours. The mixture was poured into water and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate = 98 / 2 to 90 / 10) to obtain 1-octadecylimidazole-2-carboxaldehyde (6.45 g, 89%).

[0429] 1H NMR(CDCl3)δ:0.88(3H,t),1.24-1.30(34H,m),1.75-1.79(2H,m),4.36-4.40(2H,m),7.15(1H,s),7.29(1H,d),9.81(1H,s).

[0430] [Production Example 8]

[0431] Synthesis of 2-(Nodecen-1-yl)-1-octadecyl imidazole

[0432] To a mixture of 1-octadecylimidazole-2-carboxaldehyde (5.0 g, 14 mmol), octadecyltriphenylphosphonium bromide (10 g, 16.8 mmol), and tetrahydrofuran (50 mL) obtained in Preparation Example 7 was added potassium tert-butoxide (2.0 g, 17.8 mmol) at room temperature. The mixture was stirred at 60°C for 2 hours and then cooled to room temperature. The reaction mixture was carefully added to water and extracted with ethyl acetate. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was suspended in diethyl ether, the insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 98 / 2 to 90 / 10) to obtain 2-(nonadecen-1-yl)-1-octadecylimidazole (E / Z mixture; 7.5 g, 89%).

[0433] 1 H NMR(CDCl3)δ:0.88(6H,t),1.11-1.73(64H,m),2.20-2.26(2H,m),3.85-3.90(2H ,m),6.11-6.23(1H,m),6.67-6.74(1H,m),6.81-6.82(1H,m),6.98-7.09(1H,m).

[0434] [Production Example 9]

[0435] Synthesis of 2-nonadecanyl-1-octadecyl imidazole

[0436] A mixture of 2-(nonadecen-1-yl)-1-octadecyl imidazole (E / Z mixture; 1.5 g, 2.6 mmol) obtained in Preparation Example 8, 10% Pd / C (50% aqueous; 0.30 g), and tetrahydrofuran (100 mL) was stirred under a hydrogen atmosphere at room temperature and atmospheric pressure for 15 hours. The mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane / ethyl acetate = 95 / 5) to obtain 2-nonadecanyl-1-octadecyl imidazole (1.0 g, 67%).

[0437] 1 H NMR(CDCl3)δ:0.88(6H,t),1.25-1.75(66H,m),2.60-2.64(2H,m),3.79-3.82(2H,m),6.79(1H,d),6.93(1H,d).

[0438] [Production Example 10]

[0439] Synthesis of 2-nonadecanyl-1-octadecyl imidazole hydrochloride

[0440] To a suspension of 2-nonadecyl-1-octadecylimidazole (0.88 g, 1.5 mmol) obtained in Preparation Example 9 and n-hexane (100 mL) was added a 1 M hydrogen chloride-ether solution (10 mL) at room temperature, and the mixture was stirred for 1 hour. The solvent of the resulting suspension was distilled off under reduced pressure to obtain 2-nonadecyl-1-octadecylimidazole hydrochloride (0.98 g, 100%).

[0441] 1 H NMR(CDCl3)δ:0.88(6H,t),1.25-1.40(62H,m),1.80-1.88(4H,m),3.02-3.07(2H,t),3.96-4.00(2H,t),6.97(1H,d),7.29(1H,d).

[0442] [Production Example 11]

[0443] Synthesis of 2-nonadecanyl-1-octadecylimidazolium tetrakis(pentafluorophenyl)borate

[0444] 2-Nonadecyl-1-octadecyl imidazole hydrochloride (0.98 g, 1.57 mmol) obtained in Preparation Example 10 and lithium tetrakis(pentafluorophenyl)borate etherate complex (1.19 g, 1.57 mmol) were suspended in cyclohexane (30 mL) and stirred at room temperature for 1 hour. Brine was added, the organic phase was washed, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dried under reduced pressure at 45°C to obtain 2-Nonadecyl-1-octadecyl imidazole tetrakis(pentafluorophenyl)borate (0.82 g, 94%).

[0445] 1 H NMR(CDCl3)δ:0.88(6H,t),1.25-1.43(62H,m),1.66-1.82(4H,m),2.81(2H,t),3.94(2H,t),6.99(1H,d),7.03(1H,d);

[0446] 19F NMR(CDCl3)δ:-133.9(8F,t),-164.1(4F,t),-167.9(8F,t).

[0447] [Example 5]

[0448] Composition containing 2-nonadecyl-1-octadecyl imidazole and 2-nonadecyl-1-octadecyl imidazolium tetrakis(pentafluorophenyl)borate

[0449] 2-Nonadecyl-1-octadecyl imidazole (24.1 mg, 0.04 mmol) obtained in Preparation Example 9 and 2-Nonadecyl-1-octadecyl imidazole tetrakis(pentafluorophenyl)borate (126.7 mg, 0.1 mmol) obtained in Preparation Example 11 were dissolved in cyclohexane (0.5 mL) to obtain a 20 wt% cyclohexane solution. This solution was concentrated under reduced pressure to obtain the title composition.

[0450] 1 H NMR(CDCl3)δ:0.88(6H,t),1.22-1.33(62H,m),1.66-1.82(4H,m),2.81(2H,t),3.94(2H,t),6.99(1H,d),7.03(1H,d);

[0451] 19 F NMR(CDCl3)δ:-133.9(8F,t),-164.1(4F,t),-167.9(8F,t).

[0452] It was confirmed that the composition obtained in Example 5 was dissolved in cyclohexane at a concentration of 20% by weight.

[0453] [Production Example 12]

[0454] Synthesis of 2-Heptadecanyl-1-octadecylbenzimidazole

[0455] 2-Heptadecanyl-1H-benzimidazole (1.5 g, 4.2 mmol), potassium carbonate (1.1 g, 8.0 mmol) and 1-octadecane bromide (1.5 g, 4.5 mmol) obtained by the same method as a known example (e.g., Australian Journal of Chemistry (2015), 68 (1), 145-155) were mixed in DMF (30 mL), and the mixture was stirred at 60°C for 16 hours. The reaction mixture was cooled to room temperature and poured into water. After stirring the suspension at room temperature for 1 hour, the precipitate was filtered off. The obtained solid was dried at 80°C under reduced pressure to obtain the title compound (2.25 g, 88%).

[0456] 1 H NMR(CDCl3)δ:0.88-0.92(6H,m),1.25-1.45(60H,m),1,75-1.93(4H,m),2.84(2H,t),4.08(2H,t),7.196-7.30(3H,m),7.70-7.73(1H,m).

[0457] [Production Example 13]

[0458] 2-Heptadecanyl-1-octadecylbenzimidazolium tetrakis(pentafluorophenyl)borate

[0459] 2-Heptadecanyl-1-octadecylbenzimidazole (0.61 g, 1.0 mmol) obtained in Preparation Example 12 and a triethyl ether complex of lithium tetrakis(pentafluorophenyl)borate (0.91 g, 1.0 mmol) were suspended in cyclohexane (30 mL). 1.0 M hydrogen chloride-ether solution (1.0 mL) was added dropwise, and the mixture was 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 the title compound (1.22 g, 80%).

[0460] 1 H NMR(CDCl3)δ:0.88(6H,t),1.22-1.44(60H,m),1.86-1.92(4H,m),3.10(2H,t),4.28(2H,t),7.58-7.70(4H,m);

[0461] 19 F NMR(CDCl3)δ:-134.0(8F,m),-163.7(4F,t),-167.7(8F,t).

[0462] [Example 6]

[0463] Composition containing 2-heptadecanyl-1-octadecylbenzimidazolium tetrakis(pentafluorophenyl)borate and 2-heptadecanyl-1-octadecylbenzimidazole

[0464] 2-Heptadecanyl-1-octadecylbenzimidazolium tetrakis(pentafluorophenyl)borate (500 mg, 0.4 mmol) obtained in Preparation Example 13 and 2-Heptadecanyl-1-octadecylbenzimidazole (47 mg, 0.15 mmol) obtained in Preparation Example 12 were mixed, and n-hexane was added. The mixture was concentrated under reduced pressure and then dried under reduced pressure for 16 hours to obtain the title composition.

[0465] 1H NMR(CDCl3)δ:0.88(6H,t),1.16-1.41(60H,m),1.84-1.91(4H,m),3.06(2H,t),4.25(2H,t),7.44-7.63(4H,m);

[0466] 19 F NMR(CDCl3)δ:-133.9(8F,d),-164.0(4F,t),-167.9(8F,t).

[0467] It was confirmed that the composition obtained in Example 6 was dissolved in n-hexane at a concentration of 10% by weight.

[0468] [Example 7]

[0469] Composition containing 2-nonadecyl-5-octadecyloxypyridinium tetrakis(pentafluorophenyl)borate and tetradecyl ether

[0470] 2-Nonadecyl-5-octadecyloxypyridinium tetrakis(pentafluorophenyl)borate (39 mg, 0.03 mmol), tetradecyl ether (12.3 mg, 0.03 mmol), and n-hexane (351 mg) were mixed and stirred at 25°C. The mixture became a homogeneous solution. The mixture was concentrated under reduced pressure and then dried under reduced pressure at 50°C to obtain the title compound.

[0471] 1 H NMR(CDCl3)δ:0.86-0.90(12H,m),1.23-1.84(114H,m),2.91(2H,t),3.41(4H,t),4.03(2H,t),7.62(1H,d),7.85-7.89(2H,m);

[0472] 19 F NMR(CDCl3)δ:-134.1(8F,t),-163.4(4F,t),-167.4(8F,t).

[0473] It was confirmed that the composition obtained in Example 7 was dissolved in n-hexane at a concentration of 10% by weight.

[0474] [Example 8]

[0475] Composition containing 2,6-di(nonadecyl)pyridinium tetrakis(pentafluorophenyl)borate and tetradecyl ether

[0476] 2,6-Dinonadecylpyridinium tetrakis(pentafluorophenyl)borate (39 mg, 0.03 mmol) obtained in Preparation Example 4, tetradecyl ether (12.3 mg, 0.03 mmol), and n-hexane (351 mg) were mixed and stirred at 25°C. The mixture became a homogeneous solution. The mixture was concentrated under reduced pressure and then dried under reduced pressure at 50°C to obtain the title composition.

[0477] 1 H NMR(CDCl3)δ:0.88(12H,t),1.25-1.40(76H,m),1.52-1.60(4H,m),1.70-1.78(4H,m),2.97(4H,t),3.39(4H,t),7.57(2H,d),8.28(1H,t);

[0478] 19 F NMR(CDCl3)δ:-138.8(8F,s),-163.6(4F,t),-167.7(8F,t).

[0479] It was confirmed that the composition obtained in Example 8 was dissolved in n-hexane at a concentration of 10% by weight.

[0480] [Example 9]

[0481] Composition containing 2-heptadecanyl-1-octadecylbenzimidazolium tetrakis(pentafluorophenyl)borate and tetradecyl ether

[0482] 2-Heptadecanyl-1-octadecylbenzimidazolium tetrakis(pentafluorophenyl)borate (39 mg, 0.03 mmol) obtained in Preparation Example 13, tetradecyl ether (12.3 mg, 0.03 mmol), and n-hexane (351 mg) were mixed and stirred at 25°C. The mixture became a homogeneous solution. The mixture was concentrated under reduced pressure and then dried under reduced pressure at 50°C to obtain the title composition.

[0483] 1 H NMR(CDCl3)δ:0.85-0.88(12H,m),1.22-1.57(82H,m),1.85-1.91(4H,m),3 .09(2H,t),3.38(4H,t),4.27(2H,t),7.56-7.60(2H,m),7.62-7.70(1H,m);

[0484] 19 F NMR(CDCl3)δ:-133.9(8F,s),-163.7(4F,t),-167,7(8F,m).

[0485] It was confirmed that the composition obtained in Example 9 was dissolved in n-hexane at a concentration of 10% by weight.

[0486] [Example 10]

[0487] Composition containing 2-nonadecyl-1-octadecylimidazolium tetrakis(pentafluorophenyl)borate and tetradecyl ether

[0488] 2-Nonadecyl-1-octadecylimidazolium tetrakis(pentafluorophenyl)borate (39 mg, 0.03 mmol), tetradecyl ether (73.8 mg, 0.15 mmol), and n-hexane (351 mg) obtained in Preparation Example 11 were mixed and stirred at 25°C. The mixture became a homogeneous solution. The mixture was concentrated under reduced pressure and then dried under reduced pressure at 50°C to obtain the title composition.

[0489] 1 H NMR(CDCl3)δ:0.84-0.90(36H,m),1.11-1.83(302H,m),2.85-2.89(2H,m),3.93(20H,t),4.00(2H,t),7.10(1H,d),7.13(1H,d);

[0490] 19 F NMR(CDCl3)δ:-134.0(8F,s),-163.6(4F,t),-167.7(8F,t).

[0491] It was confirmed that the composition obtained in Example 10 was dissolved in n-hexane at a concentration of 10% by weight.

[0492] [Comparative Example 1]

[0493] N,N-Dioctadecylanilinium tetrakis(pentafluorophenyl)borate

[0494] N,N-Dioctadecylaniline (3.3 g, 5.5 mmol) and lithium tetrakis(pentafluorophenyl)borate triethyl ether complex (5.0 g, 5.5 mmol) were suspended in n-hexane (50 mL). 1.0 M hydrogen chloride-ether solution (5.5 mL) 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 the title compound (7.0 g, 90%).

[0495] 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);

[0496] 19 F NMR(CDCl3)δ:-133.8(8F,t),-163.3(4F,t),-167.4(8F,t).

[0497] The compound obtained in Comparative Example 1 was poorly soluble in n-hexane at a concentration of 20% by weight.

[0498] [Production Example 14]

[0499] Synthesis of 2-nonadecanyl-5-octadecyloxypyridine hydrochloride

[0500] To a suspension of 2-nonadecyl-5-octadecyloxypyridine (1.0 g, 1.6 mmol) and n-hexane (100 mL) obtained in Preparation Example 6 was added a 1 M hydrogen chloride-ether solution (10 mL) at room temperature, and the mixture was stirred for 1 hour. The solvent in the reaction suspension was distilled off under reduced pressure to obtain 2-nonadecyl-5-octadecyloxypyridine hydrochloride (0.98 g, 93%).

[0501] 1 H NMR(CDCl3)δ:0.88(6H,t),1.24-1.50(64H,m),1.78-1.85(4H,m),3.13(2H,t),4.06(2H,t),7.74(1H,d),7.74(1H,dd),8.21(1H,d).

[0502] [Comparative Example 2]

[0503] 2-Nonadecyl-5-octadecyloxypyridinium tetrakis(pentafluorophenyl)borate

[0504] 2-Nonadecyl-5-octadecyloxypyridine hydrochloride (0.25 g, 0.38 mmol) obtained in Preparation Example 14 and lithium tetrakis(pentafluorophenyl)borate etherate complex (0.29 g, 0.38 mmol) were suspended in cyclohexane (50 mL) and stirred at room temperature for 1 hour. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dried under reduced pressure at 45°C to obtain the title compound (0.45 g, 90%).

[0505] 1 H NMR(CDCl3)δ:0.86-0.90(6H,m),1.23-1.43(64H,m),1.72-1.86(4H,m),2.92(2H,t),4.03(2H,t),7.64(1H,d),7.85(1H,d),7.91(1H,dd);

[0506] 19 F NMR(CDCl3)δ:-134.0(8F,t),-163.4(4F,t),-167.5(8F,t).

[0507] The compound obtained in Comparative Example 2 was poorly soluble in n-hexane at a concentration of 20% by weight.

[0508] [Comparative Example 3]

[0509] N,N-Dinonylanilinium tetrakis(pentafluorophenyl)borate

[0510] N,N-dinonylaniline (0.98 g, 2.8 mmol) and lithium tetrakis(pentafluorophenyl)borate triethyl ether complex (2.54 g, 2.8 mmol) were suspended in n-hexane (30 mL). 1.0 M hydrogen chloride-ether solution (2.8 mL) was added dropwise, and the mixture was stirred at room temperature for 2 hours. The resulting suspension was filtered, and the residue was washed with chloroform. The filtrate was concentrated under reduced pressure at 50°C to obtain the title compound (2.19 g, 76%).

[0511] 1 H NMR(CDCl3)δ:0.84(6H,t),1.14-1.56(64H,m),3.43(4H,br),7.29(2H,d),7.56-7.60(3H,m);

[0512] 19 F NMR(CDCl3)δ:-133.5(8F,t),-163.4(4F,t),-167.4(8F,t)

[0513] The compound obtained in Comparative Example 3 was poorly soluble in n-hexane at a concentration of 20% by weight.

[0514] [Comparative Example 4]

[0515] Composition containing N,N-dinonylaniline tetrakis(pentafluorophenyl)borate and N,N-dinonylaniline

[0516] N,N-dinonylaniline tetrakis(pentafluorophenyl)borate (125 mg, 0.12 mmol) obtained in Comparative Example 3 was added to n-hexane (500 mg) to prepare a 20 wt% n-hexane solution. The solution separated into two layers. N,N-dinonylaniline (430 mg, 1.25 mmol) was further added to the solution, stirred, and allowed to stand overnight. The solution then separated into two layers. This indicates that the title composition is poorly soluble in n-hexane at a concentration of 20 wt%.

[0517] [Comparative Example 5]

[0518] Composition containing bis(hydrogenated tallow alkyl)methylammonium tetrakis(pentafluorophenyl)borate and bis(hydrogenated tallow alkyl)methylamine

[0519] Bis(hydrogenated tallow alkyl)methylammonium tetrakis(pentafluorophenyl)borate (used as [Comparative Example 6] in the following test examples) (133.2 mg) obtained by a known method (Japanese Patent Publication No. 2000-507157) and bis(hydrogenated tallow alkyl)methylamine (Amin M2HT (registered trademark)) (11.2 mg) were mixed with n-hexane (533 mg) and stirred at room temperature. The mixture became a homogeneous solution. The mixture was concentrated under reduced pressure to obtain the title compound.

[0520] 19 F NMR(CDCl3)δ:-134.1(8F,d),-163.0(4F,t),-167.3(8F,t).

[0521] [Test Example] (Polymerization Performance Evaluation)

[0522] A typical polymerization method using the compound or composition of the present invention as a co-catalyst is shown below.

[0523] In a glove box, 1-octene, triisobutylaluminum (TIBA, 0.55M n-hexane solution), and a solvent (methylcyclohexane (MCH)) were added to a 100mL autoclave to prepare a comonomer solution. A polymerization catalyst (dimethylsilylene (tert-butylamide)-(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 transferred to a Schlenk tube. A cocatalyst was dissolved in a solvent to prepare a cocatalyst solution of a predetermined concentration, which was transferred to a Schlenk tube. When the comonomer solution, catalyst solution, and cocatalyst solution were mixed and reacted, the total amount of solvent and triisobutylaluminum was prepared in a manner to be constant. After purging the autoclave with ethylene gas, the catalyst solution and cocatalyst solution were added to the autoclave in sequence, the ethylene pressure was immediately adjusted to a predetermined pressure, and stirring was performed at a predetermined temperature (25°C) for a predetermined time. The reaction mixture was ice-cooled, ethylene gas was vented, and the mixture was poured into methanol (100 mL) containing hydrochloric acid (3 mL) and stirred at room temperature for 30 minutes. The precipitate was filtered and dried at 60° C. under reduced pressure to obtain an ethylene-octene copolymer.

[0524] (Melting point determination)

[0525] The measurement was performed by differential scanning calorimetry (DSC) using a DSC6220 device (Seiko Instruments Inc.). The sample (polymer) was heated from 40° C. to 150° C. at a rate of 10° C. / min to measure the melting point.

[0526] Table 1 shows the results of polymerization reactions at 25° C. using various co-catalysts.

[0527] [Table 1]

[0528]

[0529] Reaction conditions: catalyst: CGC, catalyst: cocatalyst = 1:1, TIBA (total 3000 μmol), solvent: methylcyclohexane, total solvent (40 mL), 1-octene (1 mL), ethylene pressure (8 atmospheres), 25 ° C

[0530] 1) Bis(hydrogenated tallow alkyl)methylammonium tetrakis(pentafluorophenyl)borate

[0531] According to Table 1, Examples 1, 3, and 4 all showed polymerization activities equal to or higher than those of Comparative Examples 1, 5, or 6.

[0532] Industrial applicability

[0533] The composition of the present invention is soluble (or easily soluble) in hydrocarbon solvents, particularly aliphatic hydrocarbon solvents, and does not act as a catalyst poison. Therefore, it is useful as a cocatalyst for the polymerization of olefins and dienes.

[0534] This application is based on Japanese Patent Application No. 2020-043246 filed on March 12, 2020, and Japanese Patent Application No. 2020-209070 filed on December 17, 2020, the contents of which are incorporated herein in their entirety.

Claims

1. A composition comprising (I) a base A; and (II) a compound represented by the following formula (1), In formula (1), R 1 、R 2 、R 3 and R 4 all represent pentafluorophenyl, and [AH] + represents a cation derived from base A, in, The base A represents: By the same or different 2 C 14-30 Alkyl or C 14-30 Alkyloxy-substituted pyridine, imidazole or benzimidazole with a total carbon number of 25 or more, The content of the base A is in the range of 0.01 to 10 mol relative to 1 mol of the compound represented by the formula (1). 2 . A co-catalyst for the polymerization of at least one monomer selected from the group consisting of olefins and dienes, the co-catalyst comprising the composition according to claim 1 .

3. A method for producing the composition according to claim 1, characterized in that: comprising the step of reacting the compound represented by formula (3) with the base A, wherein the base A is used in an amount exceeding 1 mole relative to 1 mole of the compound represented by formula (3), In formula (3), R 1 、R 2 、R 3 and R 4 All represent pentafluorophenyl groups.

4. The manufacturing method according to claim 3, wherein: The amount of base A used is in the range of 1.01 to 3 mol relative to 1 mol of the compound represented by formula (3).

5. A method for producing the composition according to claim 1, characterized in that: comprising the step of reacting a compound represented by formula (4), the base A, and a protonic acid, wherein the base A is used in an amount exceeding 1 mol relative to 1 mol of the compound represented by formula (4), In formula (4), R 1 、R 2 、R 3 and R 4 All represent pentafluorophenyl groups, M represents an alkali metal or an alkaline earth metal, and n represents 1 or 2.

6. A method for producing the composition of claim 1, comprising: a step of reacting the compound represented by formula (4), 1 mol of the base A relative to 1 mol of the compound represented by formula (4), and a protonic acid; and, thereafter, a step of adding a compound having a total carbon number of 8 or more represented by formula (5) in an amount of 0.1 mol or more relative to 1 mol of the compound represented by formula (4), In formula (4), R 1 、R 2 、R 3 and R 4 All represent pentafluorophenyl groups, M represents an alkali metal or an alkaline earth metal, and n represents 1 or 2, In formula (5), R and R' each independently represent an optionally substituted C 1-30 Alkyl, optionally substituted C 3-15 Cycloalkyl or optionally substituted C 6-14 Aryl.

7. A method for producing a polymer, comprising: At least one monomer selected from the group consisting of olefins and dienes is polymerized using the composition according to claim 1 as a co-catalyst.

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