Aromatic ether nitrile composition and production method therefor

Abstract

The present invention addresses the problem of providing an additive which reduces a melt viscosity without impairing the heat resistance of a heat-resistant resin represented by a super engineering plastic and having a high melt viscosity, and which does not generate a volatile component such as gas during molding and improves moldability. To solve the problem, provided is an aromatic ether nitrile composition which contains a dihydroxy compound represented by general formula (1) and satisfies formations (i) and (ii) in liquid chromatography (LC) analysis using, as a detector, ultraviolet rays having a wavelength of 280 nm.　Formation (i): The area percentage of the dihydroxy compound represented by general formula (1) with respect to all the components detected by the LC analysis is in the range of 10-95%.　Formation (ii): The sum of the area percentages of a compound represented by general formula (2), a dihalobenzonitrile compound represented by general formula (3), and a dihydroxy compound represented by general formula (4) with respect to all the components detected by the LC analysis is at most 5%.

Description

Aromatic ether nitrile composition and method for producing same

[0001] The present invention relates to an additive for heat-resistant resins, and more particularly to an aromatic ether nitrile composition that can significantly improve the moldability of heat-resistant resins without impairing the excellent heat resistance of the heat-resistant resins, and a method for producing the same.

[0002] Engineering plastics, particularly resins known as "super engineering plastics," such as aromatic polyether nitriles, aromatic polyether ether ketones, and aromatic polyether sulfones, are useful resins that not only exhibit excellent heat resistance, flame retardancy, chemical resistance, and mechanical strength, but also are thermoplastic and heat-moldable, making them useful for producing various molded products such as filaments, films, sheets, tubes, pipes, and round bars using molding methods such as injection molding, extrusion molding, and hot compression molding. However, due to their excellent heat resistance, these resins have a major problem: their high melting points and high melt viscosities result in poor moldability. To address this problem, a compound obtained by reacting 4-phenylphenol with a dihalide selected from 4,4'-dihalogenobenzophenone, 4,4'-dihalogenodiphenyl sulfone, and dihalogenobenzonitrile has been proposed as a plasticizer that reduces the melt viscosity of super engineering plastics and improves their moldability (Patent Document 1).

[0003] Japanese Patent Application Publication No. 3-134055

[0004] However, while these plasticizers described in Patent Document 1 can reduce the melt viscosity of resins, they have the problem of volatilizing as a gas during molding of super engineering plastics, which require molding temperatures of 380°C or higher, and this can easily cause molding defects.The present invention aims to provide an additive that reduces the melt viscosity of heat-resistant resins with high melt viscosity, such as super engineering plastics, without impairing the heat resistance, and that does not generate volatile components such as gases during molding, thereby improving molding processability.

[0005] As a result of intensive investigations aimed at solving the above problems, the present inventors have found that an aromatic ether nitrile composition having a specific composition can give a heat-resistant resin having a reduced melt viscosity without generating gas during molding and without impairing heat resistance, thereby completing the present invention. Furthermore, they have also found a rational method for producing the aromatic ether nitrile composition of the present invention.

[0006] The present invention is as follows: 1. An aromatic ether nitrile composition containing a dihydroxy compound represented by general formula (1) and satisfying compositions (i) and (ii) in liquid chromatography (LC) analysis using ultraviolet light at a wavelength of 280 nm as a detector. Composition (i): The area percentage of the dihydroxy compound represented by general formula (1) is in the range of 10% to 95% of all components detected by the LC analysis. Composition (ii): The total area percentage of the compound represented by general formula (2), the dihalobenzonitrile compound represented by general formula (3), and the dihydroxy compound represented by general formula (4) is 5% or less of all components detected by the LC analysis. (In general formulas (1), (2), and (4), R each independently represents a divalent group represented by general formula (1a) or (1b), and in general formulas (2) and (3), X each independently represents a halogen atom.) (In general formula (1a), R １ each independently represents a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, a cyclic alkyl group having 5 or 6 carbon atoms, a phenyl group, a phenoxy group, or a phenylalkyl group having 7 to 10 carbon atoms; m represents 0 or an integer of 1 to 4; n represents 0 or 1; p and q represent 0, 1, or 2; and * represents each bonding position. (In general formula (1b), R １and m are the same as defined in general formula (1a), Y represents an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, an alkylidene group having 1 to 15 carbon atoms, a fluorine-containing alkylidene group having 2 to 15 carbon atoms, a cycloalkylidene group having 5 to 15 carbon atoms, a phenylmethylidene group, a phenylethylidene group, a phenylene group, or a fluorenylidene group, Z represents an oxygen atom, a sulfur atom, or unbridged, each Ar independently represents an aryl group having 6 to 8 carbon atoms, and * represents a bonding position.) 2. The aromatic ether nitrile composition according to 1., wherein R in general formulas (1), (2), and (4) is not independent and represents a phenylene group, a naphthylene group, or a biphenylene group. 3. The aromatic ether nitrile composition according to 1., further comprising a polymer having a repeating unit represented by general formula (5). (R in general formula (5) is common to general formulae (1), (2) and (4), and each R is independently a divalent group represented by general formula (1a) or general formula (1b).) 4. The aromatic ether nitrile composition according to 1., having a weight average molecular weight (Mw) of 500 or more and 8000 or less in terms of polystyrene as measured by gel permeation chromatography (GPC) analysis. 1. A method for producing an aromatic ether nitrile composition according to 1., comprising: an etherification reaction step of reacting the dihalobenzonitrile compound represented by the general formula (3) with the dihydroxy compound represented by the general formula (4) in the presence of a basic compound that forms a salt with the hydroxyl group of the dihydroxy compound represented by the general formula (4) to obtain a reaction product containing the dihydroxy compound represented by the general formula (1); and an alkali washing step of washing the reaction product obtained in the etherification reaction step with an aqueous solution of a basic compound, wherein in the etherification reaction step, the dihydroxy compound represented by the general formula (4) is used in an amount of 1.5 times or more by mole relative to the dihalobenzonitrile compound represented by the general formula (3), and the basic compound that forms a salt with the terminal hydroxyl group of the dihydroxy compound represented by the general formula (4) is used in an amount of 2 times or more by mole relative to the dihydroxy compound represented by the general formula (4).

[0007] When used as an additive, the aromatic ether nitrile composition of the present invention reduces the melt viscosity of heat-resistant resins having high melt viscosity, such as super engineering plastics, without impairing the heat resistance, and improves molding processability without generating volatile matter such as gas during molding, thereby providing molded articles excellent in heat resistance, mechanical strength, and in some cases, crystallinity.The method for producing the aromatic ether nitrile composition of the present invention converts a low-molecular-weight product compound having a low weight loss temperature into a target high-molecular-weight compound having a high weight loss temperature during the reaction, and then removes the remaining raw materials by purification after the reaction, thereby obtaining the target aromatic ether nitrile composition.

[0008] (Aromatic Ethernitrile Composition of the Present Invention) The aromatic ethernitrile composition of the present invention contains a dihydroxy compound represented by general formula (1), and is characterized in that, in liquid chromatography (LC) analysis using ultraviolet light at a wavelength of 280 nm as a detector, it satisfies the following two requirements: composition (i) and (ii). composition (i): the area percentage of the dihydroxy compound represented by general formula (1) is in the range of 10% to 95% of all components detected by the LC analysis. composition (ii): the sum of the area percentages of the compound represented by general formula (2), the dihalobenzonitrile compound represented by general formula (3), and the dihydroxy compound represented by general formula (4) is 5% or less of all components detected by the LC analysis.

[0009] (In general formulas (1), (2), and (4), R each independently represents a divalent group represented by general formula (1a) or (1b), and in general formulas (2) and (3), X each independently represents a halogen atom.) (In general formula (1a), R １each independently represents a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, a cyclic alkyl group having 5 or 6 carbon atoms, a phenyl group, a phenoxy group, or a phenylalkyl group having 7 to 10 carbon atoms; m represents 0 or an integer of 1 to 4; n represents 0 or 1; p and q represent 0, 1, or 2; and * represents each bonding position. (In general formula (1b), R １ and m are the same as defined in general formula (1a); Y represents an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, an alkylidene group having 1 to 15 carbon atoms, a fluorine-containing alkylidene group having 2 to 15 carbon atoms, a cycloalkylidene group having 5 to 15 carbon atoms, a phenylmethylidene group, a phenylethylidene group, a phenylene group, or a fluorenylidene group; Z represents an oxygen atom, a sulfur atom, or no bridge; each Ar independently represents an aryl group having 6 to 8 carbon atoms; and * represents a bonding position.

[0010] Liquid chromatography (LC) analysis of the aromatic ether nitrile composition of the present invention using ultraviolet light at a wavelength of 280 nm as a detector can be performed in detail by the method described in the Examples below. The lower limit of the numerical range of the composition (i) of the aromatic ether nitrile composition of the present invention is preferably 15% or more, more preferably 20% or more, and particularly preferably 30% or more, from the viewpoint of reducing melt viscosity and improving crystallinity. The upper limit of the numerical range of the composition (ii) of the aromatic ether nitrile composition of the present invention is preferably 3% or less, more preferably 2% or less, and particularly preferably 1% or less, from the viewpoint of suppressing weight loss at high temperatures during molding, i.e., gas generation. The lower limit of this numerical range is not limited, as the smaller the value, the better, but it may be 0.01% or more, or even 0.001% or more.

[0011] R in general formula (1a) １each independently represents a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, a cyclic alkyl group having 5 or 6 carbon atoms, a phenyl group, a phenoxy group, or a phenylalkyl group having 7 to 10 carbon atoms; a linear alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 or 4 carbon atoms, a cyclic alkyl group having 5 or 6 carbon atoms, or a phenyl group is preferred; a linear alkyl group having 1 to 4 carbon atoms, a branched alkyl group having 3 or 4 carbon atoms, or a phenyl group is more preferred, and a methyl group is particularly preferred. Note that a "phenylalkyl group having 7 to 10 carbon atoms" refers to a group represented by a phenyl group and an alkylene group having 1 to 4 carbon atoms bonded to the phenyl group. An "alkylene group having 1 to 4 carbon atoms" refers to a linear alkylene group having 1 to 4 carbon atoms or a branched alkylene group having 3 or 4 carbon atoms. The alkylene group having 1 to 4 carbon atoms is preferably a methylene group or a branched alkylene group having 3 carbon atoms, and more preferably a methylene group or an isopropylidene group. In general formula (1a), m represents 0 or an integer of 1 to 4, preferably 0, 1, or 2, more preferably 0 or 1, and particularly preferably 0. In general formula (1a), n represents 0 or 1, and preferably 1. In general formula (1a), p and q each independently represent 0, 1, or 2, and preferably each independently represent 0 or 1, and particularly preferably 0. When n is 1 and p and q are 0, general formula (1a) is represented as general formula (1a'). (In the formula, R １ , m, and * are defined as in general formula (1a). In general formula (1a'), the bonding position indicated by * is preferably the ortho-position or para-position relative to the direct bonding position of the two benzene rings (i.e., 2,2-biphenylene group or 4,4-biphenylene group), and particularly preferably the para-position (i.e., 4,4-biphenylene group). R in general formula (1a') １ When m is 1 or 2, the bonding position of R is preferably the meta position with respect to the direct bonding position of the two benzene rings. １The preferred embodiments of n, p and q are the same as those in formula (1a). When n, p and q are 0, formula (1a) is represented by formula (1a''). (In the formula, R １ , m, and * are defined as in general formula (1a). In general formula (1a″), the bonding position indicated by * is preferably the para-position or meta-position relative to the other bonding position (i.e., a 1,4-phenylene group or a 1,3-phenylene group), and particularly preferably the para-position (i.e., a 1,4-phenylene group). R １ The preferred embodiments of n and q are the same as those in general formula (1a). When n and q are 0 and p is 1, general formula (1a) is represented as general formula (1a'''). (In the formula, R １ , m, and * are defined as in general formula (1a). In general formula (1a'''), the two bonding positions indicated by * are preferably the 1st and 5th positions, the 2nd and 6th positions, or the 2nd and 7th positions of the naphthalene ring (i.e., a 1,5-naphthylene group, a 2,6-naphthylene group, or a 2,7-naphthylene group), more preferably the 2nd and 6th positions, or the 2nd and 7th positions of the naphthalene ring (i.e., a 2,6-naphthylene group or a 2,7-naphthylene group), and particularly preferably the 2nd and 6th positions of the naphthalene ring (i.e., a 2,6-naphthylene group). R １ The preferred embodiments of R and m are the same as those in general formula (1a). １and m are the same as those defined in general formula (1a), and preferred embodiments are also the same. In general formula (1b), Y represents an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, an alkylidene group having 1 to 15 carbon atoms, a fluorine-containing alkylidene group having 2 to 15 carbon atoms, a cyclic alkylidene group having 5 to 15 carbon atoms, a phenylmethylidene group, a phenylethylidene group, a phenylene group, or a fluorenylidene group, and the cyclic alkylidene group having 5 to 15 carbon atoms may contain an alkyl group as a branched chain. Specific examples of the cyclic alkylidene group include a cyclopentylidene group (5 carbon atoms), a cyclohexylidene group (6 carbon atoms), a 3-methylcyclohexylidene group (7 carbon atoms), a 4-methylcyclohexylidene group (7 carbon atoms), a 3,3,5-trimethylcyclohexylidene group (9 carbon atoms), a cycloheptylidene group (7 carbon atoms), and a cyclododecanylidene group (12 carbon atoms). Y in the general formula (1b) is preferably a sulfonyl group, a carbonyl group, an alkylidene group having 1 to 6 carbon atoms, a fluorine-containing alkylidene group having 2 to 6 carbon atoms, a cyclic alkylidene group having 5 to 12 carbon atoms, a phenylmethylidene group, a phenylethylidene group, a phenylene group, or a fluorenylidene group, and more preferably a sulfonyl group, a carbonyl group, an alkylidene group having 1 to 3 carbon atoms, a fluorine-containing alkylidene group having 2 to 3 carbon atoms, a cyclic alkylidene group having 6 to 12 carbon atoms, a phenylmethylidene group, or a fluorenylidene group. A fluorenylidene group is more preferred, an alkylidene group having 3 carbon atoms, i.e., a propylidene group, a fluorine-containing alkylidene group having 3 carbon atoms, i.e., a fluorine-containing propylidene group, a cyclic alkylidene group having 6 to 12 carbon atoms, and a fluorenylidene group are even more preferred, and a 2,2-propylidene group, a 1,1,1,3,3,3-hexafluoro-2,2-propylidene group, a cyclohexylidene group, a 3,3,5-trimethylcyclohexylidene group, a cyclododecanylidene group, and a fluorenylidene group are particularly preferred. Z in general formula (1b) represents an oxygen atom, a sulfur atom, or no bridge, and is preferably an oxygen atom or no bridge, and more preferably no bridge. Ar in general formula (1b) represents an aryl group having 6 to 8 carbon atoms, and is more preferably a phenyl group.X in general formulas (2) and (3) each independently represent a halogen atom, preferably each independently represent a fluorine atom, chlorine atom, bromine atom, or iodine atom, more preferably each independently represent a fluorine atom or a chlorine atom, and particularly preferably both represent a chlorine atom. R in general formulas (1), (2), and (4) are preferably each not independently a divalent group represented by general formula (1a), more preferably each not independently a divalent group represented by general formula (1a'), a divalent group represented by general formula (1a''), or a divalent group represented by general formula (1a'''), further preferably each not independently a phenylene group, a naphthylene group, or a biphenylene group, even more preferably each not independently a 1,3-phenylene group, a 1,4-phenylene group, or a 4,4-biphenylene group, and particularly preferably each not independently a 4,4-biphenylene group. A particularly preferred embodiment of R in the general formulas (1), (2), and (4) where R is not independent and is a 4,4-biphenylene group will be specifically described. This means that groups corresponding to R are all 4,4-biphenylene groups, as in the compounds represented by the chemical formulas (1-1), (2-1), and (4-1) described below.

[0012] The aromatic ether nitrile composition of the present invention may contain, in addition to the compounds represented by the general formulae (1), (2), (3), and (4), a polymer having a repeating unit of the general formula (5) produced by the reaction of the compounds represented by the general formulae (3) and (4). (R in general formula (5), together with general formulas (1), (2), and (4), each independently represents a divalent group represented by general formula (1a) or general formula (1b).) There are no particular restrictions on the terminal structure of such a polymer. Both terminals may be hydroxy groups derived from the dihydroxy compound represented by general formula (4), which is the raw material, or both terminals may be halogen atoms derived from the dihalobenzonitrile compound represented by general formula (3), which is the raw material, or one terminal may be the hydroxy group and the other terminal may be the halogen atom. A preferred embodiment of R in general formula (5) is the same as R in general formulas (1), (2), and (4). A particularly preferred embodiment of R in general formula (5), in which R is not independent and is a 4,4-biphenylene group, will be specifically described. This means that, like the compounds represented by chemical formulas (1-1), (2-1), and (4-1) and a polymer having a repeating unit represented by chemical formula (5-1), which will be described later, the groups corresponding to R are all 4,4-biphenylene groups.

[0013] The aromatic ether nitrile composition of the present invention preferably has a weight average molecular weight (Mw) of 500 or more and 8000 or less, calculated as polystyrene, as measured by gel permeation chromatography (GPC). If the weight average molecular weight (Mw) is 8000 or more, a large amount may need to be added to the heat-resistant resin to achieve the effects of the present invention, which is not preferred. Furthermore, if the weight average molecular weight is less than 500, the composition of the aromatic ether nitrile composition of the present invention may deviate from the composition of the present invention. In order to improve the melt viscosity reduction and the like of the aromatic ether nitrile composition of the present invention with a small amount added to the heat-resistant resin, the weight average molecular weight (Mw) is more preferably in the range of 500 or more and 4000 or less, even more preferably in the range of 500 or more and 3000 or less, and particularly preferably in the range of 500 or more and 2000 or less.

[0014] (Method for Producing Aromatic Ethernitrile of the Present Invention) The aromatic ether nitrile composition of the present invention can be produced by a method comprising: an etherification reaction step in which a dihalobenzonitrile compound represented by the general formula (3), a dihydroxy compound represented by the general formula (4), and a basic compound that forms a salt with the hydroxyl group of the dihydroxy compound represented by the general formula (4) are reacted to obtain a reaction product containing the dihydroxy compound represented by the general formula (1); and an alkali washing step in which the reaction product obtained by the etherification reaction step is washed with an aqueous solution of a basic compound, wherein the dihydroxy compound represented by the general formula (4) is used in an amount of 1.5 or more times by mole relative to the dihalobenzonitrile compound represented by the general formula (3), and the basic compound that forms a salt with the terminal hydroxyl group of the dihydroxy compound represented by the general formula (4) is used in an amount of 2 or more times by mole relative to the dihydroxy compound represented by the general formula (4).

[0015] The dihydroxy compound of general formula (1) is produced by the following reaction between a dihalobenzonitrile compound of general formula (3) and two moles of the dihydroxy compound of general formula (4) in the presence of a basic compound that forms a salt with the hydroxyl group of the dihydroxy compound of general formula (4): The compound of general formula (2) is produced by the reaction between a dihalobenzonitrile compound of general formula (3) and one mole of the dihydroxy compound of general formula (4). Alternatively, in the etherification reaction step, a salt of the dihydroxy compound represented by general formula (4) may be synthesized in advance by converting the hydroxyl group of the dihydroxy compound represented by general formula (4) with a basic compound, and then the salt may be reacted with the dihalobenzonitrile compound represented by general formula (3). Since the above reaction involves a reaction between bifunctional monomers, a polymerization reaction also occurs in parallel, resulting in a composition containing not only the dihydroxy compound represented by general formula (1) but also compounds with lower and higher molecular weights. During the desalting reaction, water is generated, but this water may or may not be removed from the system. For example, the reaction may be carried out in the presence of a solvent that forms an azeotrope with water at a temperature at which the desalting reaction proceeds. During this time, water may be distilled off from the reaction mixture using a solvent that forms an azeotrope with water, or the azeotrope may be refluxed as is. The temperature at which the desalting reaction begins is usually around 130°C, depending on the raw materials. For example, when 4,4'-biphenol is used as the dihydroxy compound of general formula (4) and 2,6-dichlorobenzonitrile is used as the dihalobenzonitrile compound of general formula (3), potassium carbonate, sulfolane (boiling point 285°C) as the aprotic solvent, and toluene as the solvent that forms an azeotrope with water, the reaction temperature is preferably in the range of 130 to 170°C. The reaction is carried out in an inert atmosphere, for example, in a nitrogen atmosphere, at atmospheric pressure, but may also be carried out under elevated or reduced pressure.

[0016] <Dihydroxy Compound Represented by General Formula (4)> Specific examples of the dihydroxy compound represented by general formula (4) used as a component of the aromatic ether nitrile composition of the present invention or a raw material for producing the same include hydroquinone, resorcinol, 2-phenylhydroquinone, 4,4'-biphenol, 3,3'-biphenol, 2,2'-biphenol, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,1'-bi-2-naphthol, 2,2'-bi-1-naphthol, 1,3-bis[1-methyl-1-(4-hydroxyphenyl)ethyl]benzene, 1,4 -bis[1-methyl-1-(4-hydroxyphenyl)ethyl]benzene, 1,3-(4-hydroxybenzoylbenzene), 1,4-(4-hydroxybenzoylbenzene), 1,3-bis(4-hydroxyphenoxy)benzene, 1,4-bis(4-hydroxyphenoxy)benzene, 1,4-bis(4-hydroxyphenyl)benzene, 1,3-bis(4-hydroxyphenyl)benzene, 4,4'-isopropylidenebiphenol (Bis-A), 2,2-bis(4-hydroxyphenyl)-1,1,1,3,3, 3-Hexafluoropropane, 4,4'-bishydroxybenzophenone, 4,4'-bishydroxydiphenyl sulfone, 4,4'-dihydroxydiphenyl ether, bis(4-hydroxyphenyl)methane, 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis(3-phenyl-4-hydroxyphenyl)fluorene, 9,9-bis(3,5-diphenyl-4-hydroxyphenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy- 3,5-dimethylphenyl)fluorene, 9,9-bis(4-hydroxy-3-cyclohexylphenyl)fluorene, 4,4'-isopropylidenebis(2-phenylphenol), bisphenol Z (1,1-bis(4-hydroxyphenyl)cyclohexane), bisphenol TMC (1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane), 1,1-bis(4-hydroxyphenyl)cyclododecane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, and the like.Among these, hydroquinone, resorcinol, and 4,4'-biphenol are preferred, with 4,4'-biphenol being particularly preferred.

[0017] <Dihalobenzonitrile Compound Represented by General Formula (3)> Specific examples of the dihalobenzonitrile compound represented by general formula (3) used as a component of the aromatic ether nitrile composition of the present invention or a raw material for producing the same include 2,6-difluorobenzonitrile, 2,5-difluorobenzonitrile, 2,4-difluorobenzonitrile, 2,6-dichlorobenzonitrile, 2,5-dichlorobenzonitrile, 2,4-dichlorobenzonitrile, 2,6-dibromobenzonitrile, 2,5-dibromobenzonitrile, 2,4-dibromobenzonitrile, 2,6-dinitrobenzonitrile, 2,5-dinitrobenzonitrile, 2,4-dinitrobenzonitrile, and 1,4-dichloro-2,5-dicyanobenzene. In the etherification reaction step, in addition to the dihalobenzonitrile compound represented by general formula (3), reactive derivatives of these compounds may also be included. The reactive derivatives are compounds that can react with dihydroxy compounds represented by general formulas (1) and (4), such as those represented by the following formulas, taking a structure derived from 2,6-dihalobenzonitrile as an example. These mean compounds derived by reacting two 2,6-dihalobenzonitriles or a 2,6-dihalobenzonitrile with a dihydroxy compound represented by general formula (4). (In the formula, R is defined as in general formula (4), and X is defined as in general formula (3). Among these, 2,6-difluorobenzonitrile and 2,6-dichlorobenzonitrile are preferably used from the viewpoints of reactivity, economy, etc. Two or more of these compounds can also be used in combination.

[0018] <Amount of Raw Material Used> In the production method of the present invention, the dihydroxy compound represented by general formula (4) is preferably used in an amount of 1.5 or more times by mole relative to the dihalobenzonitrile compound represented by general formula (3), and from the viewpoint of efficient use of raw materials, it is more preferable to use it in an amount of 1.5 to 10 times by mole, even more preferably in an amount of 1.5 to 5 times by mole, and particularly preferably in an amount of 1.5 to 3 times by mole. In the production method of the present invention, in order to maximize the selectivity of the compound represented by general formula (1), it is suitable to use the dihydroxy compound represented by general formula (4) in an amount of 2 times by mole relative to the dihalobenzonitrile compound represented by general formula (3).

[0019] <Basic Compound> The basic compound may be any compound, whether organic or inorganic, that promotes the desalting polycondensation reaction and does not affect the quality. Of the organic and inorganic basic compounds, inorganic basic compounds are preferred, and among these, alkali metal compounds and alkaline earth metal compounds are more preferred, with alkali metal compounds being particularly preferred. Examples of organic basic compounds include tetramethylammonium hydroxide, triethylamine, N,N-diisopropylethylamine, 1,1,3,3-tetramethylguanidine (TMG), N,N-dimethyl-4-aminopyridine (DMAP), 2,6-lutidine, pyridine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), 1,5-diazabicyclo[4.3.0]-5-nonene (DBN), 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), ... Diazabicyclo[4.4.0]dec-5-ene (TBD), 1,8-bis(dimethylaminonaphthalene) (DMAN), 1,4-diazabicyclo[2.2.2]octane (DABCO), tert-butylimino-tri(pyrrolidino)phosphorane, tert-butylimino-tris(dimethylamino)phosphorane, 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine, tert-octylimino-tris(dimethylamino)phosphorane, phosphazene base P ２ -Et, phosphazene base P ２-t-Bu, phosphazene base P ３ -t-Bu, phosphazene base P ４ -t-Bu, phosphazene base P ４ -t-Oct. Among the inorganic base compounds, examples of alkali metal compounds include alkali metals such as lithium, rubidium, cesium, potassium, and sodium; alkali metal hydrides such as lithium hydride, rubidium hydride, cesium hydride, potassium hydride, and sodium hydride; alkali metal hydroxides such as lithium hydroxide, rubidium hydroxide, cesium hydroxide, potassium hydroxide, and sodium hydroxide; alkali metal carbonates such as lithium carbonate, rubidium carbonate, cesium carbonate, potassium carbonate, and sodium carbonate; and alkali metal bicarbonates such as lithium bicarbonate, rubidium bicarbonate, cesium bicarbonate, potassium bicarbonate, and sodium bicarbonate. These compounds can be used alone or in combination of two or more. The specific surface area of ​​these alkali metal compounds is 0.3 m or less. ２ By using an alkali metal compound catalyst having a specific surface area of ​​0.8 m / g or more, the desalination polycondensation reaction can be carried out with high efficiency. ２ / g or more, and ２ / g or more is more preferable. By using an alkali metal compound with a larger specific surface area, the contact opportunity between the catalyst and the reaction raw materials increases, and it becomes possible to carry out the desalination polycondensation reaction with even higher efficiency. ２ When the specific surface area is less than 0.3 m / g, the desalting polycondensation reaction cannot be carried out with sufficiently high efficiency unless the amount of catalyst is increased, but increasing the amount of catalyst is not preferred because it affects the quality of the polymer. From the above, the basic compound in the production method of the present invention is preferably an alkali metal carbonate such as lithium carbonate, rubidium carbonate, cesium carbonate, potassium carbonate, or sodium carbonate, more preferably lithium carbonate, potassium carbonate, or sodium carbonate, and particularly preferably a basic compound having a specific surface area of ​​0.3 m / g from the viewpoint of availability. ２The amount of the basic compound used in the production method of the present invention is, for example, in the case of an alkali metal compound, 2 moles or more of the alkali metal ions contained therein relative to the dihydroxy compound represented by general formula (4), but if used in large excess, side reactions such as cleavage of ether bonds occur during polymerization, so the range of 2 moles to 4 moles is more preferable, the range of 2 moles to 2.4 moles is even more preferable, and the range of 2 moles to 2.2 moles is particularly preferable.

[0020] <Solvent> In the etherification reaction step, a reaction solvent can be used, and it is preferable to use an aprotic solvent as the reaction solvent. Specific examples of aprotic solvents include N,N-dimethylacetamide, N,N-dimethylformamide, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, γ-butyrolactone, sulfolane, dimethyl sulfoxide, diethyl sulfoxide, dimethyl sulfone, diethyl sulfone, diisopropyl sulfone, diphenyl sulfone, diphenyl ether, benzophenone, dialkoxybenzenes (alkoxy groups having 1 to 4 carbon atoms), and trialkoxybenzenes (alkoxy groups having 1 to 4 carbon atoms). Among these solvents, polar organic solvents with high dielectric constants, such as N-methyl-2-pyrrolidone, N,N-dimethylacetamide, sulfolane, diphenyl sulfone, and dimethyl sulfoxide, are particularly preferred. These solvents can be used alone or in combination of two or more. The amount of aprotic solvent used is not particularly limited, as long as it uniformly dissolves the raw materials and satisfactorily disperses the alkali metal salt. It is sufficient to select an amount that maximizes the volumetric efficiency of the polymerization vessel relative to the raw materials used and the target composition. Typically, the amount is selected within a range of 0.5 to 20 times the total weight of the raw materials and the alkali metal salt. Specific examples of solvents that form an azeotrope with water include aromatic hydrocarbons such as benzene, toluene, xylene, hexane, cyclohexane, octane, chlorobenzene, dioxane, tetrahydrofuran, anisole, and phenetole. These solvents may be used alone or in combination of two or more. When a solvent that forms an azeotrope with water is used, it is preferable to use 1 to 100 parts by weight of the solvent that forms an azeotrope with water per 100 parts by weight of the aprotic solvent. From the viewpoints of volumetric efficiency and solvent recovery, a range of 1 to 10 parts by weight is more preferable, and a range of 2 to 5 parts by weight is even more preferable.

[0021] <Reaction Temperature> The reaction temperature in the etherification reaction step is preferably in the range of 140 to 200°C, more preferably in the range of 150 to 170°C, and even more preferably in the range of 155 to 165°C.

[0022] <Reaction Time> The reaction time for the etherification reaction step varies depending on the reaction conditions and the raw materials used, but is typically 3 to 20 hours. The reaction time is preferably continued until the amounts of the compounds represented by general formulas (2), (3), and (4) are minimized, but is not particularly limited. For example, when 2 moles of 4,4'-biphenol and 1 mole of 2,6-dichlorobenzonitrile are reacted at 160°C using 2 moles of potassium carbonate, sulfolane as an aprotic solvent, and toluene as a solvent that forms an azeotrope with water, all of the 2,6-dichlorobenzonitrile corresponding to the dihalobenzonitrile compound represented by general formula (3) is consumed within 4 hours. The compound represented by chemical formula (2-1) described below, which corresponds to the compound represented by general formula (2), is produced in about 20% in the first hour after the start of the reaction, but this amount decreases as the reaction time elapses, and is completely consumed after 8 hours, reaching a maximum amount of the compound corresponding to general formula (1).

[0023] (Treatment after Etherification Reaction Step) After the etherification reaction step is completed, the reaction product is extracted from the reactor, cooled and solidified, and then pulverized to be subjected to the subsequent alkali washing step. Alternatively, the reaction product extracted from the reactor may be directly charged into a washing tank for the alkali washing step. Alternatively, a solvent to be used in the alkali washing step described below may be injected into the reactor after the reaction is completed, and the reaction product may be transferred to the alkali washing step in the form of a slurry or wax.

[0024] The alkali washing step is a washing step for removing the salts and reaction solvent contained in the reaction product obtained in the etherification reaction step, as well as the remaining dihydroxy compound of general formula (4). Prior to this alkali washing step, the reaction solvent in the reaction product is preferably extracted and washed using a solvent such as an alcohol, ketone, aromatic hydrocarbon, aliphatic hydrocarbon, or water, and then the salts formed by the desalting reaction in the reaction product are preferably washed and removed using water. After removing the solvent and salt, the remaining dihydroxy compound of general formula (4) is removed using an aqueous solution of a basic compound. The washing is then completed by neutralization with an acid or an aqueous solution thereof. Specifically, the reaction product in a pulverized, slurry, or waxy state is transferred to a container equipped with a stirrer, and the stirring, washing, and filtration procedures with a washing solvent are repeated until the reaction solvent, salt, and dihydroxy compound of general formula (4) are reduced to or below the target content. As the apparatus, a washing tank and a pressure filter or a centrifuge, as well as a multifunctional filter capable of washing, filtration, and drying in one device, may be used. Specific examples of the extraction and washing solvent for the reaction solvent other than water include alcohols such as methanol, ethanol, propyl alcohol, isopropyl alcohol, butyl alcohol, isobutyl alcohol, sec-butyl alcohol, t-butyl alcohol, n-amyl alcohol, isoamyl alcohol, t-amyl alcohol, n-hexyl alcohol, cyclohexanol, n-octyl alcohol, capryl alcohol, etc. Specific examples of ketones include acetone, methyl ethyl ketone, methyl-n-propyl ketone, diethyl ketone, 2-hexanone, 3-hexanone, methyl-t-butyl ketone, di-n-propyl ketone, diisopropyl ketone, diisobutyl ketone, di-n-amyl ketone, diacetyl, acetylacetone, cyclohexanone, benzophenone, etc.Examples of aliphatic hydrocarbons include saturated aliphatic hydrocarbons such as n-hexane, 2-methylheptane, 3-methylheptane, 2,2-dimethylbutane, 2,3-dimethylbutane, n-heptane, 2-methylhexane, 3-methylhexane, 2,2-dimethylpentane, 2,3-dimethylpentane, 2,4-dimethylpentane, 3,3-dimethylpentane, 3-ethylpentane, 2,2,3-trimethylbutane, and cyclohexane; and unsaturated hydrocarbons such as 1-hexene, 1-heptene, 1-octene, and cyclohexene. Examples of aromatic hydrocarbons include benzene, toluene, o-xylene, m-xylene, p-xylene, ethylbenzene, n-propylbenzene, cumene, n-butylbenzene, t-butylbenzene, styrene, and allylbenzene. Among these, methanol, ethanol, acetone, methyl ethyl ketone, xylene, and toluene are preferred, with acetone and methanol being particularly preferred from the viewpoints of operability and ease of distillation recovery of the reaction solvent after washing. Water is preferred for washing alkali metal salts such as potassium chloride produced in the desalting condensation reaction, but acidic water containing low concentrations of hydrochloric acid, oxalic acid, or acetic acid may also be used. The basic compound used in the aqueous solution of basic compounds for removing the remaining dihydroxy compound represented by general formula (4) is preferably the basic compound described in the etherification reaction step. The concentration of the aqueous solution of basic compounds is preferably several percent to 10%. From a cost perspective, an aqueous solution of sodium hydroxide or potassium hydroxide is preferred. After removing the dihydroxy compound represented by general formula (4) in the alkali washing step, the excess basic compound is neutralized with acidic water containing hydrochloric acid, oxalic acid, or acetic acid, and the excess acidic compound is removed with water to complete the washing operation. The conditions for this washing step, such as the amount of washing solvent used, the number of washes, and the washing temperature, can be appropriately selected depending on the amounts of residual reaction solvent, residual salt, and remaining dihydroxy compound represented by general formula (4) to be removed.

[0025] The drying step is a step of drying the composition obtained in the washing step. The composition containing water after washing is dried by a known method. Known devices such as an evaporator, a tray oven, or a tumbler can be used as the dryer. The target water content is usually 0.5% by weight or less, preferably 0.4% by weight or less, and more preferably 0.3% by weight or less. The conditions for this drying step may be any conditions that allow removal of water at a temperature below the melting point of the composition. To minimize contact with air, the drying step is preferably carried out in an inert gas (nitrogen, argon, etc.) atmosphere, in an inert gas stream, or under reduced pressure.

[0026] The aromatic ether nitrile composition obtained as described above can be blended in any ratio with a resin having a high melt viscosity, such as an aromatic polyether nitrile, aromatic polyether ether ketone, or aromatic polyether sulfone, which are known as super engineering plastics, using a melt kneading device such as a single-screw, twin-screw, or multi-screw extruder, a Banbury mixer, a kneader, or a roller, to provide a highly heat-resistant resin composition that generates little gas, has high melt fluidity, and has improved moldability.

[0027] The aromatic ether nitrile composition of the present invention can be used as a molding material by the above-mentioned method, or can be used to produce molded articles and parts, and has heat resistance, chemical resistance, flame retardancy, and high mechanical properties. For example, it can be used in electrical and electronic applications such as personal computers and semiconductor parts, automotive applications such as gears, bearings, and engine housings, medical devices, and aerospace applications. It can also be used as a raw material for polyethers, polyesters, polycarbonates, epoxy resins, and other applications, not limited to super engineering plastics.

[0028] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0029] The analytical methods used in the present invention are as follows. <Analytical Methods> (1) Compositional Analysis of Aromatic Ethernitrile Composition and Each Compound The compounds represented by the following chemical formulas in the obtained aromatic ethernitrile composition and each compound were quantified by dissolving samples in tetrahydrofuran (THF) solvent and subjecting them to high performance liquid chromatography (HPLC) using the following equipment and conditions, based on the area ratio detected at a wavelength of 280 nm. The compound represented by chemical formula (5-1) is a polymer having the repeating unit. Measurement equipment: Ultra-high performance liquid chromatograph (UFLC) manufactured by Shimadzu Corporation Detector: UV [Measurement conditions] Column: HALO 90A C18 manufactured by Shimadzu GLC Corporation Flow rate: 0.8 mL / min Eluent: 0.1% aqueous phosphoric acid solution, tetrahydrofuran (THF) Temperature: 50°C Detection wavelength: 280 nm (2) Measurement of molecular weight The weight average molecular weight (Mw) and number average molecular weight (Mn) of the obtained aromatic ether nitrile composition, compound, aromatic polyether nitrile, and aromatic polyether nitrile resin composition were measured by diluting a 1% p-chlorophenol solution of the sample 10 times with chloroform, and measuring the solution using the following equipment and conditions. The molecular weight distribution Mw / Mn was calculated from this value. Apparatus: Gel permeation chromatography: 515 HPLC pump, 717plus automatic injection device, 2487 UV-visible detector (manufactured by Nihon Waters K.K.) Column: 2 × PLgel 5 μ MIXED-D, 7.5 × 300 mm (manufactured by Agilent Technologies Inc.) Column temperature: 40 ° C. Flow rate: 1.0 mL / min Injection amount: 2.5 μL Detection: UV-visible detector: 254 nm Column calibration: monodisperse polystyrene (EasiCal PS-1 manufactured by Agilent Technologies Inc.) Molecular weight calibration: relative calibration method (polystyrene equivalent) Analysis software: Empower3 (manufactured by Nihon Waters K.K.) (3) Glass transition temperature (Tg) Using a differential scanning calorimeter (manufactured by Shimadzu Corporation: DSC-60), the glass transition temperature (Tg) of the obtained aromatic polyether nitrile resin composition and the aromatic polyether nitrile was measured under the following conditions. <Conditions> Sample: 10 mg Nitrogen flow rate: 50 mL / min. Temperature change range: 50 to 370°C Temperature change rate: 10°C / min. (4) 1% weight loss temperature (Td1) The 1% weight loss temperature (Td1) of the obtained aromatic polyethernitrile resin composition was measured under the following conditions using a DTG NEXTA STA manufactured by Hitachi High-Tech Science Corporation. Sample: 10 mg Nitrogen flow rate: 100 mL / min. Temperature change range: 30 to 550°C Temperature increase rate: 10°C / min Sampling interval: 0.5 seconds

[0030] Example 1 A four-necked, 3-liter reaction vessel equipped with a mechanical stirrer, a thermometer, a dry nitrogen inlet, and a reflux condenser was charged with 149.23 g (0.868 mol) of 2,6-dichlorobenzonitrile (hereinafter referred to as "DCBN"; its purity as determined by high-performance liquid chromatography was 99.90% by weight; the same applies hereinafter), which is compound (3-1), 323.08 g (1.735 mol) of 4,4'-biphenol (hereinafter referred to as "BP"; its purity as determined by high-performance liquid chromatography was 99.95% by weight; the same applies hereinafter), which is compound (4-1), 239.79 g (1.735 mol: 1.00 times the molar equivalent of BP), 60 g of toluene, and 1562 g of anhydrous sulfolane. This mixture was heated from room temperature in a nitrogen stream and, while stirring at 250 rpm, heated to 160°C under reflux. At temperatures above 130°C, carbon dioxide was generated from the reaction of potassium carbonate and BP. The reaction was allowed to proceed at 160°C while refluxing toluene and the generated water. After 8 hours, the reaction product was extracted from the bottom of the reaction vessel and allowed to cool and solidify. HPLC analysis confirmed that compound (2-1) and the raw material DCBN were not detected in the solidified product, and 19.2% of the raw material BP remained. This solidified product was washed with 2.5 times its weight of water and filtered three times, then washed with 1.5 times its weight of a 4 wt% aqueous solution of sodium hydroxide and filtered four times, and HPLC confirmed that the BP content had decreased to less than 1%. The solidified product was then washed with 1.5 times its weight of 4 wt% hydrochloric acid, filtered, washed with 1.5 times its weight of water, filtered three times, and dried at 120°C for 5 hours under nitrogen to obtain 197 g of a white powder (hereinafter referred to as "aromatic ether nitrile composition α"). The contents of potassium and sodium in the aromatic ether nitrile composition α were each 10 ppm or less. The results of the composition and molecular weight of the aromatic ether nitrile composition α obtained by the above analytical methods are shown in Table 1.

[0031] Comparative Example 1 A solidified product was obtained in the same manner as in Example 1, except that the amount of DCBN was 298.45 g (1.735 mol), the amount of anhydrous potassium carbonate was 143.87 g (1.041 mol: 0.60 times the molar amount of BP), and the reaction was carried out at 160°C for 5 hours. HPLC analysis confirmed that the solidified product contained 26.8% of compound (2-1), no detectable DCBN from the raw material, and 10.8% of the raw material BP remaining. This solidified product was subjected to the same procedure as in Example 1 to obtain 328 g of a white powder (hereinafter referred to as "aromatic ether nitrile composition β"). The potassium and sodium contents of aromatic ether nitrile composition β were each 10 ppm or less. The composition and molecular weight of aromatic ether nitrile composition β determined by the above analytical methods are shown in Table 1.

[0032] Synthesis Example 1 A four-necked, 3-liter reaction vessel equipped with a mechanical stirrer, a thermometer, a dry nitrogen inlet, and a reflux condenser was charged with 149.23 g (0.868 mol) of DCBN, 295.48 g (1.735 mol) of 4-phenylphenol (hereinafter referred to as "PPP"; a reagent manufactured by Tokyo Chemical Industry Co., Ltd. with a gas chromatography purity of 99% or higher), 143.877 g (1.041 mol: 0.60 times the molar ratio of PPP), 60 g of toluene, and 1562 g of anhydrous sulfolane. This mixture was heated from room temperature in a nitrogen stream and, while stirring at 250 rpm, heated to 160°C under reflux. At temperatures above 130°C, carbon dioxide was generated from the reaction of potassium carbonate and PPP. The reaction was continued at 160°C while refluxing the toluene and the generated water. After 9 hours, the reaction product was withdrawn from the bottom of the reaction vessel and allowed to cool and solidify. This solidified product was washed with 2.5 times its weight of water and filtered three times, then washed with 1.5 times its weight of methanol and filtered three times, and dried at 120°C for 5 hours in nitrogen to obtain 433 g of a white powder of a compound represented by chemical formula (6) (compound (6)) with a purity of 98.3%. The potassium and sodium contents of the obtained compound (6) were each 10 ppm or less. The composition and molecular weight of the obtained compound (6) obtained by the above analytical methods are shown in Table 1.

[0033] Synthesis Example 2: A four-necked, 3-liter reaction vessel equipped with a mechanical stirrer, a thermometer, a dry nitrogen inlet, and a reflux condenser was charged with 298.45 g (1.735 mol) of DCBN, 323.08 g (1.735 mol) of BP, 251.79 g (1.822 mol: 1.05 times the molar ratio of BP) of anhydrous potassium carbonate, 60 g of toluene, and 1,562 g of anhydrous sulfolane. This mixture was heated from room temperature to 160°C under reflux while stirring at 250 rpm in a nitrogen stream. At temperatures above 130°C, carbon dioxide was generated from the reaction of potassium carbonate and BP. After 3 hours at 160°C, the oligomerization reaction between DCBN and BP was completed. The cooling water for the reflux condenser was then switched to hot water, and the temperature was raised to 220°C by removing water and toluene from the reflux condenser outlet, and the polycondensation reaction was carried out for 3 hours. After the polycondensation reaction, the polycondensation reaction product was removed from the bottom of the reaction vessel and allowed to cool and solidify. The solid product was pulverized in a Waring blender, washed with acetone, 1% oxalic acid water, and distilled water, and dried in a vacuum oven at 120°C for 16 hours to obtain 470 g of powder raw material polyethernitrile (hereinafter referred to as "aromatic polyethernitrile α") (yield 95%). The potassium content of the obtained aromatic polyethernitrile α was 10 ppm or less. The molecular weight of the obtained aromatic polyethernitrile α measured by the above analytical method is shown in Table 1.

[0034]

[0035] Examples 2 to 4, Comparative Examples 2 to 5, Reference Example The aromatic polyethernitrile α obtained in Synthesis Example 2 was powder-mixed with the aromatic ethernitrile composition α obtained in Example 1, the aromatic ethernitrile composition β obtained in Comparative Example 1, and the compound (6) obtained in Synthesis Example 1 as additives in the amounts shown in Table 2, and then melt-kneaded at 380°C under a nitrogen atmosphere under the following conditions, and a strand was obtained while measuring the melt viscosity of the aromatic polyethernitrile resin composition. (Melt-kneading conditions) Apparatus: Circulation kneader [Xplore MC15HT] (manufactured by Xplore Instrument) Temperature / time: 380°C / 5 min. Rotation speed: 100 rpm Screw shape: Conical twin screw Kneading environment: N ２The weight average molecular weight (Mw), number average molecular weight (Mn), glass transition temperature (Tg), and 1% weight loss temperature (Td1) of the resulting aromatic polyethernitrile resin composition and the aromatic polyethernitrile α obtained in Synthesis Example 2 were measured by the above-mentioned methods, and the results are shown in Table 2. The measurement results of the aromatic polyethernitrile α obtained in Synthesis Example 2 to which no additive was added are shown as Reference Examples.

[0036]

[0037] The above Examples 2 to 4, Comparative Examples 2 to 5, and Reference Example confirmed that aromatic ether nitrile compositions α and β, and compound (6), when blended with aromatic polyether nitrile α, have the effect of lowering melt viscosity. The 1% weight loss temperatures of the aromatic polyether nitrile resin compositions containing the additives used in Comparative Examples 2 to 5 were 380°C or lower, and all of them generated gas during molding, such as injection or extrusion, which is likely to result in mold contamination and defective molded products. This result is believed to be due to the fact that compound (2-1) contained in aromatic ether nitrile composition β has a small molecular weight of 322 and is highly volatile at low temperatures. The difference in thermal weight loss between the aromatic polyether nitrile resin compositions obtained using aromatic ether nitrile composition α and compound (6) as additives is believed to be due to the slight difference between the molecular weights of compound (1-1) (471) and compound (6) (439), or the difference in affinity with polyether nitrile due to the presence or absence of hydroxyl groups in compound (1-1) and compound (6). As described above, the aromatic ether nitrile composition of the present invention can reduce the melt viscosity of resins with high melting points, known as super engineering plastics, such as polyether nitriles and PEEK, without impairing the heat resistance, and can improve the moldability without causing problems such as gas generation, thereby providing high-quality molded articles.

Claims

1. An aromatic ether nitrile composition containing a dihydroxy compound represented by general formula (1) and satisfying compositions (i) and (ii) in liquid chromatography (LC) analysis using 280 nm ultraviolet light as a detector. Composition (i): The area percentage of the dihydroxy compound represented by general formula (1) is in the range of 10% to 95% of all components detected by the LC analysis. Composition (ii): The sum of the area percentages of the compound represented by general formula (2), the dihalobenzonitrile compound represented by general formula (3), and the dihydroxy compound represented by general formula (4) is 5% or less of all components detected by the LC analysis. (In general formulas (1), (2), and (4), R each independently represents a divalent group represented by general formula (1a) or (1b), and in general formulas (2) and (3), X each independently represents a halogen atom.) (In general formula (1a), R １ each independently represents a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, a cyclic alkyl group having 5 or 6 carbon atoms, a phenyl group, a phenoxy group, or a phenylalkyl group having 7 to 10 carbon atoms; m represents 0 or an integer of 1 to 4; n represents 0 or 1; p and q represent 0, 1, or 2; and * represents each bonding position. (In general formula (1b), R １ and m are the same as defined in general formula (1a); Y represents an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, an alkylidene group having 1 to 15 carbon atoms, a fluorine-containing alkylidene group having 2 to 15 carbon atoms, a cycloalkylidene group having 5 to 15 carbon atoms, a phenylmethylidene group, a phenylethylidene group, a phenylene group, or a fluorenylidene group; Z represents an oxygen atom, a sulfur atom, or no bridge; each Ar independently represents an aryl group having 6 to 8 carbon atoms; and * represents a bonding position.

2. The aromatic ether nitrile composition according to claim 1, wherein R in said general formulas (1), (2) and (4) is independently a phenylene group, a naphthylene group or a biphenylene group.

3. The aromatic ether nitrile composition according to claim 1, further comprising a polymer having a repeating unit represented by general formula (5). (R in general formula (5) is common to general formulas (1), (2), and (4), and each R is independently a divalent group represented by general formula (1a) or general formula (1b).) 4. The aromatic ether nitrile composition according to claim 1, which has a weight average molecular weight (Mw) of 500 or more and 8,000 or less in terms of polystyrene as measured by gel permeation chromatography (GPC).

5. A method for producing the aromatic ether nitrile composition according to claim 1, comprising: an etherification reaction step in which the dihalobenzonitrile compound represented by general formula (3) and the dihydroxy compound represented by general formula (4) are reacted in the presence of a basic compound which forms a salt with the hydroxyl group of the dihydroxy compound represented by general formula (4) to obtain a reaction product containing the dihydroxy compound represented by general formula (1); and an alkali washing step in which the reaction product obtained in the etherification reaction step is washed with an aqueous solution of a basic compound, wherein in the etherification reaction step, the dihydroxy compound represented by general formula (4) is used in an amount of 1.5 or more times by mole relative to the dihalobenzonitrile compound represented by general formula (3), and the basic compound which forms a salt with the terminal hydroxyl group of the dihydroxy compound represented by general formula (4) is used in an amount of 2 or more times by mole relative to the dihydroxy compound represented by general formula (4).