JP2016040344A - Resin composition, method for producing aromatic poly (thio) ether, and molded article - Google Patents

Abstract

Disclosed are a resin composition, a method for producing an aromatic poly (thio) ether, and a molded product, which can suppress coloring of the molded product and can be produced advantageously in a process. The present invention provides a resin composition containing an organic solvent and an aromatic poly (thio) ether, wherein the organic solvent is a compound represented by the following formula (1): diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, Triethylene glycol dimethyl ether, or a combination of two or more thereof. In formula (1), R is a C1-C5 monovalent organic group other than an amide group. n is an integer of 0-5. When n is 2 or more, the plurality of R may be the same or different. The organic solvent is preferably benzonitrile, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, or triethylene glycol dimethyl ether. [Selection figure] None

Description

  The present invention relates to a resin composition, a method for producing an aromatic poly (thio) ether, and a molded article.

  Aromatic poly (thio) ethers are generally synthesized in aprotic polar solvents. By thus synthesizing the aromatic poly (thio) ether in an aprotic polar solvent, the aromatic nucleophilic substitution reaction is promoted and a high molecular weight product can be obtained.

  Examples of the aprotic polar solvent used for the synthesis of aromatic poly (thio) ether include N-methylpyrrolidone (NMP), dimethylacetamide (DMAc), N, N-dimethylformamide (DMF), sulfolane, dimethyl sulfoxide ( DMSO) (see JP-A-5-339364, JP-A-2010-95614 and JP-B-8-5959).

  Also known is a method in which diphenylsulfone, which is a solid at room temperature, is melted at a high temperature of about 300 ° C. to advance the reaction (see JP 2013-47331 A).

  However, conventionally known aprotic polar solvents used for the synthesis of aromatic poly (thio) ethers have various disadvantages, and development of alternative solvents is required.

  For example, amide solvents such as NMP, DMAc, and DMF are feared for biotoxicity. In addition, amide solvents are generally easily decomposed, and there is a risk that decomposition products may inhibit the polymerization reaction. For example, it is known that NMP decomposes into hydroxy-N-methylpyrrolidone and it is difficult to obtain a high molecular weight product because this decomposition product inhibits the polymerization reaction (Japanese Patent Laid-Open No. 11-158264). reference). In addition, the decomposition product of the amide solvent also causes coloring of the molded product obtained from the composition containing the aromatic polyether. For example, DMAc is known to easily undergo a decomposition reaction in the presence of oxygen and water, and a decomposition product generated at this time is known to cause coloring (see JP-A-7-173119). . It is very difficult to remove the colored substance, and in order to improve the hue, it is important to suppress the generation of the colored substance.

  In addition, although sulfolane does not have a problem of biotoxicity, it itself has a pale yellow color due to the influence of impurities, and further easily turns yellow upon heating. In addition, there is a process inconvenience due to solidification at room temperature. Similarly, since diphenyl sulfone is solid at room temperature (melting point: 127 ° C., boiling point: 379 ° C.), it is difficult to handle and there are inconveniences in the process. In addition, in order to remove diphenylsulfone after the synthesis of the aromatic polyether, there is a disadvantage that extraction must be repeated with an organic solvent.

  In particular, when aromatic poly (thio) ether is applied to applications requiring high colorless transparency, such as heat-resistant transparent films, transparent circuit boards, lenses, solar battery substrates, etc., coloring of the molded products is suppressed. The necessity is high. Therefore, the resin composition for obtaining a molded body is required to eliminate coloring factors as much as possible, and is required to be able to be produced advantageously in the process.

JP-A-5-339364 JP 2010-95614 A Japanese Patent Publication No. 8-5959 JP 2013-47331 A Japanese Patent Laid-Open No. 11-158264 Japanese Unexamined Patent Publication No. 7-173119

  The present invention has been made based on the circumstances as described above, and can provide a resin composition, an aromatic poly (thio) ether manufacturing method, and a molded body that can suppress coloring of the molded body and can be advantageously manufactured in a process. The purpose is to provide.

（式（１）中、Ｒは、アミド基以外の炭素数１〜５の１価の有機基である。ｎは、０〜５の整数である。ｎが２以上の場合、複数のＲは同一であっても異なっていてもよい。） The present invention made in order to solve the above problems is a resin composition containing an organic solvent and an aromatic poly (thio) ether, wherein the organic solvent is a compound represented by the following formula (1): diethylene glycol dimethyl ether , Diethylene glycol ethyl methyl ether, triethylene glycol dimethyl ether, or a combination of two or more thereof.

(In Formula (1), R is a C1-C5 monovalent organic group other than an amide group. N is an integer of 0 to 5. When n is 2 or more, a plurality of R are They may be the same or different.)

  Another aspect of the present invention made to solve the above problems is a method for producing an aromatic poly (thio) ether by polycondensation reaction using an organic solvent, wherein the organic solvent is represented by the formula (1). The compound is diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, triethylene glycol dimethyl ether, or a combination of two or more thereof.

  Yet another aspect of the present invention made to solve the above problems is a molded article containing an organic solvent and a aromatic aromatic poly (thio) ether, wherein the organic solvent is a compound represented by the above formula (1). , Diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, triethylene glycol dimethyl ether, or a combination of two or more thereof.

  Here, the “organic group” is a group containing at least one carbon atom, and the “organic group” may contain a hetero atom.

  ADVANTAGE OF THE INVENTION According to this invention, the coloring of a molded object can be suppressed and the manufacturing method and molded object of an aromatic poly (thio) ether which can be manufactured advantageously on a process can be provided.

  The present invention includes a resin composition, a molded article, and a method for producing an aromatic poly (thio) ether. These will be described in detail below.

<Resin composition>
The resin composition of the present invention contains an organic solvent and an aromatic poly (thio) ether. The said resin composition may contain the arbitrary component in the range which does not impair the effect of this invention.

[Organic solvent]
The organic solvent contained in the resin composition is a compound represented by the following formula (1) (hereinafter also referred to as “specific benzonitrile-based solvent”), diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, or triethylene glycol dimethyl ether ( These ether solvents are collectively referred to as “specific ether solvents”). In the following, “specific benzonitrile-based solvent” and “specific ether-based solvent” are also collectively referred to as “specific organic solvent”.

(Specific benzonitrile solvents)
The specific benzonitrile-based solvent does not contain an amide group. The specific benzonitrile-based solvent may be used alone or in combination.

  In formula (1), R is a C1-C5 monovalent organic group other than an amide group. n is an integer of 0-5. When n is 2 or more, the plurality of R may be the same or different.

  Examples of the monovalent organic group having 1 to 5 carbon atoms other than the amide group include hydrocarbon groups such as a chain hydrocarbon group having 1 to 5 carbon atoms, an alicyclic hydrocarbon group having 3 to 5 carbon atoms, and the like. A heteroatom-containing group having a heteroatom between carbon-carbons of the hydrocarbon group (excluding those having an amide group), part or all of the hydrogen atoms of the hydrocarbon group and heteroatom-containing group are substituents. Examples include substituted groups.

Examples of the chain hydrocarbon group having 1 to 5 carbon atoms include:
Alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, t-butyl and n-pentyl;
Alkenyl groups such as ethenyl group, propenyl group, butenyl group, pentenyl group;
Examples thereof include alkynyl groups such as ethynyl group, propynyl group, butynyl group, and pentynyl group.

  Examples of the alicyclic hydrocarbon group having 3 to 5 carbon atoms include a cyclopropyl group, a cyclobutyl group, and a cyclopentyl group.

  Examples of the hetero atom include an oxygen atom, a nitrogen atom, a silicon atom, a phosphorus atom, a sulfur atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

  Examples of the substituent include halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom, hydroxy group, carboxy group, cyano group, nitro group, alkoxy group, alkoxycarbonyl group, alkoxycarbonyloxy group, acyl group, and acyloxy. Group other than amide group such as oxy group.

  As the specific benzonitrile-based solvent, benzonitrile (n = 0 in the above formula (1)) is preferable.

(Specific ether solvent)
The specific ether solvent does not contain an amide group. The specific ether solvent may be used alone or in combination, or may be used in combination with a specific benzonitrile solvent. As the specific ether solvent, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, and triethylene glycol dimethyl ether are preferable. Among these, as the specific ether solvent, diethylene glycol dimethyl ether (diglyme) is preferably used alone, or diethylene glycol dimethyl ether (diglyme) is preferably used in combination with another ether solvent.

  A specific benzonitrile-based solvent or a specific ether-based solvent may be used in combination with another solvent. Any other solvent may be used as long as it does not have an amide group, and examples thereof include aprotic polar solvents other than specific organic solvents and azeotropic solvents.

  Examples of the aprotic polar solvent other than the specific organic solvent include dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butyl methyl ether, triethylene glycol Propylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl Ether, polyethylene glycol monomethyl ether.

  Examples of the azeotropic solvent include hexane, benzene, toluene, xylene, cumene, chlorobenzene, and o-dichlorobenzene.

  The content of the specific organic solvent in the resin composition ensures the moldability according to the form of the molded body to be obtained from the resin composition while ensuring the handleability of the resin composition. What is necessary is just to select suitably. For example, when the resin composition is applied to a casting method, the content of the specific organic solvent is usually 50% by mass or more and 95% by mass or less, and 60% by mass or more and 95% by mass in the total amount of the resin composition. % Or less is preferable, and 70 mass% or more and 90 mass% or less are more preferable. In addition, when the resin composition is concentrated and processed into pellets used in an injection molding method, an extrusion molding method, or the like, the content of the specific organic solvent in the resin composition before concentration is usually the resin composition. It is 50 mass% or more and 90 mass% or less in the whole quantity of a thing, 60 mass% or more and 80 mass% or less are preferable, and 65 mass% or more and 75 mass% or less are more preferable.

[Aromatic poly (thio) ether]
An aromatic poly (thio) ether is a polymer containing a structural unit having an aromatic ring and an ether bond, an aromatic ring and a thioether bond, or an aromatic ring, an ether bond and a thioether bond (hereinafter also referred to as “essential structural unit”). It refers to polymers such as aromatic polyethers and aromatic polythioethers. This aromatic poly (thio) ether may contain structural units other than the essential structural units (hereinafter also referred to as “arbitrary structural units”).

{Aromatic polyether}
Although there is no restriction | limiting in particular as aromatic polyether which can be used for the said resin composition, The thing in which the adjacent aromatic rings are connected through the ether bond is preferable. Examples of such aromatic polyethers include aromatic polyether nitriles, aromatic polyether ketones, and aromatic polyether sulfones. Naturally, aromatic polyether nitrile, aromatic polyether ketone, aromatic polyether sulfone include aromatic polyether ether nitrile, aromatic polyether ether ether nitrile, aromatic polyether ether ketone, aromatic polyether sulfone. Ether ether ether ketone, aromatic polyether ether sulfone, aromatic polyether ether ether sulfone and the like are also included.

(Aromatic polyether nitrile)
In the aromatic polyether nitrile, the essential structural unit has an aromatic ring having an nitrile group and an ether bond. This aromatic polyether nitrile can be synthesized, for example, by copolymerizing a dihalide benzonitrile that provides an aromatic ring having a nitrile group and a diol that provides an ether bond. Each of dihalide benzonitrile and diol may be used alone or in combination of two or more. Of course, the nitrile group, the aromatic ring and the ether bond in the essential structural unit of the aromatic polyether nitrile may be derived from compounds other than dihalide benzonitrile and diol.

  Examples of the dihalide benzonitrile include 2,6-difluorobenzonitrile, 2,4-difluorobenzonitrile, 2,6-dichlorobenzonitrile, 2,4-dichlorobenzonitrile, and precursors and derivatives thereof.

  Examples of the diol include dihydroxybenzene, dihydroxynaphthalene, and bisphenol.

  Examples of dihydroxybenzene include catechol, resorcinol, and hydroquinone.

  Examples of the dihydroxynaphthalene include 1,2-dihydroxynaphthalene, 1,3-dihydroxynaphthalene, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 2, Examples include 3-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, and 2,7-dihydroxynaphthalene.

  Examples of the bisphenol include 4,4′-biphenol, bis (4-hydroxyphenyl) sulfide, dihydroxybenzophenone, 2,2-bis (4-hydroxyphenyl) propane, and 1,1-bis (4-hydroxyphenyl) -1. -Phenylethane, bis (4-hydroxyphenyl) diphenylmethane, 5,5 '-(1-methylethylidene) -bis [1,1'-(bisphenyl) -2-ol] propane, bis (4-hydroxy-3) -Methylphenyl) sulfide, bis (4-hydroxyphenyl) sulfone, 9,9-bis (4-hydroxyphenyl) fluorene, 9,9-bis (4-hydroxy-3-methylphenyl) fluorene, 9,9-bis (3-Phenyl-4-hydroxy) phenylfluorene, 9,9-bis (6-hydro) Sinaftyl) fluorene, 3,3-bis (4-hydroxyphenyl) isobenzofuran-1 (3H) -one, 1,1-bis (4-hydroxyphenyl) -3,3,5-trimethylcyclohexane, 1,1- Bis (4-hydroxyphenyl) cyclohexane, precursors and derivatives thereof are mentioned.

(Aromatic polyether ketone)
The aromatic polyether ketone has an essential structural unit having a ketone group, an aromatic ring and an ether bond. This aromatic polyether ketone can be synthesized by copolymerizing a dihalide benzophenone that provides a ketone group and an aromatic ring and a diol that provides an ether bond. Each of dihalide benzophenone and diol may be used alone or in combination of two or more. Of course, the ketone group, aromatic ring and ether bond in the essential structural unit of the aromatic polyether ketone may be derived from compounds other than dihalide benzophenone and diol.

  Examples of the dihalide benzophenone include 4,4'-difluorobenzophenone, 4,4'-dichlorobenzophenone, 2,4'-difluorobenzophenone, 2,4'-dichlorobenzophenone, and reactive derivatives thereof.

  Examples of the diol include the same diol that gives an ether bond in an aromatic polyether nitrile.

(Aromatic polyethersulfone)
The aromatic polyether sulfone has an essential structural unit having a sulfonyl group, an aromatic ring and an ether bond. This aromatic polyethersulfone can be synthesized by copolymerizing a dihalide diphenylsulfone that gives a sulfonyl group and a diol that gives an ether bond. Dihalide diphenyl sulfone and diol may be used individually by 1 type, and may be used in combination of multiple types. Of course, the sulfonyl group, aromatic ring and ether bond in the essential structural unit of the aromatic polyethersulfone may be derived from compounds other than dihalide diphenylsulfone and diol.

  Examples of the dihalide diphenyl sulfone include 4,4′-difluorodiphenyl sulfone, 4,4′-dichlorodiphenyl sulfone, 2,4′-difluorodiphenyl sulfone, 2,4′-dichlorodiphenyl sulfone, and reactive derivatives thereof. Can be mentioned.

  Examples of the diol include the same diol that gives an ether bond in an aromatic polyether nitrile.

(Polyphenylene oxide)
Polyphenylene oxide is a polymer represented by the general formula (—C ₆ H ₂ (CH ₃ ) ₂ —O—) n (n is 10 to 1,000). This polyphenylene oxide is obtained by condensation polymerization of 2,6-dimethylphenol (2,6-xylenol).

{Aromatic polythioether}
The aromatic polythioether is an essential structural unit in which an aromatic ring and another aromatic ring are connected via a thioether bond. Although there is no restriction | limiting in particular as aromatic polythioether which can be used for the said resin composition, The thing in which the adjacent aromatic rings are connected through the thioether bond is preferable. Examples of such aromatic polythioethers include polyphenylene sulfide.

  The aromatic polythioether can be synthesized, for example, by copolymerizing a dihalide compound and sodium sulfide. Examples of the dihalide compound include orthodichlorobenzene, metadichlorobenzene, paradichlorobenzene, 4,4'-dichlorobenzophenone, 4,4'-dichlorodiphenyl sulfone, 4,4'-dichlorobiphenyl, and the like.

  The glass transition temperature (Tg) of the aromatic poly (thio) ether is usually 150 ° C to 350 ° C, preferably 250 ° C to 300 ° C. When the glass transition temperature is 150 ° C. or higher, the thermal stability of the obtained molded body is increased. On the other hand, when the glass transition temperature is 350 ° C. or lower, thermal decomposition during molding can be suppressed. In addition, glass transition temperature (Tg) is the value measured by the method as described in the Example mentioned later.

  The weight average molecular weight (Mw) of the aromatic poly (thio) ether is usually 15,000 to 250,000, preferably 20,000 to 200,000. When the weight average molecular weight (Mw) is less than 15,000, the viscosity of the resin composition becomes small, and the injection moldability and the like may be deteriorated. When the weight average molecular weight (Mw) exceeds 250,000, the viscosity when the aromatic poly (thio) ether is melted increases, and the moldability and the like may be deteriorated. In addition, a weight average molecular weight (Mw) is the value measured by the method as described in the Example mentioned later.

  The content of the aromatic poly (thio) ether in the resin composition is the same as in the case of the content of the specific organic solvent as described above, while ensuring the handleability of the resin composition. Therefore, it may be selected as appropriate so that the moldability and the like according to the form of the molded body to be obtained can be suitably secured. For example, when the resin composition is applied to a casting method, the content of the aromatic poly (thio) ether in the resin composition is usually 5% by mass or more and 50% by mass or less based on the total amount of the resin composition. 5 mass% or more and 40 mass% or less are preferable, and 10 mass% or more and 30 mass% or less are more preferable. In addition, when the resin composition is concentrated and processed into pellets for use in an injection molding method, an extrusion molding method, or the like, the content of the aromatic poly (thio) ether in the resin composition before concentration is usually It is 10 mass% or more and 50 mass% or less in the whole quantity of a resin composition, 20 mass% or more and 40 mass% or less are preferable, and 25 mass% or more and 35 mass% or less are more preferable.

  The viscosity of the resin composition depends on the molecular weight and content of the aromatic poly (thio) ether, but when prepared as a composition for forming a sheet or film, it is usually from 2,000 mPa · s to 100,000 mPa · s. s, preferably 3,000 mPa · s to 50,000 mPa · s. By setting the viscosity of the resin composition within such a range, the composition can be easily retained during film formation, and the thickness can be easily adjusted. Therefore, the sheet or film can be easily molded.

[Optional ingredients]
The resin composition may contain an optional component in addition to the specific organic solvent and the aromatic poly (thio) ether. There is no restriction | limiting in particular as such an arbitrary component, What is necessary is just to select suitably according to the kind etc. of the molded object which should be obtained from the said resin composition. Examples of optional components include antioxidants, lubricants, flame retardants, antibacterial agents, colorants, mold release agents, and foaming agents. These arbitrary components may be used individually by 1 type, and may be used in combination of multiple types.

<Method for producing aromatic poly (thio) ether>
Aromatic poly (thio) ether includes, for example, a compound that gives an aromatic ring in a specific organic solvent (hereinafter also referred to as “compound (A)”) and a compound that gives a (thio) ether bond (hereinafter referred to as “compound (B)”). Can be produced by condensation polymerization under predetermined reaction conditions. In synthesizing the aromatic poly (thio) ether, if necessary, a compound giving another structural unit, an alkali metal compound, another solvent, and the like may be mixed in a specific organic solvent.

[Compound (A)]
The compound (A) may be selected according to the type of aromatic poly (thio) ether to be synthesized. Examples of the compound (A) include dihalide benzonitrile when synthesizing polyether nitrile, dihalide benzophenone when synthesizing polyether ketone, and dihalide diphenyl sulfone when synthesizing polyether sulfone. It is done.

  Examples of the dihalide benzonitrile, dihalide benzophenone, and dihalide diphenyl sulfone include the same compounds as those exemplified as the compound that gives an aromatic ring in the essential structural unit of the resin composition.

[Compound (B)]
Examples of the compound (B) include the same compounds as those exemplified as the compound giving a (thio) ether bond in the essential structural unit of the resin composition.

[Specific organic solvent]
The specific organic solvent is a specific benzonitrile-based solvent represented by the above formula (1) or a specific ether-based solvent as described above, and the specific benzonitrile-based solvent contained in the resin composition and The thing similar to a specific ether solvent can be illustrated. A specific organic solvent may be used individually by 1 type, and may be used in combination of multiple types.

[Other solvents]
Any other solvent may be used as long as it does not have an amide group. For example, an aprotic polar solvent other than a specific organic solvent or an azeotropic solvent is used in the same manner as other solvents contained in the resin composition. can do.

[Alkali metal compounds]
The alkali metal compound forms an alkali metal salt by reacting with a diol or the like in the process of synthesis of the aromatic poly (thio) ether. Examples of such alkali metal compounds include alkali metals such as lithium, sodium, and potassium;
Alkali metal hydrides such as lithium hydride, sodium hydride, potassium hydride;
Alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide;
Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate;
Examples thereof include alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate. Of these, alkali metal carbonates are preferred, and potassium carbonate is more preferred.

  With respect to the amount of the alkali metal compound used, the amount of metal atoms in the alkali metal compound is usually 1 to 3 equivalents, preferably 1 with respect to the hydroxyl groups of all compounds used for the synthesis of the aromatic poly (thio) ether. .1 times equivalent to 2 times equivalent, more preferably 1.2 times equivalent to 1.5 times equivalent.

[Reaction conditions]
The reaction conditions for synthesizing the aromatic poly (thio) ether may be appropriately set according to the composition of the reaction solution at the time of synthesis, but the reaction temperature is usually 100 ° C. to 250 ° C., and the reaction time is 0.00. 5 to 20 hours.

  According to the method for producing the aromatic poly (thio) ether, the aromatic nucleophilic substitution reaction during the synthesis of the aromatic poly (thio) ether is promoted by containing a specific organic solvent, For example, an aromatic poly (thio) ether having the above-described weight average molecular weight (Mw) can be suitably obtained.

  In addition, the specific organic solvent used for the production of the aromatic poly (thio) ether is the same as the specific organic solvent contained in the resin composition, that is, a substance that does not contain an amide group. There is no problem of toxicity. Furthermore, by using a specific organic solvent, inconveniences caused by the decomposition products of the solvent, for example, inhibition of synthesis of aromatic poly (thio) ether and coloring of the polymer solution after synthesis can be suppressed.

  In addition, since the specific organic solvent has no problem of biotoxicity and can suppress coloring of the polymer solution after the synthesis of the aromatic poly (thio) ether, without replacing the aprotic polar solvent after the synthesis, A polymer solution can be used as the resin composition. That is, it is necessary to prepare the composition by precipitating the aromatic poly (thio) ether and then re-dissolving it in the solvent for reasons such as suppressing coloring of the molded product after the synthesis of the aromatic poly (thio) ether. Therefore, the resin composition can be advantageously prepared in a process. Thus, according to the production of the aromatic poly (thio) ether, it is possible to provide a resin composition that can suppress coloring of the molded body and can be advantageously prepared in a process.

<Method for preparing resin composition>
The resin composition of this invention can be prepared by mixing another solvent and arbitrary components with the liquid mixture of aromatic poly (thio) ether and a specific organic solvent as needed. The mixed liquid of the aromatic poly (thio) ether and the specific organic solvent was obtained by re-dissolving the aromatic poly (thio) ether powder obtained from the polymer solution after the synthesis of the aromatic poly (thio) ether in the solvent. Although a thing can be used, it is preferable to use the polymer solution after aromatic poly (thio) ether synthesis | combination as mentioned above. This polymer solution may be used for the preparation of the resin composition as it is, or a part of the solvent (for example, a polar solvent as another solvent) is removed or the solvent (for example, aromatic poly (thio) ether). The resin composition may be prepared by adjusting the content of the aromatic poly (thio) ether by adding a specific benzonitrile solvent or a specific ether solvent used in the synthesis.

  According to the resin composition, since the specific organic solvent does not contain an amide group, there is no problem of biotoxicity, polymerization inhibition and polymerization caused by the decomposition product of the solvent during the synthesis of aromatic poly (thio) ether. It becomes possible to suppress coloring of a solution or a molded object.

  In addition, the specific benzonitrile solvent and the specific ether solvent contained as essential components in the resin composition can be used for the synthesis of aromatic poly (thio) ether, and have a colorless, transparent or close hue. Have. Therefore, as described above, it is not necessary to replace the solvent after the synthesis of the aromatic poly (thio) ether, and the polymer solution after the synthesis of the aromatic poly (thio) ether is used as it is or by adjusting the solvent concentration. Since it can be used as a resin composition, it is advantageous in terms of process. Therefore, the said resin composition can be used conveniently for the use as which high transparency is calculated | required, for example, formation of a heat-resistant transparent film, a transparent circuit board, a lens, a solar cell board | substrate, etc.

<Molded body>
The molded product of the present invention is a molded product containing a specific organic solvent and an aromatic poly (thio) ether. Here, in the present invention, the “molded body” refers to a solid material having no fluidity formed from a resin composition. The “molded product” in the present invention includes at least a pellet, a film, a sheet, and an injection molded product.

  The specific organic solvent in the molded body is the specific benzonitrile solvent or the specific ether solvent described above. The specific organic solvent content (residual solvent concentration) in the molded article is preferably 5 ppm or more and 5,000 ppm or less. As an upper limit of content (residual solvent concentration) of a specific organic solvent, 3,000 ppm is more preferable, and 2,000 ppm is more preferable. In addition, content (residual solvent density | concentration) of the specific organic solvent in the said molded object is the value measured by the method as described in the Example mentioned later.

  The aromatic poly (thio) ether in the molded article is not particularly limited, and examples thereof include aromatic polyether nitrile, aromatic polyether ketone, aromatic polyether ether ketone, aromatic polyether sulfone, polyphenylene oxide, and polyphenylene. And sulfide. Among these, aromatic polyether nitrile, aromatic polyether ketone, and aromatic polyether sulfone are preferable.

The hue change (Δb ^* ) of the molded article is preferably 1.25 or less, more preferably 1.15 or less, further preferably 1.10 or less, particularly preferably 1.05 or less, and most preferably 1.00 or less. preferable. The hue change (Δb ^* ) is a value measured by the method described in Examples described later.

[pellet]
The pellet is a material for forming a molded body by injection molding, extrusion molding, or the like, and has, for example, a granular or columnar form. The size of the pellet is not particularly limited, and may be set as appropriate depending on the form of the molded body to be obtained, the size of the molding apparatus to be used, and the like. In this case, the length is 1 mm to 10 mm, and the width (diameter) is 0.5 mm to 5 mm. The average particle diameter of pellets is the median diameter calculated from the volume particle size distribution measured in a laser diffraction method (d _50).

(Pellet production method)
Although there is no restriction | limiting in particular as a manufacturing method of a pellet, For example, the method of cut | disconnecting to the predetermined dimension after melt-extruding the said resin composition is mentioned. Specifically, pellets can be obtained by demelting the resin composition using a twin screw extruder, cutting and pulverizing the extruded strand after melt-kneading into a predetermined size with a pelletizer.

  The pellets can also be produced by extruding the resin composition in a poor solvent, precipitating and / or solidifying it, washing and / or drying it, and cutting and pulverizing it to a desired size.

[Film and sheet]
The film and sheet are applied to, for example, an optical sheet, a heat-resistant transparent film, a transparent circuit board, a solar cell substrate film, and the like. The film is formed by using a resin composition containing a specific organic solvent and an aromatic poly (thio) ether, for example, an average thickness of less than 200 μm using the resin composition. On the other hand, a sheet means what was shape | molded so that average thickness might be 200 micrometers or more. Here, “average thickness” refers to a value measured according to JIS K 7130: 1999.

(Film and sheet manufacturing method)
Although there is no restriction | limiting in particular as a manufacturing method of a film and a sheet | seat, For example, the solvent cast method and the melt extrusion molding method are mentioned.

  In the case of the solvent casting method, the film and the sheet can be produced by drying a coating film formed by applying a resin composition to a substrate and firing the coating film as necessary. In this case, the film and sheet may be formed on the substrate or may be peeled off from the substrate.

  Examples of the coating method of the resin composition include a spray method, a roll coating method, a spin coating method (spin coating method), a slit die coating method, a bar coating method, and an ink jet method.

  The coating film can be dried by, for example, heating with a heating device, vacuum drying with a vacuum dryer, warm air (hot air) drying with a warm air (hot air) generator, natural drying, or a combination of two or more of these. The conditions for drying the coating film by heating, vacuum drying and warm air (hot air) should be set appropriately according to the melting point of the aromatic poly (thio) ether, the boiling point of the solvent such as a specific organic solvent, the capacity of the solvent, etc. For example, it is set to 50 ° C. to 250 ° C., 5 minutes to 1 hour.

  The coating film can be baked by, for example, heating with a heating device, vacuum drying with a vacuum dryer, hot air drying with a hot air generator, or a combination of two or more of these. What is necessary is just to set suitably the baking conditions of the coating film by a heating, decompression drying, and warm air according to melting | fusing point etc. of aromatic poly (thio) ether, for example, it is 250 to 400 degreeC, and it is 5 minutes to 1 hour. In addition, baking of a coating film can be abbreviate | omitted and you may carry out simultaneously with drying of a coating film.

  On the other hand, examples of the extrusion molding method include a melt extrusion method and a semi-melt extrusion method, and the melt extrusion method is preferable. Examples of the melt extrusion method include methods using dies having various shapes, and among these, methods using a T die and a coat hanger die are preferable. The film or sheet obtained by the extrusion method may be subjected to stretching treatment. Thereby, it becomes possible to apply a film or a sheet to an optical film.

  In such melt-extrusion, a heat-melted resin composition is extruded from a die, and is then brought into close contact with a metal belt, a cooling roll or the like to form a sheet. A sheet is obtained.

[Injection molded body]
The injection-molded product refers to a material molded by injecting a material obtained by heating and melting a resin composition (aromatic poly (thio) ether) into a mold, and cooling and solidifying the material. Examples of such injection-molded bodies include optical components. Examples of the optical component include optical films such as a wave plate and a retardation plate, various special lenses such as a conical lens, a spherical lens, and a cylindrical lens, and a lens array.

  Hereinafter, based on an Example, this invention is demonstrated more concretely. However, the present invention is not limited to the following examples.

<Synthesis of aromatic polyether nitrile and preparation of resin composition>
[Example 1]
A four-necked flask was equipped with a thermometer, a stirrer, a three-way cock with a nitrogen inlet tube, a Dean-Stark tube and a condenser tube, and 34.91 g (0.251 mol) of 2,6-difluorobenzonitrile, 9,9-bis 87.53 g (0.250 mol) of (4-hydroxyphenyl) fluorene (hereinafter also referred to as “BPFL”), 44.92 g (0.325 mol) of potassium carbonate, and 490 g of benzonitrile (hereinafter also referred to as “BN”). And 122 g of toluene were added.

  Next, after the atmosphere in the flask was replaced with nitrogen, the obtained solution was reacted at 130 ° C. for 3 hours, and water produced was removed from the Dean-Stark tube as needed. When no more water was observed, the temperature was gradually raised to 150 ° C. while removing toluene, and the reaction was allowed to proceed at that temperature for 6 hours.

  After cooling to room temperature (25 ° C.), the produced salt was removed with filter paper, the filtrate was poured into methanol to reprecipitate, and the precipitate was isolated by filtration. The isolated precipitate was vacuum-dried at 100 ° C. overnight to obtain a white powder (polymer) (yield 107 g, yield 95%).

  This white powder was dissolved in the same BN as the polymerization solvent to prepare a resin composition having an aromatic polyether nitrile concentration of 10% by mass.

[Example 2]
The aromatic polyether nitrile was synthesized and purified in the same manner as in Example 1 except that 490 g of diethylene glycol dimethyl ether (diglyme) was used instead of BN as the polymerization solvent. As a result, a white powder (polymer) was obtained (yield 105 g, yield 93%).

  This white powder was dissolved in the same diglyme as the polymerization solvent to prepare a resin composition having an aromatic polyether nitrile concentration of 10% by mass.

[Comparative Example 1]
The aromatic polyether nitrile was synthesized and purified in the same manner as in Example 1 except that 490 g of dimethylacetamide (DMAc) was used instead of BN as the polymerization solvent. As a result, white powder (polymer) was obtained (yield 106 g, yield 94%).

  This white powder was dissolved in the same DMAc as the polymerization solvent to prepare a resin composition having an aromatic polyether nitrile concentration of 10% by mass.

[Comparative Example 2]
The aromatic polyether nitrile was synthesized and purified in the same manner as in Example 1 except that 490 g of N-methylpyrrolidone (NMP) was used instead of BN as the polymerization solvent. As a result, a white powder (polymer) was obtained (yield: 108 g, yield: 95%).

  The obtained white powder was dissolved in NMP to prepare a resin composition having an aromatic polyether nitrile concentration of 10% by mass.

[Comparative Example 3]
Synthesis of an aromatic polyether nitrile was attempted in the same manner as in Example 1 except that 490 g of anisole was used instead of BN as a polymerization solvent. The progress of the polymerization reaction was confirmed by gel filtration chromatography (GPC), but no increase in molecular weight was confirmed.

[Comparative Example 4]
Synthesis of an aromatic polyether nitrile was attempted in the same manner as in Example 1 except that 490 g of orthodichlorobenzene was used instead of BN as the polymerization solvent. The progress of the polymerization reaction was confirmed by GPC, but no increase in molecular weight was confirmed.

[Comparative Example 5]
The aromatic polyether nitrile was synthesized and purified in the same manner as in Example 1 except that 490 g of gamma butyrolactone was used instead of BN as the polymerization solvent. As a result, the viscosity of the reaction solution was remarkably increased, making it very difficult to purify the aromatic polyether nitrile.

  In order to analyze the reaction solution, a small amount of the reaction solution was sampled and coagulated with 10 times the amount of methanol, and the liquid phase part was measured by gas chromatography (GC). As a result, it was confirmed that the polymerization solvent gamma-butyrolactone was decomposed. It is considered that the viscosity of the reaction solution was remarkably increased because a part of gamma-butyrolactone as a polymerization solvent was decomposed into a compound presumed to be a gamma-butyrolactone ring-opened product.

[Comparative Example 6]
A polymer powder of aromatic polyether nitrile of Comparative Example 1 synthesized and purified using DMAc as a polymerization solvent was dissolved in a mixed solvent containing DMAc and anisole in a mass ratio of 50:50, and A resin composition having a concentration of 10% by mass was prepared.

[Comparative Example 7]
The aromatic polyether nitrile polymer powder of Comparative Example 2 synthesized and purified using NMP as a polymerization solvent was dissolved in a mixed solvent containing NMP and anisole at a mass ratio of 50:50, and the aromatic polyether nitrile polymer powder was dissolved. A resin composition having a concentration of 10% by mass was prepared.

[Example 3]
First, an aromatic polyether nitrile was polymerized in the same manner as in Example 1 to obtain a reaction solution. BN was added to the reaction solution for dilution, and the salt was filtered off using filter paper. An appropriate amount of ion exchange resins (“Diaion RCP160M” and “Diaion WA21J” manufactured by Mitsubishi Chemical Corporation) was added to the filtered reaction solution, and the mixture was stirred for 2 hours with a mix rotor. After completion of the stirring, the ion exchange resin was filtered off to obtain a polymer solution. The polymer solution was concentrated using an evaporator to prepare a 10% by mass resin composition. A small amount of this resin composition was sampled, coagulated with methanol, filtered and dried to prepare a sample for GPC measurement.

[Example 4]
First, an aromatic polyether nitrile was polymerized in the same manner as in Example 2 to obtain a reaction solution. Diglime was added to the reaction solution for dilution, and the salt was filtered off using filter paper. An appropriate amount of ion exchange resins (“Diaion RCP160M” and “Diaion WA21J” manufactured by Mitsubishi Chemical Corporation) was added to the filtered reaction solution, and the mixture was stirred for 2 hours with a mix rotor. After completion of the stirring, the ion exchange resin was filtered off to obtain a polymer solution. The polymer solution was concentrated using an evaporator to prepare a 10% by mass resin composition. A small amount of this resin composition was sampled, coagulated with methanol, filtered and dried to prepare a sample for GPC measurement.

[Comparative Example 8]
First, an aromatic polyether nitrile was polymerized in the same manner as in Comparative Example 1 to obtain a reaction solution. DMAc was added to the reaction solution for dilution, and the salt was filtered off using filter paper. An appropriate amount of ion exchange resins (“Diaion RCP160M” and “Diaion WA21J” manufactured by Mitsubishi Chemical Corporation) was added to the filtered reaction solution, and the mixture was stirred for 2 hours with a mix rotor. After completion of the stirring, the ion exchange resin was filtered off to obtain a polymer solution. The polymer solution was concentrated using an evaporator to prepare a 10% by mass resin composition. A small amount of this resin composition was sampled, coagulated with methanol, filtered and dried to prepare a sample for GPC measurement.

[Comparative Example 9]
First, an aromatic polyether nitrile was polymerized in the same manner as in Comparative Example 2 to obtain a reaction solution. NMP was added to the reaction solution for dilution, and the salt was filtered off using filter paper. An appropriate amount of ion exchange resins (“Diaion RCP160M” and “Diaion WA21J” manufactured by Mitsubishi Chemical Corporation) was added to the filtered reaction solution, and the mixture was stirred for 2 hours with a mix rotor. After completion of the stirring, the ion exchange resin was filtered off to obtain a polymer solution. The polymer solution was concentrated using an evaporator to prepare a 10% by mass resin composition. A small amount of this resin composition was sampled, coagulated with methanol, filtered and dried to prepare a sample for GPC measurement.

<Synthesis of aromatic polyethersulfone and preparation of resin composition>
[Example 5]
In a 2 L four-necked flask, 72.51 g (0.2525 mol) of 4,4′-dichlorodiphenylsulfone (hereinafter also referred to as “DCDPS”), 9,9-bis (4-hydroxyphenyl) fluorene (BPFL) 70 0.03 g (0.2000 mol), 2,2-bis (4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane 16.81 g (0.0500 mol), potassium carbonate 41.46 g ( 0.3000 mol), 640 g of BN and 160 g of toluene were added. Subsequently, a thermometer, a stirrer, a three-way cock with a nitrogen introduction tube, a Dean-Stark tube and a cooling tube were attached to the four-necked flask.

  Next, after the atmosphere in the flask was replaced with nitrogen, the obtained solution was reacted at 130 ° C. for 3 hours, and water produced was removed from the Dean-Stark tube as needed. When no more water was observed, the temperature was gradually raised to 150 ° C. and reacted at that temperature for 5 hours.

  After cooling to room temperature (25 ° C.), the produced salt was removed with a filter paper, the filtrate was poured into methanol for reprecipitation, and the precipitate was isolated by filtration. The isolated precipitate was vacuum-dried overnight at 60 ° C. to obtain a white powder (polymer) (yield 133 g, yield 94%).

  The obtained white powder was dissolved in BN to prepare a resin composition having an aromatic polyethersulfone concentration of 10% by mass.

[Example 6]
An aromatic polyether sulfone was synthesized in the same manner as in Example 5 except that 640 g of diglyme was used instead of BN as a polymerization solvent. As a result, a white powder (polymer) was obtained (yield 105 g, yield 93%).

  The obtained white powder was dissolved in diglyme to prepare a resin composition having an aromatic polyethersulfone concentration of 10% by mass.

[Comparative Example 10]
An aromatic polyether sulfone was synthesized in the same manner as in Example 5 except that 640 g of DMAc was used instead of BN as a polymerization solvent. As a result, a white powder (polymer) was obtained (yield 105 g, yield 93%).

  The obtained white powder was dissolved in DMAc to prepare a resin composition having an aromatic polyethersulfone concentration of 10% by mass.

[Comparative Example 11]
An aromatic polyether sulfone was synthesized in the same manner as in Example 5 except that 640 g of NMP was used instead of BN as a polymerization solvent. As a result, a white powder (polymer) was obtained (yield 105 g, yield 93%).

  The obtained white powder was dissolved in NMP to prepare a resin composition having an aromatic polyethersulfone concentration of 10% by mass.

<Evaluation>
For the aromatic polyethers (aromatic polyether nitriles or aromatic polyether sulfones) and resin compositions of Examples 1 to 6, Comparative Examples 1, 2 and 6 to 11, the weight average molecular weight (Mw), residual Changes in solvent concentration and hue were evaluated. These evaluation results are shown in Table 1. In Comparative Examples 3 and 4, aromatic polyether nitrile could not be synthesized, and in Comparative Example 5, it was difficult to purify aromatic polyether nitrile. Therefore, Comparative Examples 3 to 5 were not evaluated as follows. .

[Weight average molecular weight (Mw) [-]]
The weight average molecular weight (Mw) of the aromatic polyether was measured using the “HLC-8220 GPC apparatus (column: TSKgel α-M)” manufactured by Tosoh Corporation under the following conditions.

(Analysis conditions)
Elution solvent: Tetrahydrofuran Flow rate: 0.6 mL / min Sample concentration: 0.2% by mass
Sample injection volume: 100 μL
Column temperature: 40 ° C
Detector: Differential refractometer Standard material: Monodisperse polystyrene

[Residual solvent concentration [ppm]]
In measuring the residual solvent concentration, a film sample was first prepared. The film sample was prepared by coating the resin composition on a glass substrate with a spin coater, then heating the coating solution on a hot plate at 70 ° C. for 15 minutes and 120 ° C. for 15 minutes, and further using a vacuum dryer at 200 ° C. And dried under reduced pressure for 2 hours to produce a glass substrate with a film. The film was peeled from this glass substrate with a film to obtain a film sample having a film thickness of 50 μm.

  The residual solvent concentration was measured using “EXSTAR TG / DTA6200” manufactured by Seiko Instruments Inc. and using a differential thermothermal gravimetric simultaneous measurement apparatus (TG-DTA). Specifically, the residual solvent concentration was determined by placing the film sample on an aluminum pan, raising the temperature rising rate from room temperature to 350 ° C. under a nitrogen atmosphere at a rate of temperature increase of 10 ° C./min, and determining from the mass of the film sample at 100 ° C. to 350 It calculated as a value (mass reduction | decrease part) which made the difference the mass of the film sample in ° C.

[Hue change]
In measuring the hue change, first, a glass substrate with a film was prepared in the same manner as in the case of measuring the residual solvent concentration. About the film of this glass substrate with a film, the hue was measured using "SPECTROTOPOMETER DOT-3C" of Murakami Color Research Laboratory.

  Subsequently, the glass substrate with a film was baked using "High-temperature thermostatic oven super high temp oven SSPH-101" of ESPEC. The film was baked under a nitrogen atmosphere by raising the temperature from room temperature to 340 ° C. at a rate of temperature rise of 15 ° C./min, holding at 340 ° C. for 5 minutes, and then allowing to cool. The film hue in the glass substrate with film after firing was measured in the same manner as described above.

Calculate the hue change “Δb ^* ” using the following equation, where the measured value of the hue of the film before baking is the “initial b ^* value” and the measured value of the hue of the film after baking is the “b ^* value after baking”. did.
Δb ^* = (b ^* value after firing) − (initial b ^* value)

  As is apparent from Table 1, the film formed from the aromatic polyether nitriles of Examples 1 to 4 synthesized using BN or diglyme (diethylene glycol dimethyl ether) as a polymerization solvent has a small hue change before and after firing. It was.

  On the other hand, the films formed from the aromatic polyether nitriles of Comparative Examples 1, 2, 8 and 9 using DMAc or NMP as the polymerization solvent are different from those of Examples 1 and 2 in hue change before and after firing. It was bigger than.

  When anisole or orthochlorobenzene is used as a polymerization solvent (Comparative Example 3 or 4), aromatic polyether nitrile cannot be synthesized, and when gamma-butyrolactone is used (Comparative Example 5), decomposition of the solvent Therefore, it was difficult to purify the aromatic polyether nitrile.

  Furthermore, after synthesizing and purifying an aromatic polyether nitrile using DMAc or NMP, the films of Comparative Examples 6 and 7 dissolved in a mixed solvent of DMAc and anisole or a mixed solvent of NMP and anisole also, The hue change was greater than the aromatic polyether nitrile films of Examples 1 and 2.

  Thus, the polymerization solvent used for the synthesis of the aromatic polyether nitrile affects the hue change before and after baking of the film obtained from the aromatic polyether nitrile, and also affects the polymerizability of the aromatic polyether nitrile. Confirmed to give. By using an aprotic polar solvent such as BN as a benzonitrile solvent or diglyme as an ether solvent as a polymerization solvent, an aromatic solvent can be used as compared with the case where DMAc or NMP as an amide solvent is used. It was also confirmed that the hue change before and after baking of the film obtained from polyether nitrile can be suppressed.

  Here, Examples 1 and 2 and Comparative Examples 1 and 2 are different from Examples 3 and 4 and Comparative Examples 8 and 9 in the purification method after synthesis of the aromatic polyether nitrile. That is, the aromatic polyether nitriles of Examples 1 to 4 synthesized using BN or diglyme (diethylene glycol dimethyl ether) as a polymerization solvent are calcined without being affected by the general purification method. It is presumed that the hue change before and after becomes small.

  On the other hand, as can be seen from a comparison between Examples 5 and 6 and Comparative Examples 10 and 11, the same results as in the case of synthesizing the aromatic polyether nitrile can be obtained when synthesizing the aromatic polyether sulfone. It was. That is, by using a specific organic solvent such as BN as a benzonitrile-based solvent or diglyme as an ether solvent as a polymerization solvent, an aromatic polyether is used as compared with the case where DMAc or NMP as an amide-based solvent is used. It was confirmed that the hue change before and after baking of the film obtained from sulfone can be suppressed.

  In this example, the aromatic polyether was purified into a powder form and then dissolved in the same solvent as the polymerization solvent, or a salt was obtained from the polymer solution after the synthesis of the aromatic polyether. The resin composition obtained by concentration after removal is used. Therefore, a molded body formed from such a resin composition is considered to be a molded body in which the hue change before and after firing, that is, coloring is suppressed.

  ADVANTAGE OF THE INVENTION According to this invention, the coloring of a molded object can be suppressed and the manufacturing method and molded object of an aromatic poly (thio) ether which can be manufactured advantageously on a process can be provided.

Claims (11)

A resin composition containing an organic solvent and an aromatic poly (thio) ether,
A resin composition, wherein the organic solvent is a compound represented by the following formula (1), diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, triethylene glycol dimethyl ether, or a combination of two or more thereof.

(In Formula (1), R is a C1-C5 monovalent organic group other than an amide group. N is an integer of 0 to 5. When n is 2 or more, a plurality of R are They may be the same or different.)   The resin composition according to claim 1, wherein the organic solvent is benzonitrile, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, or triethylene glycol dimethyl ether.   The resin composition according to claim 1 or 2, wherein the aromatic poly (thio) ether is an aromatic polyether nitrile, an aromatic polyether ketone, an aromatic polyether sulfone, a polyphenylene oxide, or a polyphenylene sulfide. A method for producing an aromatic poly (thio) ether by polycondensation reaction using an organic solvent,
The organic solvent is a compound represented by the following formula (1), diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, triethylene glycol dimethyl ether, or a combination of two or more thereof. Production method.

(In Formula (1), R is a C1-C5 monovalent organic group other than an amide group. N is an integer of 0 to 5. When n is 2 or more, a plurality of R are They may be the same or different.)   The method for producing an aromatic poly (thio) ether according to claim 4, wherein the organic solvent is benzonitrile, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, or triethylene glycol dimethyl ether.   The aromatic poly (thio) ether according to claim 4 or 5, wherein the aromatic poly (thio) ether is an aromatic polyether nitrile, an aromatic polyether ketone, an aromatic polyether sulfone, a polyphenylene oxide, or a polyphenylene sulfide. Method for producing thio) ether. A molded article containing an organic solvent and an aromatic poly (thio) ether,
A molded article, wherein the organic solvent is a compound represented by the following formula (1), diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, triethylene glycol dimethyl ether, or a combination of two or more thereof.

(In Formula (1), R is a C1-C5 monovalent organic group other than an amide group. N is an integer of 0 to 5. When n is 2 or more, a plurality of R are They may be the same or different.)   The molded product according to claim 7, wherein the content of the organic solvent is 5 ppm or more and 2,000 ppm or less.   The molded article according to claim 7 or 8, which is a pellet, a film, a sheet, or an injection molded article.   The molded article according to claim 7, 8 or 9, wherein the organic solvent is benzonitrile, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, or triethylene glycol dimethyl ether.   The aromatic poly (thio) ether is an aromatic polyether nitrile, an aromatic polyether ketone, an aromatic polyether sulfone, a polyphenylene oxide, or a polyphenylene sulfide. Molded body.