WO2019167782A1 - Procédé de production de sulfure de polyarylène - Google Patents

Procédé de production de sulfure de polyarylène Download PDF

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WO2019167782A1
WO2019167782A1 PCT/JP2019/006499 JP2019006499W WO2019167782A1 WO 2019167782 A1 WO2019167782 A1 WO 2019167782A1 JP 2019006499 W JP2019006499 W JP 2019006499W WO 2019167782 A1 WO2019167782 A1 WO 2019167782A1
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sulfur
mixture
dehydrated
dehydration
sulfur source
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PCT/JP2019/006499
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English (en)
Japanese (ja)
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鎮 植田
康弘 小路
直人 川谷内
慎也 石神
貞歳 石井
美里 田中
俊明 大内
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株式会社クレハ
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/0204—Polyarylenethioethers
    • C08G75/025—Preparatory processes
    • C08G75/0259—Preparatory processes metal hydrogensulfides

Definitions

  • the present invention relates to a method for producing polyarylene sulfide.
  • Polyarylene sulfide represented by polyphenylene sulfide (hereinafter also referred to as “PPS”) has heat resistance, chemical resistance, flame resistance, mechanical strength, electrical properties, and dimensions.
  • Engineering plastic with excellent stability. PAS can be molded into various molded products, films, sheets, fibers, etc. by general melt processing methods such as extrusion molding, injection molding, compression molding, etc., so electrical equipment, electronic equipment, automotive equipment, packaging materials, etc. Widely used in a wide range of technical fields.
  • Patent Document 1 discloses a technique for dehydrating a raw material solution by raising the temperature to 200 ° C. over about 2 hours in a nitrogen gas atmosphere.
  • the raw material of PAS contains Na 2 S, which is highly corrosive under high temperature conditions.
  • the reaction vessel used for dehydration corrodes, so that the corrosion resistance is very high.
  • a container containing Zr or Ti There is a problem that it is necessary to use a container containing Zr or Ti.
  • the present invention has been made in view of the above problems, and can suppress foaming in the dehydration process and does not require the use of a high-grade material having high corrosion resistance, for example, a material such as Ti or Zr. It aims at providing the manufacturing method of.
  • the present inventors have found that the above object can be achieved by performing dehydration in the dehydration step in a state where the phase separation between the organic phase and the aqueous phase is eliminated, and have completed the present invention.
  • the PAS manufacturing method includes: A method for producing PAS by polymerizing a sulfur source and a polyhaloaromatic compound in an organic polar solvent, The method A non-dehydrated sulfur-containing source mixture containing a sulfur source, an alkali metal hydroxide, an organic polar solvent, and water is subjected to heating at a temperature not higher than 25 ° C. below the boiling point of the non-dehydrated sulfur-containing source mixture.
  • the amount of water in the non-dehydrated sulfur-containing source mixture after the homogenization step is 0.03 times or more and 1 time the amount of water in the non-dehydrated sulfur-containing source mixture before the homogenization step. The following is acceptable.
  • the homogenization step may be performed in a closed system.
  • the homogenization step may be performed at least when the undehydrated sulfur-containing source mixture is supplied to a reaction vessel in which the dehydration step is performed.
  • the material of the reaction vessel for performing the dehydration step is stainless steel.
  • the present invention it is possible to provide a PAS manufacturing method that can suppress foaming in the dehydration step and that does not require the use of a high-grade material having high corrosion resistance, such as Ti or Zr. . According to this method, it is possible to prevent an increase in the size of the apparatus, deterioration in productivity, and increase in dehydration time when manufacturing PAS.
  • Example 1 and Comparative Example 1 it is a graph which shows the relationship between the elapsed time after boiling and bubble height.
  • Example 4 it is a graph which shows the relationship between the elapsed time after boiling and the amount of water per 1 mol of sulfur sources of a dehydration sulfur-containing source mixture.
  • Example 5 it is a graph which shows the relationship between the elapsed time from a heating start, and bubble height.
  • the PAS manufacturing method in the present embodiment includes a homogenization step and a dehydration step as essential steps.
  • the PAS production method in the present embodiment usually includes a polymerization step after the dehydration step, and may optionally include a preparation step, a cooling step, a post-treatment step, and the like.
  • organic polar solvent sulfur source, polyhaloaromatic compound, and alkali metal hydroxide
  • organic polar solvent sulfur source, polyhaloaromatic compound, and alkali metal hydroxide
  • those usually used in the production of PAS can be used.
  • Each of the organic polar solvent, the sulfur source, the polyhaloaromatic compound, and the alkali metal hydroxide may be used alone or in combination of two or more as long as the PAS can be produced. May be.
  • Examples of the organic polar solvent include an organic amide solvent; an aprotic organic polar solvent composed of an organic sulfur compound; and an aprotic organic polar solvent composed of a cyclic organic phosphorus compound.
  • Examples of the organic amide solvent include amide compounds such as N, N-dimethylformamide and N, N-dimethylacetamide; N-alkylcaprolactam compounds such as N-methyl- ⁇ -caprolactam; N-methyl-2-pyrrolidone (hereinafter, “ NMP ”), N-alkylpyrrolidone compounds such as N-cyclohexyl-2-pyrrolidone or N-cycloalkylpyrrolidone compounds; N, N-dialkylimidazolidinones such as 1,3-dialkyl-2-imidazolidinone Compounds; tetraalkylurea compounds such as tetramethylurea; hexaalkylphosphate triamide compounds such as hexamethylphosphate triamide,
  • Examples of the aprotic organic polar solvent composed of an organic sulfur compound include dimethyl sulfoxide and diphenyl sulfone.
  • Examples of the aprotic organic polar solvent comprising a cyclic organophosphorus compound include 1-methyl-1-oxophosphorane.
  • organic amide solvents are preferable in terms of availability, handling, and the like, and N-alkylpyrrolidone compounds, N-cycloalkylpyrrolidone compounds, N-alkylcaprolactam compounds, and N, N-dialkylimidazolidinone compounds are more preferable.
  • NMP, N-methyl- ⁇ -caprolactam, and 1,3-dialkyl-2-imidazolidinone are even more preferred, and NMP is particularly preferred.
  • Examples of the sulfur source include alkali metal sulfides, alkali metal hydrosulfides, and hydrogen sulfide, and alkali metal sulfides and alkali metal hydrosulfides are preferable.
  • the sulfur source can be handled, for example, in either an aqueous slurry or an aqueous solution, and is preferably in the state of an aqueous solution from the viewpoint of handling properties such as meterability and transportability.
  • Examples of the alkali metal sulfide include lithium sulfide, sodium sulfide, potassium sulfide, rubidium sulfide, and cesium sulfide.
  • Examples of the alkali metal hydrosulfide include lithium hydrosulfide, sodium hydrosulfide, potassium hydrosulfide, rubidium hydrosulfide, and cesium hydrosulfide.
  • a polyhaloaromatic compound refers to an aromatic compound in which two or more hydrogen atoms directly bonded to an aromatic ring are substituted with halogen atoms, and an aromatic compound in which two hydrogen atoms directly bonded to an aromatic ring are substituted with halogen atoms Even a compound (that is, a dihaloaromatic compound) or an aromatic compound in which 3 or more hydrogen atoms directly bonded to an aromatic ring are substituted with a halogen atom (also referred to as “polyhaloaromatic compound having 3 or more halogen substitutions”). Good.
  • polyhaloaromatic compounds include o-dihalobenzene, m-dihalobenzene, p-dihalobenzene, dihalotoluene, dihalonaphthalene, methoxy-dihalobenzene, dihalobiphenyl, dihalobenzoic acid, dihalodiphenyl ether, dihalodiphenylsulfone, dihalo Dihaloaromatic compounds such as diphenyl sulfoxide and dihalodiphenyl ketone; 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, 1,3,5-trichlorobenzene, hexachlorobenzene, 1,2,3 4-tetrachlorobenzene, 1,2,4,5-tetrachlorobenzene, 1,3,5-trichloro-2,4,6-trimethylbenzene, 2,4,6-trichlorotoluene, 1,2,3-trich
  • a halogen atom refers to each atom of fluorine, chlorine, bromine, and iodine, and two or more halogen atoms in the polyhaloaromatic compound may be the same or different.
  • p-dihalobenzene, m-dihalobenzene, and a mixture of both are preferable in terms of availability, reactivity, and the like, p-dihalobenzene is more preferable, and p-dichlorobenzene (hereinafter also referred to as “pDCB”). Particularly preferred.
  • alkali metal hydroxide examples include lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide, and cesium hydroxide.
  • the homogenization step in the present embodiment is a heating of an undehydrated sulfur-containing source mixture containing a sulfur source, an alkali metal hydroxide, an organic polar solvent, and water, resulting in phase separation between the organic phase and the aqueous phase.
  • This is a step of homogenizing the non-dehydrated sulfur-containing source mixture from a heterogeneous system to a homogeneous system in which phase separation between the organic phase and the aqueous phase has been eliminated.
  • the liquid temperature for homogenization may be 25 ° C. or more below the boiling point of the non-dehydrated sulfur-containing source mixture. For example, the liquid temperature that was 25 ° C. at the start of homogenization is 60 ° C.
  • the temperature may be raised to a temperature of 100, 115, 120, or 130 ° C., and the temperature may be maintained until a uniform liquid phase is obtained.
  • a dehydration step described later may be performed as it is.
  • the non-dehydrated sulfur-containing source mixture can be homogenized from the heterogeneous system to the homogeneous system.
  • the homogenization in the present embodiment means that the non-dehydrated sulfur-containing source mixture is in a uniform liquid phase.
  • the organic polar solvent and the aqueous solution containing other raw materials are initially in a phase-separated state when charged into the reaction vessel. That is, in the undehydrated sulfur-containing source mixture at the beginning of the preparation, an organic polar solvent as a main component, an organic phase containing a sulfur source and water, and a phase comprising a sulfur source, an alkali metal hydroxide, and an aqueous phase containing water. Separation has occurred. If the dehydration step is carried out in this state, the mixture will foam violently, and nozzle clogging tends to occur.
  • foaming is suppressed by performing the dehydration step after the phase separation state is eliminated through the homogenization step, and nozzle clogging and the like can be effectively suppressed. Accordingly, dehydration can be performed at a stretch, so that the dehydration time can be shortened and productivity can be improved.
  • the reaction between the organic polar solvent and the alkali metal hydroxide sufficiently proceeds as a result of heating, and the phase separation between the organic phase and the aqueous phase is eliminated by the reaction product.
  • the organic polar solvent is NMP and the alkali metal hydroxide is sodium hydroxide
  • SMAB is a reaction product of NMP and sodium hydroxide.
  • the place where the homogenization step is performed is not particularly limited, and the homogenization step may be performed, for example, in the same reaction vessel as that in which the dehydration step described below is performed, or may be performed in a container dedicated to the homogenization step, You may carry out in piping. Or you may perform a homogenization process at the time of supply of the said non-dehydrating sulfur-containing source mixture to the reaction container which performs a dehydration process at least. If the homogenization step is performed at the time of supplying the non-dehydrated sulfur-containing source mixture to the reaction vessel, it takes time to perform only the homogenization step between the supply of the non-dehydrated sulfur-containing source mixture and the dehydration step. Since it does not need to be pinched, cycle time is shortened and productivity is easily improved.
  • the amount of water per 1 mol of the sulfur source of the non-dehydrated sulfur-containing mixture after the homogenization step is not particularly limited, and is preferably 0.03 times the amount of water per 1 mol of the sulfur source of the non-dehydrated sulfur-containing mixture before the homogenization step. It is 1 to 1 time, more preferably 0.1 to 1 time, and even more preferably 0.9 to 1 time.
  • the amount of water after the homogenization step is preferably 0.03 or more and less than 1 time, more preferably 0.1 or more and less than 1 time, and even more preferably 0.9 or more times the amount of water before the homogenization step.
  • the upper limit of the heating temperature in the homogenization step is not particularly limited as long as it is not higher than the boiling point of the non-dehydrated sulfur-containing source mixture, and may be lower than the boiling point of the non-dehydrated sulfur-containing source mixture, for example, 140 ° C. or lower.
  • the temperature is preferably 135 ° C. or lower.
  • the lower limit of the heating temperature in the homogenizing step is not particularly limited as long as it is 25 ° C. or higher. For example, it may be 60 ° C. or higher, and may be 95 ° C. or higher.
  • the dehydration step is a step of dehydrating the non-dehydrated sulfur-containing source mixture to obtain a dehydrated sulfur-containing source mixture, and is performed after the homogenizing step. Through the dehydration step, distillate containing water is discharged out of the system containing the non-dehydrated sulfur-containing source mixture.
  • the polymerization reaction between the sulfur source and the polyhaloaromatic compound is influenced by being promoted or inhibited by the amount of water present in the polymerization reaction system.
  • a dehydration process aims at reducing the said moisture content so that the moisture content which exists in a polymerization reaction system may not inhibit a polymerization reaction.
  • the water to be dehydrated in the dehydration step is water charged to prepare the non-dehydrated sulfur-containing source mixture, water contained in each raw material other than water charged to prepare the non-dehydrated sulfur-containing source mixture, aqueous An aqueous medium of the mixture, water by-produced by a reaction between the raw materials, and the like.
  • the heating temperature in the dehydration step is not particularly limited as long as it is 300 ° C. or less, and is preferably 100 to 250 ° C.
  • the heating time is preferably 15 minutes to 24 hours, and more preferably 30 minutes to 10 hours.
  • dehydration is performed until the water content falls within a predetermined range. That is, in the dehydration step, dehydration is preferably performed until the amount is preferably 0.5 to 2.4 mol with respect to 1.0 mol of the sulfur source. When the amount of water becomes too small in the dehydration step, water may be added to adjust the desired amount of water in the preparation step prior to the polymerization step.
  • the material of the reaction vessel for performing the dehydration step is not particularly limited, and for example, a material having low corrosion resistance compared to Ti and Zr, such as stainless steel, can be used.
  • a material having low corrosion resistance compared to Ti and Zr such as stainless steel
  • the reaction between the organic polar solvent and the alkali metal hydroxide sufficiently proceeds to generate a reaction product that eliminates phase separation between the organic phase and the aqueous phase. It is considered a thing.
  • This reaction product reacts with a highly corrosive sulfur source to produce a material with low metal corrosivity.
  • the material of the reaction vessel for performing the dehydration process is not corrosion-resistant Zr and Ti but stainless steel, corrosion of the reaction vessel can be effectively suppressed.
  • the organic polar solvent is NMP
  • the alkali metal hydroxide is sodium hydroxide
  • the sulfur source is sodium sulfide
  • water coexists in the system, the reaction product of NMP, sodium hydroxide, and water
  • a highly corrosive sodium sulfide produces a less corrosive SMAB-NaSH complex, effectively suppressing the corrosion of the reaction vessel. be able to.
  • the charging step is a step of preparing a mixture containing an organic polar solvent, a sulfur source, a polyhaloaromatic compound, and water by mixing the dehydrated sulfur-containing source mixture and the polyhaloaromatic compound.
  • a mixture charged in the charging step is also referred to as a “charged mixture”.
  • the amount of sulfur source in the charged mixture (hereinafter also referred to as “the amount of charged sulfur source” (effective sulfur source)) is obtained by subtracting the molar amount of hydrogen sulfide volatilized in the dehydration process from the molar amount of sulfur source charged as a raw material. Can be calculated.
  • an alkali metal hydroxide and water can be added to the mixture remaining in the system after the dehydration step, if necessary.
  • the alkali metal hydroxide is added in consideration of the amount of hydrogen sulfide generated during dehydration and the amount of alkali metal hydroxide generated during dehydration.
  • the amount of each of the organic polar solvent and the polyhaloaromatic compound used is set, for example, within the range shown in the following description of the polymerization step with respect to 1 mol of the charged sulfur source.
  • the polymerization reaction in the main polymerization step is performed by heating a mixture containing the sulfur source and the polyhaloaromatic compound.
  • the polymerization reaction may be carried out in two or more stages.
  • the first stage polymerization reaction is a polymerization reaction in which a mixture containing the sulfur source and the polyhaloaromatic compound is heated to start the polymerization reaction, and a prepolymer having a polyhaloaromatic compound conversion rate of 50% or more is generated. is there.
  • the second stage polymerization step may be performed in the presence of a phase separation agent such as water, an organic carboxylic acid metal salt, or a combination thereof.
  • the polymerization reaction it is preferable to carry out the polymerization reaction under heating at a temperature of 170 to 300 ° C. from the viewpoint of the efficiency of the polymerization reaction.
  • the polymerization temperature in the polymerization reaction is more preferably in the range of 180 to 280 ° C. in order to suppress side reactions and decomposition reactions.
  • the polymerization reaction is started under heating at a temperature of 170 to 270 ° C., and a prepolymer having a polyhaloaromatic compound conversion of 50% or more is generated. It is preferable.
  • the polymerization temperature in the first stage polymerization reaction is preferably selected from the range of 180 to 265 ° C. in order to suppress side reactions and decomposition reactions.
  • the conversion rate of the polyhaloaromatic compound in the pre-stage polymerization reaction is preferably 50 to 98%, more preferably 60 to 97%, still more preferably 65 to 96%, and particularly preferably 70 to 95%.
  • the conversion rate of the polyhaloaromatic compound is calculated based on the amount of the polyhaloaromatic compound remaining in the reaction mixture by gas chromatography and based on the remaining amount, the charged amount of the polyhaloaromatic compound, and the charged amount of the sulfur source. Can do.
  • the polymerization reaction in the main polymerization step may be performed batchwise or continuously. For example, supply of at least an organic polar solvent, a sulfur source, and a polyhaloaromatic compound, production of PAS by polymerization of the sulfur source and the polyhaloaromatic compound in the organic polar solvent, and recovery of a reaction mixture containing PAS ,
  • the polymerization reaction can be carried out continuously by carrying out in parallel.
  • the amount of the organic polar solvent used is preferably from 1 to 30 mol, more preferably from 3 to 15 mol, based on 1 mol of the sulfur source from the viewpoint of the efficiency of the polymerization reaction.
  • the amount of the polyhaloaromatic compound to be used is preferably 0.90 to 1.50 mol, more preferably 0.92 to 1.10 mol, and still more preferably with respect to 1 mol of the charged sulfur source. 0.95 to 1.05 mol.
  • the amount used is within the above range, a decomposition reaction is unlikely to occur, a stable polymerization reaction can be easily performed, and a high molecular weight polymer is easily generated.
  • the cooling step is a step of cooling the reaction mixture after the polymerization step. Specific operations in the cooling step are as described in, for example, Japanese Patent No. 6062924.
  • the post-treatment step after the polymerization reaction can be performed by a conventional method, for example, by the method described in JP-A-2016-056232.
  • Example 1 and Comparative Example 1 Into a 2 L reaction vessel, NMP 160 g / mol-S, 48 mass% sodium hydroxide aqueous solution 0.9 mol-NaOH / mol-S, and 45 mass% sodium hydrosulfide aqueous solution were charged. The resulting mixture was heated from 25 ° C. to 130 ° C. in a boil for at least about 10 minutes in the following state 1 (Comparative Example 1). Alternatively, when the resulting mixture is heated to the following state 2 (Example 1), it is heated from the corresponding heating temperature to 130 ° C. at once (if the heating temperature is 130 ° C., the heating is performed at the same temperature as it is. Continued) and boiled for at least about 10 minutes.
  • Example 1 the system heated and boiled after eliminating phase separation was generated in Comparative Example 1 than the system heated and boiled without eliminating phase separation.
  • the height of the foam was low.
  • Comparative Example 1 it is considered that the reason why the height of the bubbles is decreasing at the peak of 2 minutes is that the phase separation has been eliminated as the reaction proceeds.
  • Example 1 or Comparative Example 1 the same experiment was conducted by specifying the material of the 2 L reaction vessel as stainless steel or titanium, and the degree of corrosion of the reaction vessel after the experiment was evaluated according to the following criteria. The results are shown in Table 1. D: The degree of corrosion was relatively high, and the reaction vessel hardly resisted corrosion. A: The degree of corrosion was relatively low, and the reaction vessel resisted corrosion. AA: The degree of corrosion was relatively lower, and the reaction vessel withstood the corrosion well.
  • the degree of corrosion of the reaction vessel using stainless steel can be suppressed to the same level as that of the reaction vessel using titanium.
  • Titanium is a commonly used material in PAS manufacturing and is rarer and more expensive than stainless steel. According to the present invention, it is possible to change the material of the reaction vessel from titanium to stainless steel while suppressing the corrosion of the reaction vessel equally, so that resource saving and cost reduction can be realized.
  • Example 4 In the same manner as in Example 1, heating was performed from 25 ° C. to 130 ° C. all at once to start boiling. Thereafter, the amount of heat was controlled so that the liquid temperature was always at the boiling point, and all the liquid vapor was discharged out of the system. The heating was performed using an oil bath. The amount of water per 1 mol of the sulfur source in the dehydrated sulfur-containing source mixture was measured along the elapsed time after boiling. The results are shown in FIG.
  • the amount of water decreased as the time elapsed from boiling. Therefore, according to the present invention, the amount of water present in the polymerization reaction system can be sufficiently reduced, so that the polymerization reaction in the polymerization step is hardly inhibited.
  • Example 5 In the same manner as in Example 1, NMP, 48 mass% sodium hydroxide aqueous solution, and 45 mass% sodium hydrosulfide aqueous solution were charged into the reaction vessel, and the resulting mixture was heated from 25 ° C. and boiled to generate.
  • the height of the foam is 30 mm (corresponding to an acceptable foaming amount.
  • (1) The height from the liquid surface to the nozzle is 40 mm, and (2) 2 is acceptable if the height from the foam to the nozzle is 10 mm. From the facts, the allowable amount of foaming was set at 30 mm.
  • the homogenization process was completed in about 6 minutes from the start of heating, and after confirming that the bubble height had decreased, the amount of heat was increased and the dehydration process was performed.
  • the heating was performed using an oil bath in the same manner as in Example 4, and all the liquid vapor was discharged out of the system.
  • the foam height was measured along the elapsed time from the start of heating. The results are shown in FIG.
  • the homogenization process was completed in about 6 minutes (third plot) from the start of heating. Accordingly, it can be seen that the bubble height decreased after the homogenization step.
  • the amount of water per 1 mol of the sulfur source of the non-dehydrated sulfur-containing source mixture was 6.40 mol / mol-S at the start of heating, whereas it was 6.27 mol / mol-S at the end of the homogenization step. Therefore, the amount of water per 1 mol of the sulfur source of the non-dehydrated sulfur-containing mixture after the homogenization step was about 0.98 times the amount of water per 1 mol of the sulfur source of the non-dehydrated sulfur-containing mixture before the homogenization step.
  • FIG. 3 it was confirmed that the cycle time was shortened and the productivity was improved because the amount of dehydration decreased in the dehydration step.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

L'invention concerne un procédé qui permet de produire un sulfure de polyarylène (ci-après désigné « PAS ») et dans lequel le moussage dans un processus de déshydratation peut être empêché, et l'utilisation d'un matériau coûteux présentant une résistance élevée à la corrosion tel que Ti ou Zr n'est pas nécessaire. Le procédé de production d'un PAS selon la présente invention produit le PAS par polymérisation d'une source de soufre et d'un composé polyhaloaromatique dans un solvant polaire organique, et comprend : une étape d'homogénéisation consistant à chauffer un mélange contenant une source de soufre non déshydraté comprenant une source de soufre, un hydroxyde de métal alcalin, un solvant polaire organique et de l'eau à une température comprise entre 25 °C et le point d'ébullition du mélange contenant une source de soufre non déshydraté, et à homogénéiser et transformer le mélange contenant une source de soufre non déshydraté d'un système non homogène dans lequel a lieu une séparation de phase entre une phase organique et une phase aqueuse en un système homogène dans lequel la séparation de phase entre la phase organique et la phase aqueuse a été résolue ; et une étape de déshydratation consistant à déshydrater le mélange contenant une source de soufre non déshydraté pour obtenir un mélange contenant une source de soufre déshydraté, l'étape de déshydratation étant effectuée après l'étape d'homogénéisation.
PCT/JP2019/006499 2018-02-27 2019-02-21 Procédé de production de sulfure de polyarylène WO2019167782A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7463838B2 (ja) 2020-05-19 2024-04-09 Dic株式会社 ポリアリーレンスルフィド樹脂の製造方法および洗浄方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5023315A (en) * 1990-04-18 1991-06-11 Phillips Peteroleum Company Process for preparing arylene sulfide polymers
WO2010058713A1 (fr) * 2008-11-21 2010-05-27 Dic株式会社 Procédé de fabrication d'une résine de poly(sulfure d'arylène)
JP2013241590A (ja) * 2012-04-27 2013-12-05 Toray Ind Inc 環式ポリアリーレンスルフィドの製造方法
US20160244568A1 (en) * 2015-02-19 2016-08-25 Ticona Llc Method for Forming a High Molecular Weight Polyarylene Sulfide
JP2016536377A (ja) * 2013-09-25 2016-11-24 ティコナ・エルエルシー ポリアリーレンスルフィドを形成するためのスクラビングプロセス

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5023315A (en) * 1990-04-18 1991-06-11 Phillips Peteroleum Company Process for preparing arylene sulfide polymers
WO2010058713A1 (fr) * 2008-11-21 2010-05-27 Dic株式会社 Procédé de fabrication d'une résine de poly(sulfure d'arylène)
JP2013241590A (ja) * 2012-04-27 2013-12-05 Toray Ind Inc 環式ポリアリーレンスルフィドの製造方法
JP2016536377A (ja) * 2013-09-25 2016-11-24 ティコナ・エルエルシー ポリアリーレンスルフィドを形成するためのスクラビングプロセス
US20160244568A1 (en) * 2015-02-19 2016-08-25 Ticona Llc Method for Forming a High Molecular Weight Polyarylene Sulfide

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7463838B2 (ja) 2020-05-19 2024-04-09 Dic株式会社 ポリアリーレンスルフィド樹脂の製造方法および洗浄方法

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