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WO2018164010A1 - Procédé de production de poly(sulfure d'arylène) - Google Patents

Procédé de production de poly(sulfure d'arylène) Download PDF

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Publication number
WO2018164010A1
WO2018164010A1 PCT/JP2018/008128 JP2018008128W WO2018164010A1 WO 2018164010 A1 WO2018164010 A1 WO 2018164010A1 JP 2018008128 W JP2018008128 W JP 2018008128W WO 2018164010 A1 WO2018164010 A1 WO 2018164010A1
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WIPO (PCT)
Prior art keywords
reaction tank
zirconium
valve
supply path
pas
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Ceased
Application number
PCT/JP2018/008128
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English (en)
Japanese (ja)
Inventor
崇之 木村
義宏 一ノ瀬
精孝 ▲但▼野
小林　正則
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Kureha Corp
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Kureha Corp
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Filing date
Publication date
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Publication of WO2018164010A1 publication Critical patent/WO2018164010A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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

Definitions

  • the present invention relates to an apparatus 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.
  • Examples of the method for producing PAS include a method for producing PAS by polymerizing a sulfur source and a dihaloaromatic compound in an organic amide solvent (for example, Patent Documents 1 and 2).
  • the valve provided in the supply path for supplying the raw material sulfur source to the reaction tank is one in which the reaction solution does not directly pass through. in use.
  • This invention is made in view of said subject, Comprising: The frequency which replace
  • An object of the present invention is to provide an apparatus for manufacturing a PAS that can be used.
  • the present inventors have found that the above object can be achieved by using a valve formed of a zirconium-containing material, and have completed the present invention.
  • the PAS manufacturing apparatus comprises: A reaction vessel for polymerizing a sulfur source and a dihaloaromatic compound in an organic polar solvent to produce PAS; A supply path communicating with the reaction tank and supplying the sulfur source to the reaction tank; At least one valve provided in the supply path for opening and closing the supply path; With At least one of the valves is formed from a zirconium-containing material.
  • a valve closest to the reaction vessel among the at least one valve is formed of the zirconium-containing material.
  • the zirconium content in the zirconium-containing material is preferably 95 to 100% by mass.
  • the manufacturing apparatus of PAS which can reduce the frequency which replace
  • the manufacturing apparatus according to the present invention can be applied to a PAS manufacturing apparatus in which a corrosive material such as strong alkali is introduced into a reaction tank to perform a polymerization reaction.
  • PAS production method The method for producing PAS is not particularly limited as long as the gist of the present invention is not impaired, and generally, a charging step, a polymerization step (a two-stage polymerization step comprising a pre-stage polymerization step and a post-stage polymerization step) And a method of further comprising a dehydration step.
  • the dehydration step is a step of discharging a distillate containing water from the reaction system during the polymerization reaction, which contains a mixture containing an organic polar solvent and a sulfur source, before the preparation step.
  • the polymerization reaction between the sulfur source and the dihaloaromatic compound is affected by being accelerated or inhibited by the amount of water present in the polymerization reaction system. Therefore, the dehydration step is not indispensable as long as the water content does not inhibit the polymerization reaction, but it is preferable to reduce the water content in the polymerization reaction system by performing a dehydration treatment before the polymerization.
  • the dehydration step it is preferable to perform dehydration by heating in an inert gas atmosphere.
  • a dehydration process is performed within a reaction tank, and the distillate containing water is discharged
  • the water to be dehydrated in the dehydration step is hydrated water contained in each raw material charged in the dehydration step, an aqueous medium of an aqueous 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, it is desirable to dehydrate until the amount of water is preferably 0 to 2 mol, more preferably 0.5 to 1.8 mol with respect to 1 mol of the effective sulfur source described later. 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 preparation step is a step of preparing a mixture containing an organic polar solvent, a sulfur source, a dihaloaromatic compound, and water.
  • 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)) was volatilized in the dehydration step from the molar amount of the sulfur source charged in the dehydration step. It can be calculated by subtracting the molar amount of hydrogen sulfide.
  • 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 dihaloaromatic compound used is set, for example, within the range shown in the following description regarding the polymerization step with respect to 1 mol of the charged sulfur source.
  • PAS is produced by polymerizing a sulfur source and a dihaloaromatic compound in an organic polar solvent.
  • the polymerization reaction in the main polymerization step is performed by heating a mixture containing the sulfur source and the dihaloaromatic compound.
  • the polymerization reaction may be carried out in two or more stages.
  • the polymerization reaction is preferably, for example, a pre-polymerization reaction between the sulfur source and the dihaloaromatic compound.
  • the pre-stage polymerization reaction is a polymerization reaction in which a mixture containing the sulfur source and the dihaloaromatic compound is heated to start the polymerization reaction, and a prepolymer having a dihaloaromatic compound conversion rate of 50% or more is generated.
  • 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 dihaloaromatic compound conversion rate of 50% or more can be generated.
  • the polymerization temperature in the pre-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 dihaloaromatic 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 dihaloaromatic compound is calculated based on the amount of the dihaloaromatic compound remaining in the reaction mixture by gas chromatography and based on the remaining amount, the charged amount of the dihaloaromatic 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 dihaloaromatic compound, production of PAS by polymerization of the sulfur source and the dihaloaromatic 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.
  • organic polar solvent a sulfur source, and a dihalo aromatic compound
  • a sulfur source and a dihalo aromatic compound
  • the organic polar solvent, the sulfur source, and the dihaloaromatic compound may be used singly or in combination of two or more as long as the PAS can be produced.
  • 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.
  • 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.
  • 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 in the form of, for example, 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.
  • Dihaloaromatic compounds include o-dihalobenzene, m-dihalobenzene, p-dihalobenzene, dihalotoluene, dihalonaphthalene, methoxy-dihalobenzene, dihalobiphenyl, dihalobenzoic acid, dihalodiphenyl ether, dihalodiphenyl sulfone, dihalodiphenyl sulfoxide Dihalodiphenyl ketone, and the like.
  • Halogen atoms refer to fluorine, chlorine, bromine and iodine atoms, and the two halogen atoms in the dihaloaromatic compound may be the same or different.
  • p-dihalobenzene p-dihalobenzene
  • m-dihalobenzene p-dihalobenzene
  • pDCB p-dichlorobenzene
  • the amount of the dihaloaromatic compound to be used is preferably 0.90 to 1.50 mol, more preferably 0.92 to 1.10 mol, 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.
  • Post-treatment process (separation process, washing process, recovery process, etc.):
  • the post-treatment step after the polymerization reaction can be performed by a conventional method. For example, after the polymerization reaction is completed, the slurry containing the produced PAS polymer is kept in a high temperature state or cooled, and then diluted with water or the like as desired, and then the PAS polymer is filtered by sieving or the like, Next, the separated PAS polymer is washed with an organic solvent such as the same polar solvent as the polymerization solvent, an organic solvent such as ketones (for example, acetone), alcohols (for example, methanol), hot water, and filtration.
  • an organic solvent such as the same polar solvent as the polymerization solvent, an organic solvent such as ketones (for example, acetone), alcohols (for example, methanol), hot water, and filtration.
  • a recovery step for recovering PAS can be performed.
  • the produced PAS can be treated with a salt such as acid or ammonium chloride.
  • a salt such as acid or ammonium chloride.
  • PAS manufacturing apparatus communicates with a reaction tank for polymerizing a sulfur source and a dihaloaromatic compound in an organic polar solvent to produce polyarylene sulfide, and the reaction tank.
  • a PAS manufacturing apparatus 100 includes a reaction tank 1. As a PAS manufacturing method performed by applying the PAS manufacturing apparatus 100, the reaction tank 1 is used, and at least the charging process and the polymerization process are performed in the reaction tank 1 (therefore, the reaction tank 1 is a “polymerization tank” or Sometimes referred to as “polymerization can”), and if desired, a dehydration step is performed.
  • the reaction tank 1 is a “polymerization tank” or Sometimes referred to as “polymerization can”
  • a dehydration step is performed.
  • the reaction tank 1 provided in the PAS manufacturing apparatus 100 the same shape, structure, size, etc. as in the reaction tank conventionally provided and used in the PAS manufacturing apparatus can be applied, and the same material is used.
  • the reaction vessel 1 usually has a structure including a cylindrical body portion 11, a lid portion 12 and a bottom portion 13.
  • a stirring blade 21 and a stirring shaft 22 are usually inserted, and one or a plurality of baffles (baffle plates) 3 are provided on the inner peripheral wall.
  • the agitation shaft 22 is connected to an electric motor (not shown) disposed above the reaction tank 1 and is driven to rotate.
  • the lid 12 of the reaction tank 1 is usually a bowl-shaped member that is connected to and attached to the upper part of the cylindrical body 11, and is provided with a hole through which the stirring shaft 22 described above is inserted.
  • the reaction vessel 1 includes raw material monomers and other materials (alkali metal hydroxides and the like.
  • the raw material monomers and other materials are collectively referred to as “various”.
  • a plurality of supply passages 4 (sometimes referred to as “supply nozzles”) for charging the reaction tank 1 into the interior of the reaction tank 1 ( In FIG. 1, one supply path 4 is shown as a supply path for supplying the sulfur source to the reaction tank 1).
  • the lid 12 may be provided with an openable / closable opening or the like so that the inside of the reaction tank 1 can be inspected, cleaned, and the like.
  • the opening that can be opened and closed is usually larger in diameter than the supply path 4.
  • the lid portion 12 may be provided with a required number of baffle fixing portions for suspending and fixing the baffles 3 arranged in the reaction tank 1.
  • the bottom 13 of the reaction tank 1 is a generally bowl-shaped member that is connected to and attached to the lower part of the cylindrical body 11.
  • the bottom 13 is usually provided with a discharge pipe 131 (also referred to as a “discharge nozzle”) for discharging the PAS polymer produced by the polymerization reaction, and various raw materials are charged into the reaction tank 1 as desired. There is a case where a supply path is provided.
  • the cylindrical body 11 of the reaction tank 1 constitutes a main part of the reaction tank 1, and a charging process, a polymerization process, and a dehydration process are performed therein if desired.
  • a stirring blade 21 and a stirring shaft 22 and a baffle (baffle plate) 3 are usually arranged inside the cylindrical body 11.
  • the baffle 3 is directly attached to the inner wall of the cylindrical body 11.
  • the baffle 3 may be supported by a baffle support protruding from the inner wall of the reaction tank 1, specifically, the inner wall of the cylindrical body 11, or as mentioned above, You may make it hang and fix from the cover part 12.
  • FIG. 1 The baffle 3 is directly attached to the inner wall of the cylindrical body 11.
  • the baffle 3 may be supported by a baffle support protruding from the inner wall of the reaction tank 1, specifically, the inner wall of the cylindrical body 11, or as mentioned above, You may make it hang and fix from the cover part 12.
  • reaction tank 1 including the cylindrical body portion 11, the lid portion 12, and the bottom portion 13.
  • the electric motor that rotates the agitation shaft 22 described above is an example.
  • a heat exchange jacket for adjusting the temperature of the reaction vessel 1, particularly the cylindrical body 11, is an outer peripheral surface of the reaction vessel 1. May be provided so as to surround.
  • various pipes may be provided for the purpose of transferring various raw materials and the like, PAS polymer to be produced, circulation of a heat medium and / or refrigerant, and the like.
  • a material excellent in strength and chemical resistance in a high temperature environment is required.
  • Specific examples include corrosion resistant metals such as titanium materials (may be titanium alloys), zirconium materials (may be zirconium alloys), special austenitic steels [Carpenter (registered trademark), etc.], and these plate-like materials, A laminate in which a corrosion-resistant metal such as titanium or zirconium is provided on the inner surface of the reaction vessel 1, such as a titanium-coated steel material or a clad material, is used. The thickness and size of the corrosion-resistant metal plate material (including clad material) are appropriately determined as necessary. The same applies to materials forming members such as the baffle 3 disposed in the reaction tank 1.
  • the PAS manufacturing apparatus 100 includes a supply path 4.
  • the supply path 4 communicates with the reaction tank 1 and supplies a sulfur source to the reaction tank 1.
  • the supply path 4 is connected to the lid portion 12 of the reaction tank 1 as shown in FIG. 1, for example.
  • the PAS manufacturing apparatus 100 includes one or a plurality of supply paths for introducing various raw materials such as raw material monomers and alkali metal hydroxide into the reaction tank 1 (not shown). )
  • the diameter, length, and thickness of the supply path 4 can be appropriately set in consideration of the type of the sulfur source supplied from the supply path 4, the input amount to the reaction tank 1, the strength required for the supply path 4, and the like.
  • the supply path 4 is preferably formed from a corrosion-resistant material such as a titanium material or a zirconium material.
  • valve 5 As shown in FIG. 1, the PAS manufacturing apparatus 100 includes a valve 5.
  • the valve 5 is provided in the supply path 4 and opens and closes the supply path 4.
  • FIG. 1 shows the case where one valve is provided in the supply path 4, a plurality of valves may be provided in the supply path 4. By opening the valve 5, the sulfur source is supplied to the reaction tank 1 through the supply path 4, and by closing the valve 5, the supply of the sulfur source to the reaction tank 1 through the supply path 4 is completed.
  • the shape of the valve 5 is not particularly limited as long as the sulfur source can be supplied to the reaction tank 1.
  • a butterfly valve, a ball valve, a diaphragm valve, a globe valve, a plug valve, a ball valve, or the like can be used as the valve 5, for example, a butterfly valve, a ball valve, a diaphragm valve, a globe valve, a plug valve, a ball valve, or the like can be used.
  • a ball valve is preferable from the viewpoint of operability, flow rate adjustability, and the like.
  • the valve 5 is made of a zirconium-containing material. Thereby, even if a sulfur-containing atmosphere such as hydrogen sulfide generated in the reaction tank 1 comes into contact with the valve 5, the valve 5 is hardly corroded.
  • a plurality of valves are provided in the supply path 4, at least one of these valves is made of a zirconium-containing material, and preferably the valve closest to the reaction vessel 1 among these valves. Is formed from the zirconium-containing material.
  • the valve closest to the reaction vessel is likely to corrode due to the sulfur-containing atmosphere, and therefore needs to be replaced periodically. If the valve is formed from the zirconium-containing material, The frequency of exchange can be effectively reduced.
  • valve 5 in the present embodiment is provided in the supply path 4, it also comes into contact with a corrosive PAS raw material such as an alkali metal hydroxide.
  • a corrosive PAS raw material such as an alkali metal hydroxide.
  • the polymerization reaction of PAS is generally performed under a high temperature condition of 200 ° C. or higher. Since the valve 5 of the present embodiment is formed from a zirconium-containing material, corrosion of the valve 5 can be effectively suppressed even under high temperature conditions.
  • the zirconium-containing material is not particularly limited as long as zirconium is contained, and examples thereof include a metal material containing zirconium.
  • the zirconium content in the zirconium-containing material is not particularly limited, and is preferably 95 to 100% by mass, more preferably 97.5 to 99.5% by mass from the viewpoint of improving corrosion resistance. Even more preferably, it is 98 to 99% by mass.
  • the zirconium-containing material showed excellent corrosion resistance to any of the sodium hydrosulfide aqueous solution, the hydrogen sulfide atmosphere, and the sodium hydroxide aqueous solution. Therefore, in the PAS manufacturing apparatus, the corrosion resistance of the valve can be improved by forming the valve provided in the supply path for supplying the sulfur source as the raw material to the reaction tank with the zirconium-containing material.

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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 dispositif de production de poly(sulfure d'arylène) (ci-après, PSA), la résistance à la corrosion d'une valve placée dans un trajet d'alimentation pour alimenter une cuve de réaction par une source de soufre qui est une matière première pouvant être améliorée pour réduire la fréquence de remplacement de la valve. Le dispositif de production de PSA selon la présente invention comprend : une cuve de réaction pour produire du PSA par polymérisation d'une source de soufre et d'un composé dihalogéné aromatique dans un solvant polaire organique ; un trajet d'alimentation communiquant avec la cuve de réaction, et alimentant en source de soufre le réservoir de réaction ; et une ou plusieurs valves placées dans le trajet d'alimentation, et ouvrant et fermant le trajet d'alimentation. Au moins une des valves est constituée d'un matériau contenant du zirconium. De préférence, seule la valve la plus proche de la cuve de réaction parmi la ou les valves est constituée du matériau contenant du zirconium. De plus, de préférence, la teneur en zirconium dans le matériau contenant du zirconium est comprise entre 95 et 100 % en masse.
PCT/JP2018/008128 2017-03-06 2018-03-02 Procédé de production de poly(sulfure d'arylène) Ceased WO2018164010A1 (fr)

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JP2017-041951 2017-03-06
JP2017041951 2017-03-06

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12018129B2 (en) 2021-09-08 2024-06-25 Ticona Llc Extraction technique for recovering an organic solvent from a polyarylene sulfide waste sludge
US12024596B2 (en) 2021-09-08 2024-07-02 Ticona Llc Anti-solvent technique for recovering an organic solvent from a polyarylene sulfide waste sludge

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JPH03121133A (ja) * 1989-08-24 1991-05-23 Bayer Ag ポリアリーレンスルフイド類の製造方法
JP2004352923A (ja) * 2003-05-30 2004-12-16 Dainippon Ink & Chem Inc ポリアリーレンスルフィド樹脂の製造方法
JP2005041922A (ja) * 2003-07-23 2005-02-17 Dainippon Ink & Chem Inc ポリアリーレンスルフィド樹脂の製造方法
JP2006016567A (ja) * 2004-07-05 2006-01-19 Dainippon Ink & Chem Inc ポリアリーレンスルフィド樹脂の製造方法
WO2008020553A1 (fr) * 2006-08-17 2008-02-21 Dic Corporation Procédé de production d'une résine de sulfure de polyarylène
JP2008081542A (ja) * 2006-09-26 2008-04-10 Dainippon Ink & Chem Inc ポリアリ−レンスルフィド樹脂の製造方法
JP2008248153A (ja) * 2007-03-30 2008-10-16 Dic Corp ポリアリ−レンスルフィド樹脂の製造方法
WO2011148929A1 (fr) * 2010-05-26 2011-12-01 Dic株式会社 Composition de résine pour article évidé moulé par soufflage, article évidé moulé par soufflage, et procédés de production
WO2016047631A1 (fr) * 2014-09-22 2016-03-31 株式会社クレハ Dispositif de production de sulfure de polyarylène pourvu de déflecteur et support de déflecteur
WO2016047632A1 (fr) * 2014-09-22 2016-03-31 株式会社クレハ Dispositif de production de polysulfure d'arylène équipé d'une conduite d'alimentation

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03121133A (ja) * 1989-08-24 1991-05-23 Bayer Ag ポリアリーレンスルフイド類の製造方法
JP2004352923A (ja) * 2003-05-30 2004-12-16 Dainippon Ink & Chem Inc ポリアリーレンスルフィド樹脂の製造方法
JP2005041922A (ja) * 2003-07-23 2005-02-17 Dainippon Ink & Chem Inc ポリアリーレンスルフィド樹脂の製造方法
JP2006016567A (ja) * 2004-07-05 2006-01-19 Dainippon Ink & Chem Inc ポリアリーレンスルフィド樹脂の製造方法
WO2008020553A1 (fr) * 2006-08-17 2008-02-21 Dic Corporation Procédé de production d'une résine de sulfure de polyarylène
JP2008081542A (ja) * 2006-09-26 2008-04-10 Dainippon Ink & Chem Inc ポリアリ−レンスルフィド樹脂の製造方法
JP2008248153A (ja) * 2007-03-30 2008-10-16 Dic Corp ポリアリ−レンスルフィド樹脂の製造方法
WO2011148929A1 (fr) * 2010-05-26 2011-12-01 Dic株式会社 Composition de résine pour article évidé moulé par soufflage, article évidé moulé par soufflage, et procédés de production
WO2016047631A1 (fr) * 2014-09-22 2016-03-31 株式会社クレハ Dispositif de production de sulfure de polyarylène pourvu de déflecteur et support de déflecteur
WO2016047632A1 (fr) * 2014-09-22 2016-03-31 株式会社クレハ Dispositif de production de polysulfure d'arylène équipé d'une conduite d'alimentation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12018129B2 (en) 2021-09-08 2024-06-25 Ticona Llc Extraction technique for recovering an organic solvent from a polyarylene sulfide waste sludge
US12024596B2 (en) 2021-09-08 2024-07-02 Ticona Llc Anti-solvent technique for recovering an organic solvent from a polyarylene sulfide waste sludge

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