JPH11169870A - Waste water treating device in production of polyarylene sulfide - Google Patents
Waste water treating device in production of polyarylene sulfideInfo
- Publication number
- JPH11169870A JPH11169870A JP9346306A JP34630697A JPH11169870A JP H11169870 A JPH11169870 A JP H11169870A JP 9346306 A JP9346306 A JP 9346306A JP 34630697 A JP34630697 A JP 34630697A JP H11169870 A JPH11169870 A JP H11169870A
- Authority
- JP
- Japan
- Prior art keywords
- polyarylene sulfide
- compound
- waste water
- wastewater
- production
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Removal Of Specific Substances (AREA)
- Treatment Of Water By Oxidation Or Reduction (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、ポリアリーレンス
ルフィド製造時の排水処理方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a wastewater treatment method for producing polyarylene sulfide.
【０００２】[0002]
【従来の技術】ポリアリーレンスルフィドの製造工程に
おいては、大量の水を用いてポリマー中の硫黄系未反応
モノマー（Ｎａ2Ｓ 等）や副生成する塩（ＮａＣｌ等）
を洗浄除去する方法が一般的である。2. Description of the Related Art In a process for producing a polyarylene sulfide, a large amount of water is used to unreact sulfur-containing monomers (such as Na 2 S) and by-product salts (such as NaCl) in a polymer.
Is generally removed by washing.
【０００３】[0003]
【発明が解決しようとする課題】しかし、上述した工程
より排出される排水は著しく着色しており、そのままで
は廃棄できず、さらに大量の水で希釈して廃棄されてい
る。本発明の課題は、ポリアリーレンスルフィド製造時
の着色排水を脱色させる簡便な排水処置方法を提供する
ことにある。However, the wastewater discharged from the above-mentioned process is markedly colored and cannot be disposed of as it is, but is further diluted with a large amount of water and disposed. An object of the present invention is to provide a simple wastewater treatment method for decolorizing colored wastewater during the production of polyarylene sulfide.
【０００４】[0004]
【課題を解決するための手段】発明者らは、上述した着
色排水の脱色方法について鋭意検討した結果、着色排水
に次亜塩素酸化合物を添加すると、容易に脱色されるこ
とを見い出し、本発明を完成するに至った。Means for Solving the Problems As a result of intensive studies on the above-mentioned method for decolorizing colored wastewater, the inventors have found that when a hypochlorous acid compound is added to colored wastewater, it is easily decolorized. Was completed.
【０００５】即ち、本発明は、 （１） 有機極性溶媒中でアルカリ金属硫化物とポリハ
ロ芳香族化合物とを反応させて得られたポリアリーレン
スルフィドを含有する重合体スラリーからポリアリーレ
ンスルフィドを単離精製する工程において排出される着
色排水に次亜塩素酸化合物を添加することを特徴とする
ポリアリーレンスルフィド製造時の排水処理方法、およ
びThat is, the present invention provides (1) isolation of polyarylene sulfide from a polymer slurry containing polyarylene sulfide obtained by reacting an alkali metal sulfide with a polyhalo aromatic compound in an organic polar solvent. Wastewater treatment method at the time of production of polyarylene sulfide, characterized by adding a hypochlorite compound to colored wastewater discharged in the step of refining, and
【０００６】（２） 前記排水のｐＨを７〜１０に調整
した後、次亜塩素酸化合物を添加する上記（１）記載の
排水処理方法を提供するものである。(2) The present invention provides the method for treating wastewater according to the above (1), wherein the pH of the wastewater is adjusted to 7 to 10 and then a hypochlorite compound is added.
【０００７】[0007]
【発明の実施の形態】以下本発明について詳細に説明す
る。ポリアリーレンスルフィドの重合方法については、
当該業者周知の方法であればかまわない。それらの例と
しては、 （１）アルカリ金属硫化物、特に結晶水を有する硫化ナ
トリウム（以下、含水硫化ナトリウムと略称する）を有
機極性溶媒中で加熱して該含水硫化ナトリウムが含有す
る水を除去し、そこへジクロルベンゼンを加えて加熱重
合させる方法（米国特許第３，３５４，１２９号公報
等）、DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. Regarding the polymerization method of polyarylene sulfide,
Any method known to those skilled in the art may be used. Examples thereof include: (1) alkali metal sulfide, particularly sodium sulfide having water of crystallization (hereinafter abbreviated as sodium sulfide) is heated in an organic polar solvent to remove water contained in the sodium sulfide. A method of adding dichlorobenzene thereto and subjecting to heat polymerization (US Pat. No. 3,354,129),
【０００８】（２）有機極性溶媒、含水アルカリ金属硫
化物、ジハロ芳香族化合物等の原料を一括して仕込み、
反応系を昇温しながら脱水し、更に脱水を継続しながら
重合反応させる方法（特開昭５９−１０５０２７号公
報）、(2) Raw materials such as an organic polar solvent, a hydrated alkali metal sulfide, and a dihaloaromatic compound are charged together,
A method in which the reaction system is dehydrated while raising the temperature, and further subjected to a polymerization reaction while continuing the dehydration (JP-A-59-105027);
【０００９】（３）ジハロ芳香族化合物（芳香族トリハ
ロ芳香族化合物またはテトラハロ芳香族化合物を少量含
んでいても良い）及び有機極性溶媒の混合物に、１５０
℃以上で含水アルカリ金属硫化物を水が反応混合物から
除去され得る速度で導入し、重合反応を行う方法（特開
昭６０−１０４１３０号公報）、等が挙げられる。(3) A mixture of a dihalo aromatic compound (which may contain a small amount of an aromatic trihalo aromatic compound or a tetrahalo aromatic compound) and an organic polar solvent is mixed with
A method in which a hydrated alkali metal sulfide is introduced at a temperature at which the water can be removed from the reaction mixture at a temperature of not less than ° C and a polymerization reaction is carried out (JP-A-60-104130).
【００１０】この様にして得られた重合体スラリーから
のポリアリーレンスルフィドの単離精製としては、例え
ば （１）重合終了時にまず重合体スラリーをそのまま、あ
るいは酸または塩基を加えた後、減圧下または常圧下で
加熱して溶媒だけを留去し、ついで缶残固形物を水、ア
セトン、メチルエチルケトン、アルコール類などの溶媒
で洗浄、あるいはさらに中和、洗浄する方法、[0010] The isolation and purification of polyarylene sulfide from the polymer slurry obtained as described above include, for example, (1) first, upon completion of polymerization, the polymer slurry as it is, or after adding an acid or a base, Or heating under normal pressure to distill off only the solvent, and then washing the solid residue with water, acetone, methyl ethyl ketone, a solvent such as alcohol, or further neutralizing and washing,
【００１１】（２）重合終了後に重合体スラリーに水、
アセトン、メチルエチルケトン、アルコール類、エーテ
ル類、ハロゲン化炭化水素、芳香族炭化水素、脂肪族炭
化水素などの溶媒（使用した重合溶媒に可溶であり、か
つ少なくとも生成した重合体に対しては貧溶媒であるも
の）を沈降剤として添加し、重合体を沈降させ、それを
濾別、洗浄する方法（これらの場合の「洗浄」は、抽出
の形で実施することができる）、(2) After the polymerization is completed, water is added to the polymer slurry.
Solvents such as acetone, methyl ethyl ketone, alcohols, ethers, halogenated hydrocarbons, aromatic hydrocarbons, and aliphatic hydrocarbons (soluble in the polymerization solvent used and a poor solvent for at least the produced polymer. Is added as a precipitant to precipitate the polymer, which is filtered off and washed ("washing" in these cases can be carried out in the form of extraction),
【００１２】（３）重合体スラリーをそのまま、あるい
は重合体スラリーに反応溶媒（もしくはそれと同等の低
分子重合体の溶解度を有する溶媒）、または反応溶媒及
び酸あるいはアルカリを加えて撹拌した後、ろ別して低
分子量重合体を除き、水、アセトン、メチルエチルケト
ン、アルコール類などの溶媒で洗浄、あるいはさらに中
和、洗浄する方法、等が挙げられる。(3) The polymer slurry is stirred as it is, or after adding a reaction solvent (or a solvent having a low molecular weight polymer equivalent thereto) or a reaction solvent and an acid or alkali to the polymer slurry and stirring, Separately, a method of washing with a solvent such as water, acetone, methyl ethyl ketone, and alcohols, or further neutralizing and washing, excluding the low-molecular-weight polymer, and the like can be mentioned.
【００１３】上述した単離精製工程からの排出液中に、
重合溶媒や洗浄溶媒としての有機化合物を含有している
場合は、蒸留により分離され、溶媒及び有機化合物は回
収される。一方、無機塩等を含有した水溶液は排水とし
て処理される。この排水中には、未反応モノマーである
アルカリ金属硫化物やアルカリ金属硫化物が重合中に変
化したポリスルフィド等が残存しており、これらが原因
と推定されるかなりの着色が見られる。この着色排水に
次亜塩素酸化合物を添加することによって、着色原因と
推定される物質がチオ硫酸ナトリウムへ酸化され、退色
するものと推定している。上述した着色現象は、単離精
製工程で酸等を使用すると着色が特に激しく、この様な
場合においても次亜塩素酸化合物の添加による退色効果
は顕著である。In the effluent from the above-mentioned isolation and purification step,
When the composition contains an organic compound as a polymerization solvent or a washing solvent, it is separated by distillation, and the solvent and the organic compound are recovered. On the other hand, an aqueous solution containing an inorganic salt or the like is treated as wastewater. In the wastewater, unreacted monomers such as alkali metal sulfides and polysulfides in which alkali metal sulfides have changed during polymerization remain, and considerable coloring is presumed to be caused by these. It is presumed that by adding a hypochlorous acid compound to the colored wastewater, a substance presumed to cause coloring is oxidized to sodium thiosulfate and discolored. The coloring phenomenon described above is particularly severe when an acid or the like is used in the isolation and purification step, and even in such a case, the fading effect due to the addition of the hypochlorous acid compound is remarkable.
【００１４】本発明の廃水処理方法で用いる次亜塩素酸
化合物としては、次亜塩素酸ナトリウム及び次亜塩素酸
カリウムで挙げられるが、これらはそれぞれ単独で用い
てもよいし、２種を混合して用いてもよい。この時使用
する次亜塩素酸化合物の形状は固形、水溶液のいずれで
も良い。入手のしやすさや次亜塩素酸化合物の安定性の
面から次亜塩素酸ナトリウム水溶液を用いるのが好まし
い。その添加量は、着色排水として排出可能な着色度に
なる量であればかまわない。一般に添加濃度としては、
有効塩素１２重量％次亜塩素酸ナトリウム水溶液を前記
着色排水に１〜３０重量％になるように添加する。The hypochlorite compound used in the wastewater treatment method of the present invention includes sodium hypochlorite and potassium hypochlorite, each of which may be used alone or a mixture of two. You may use it. The hypochlorite compound used at this time may be in the form of a solid or an aqueous solution. It is preferable to use an aqueous solution of sodium hypochlorite from the viewpoint of availability and stability of the hypochlorous acid compound. The amount of addition may be any amount as long as the coloring degree can be discharged as colored wastewater. Generally, the addition concentration is
An aqueous solution of 12% by weight of available chlorine and sodium hypochlorite is added to the colored wastewater so as to be 1 to 30% by weight.
【００１５】次に次亜塩素酸化合物添加による脱色効果
は、着色排水のｐＨが低いほど添加量が少なくなる。一
般に上述した工程で排出される排水は、強アルカリ性
（ｐＨ１０〜１４）を示しており、そのｐＨで次亜塩素
酸化合物を添加してもよいが、塩酸や硫酸等でｐＨを７
〜１０に調整した後、添加した方が、次亜塩素酸化合物
の添加量が少なくて済み、経済的にも好適である。しか
し、排水のｐＨが７未満であると次亜塩素酸化合物の添
加によって塩素ガスが発生するので好ましくない。Next, the decolorizing effect by the addition of the hypochlorous acid compound decreases as the pH of the colored wastewater decreases. Generally, the wastewater discharged in the above-mentioned step shows strong alkalinity (pH 10 to 14), and a hypochlorite compound may be added at that pH, but the pH is reduced to 7 with hydrochloric acid or sulfuric acid.
After adjusting to 10 to 10, it is preferable to add the amount of the hypochlorous acid compound, which is economically preferable. However, if the pH of the waste water is less than 7, chlorine gas is generated by the addition of the hypochlorite compound, which is not preferable.
【００１６】[0016]
【実施例】以下に本発明を実施例により具体的に説明す
るが、本発明はこれら実施例にのみ限定されるものでは
ない。EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples.
【００１７】参考例１ ４リットルのオートクレーブにＮ−メチルピロリドン
（ＮＭＰ）１２６０ｇ、結晶水含有水硫化ナトリウム
（ＮａＳＨ・ｘＨ2Ｏ） ３０９．３ｇ（４．００ｍｏ
ｌ）を仕込、アルカリトラップを装備し、窒素雰囲気
下、開放系において昇温を始め、１００℃であらかじめ
水酸化ナトリウム １６４．８ｇ（４．１２ ｍｏｌ）を
水１７８．５ｇに溶かしておいた水溶液を加え、さらに
昇温を続けた。１４５℃付近で水−ＮＭＰ−Ｈ2Ｓ 混合
物が留出を始め、２００℃まで留出させた。このとき留
出した水は２３４．１ｇ、ＮＭＰは６１．２ｇ、Ｈ2Ｓ
は６９．６５ｍｍｏｌであった。ついでこの系を密閉し
て２２０℃まで昇温してｐ−ジクロロベンゼン５７７．
７ｇ（３．９３ ｍｏｌ）をＮＭＰ３５９．５ｇに溶か
した溶液を圧入添加した。そして窒素雰囲気、加圧下で
２２０℃で４時間、その後２６０℃に昇温して１時間反
応し反応終了後冷却して重合体スラリーを得た。Reference Example 1 In a 4-liter autoclave, 1260 g of N-methylpyrrolidone (NMP) and 309.3 g of sodium hydrosulfide (NaSH.xH 2 O) containing water of crystallization (4.00 mo)
1), equipped with an alkali trap, and started to raise the temperature in an open system under a nitrogen atmosphere. An aqueous solution in which 164.8 g (4.12 mol) of sodium hydroxide was previously dissolved in 178.5 g of water at 100 ° C. And the temperature was further increased. The water-NMP-H 2 S mixture started to distill at around 145 ° C., and was distilled to 200 ° C. At this time, the distilled water was 234.1 g, NMP was 61.2 g, H 2 S
Was 69.65 mmol. Then, the system was sealed and the temperature was raised to 220 ° C. to obtain p-dichlorobenzene.
A solution obtained by dissolving 7 g (3.93 mol) in 359.5 g of NMP was added under pressure. Then, the mixture was heated at 220 ° C. for 4 hours under a nitrogen atmosphere under pressure, and then heated to 260 ° C. and reacted for 1 hour. After the completion of the reaction, the mixture was cooled to obtain a polymer slurry.
【００１８】実施例１ 参考例１で得られた重合体スラリー３００ｇを減圧下加
熱し、ＮＭＰを留去して得られた缶残固形物に水２５０
ｇを添加して攪拌し濾別した後、さらに水２５０ｇで洗
浄した。このとき排出したろ液は、ｐＨが１３で黄褐色
（ガードナーカラー値１０）に着色していた。そこに有
効塩素１２重量％次亜塩素酸ナトリウム水溶液を、該水
溶液濃度が１５重量％となるように添加したところ、ろ
液は薄い黄色（ガードナーカラー値４）となった。以
下、次亜塩素酸ナトリウム水溶液は、有効塩素１２重量
％のものを使用した。Example 1 300 g of the polymer slurry obtained in Reference Example 1 was heated under reduced pressure, and NMP was distilled off.
After adding g, stirring and filtering, the mixture was further washed with 250 g of water. The filtrate discharged at this time had a pH of 13 and was colored yellow-brown (Gardner color value of 10). When an aqueous solution of 12% by weight of available chlorine and sodium hypochlorite was added thereto so that the concentration of the aqueous solution became 15% by weight, the filtrate turned pale yellow (Gardner color value 4). Hereinafter, the aqueous solution of sodium hypochlorite used was 12% by weight of available chlorine.
【００１９】実施例２ 実施例１で得られたろ液に０．１ｍｏｌ／ｄｍ３の塩酸
を添加してｐＨを９に調整した後、有効塩素１２重量％
次亜塩素酸ナトリウム水溶液をガードナーカラー値４と
なるまで添加したところ、添加後のろ液の次亜塩素酸ナ
トリウム水溶液濃度は５重量％であった。Example 2 After the pH of the filtrate obtained in Example 1 was adjusted to 9 by adding 0.1 mol / dm3 hydrochloric acid, available chlorine was 12% by weight.
When the aqueous sodium hypochlorite solution was added until the Gardner color value reached 4, the concentration of the aqueous sodium hypochlorite solution in the filtrate after addition was 5% by weight.
【００２０】実施例３ 参考例１で得られた重合体スラリー３００ｇを１Ｋｇの
水中に投入し、水洗、濾過を行った。この時の排出ろ液
を減圧蒸留し、ＮＭＰを回収した。蒸留後の釜残固形物
に水５００ｇを添加したところ、この水溶液はｐＨが１
３で濃い黄色（ガードナーカラー値８）に着色してい
た。この水溶液に有効塩素１２重量％次亜塩素酸ナトリ
ウム水溶液を、該水溶液濃度が３重量％となるように添
加したところ、薄い黄色（ガードナーカラー値４）とな
った。Example 3 300 g of the polymer slurry obtained in Reference Example 1 was put into 1 kg of water, washed with water and filtered. The filtrate discharged at this time was distilled under reduced pressure to recover NMP. When 500 g of water was added to the still residue after distillation, the pH of this aqueous solution became 1
3 was colored deep yellow (Gardner color value 8). When an aqueous solution of 12% by weight of available chlorine and sodium hypochlorite was added to the aqueous solution so that the concentration of the aqueous solution became 3% by weight, the solution turned pale yellow (Gardner color value 4).
【００２１】実施例４ 重合体スラリー３００ｇに硫酸１．００ｇを添加して１
２０℃でろ過を行ない、ろ残とＮＭＰろ液を得た。ろ残
は、水２５０ｇ中に投入し、攪拌後、ろ別した後、さら
に水２５０ｇで洗浄してろ残とろ液を得た。ＮＭＰろ液
（酸性）とろ液（アルカリ性）を混合したところ、沈殿
物（低分子量重合体）があった。この混合液（ｐＨ４）
を水酸化ナトリウムでアルカリ性にして、次いでこのろ
液を蒸留してＮＭＰを留去した。蒸発乾固した残渣に水
を加えて不溶分をろ過除去した。この様にして得られた
ろ液（ｐＨ１１）は、濃褐色（ガードナーカラー値１
８）をしていた。このろ液に有効塩素１２重量％次亜塩
素酸ナトリウム水溶液を、該水溶液濃度が１５重量％と
なるように添加したところ、薄い黄色（ガードナーカラ
ー値４）となった。Example 4 1.00 g of sulfuric acid was added to 300 g of a polymer slurry to obtain 1
Filtration was performed at 20 ° C. to obtain a residue and an NMP filtrate. The residue was put into 250 g of water, stirred, filtered, and then washed with 250 g of water to obtain a residue and a filtrate. When the NMP filtrate (acidic) and the filtrate (alkaline) were mixed, a precipitate (low molecular weight polymer) was found. This mixture (pH 4)
Was made alkaline with sodium hydroxide and then the filtrate was distilled to remove NMP. Water was added to the residue evaporated to dryness, and the insolubles were removed by filtration. The filtrate (pH 11) thus obtained is dark brown (Gardner color value 1).
8) I was doing. When an aqueous solution of 12% by weight of available chlorine and sodium hypochlorite was added to the filtrate so that the concentration of the aqueous solution became 15% by weight, the solution turned pale yellow (Gardner color value 4).
【００２２】実施例５ 実施例３で得られたろ液（ｐＨ１３）に０．１ｍｏｌ／
ｄｍ３の塩酸を添加してｐＨを９に調整した後、有効塩
素１２重量％次亜塩素酸ナトリウム水溶液をガードナー
カラー値４となるまで添加したところ、添加後のろ液の
次亜塩素酸ナトリウム水溶液濃度は８重量％であった。Example 5 The filtrate (pH 13) obtained in Example 3 was added in an amount of 0.1 mol /
After adding dm3 hydrochloric acid to adjust the pH to 9, an aqueous solution of 12% by weight of available chlorine and sodium hypochlorite was added until the Gardner color value reached 4, and the filtrate after the addition was treated with an aqueous solution of sodium hypochlorite. The concentration was 8% by weight.
【００２３】[0023]
【発明の効果】本発明の排水処理方法によれば、着色排
水の脱色が容易である。According to the wastewater treatment method of the present invention, it is easy to decolorize colored wastewater.
Claims (2)
ポリハロ芳香族化合物とを反応させて得られたポリアリ
ーレンスルフィドを含有する重合体スラリーからポリア
リーレンスルフィドを単離精製する工程において排出さ
れる着色排水に次亜塩素酸化合物を添加することを特徴
とするポリアリーレンスルフィド製造時の排水処理方
法。1. A process for isolating and purifying polyarylene sulfide from a polymer slurry containing polyarylene sulfide obtained by reacting an alkali metal sulfide with a polyhaloaromatic compound in an organic polar solvent. A wastewater treatment method for producing polyarylene sulfide, comprising adding a hypochlorite compound to colored wastewater.
後、次亜塩素酸化合物を添加する請求項１記載の排水処
理方法。2. The wastewater treatment method according to claim 1, wherein a hypochlorite compound is added after adjusting the pH of the wastewater to 7 to 10.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9346306A JPH11169870A (en) | 1997-12-16 | 1997-12-16 | Waste water treating device in production of polyarylene sulfide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9346306A JPH11169870A (en) | 1997-12-16 | 1997-12-16 | Waste water treating device in production of polyarylene sulfide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH11169870A true JPH11169870A (en) | 1999-06-29 |
Family
ID=18382516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9346306A Pending JPH11169870A (en) | 1997-12-16 | 1997-12-16 | Waste water treating device in production of polyarylene sulfide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH11169870A (en) |
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| JP2005054181A (en) * | 2003-07-24 | 2005-03-03 | Toray Ind Inc | Method for producing alkali metal sulfide having low water content, polyarylene sulfide produced by using this and method for producing the same |
| WO2012070335A1 (en) * | 2010-11-26 | 2012-05-31 | 株式会社クレハ | Method for producing polyarylene sulfide, and polyarylene sulfide |
| WO2016104381A1 (en) * | 2014-12-24 | 2016-06-30 | 株式会社クレハ | Method for treating wastewater containing sulfur-containing compounds produced in step for producing polyarylene sulfide, and method for producing polyarylene sulfide |
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| US9617387B2 (en) | 2013-09-25 | 2017-04-11 | Ticona Llc | Scrubbing process for polyarylene sulfide formation |
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| US9815942B2 (en) | 2015-03-25 | 2017-11-14 | Ticona Llc | Technique for forming a high melt viscosity polyarylene sulfide |
| US9988494B2 (en) | 2015-02-19 | 2018-06-05 | Ticona Llc | Method for forming a high molecular weight polyarylene sulfide |
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-
1997
- 1997-12-16 JP JP9346306A patent/JPH11169870A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005054181A (en) * | 2003-07-24 | 2005-03-03 | Toray Ind Inc | Method for producing alkali metal sulfide having low water content, polyarylene sulfide produced by using this and method for producing the same |
| WO2012070335A1 (en) * | 2010-11-26 | 2012-05-31 | 株式会社クレハ | Method for producing polyarylene sulfide, and polyarylene sulfide |
| US9096723B2 (en) | 2010-11-26 | 2015-08-04 | Kureha Corporation | Production process of poly(arylene sulfide) and poly(arylene sulfide) |
| JP5781086B2 (en) * | 2010-11-26 | 2015-09-16 | 株式会社クレハ | Method for producing polyarylene sulfide and polyarylene sulfide |
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| US9938379B2 (en) | 2013-09-25 | 2018-04-10 | Ticona Llc | Salt byproduct separation during formation of polyarylene sulfide |
| US9403948B2 (en) | 2013-09-25 | 2016-08-02 | Ticona Llc | Salt byproduct separation during formation of polyarylene sulfide |
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| US9388283B2 (en) | 2013-09-25 | 2016-07-12 | Ticona Llc | Method of polyarylene sulfide crystallization |
| US9868824B2 (en) | 2013-09-25 | 2018-01-16 | Ticona Llc | Method of polyarylene sulfide crystallization |
| WO2016104381A1 (en) * | 2014-12-24 | 2016-06-30 | 株式会社クレハ | Method for treating wastewater containing sulfur-containing compounds produced in step for producing polyarylene sulfide, and method for producing polyarylene sulfide |
| US9809681B2 (en) | 2015-02-19 | 2017-11-07 | Ticona Llc | Method for forming a low viscosity polyarylene sulfide |
| US9988494B2 (en) | 2015-02-19 | 2018-06-05 | Ticona Llc | Method for forming a high molecular weight polyarylene sulfide |
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| US11319441B2 (en) | 2019-12-20 | 2022-05-03 | Ticona Llc | Method for forming a polyarylene sulfide |
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