JPS60104126A - Aromatic polythioether ketone and its preparation - Google Patents
Aromatic polythioether ketone and its preparationInfo
- Publication number
- JPS60104126A JPS60104126A JP21152983A JP21152983A JPS60104126A JP S60104126 A JPS60104126 A JP S60104126A JP 21152983 A JP21152983 A JP 21152983A JP 21152983 A JP21152983 A JP 21152983A JP S60104126 A JPS60104126 A JP S60104126A
- Authority
- JP
- Japan
- Prior art keywords
- aromatic
- formula
- phosgene
- compound
- bis
- 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.)
- Granted
Links
Abstract
Description
【発明の詳細な説明】
本発明は芳香族ポリチオエーテルケトンおよびその製造
方法に関する。芳香族ポリチオエーテルけｌＪｒ規なポ
リマーである。我々は先に芳香族ポリエーテルケトンを
芳香族エーテル化合物とホスゲンとの反応により製造す
る方法を見出したが、さらに本発明基等は芳香族チオエ
ーテル化合物とホスゲンとの反応を鋭篇検削を行なった
結果、新規化合物である芳香族ポリチオエーテルケトン
を著しく安価でしかも温和な条件下で製造する方法を見
出した。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an aromatic polythioetherketone and a method for producing the same. It is a polymer similar to aromatic polythioether. We have previously discovered a method for producing aromatic polyetherketones by reacting aromatic ether compounds with phosgene, but the present invention has further investigated the reaction between aromatic thioether compounds and phosgene. As a result, we discovered a method for producing a new compound, aromatic polythioetherketone, at a significantly low cost and under mild conditions.
また本発明によシ製造さｉ″した芳香族ポリチオエーテ
ルケトンは耐熱性１機械的性質、’ＦｉＬ気的性質１寸
法安定性に優れ、吸水率が低く物性的に非常に良好なポ
リマーである。In addition, the aromatic polythioetherketone produced according to the present invention is a polymer with excellent heat resistance, mechanical properties, dimensional stability, low water absorption, and very good physical properties. .
すなわち本発明の要旨は下記の一般式ＣＤ（〔ｌ〕式中
Ｒ１〜Ｒ１２は水素原子、ノ・ロゲン原子。That is, the gist of the present invention is the following general formula CD ([l] in which R1 to R12 are hydrogen atoms and hydrogen atoms.
炭化水素基またはアルコキシ基を示１−．ｎｔ；Ｊθ〜
！の整数である）１・゛いトシ端羨ψイを乞有し、ｆ）
、ワ族チオエーテルケトンおよびその製−６シ法に存す
る。1-. Indicates a hydrocarbon group or an alkoxy group. nt; Jθ~
! (is an integer of ) 1.
, Wa group thioetherketones and their production method-6.
本発明をさらに詳細に説明するに、このような芳香族ポ
リチオエーテルケトンは一般式〔１１〕（〔■〕式中、
Ｒ’−ｗＲ”は水素原子、ハロゲン原子、炭化水素基ま
たはアルコキシ基を示し、ｎはθ〜５の整数である）
で表わされる芳香族チオエーテル類とホスゲントラルイ
ス酸の存在下で溶媒として非プロトン性有機溶剤を用い
て反応させることによシ製造される。To explain the present invention in more detail, such an aromatic polythioetherketone has the general formula [11] ([■] in the formula,
R'-wR'' represents a hydrogen atom, a halogen atom, a hydrocarbon group, or an alkoxy group, and n is an integer of θ to 5. It is produced by reaction using a protic organic solvent.
本発明をさらに詳細に説明するに、本発明に用いられる
前爪一般式〔旧で表わされる芳香族チオエーテル類とし
てはジフェニルサルファイド、ビス（３−クロロフェニ
ル）サルファイド、ビス（３−メチルフェニル）サルフ
ァイド、ビス（３，！ｒ−ジメチルフェニル）？ル７ア
イド、（３−メトキシフェニル）サルファイド、ビス（
３゜５−ジクロロフェニル）サルファイド、ビス（３−
ブロモフェニル）サルファイド、ビス（３−フルオロン
エニル）サルファイド、ビス（３，ｊジンルオロフェニ
ル）サルファイド、ビス（３−エチルフェニル）サルフ
ァイド、／、クービス（フェニルメルカ７”ト）ベンゼ
ン、ビス（クーフェニルメルカプトフェニル）サルファ
イド、／、３−ビス（フェニルメルカプト）ベンゼン。To explain the present invention in more detail, the aromatic thioethers represented by the general formula [formula] used in the present invention include diphenyl sulfide, bis(3-chlorophenyl) sulfide, bis(3-methylphenyl) sulfide, Bis(3,!r-dimethylphenyl)? 7-eyed, (3-methoxyphenyl) sulfide, bis(
3゜5-dichlorophenyl) sulfide, bis(3-
Bromophenyl) sulfide, bis(3-fluoronenyl) sulfide, bis(3,j-zinefluorophenyl) sulfide, bis(3-ethylphenyl) sulfide, /, coubis(phenylmerca 7”)benzene, bis( cuphenylmercaptophenyl) sulfide, /, 3-bis(phenylmercapto)benzene.
り、り′−ビス（ｙ−フェニルメルカプトフェニル）ジ
フェニルサルファイド、１ （＜１−フェニルメルカプ
トフェニル） ｙｔ−フェニルメルカプトジフェニルサ
ルファイド、／、Ｚ−ビス（３−メチルフェニルメルカ
プト）ベンゼン％ ／、クービス（３−クロロフェニル
メルカプト）ベンゼン、／、４ｔ−ビス（３−メトキシ
フェニルメルカプト）ベンゼン、／、３−ビス（ｉ、ｔ
−シメヂルフェニルメルカブト）ベンゼンｓ ／、３−
ビス（３−ブロモフェニルメルカプト）ベンゼン、／、
クービス（３，ｔ−シンルオロフェニルメルカブト）ベ
ンゼンなどが羊げられるが一般式（ＩＩ）で示さノ］、
るものけいずれ屯使用可能であり、とｉｔらに限定され
るものではない。これらは単独もしくは混合して使用し
てもよ（、／、＠又は／、３構造のものが好まし込。ま
たこれらの中でコストの点かラシフェニルザルファイド
、／、￥−ジフェニルメルカプトベンゼンを用いること
が最も好まし。Ri, Ri'-bis(y-phenylmercaptophenyl) diphenyl sulfide, 1 (<1-phenylmercaptophenyl) yt-phenylmercapto diphenyl sulfide, /, Z-bis(3-methylphenylmercapto)benzene% /, Kubis ( 3-chlorophenylmercapto)benzene, /, 4t-bis(3-methoxyphenylmercapto)benzene, /, 3-bis(i,t
-Shimedylphenylmerkabuto)benzene s /, 3-
Bis(3-bromophenylmercapto)benzene, /
Kubis(3,t-synfluorophenylmercabuto)benzene and the like are represented by the general formula (II)],
It can be used in any way, and is not limited to it. These may be used alone or in combination (, /, @ or /, 3-structures are preferred. Among these, from the viewpoint of cost, raciphenyl sulfide, /, \-diphenylmercaptobenzene It is most preferable to use
い。stomach.
本発明では前記一般式〔■〕で表わされる芳香族チオエ
ーテル類にホスゲンを反応させるが、ホスゲンの使用量
は該芳香族チオエーテル類１モルに対して通常ｏ３モル
以上、好ましくけ７モル以上の割合で使用される。In the present invention, the aromatic thioether represented by the general formula [■] is reacted with phosgene, and the amount of phosgene used is usually at least 3 mol, preferably at least 7 mol, per 1 mol of the aromatic thioether. used in
本発明で用いられる非プロトン性有機溶媒としては％塩
化メチレン、塩化エチレン％ ／、／、、２゜−一テト
ラクロルエタン、クロロホルム、四塩化炭素、ニトロベ
ンゼン、ニトロメタン、二硫化炭素、トルエン、キシレ
ン、ベンゼン、テトラリン、デカリン、ヘキサン、エチ
ルエーテル、ジブチルエーテル、ヘプタン、ペンタン、
オルトジク目ルベンゼンなどが用いられるが必ずしもこ
れ等に限定されるものではない。The aprotic organic solvents used in the present invention include % methylene chloride, ethylene chloride% /, /, 2°-1 tetrachloroethane, chloroform, carbon tetrachloride, nitrobenzene, nitromethane, carbon disulfide, toluene, xylene, Benzene, tetralin, decalin, hexane, ethyl ether, dibutyl ether, heptane, pentane,
Rubenzene of the order Orthodactyla and the like are used, but are not necessarily limited thereto.
溶媒の使用量は一般式ＣＩ）で表わされる芳香族エーテ
ルの／〜１００倍侶（重邦、比）好オし７〈け！〜１０
θ倍量（重量比）である。The amount of solvent to be used should be ~100 times that of the aromatic ether represented by the general formula CI). ~10
θ times the amount (weight ratio).
本発明に用いられるルイス酸としては五塩化アルミニウ
ム、三臭化アルミニウム・、三弗化側１素、剋１化第二
鉄、堪化第二錫、ムｉＡ化ｔ（４−錫、四塩化チタン、
三填化硼素、五縞化アンチモン。The Lewis acids used in the present invention include aluminum pentachloride, aluminum tribromide, trifluoride, ferric chloride, ferric chloride, aluminum trichloride (4-tin, tetrachloride), Titanium,
Tri-boron compound, penta-stripe antimony compound.
塩化亜鉛、三基〜・イヒガリウム、大地化アンチモン。Zinc chloride, three groups - Ihigallium, antimony chloride.
三塩化リン、五塩化リン、五地化アルル、三弗化硼素エ
チルエーテル錯化物、五塩化ニメブ、六塩化タングステ
ンカとが挙けら）しるが必ずしもとれらに限定されるも
のではない。こノ１らの中で三塩化アルミニウム、四塩
化スズがコストの点で最も好ましい。こ九ものルイス酸
の使用佃は酸ジハシイドに対して重量比で０．３〜！、
θ好ましくは０．９〜２．０である。Examples include, but are not limited to, phosphorus trichloride, phosphorus pentachloride, allyl pentachloride, boron trifluoride ethyl ether complex, nimeb pentachloride, and tungsten hexachloride. Among these, aluminum trichloride and tin tetrachloride are most preferred in terms of cost. The weight ratio of these nine Lewis acids to the acid dihoxide is 0.3~! ,
θ is preferably 0.9 to 2.0.
また本発明は一般式〔■〕で表わさｆするチオエーテル
類とホスゲンとを含む溶液にルイス酸を添加してもよい
し、溶媒とルイ酸の存在下でホスゲンと一般式〔■〕で
表わされるチオエーテル類を添加してもよい。本発明方
法においては反応温度は特に制限はなしが−１０℃以上
（通常７００℃以下）という〃１度でも高重合物が得ら
れる。また加圧下で反応を行につてもよい。Further, in the present invention, a Lewis acid may be added to a solution containing a thioether represented by the general formula [■] and phosgene, or a Lewis acid may be added to a solution containing phosgene and a thioether represented by the general formula [■]. Thioethers may also be added. In the method of the present invention, the reaction temperature is not particularly limited, but a high polymer can be obtained even at 1 degree above -10°C (usually below 700°C). Alternatively, the reaction may be carried out under pressure.
本発明で得た芳香族ポリチオエーテルケトンは多くの利
点を有している。すなわち引張り強度％曲げ強度、引張
、＋）弾性率１曲げ弾性率などの機械的性質、耐熱４．
４：、熱分解開始汎・１度、電気的性質、寸法安定性に
優ね、吸湿、吸水率が低０
以下１本発明を実施例によりさらに詳細に駅間する。The aromatic polythioetherketone obtained according to the present invention has many advantages. That is, mechanical properties such as tensile strength, % bending strength, tensile strength, +) elastic modulus, 1 bending elastic modulus, and heat resistance 4.
4: Thermal decomposition starts at 1 degree, has excellent electrical properties and dimensional stability, and has low moisture absorption and water absorption rate of 0.1 Below, the present invention will be explained in more detail with reference to Examples.
実施例／
ホスゲン、２２．３ ｆとジフェニルサルファイド７、
ざ２２の二硫化炭素溶液／！Ｑｍｅ Ｋ ｍ化アルミニ
ウム／り、に２を加える。この際水冷によシ反応７ｆＡ
合物の温度を１℃以下に保つ。環化アルミニウム添加終
了後、水冷撹拌丁Ｚ時間、さらに室温で／／＃間反応さ
せる。反応終了後１反応混合物をメタノールｊ′０θｆ
ｆ１．ｌ’中に注ぐとうす黄緑色粉末状重合物が得られ
る。重合物は戸別後メタノール５ｏｏ７．２％塩酸水溶
液」θ０−でλ回、さらに脱塩水６００ ｍｌで２回洗
浄し。Example / Phosgene, 22.3 f and diphenyl sulfide 7,
Carbon disulfide solution of 22/! Add 2 to Qme K m-aluminum chloride/li. At this time, the reaction is 7fA due to water cooling.
Keep the temperature of the mixture below 1°C. After the addition of aluminum cyclide is completed, the reaction is carried out under water-cooling and stirring for an additional hour at room temperature. After the reaction is completed, the reaction mixture is mixed with methanol j′0θf
f1. When poured into L', a light yellow-green powdery polymer is obtained. After the polymerized product was separated, it was washed λ times with 50 methanol and 7.2% aqueous hydrochloric acid solution, and then twice with 600 ml of demineralized water.
／オθ℃で一昼夜宵空乾燥する。収率は３θチであった
。Dry in the air at θ°C overnight. The yield was 3θ.
得られたポリマーの赤外線吸収スペクトル（ＫＢｒディ
スク）ｉｊ： ／ｌ！ｊ’ｉｍ−’、を２芳すがり°ト
ンの吸収がみられた。またポリマーの粘度（＃硫酸中３
θ℃、濃度＝／、θｔ／ｄｉで測定）はηｉ］１ｈ＝θ
、／／ｄｌ／ｆであシ１元素分析の結果は太′６１１」
値：０，７コ、０９％：Ｈ２Ｓ、６９％、６１″算値（
０，、Ｈ，Ｏ８） ： ０．７’ 、３．ｊごチ；Ｈ１
３，と０％てあった。Infrared absorption spectrum (KBr disk) of the obtained polymer ij: /l! Absorption of 2°tons was observed in the case of j'im-'. Also, the viscosity of the polymer (#3 in sulfuric acid)
θ℃, concentration=/, θt/di) is ηi]1h=θ
, //dl/f and the result of 1 elemental analysis is '611'.
Value: 0.7 pieces, 09%: H2S, 69%, 61″ calculated value (
0,, H, O8): 0.7', 3. j Gochi;H1
It was 0%.
出 願 人 三菱化成工業株式会社 ほか／名Sender: Mitsubishi Chemical Industries, Ltd. Others/names
Claims (2)
、炭化水素基またはアルコキシ基を示し、℃で測定しだ
ηｉｎｈ がＯ３θｓ ｄｔ ／ ｙ 以上である芳香
族チオエーテルケトン(1) General formula (I) ([I] In the formula, R1 to Rj2 represent a hydrogen atom, a hydrogen atom, a hydrocarbon group, or an alkoxy group, and an aromatic compound whose ηinh is O3θs dt / y or more when measured at °C group thioether ketones
子、炭化水素基またはアルコキシ基を示し。 ｎはθ〜夕の整数である） で表わされる芳香族チオエーテル類とホスゲンをルイス
酸の存在下で、溶媒として非プロトン性有機溶妓を用い
て反応させることを特徴とする芳香族ポリチオエーテル
ケトンの製造方法(2) Aromatic thioether represented by the general formula (II) (in the [I] formula, R'% R+a represents a hydrogen atom, a halogen atom, a hydrocarbon group, or an alkoxy group; n is an integer from θ to 0) and phosgene in the presence of a Lewis acid using an aprotic organic solvent as a solvent.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21152983A JPS60104126A (en) | 1983-11-10 | 1983-11-10 | Aromatic polythioether ketone and its preparation |
| EP84111574A EP0135938B1 (en) | 1983-09-29 | 1984-09-27 | Process for producing aromatic polyether ketones and polythioether ketones |
| DE8484111574T DE3472262D1 (en) | 1983-09-29 | 1984-09-27 | Process for producing aromatic polyether ketones and polythioether ketones |
| US06/656,325 US4661581A (en) | 1983-09-29 | 1984-10-01 | Process for producing aromatic polyether ketones and polythioether ketones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21152983A JPS60104126A (en) | 1983-11-10 | 1983-11-10 | Aromatic polythioether ketone and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60104126A true JPS60104126A (en) | 1985-06-08 |
| JPH0460137B2 JPH0460137B2 (en) | 1992-09-25 |
Family
ID=16607387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21152983A Granted JPS60104126A (en) | 1983-09-29 | 1983-11-10 | Aromatic polythioether ketone and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60104126A (en) |
Cited By (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61138627A (en) * | 1984-12-11 | 1986-06-26 | Mitsubishi Chem Ind Ltd | Production of aromatic polyketone |
| JPS62119230A (en) * | 1985-11-20 | 1987-05-30 | Mitsubishi Chem Ind Ltd | Production of aromatic poly(thio)ether ketone |
| JPS62241922A (en) * | 1986-04-14 | 1987-10-22 | Mitsubishi Chem Ind Ltd | Production of aromatic poly(thio)ether ketone |
| EP0293117A2 (en) | 1987-05-15 | 1988-11-30 | Kureha Kagaku Kogyo Kabushiki Kaisha | Heat-resistant molded or formed articles and production process thereof |
| EP0293113A2 (en) | 1987-05-15 | 1988-11-30 | Kureha Kagaku Kogyo Kabushiki Kaisha | Stretched poly(arylene thioether-ketone) films and production process thereof |
| EP0293118A2 (en) | 1987-05-15 | 1988-11-30 | Kureha Kagaku Kogyo Kabushiki Kaisha | Molded or formed poly(arylene thioether-ketone) articles |
| US4826906A (en) * | 1987-06-22 | 1989-05-02 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether-ketone) compositions improved in both melt stability and crystallinity |
| US4873283A (en) * | 1987-05-15 | 1989-10-10 | Kureha Kagaku Kogyo K.K. | Molded or formed poly(arylene thioether-ketone) articles |
| US4886871A (en) * | 1987-05-15 | 1989-12-12 | Kureha Kagaku Kogyo K. K. | Melt-stable poly(arylene thioetherketone) and production process thereof |
| US4895924A (en) * | 1987-05-15 | 1990-01-23 | Kureha Kagaku Kogyo K. K. | Poly(arylene thioether-ketone) fibers and production process thereof |
| US4895892A (en) * | 1987-05-15 | 1990-01-23 | Kureha Kagaku Kogyo K.K. | Melt-stable poly(arylene thioether-ketone) compositions |
| US4895893A (en) * | 1987-05-15 | 1990-01-23 | Kureha Kagaku Kogyo K.K. | Heat-resistant resin compositions, and heat-resistant molded or formed articles and production process thereof |
| US4897238A (en) * | 1987-05-15 | 1990-01-30 | Kureha Kagaku Kogyo K.K. | Stretched poly(arylene thioether-ketone) films and production process thereof |
| US4910086A (en) * | 1987-12-25 | 1990-03-20 | Kureha Kagaku Kogyo K.K. | Resin coated metal body |
| US4960806A (en) * | 1988-10-25 | 1990-10-02 | Kureha Kagaku Kagyo K.K. | Stretched poly(arylene thioether) block copolymer films and production process thereof |
| US4960555A (en) * | 1988-10-25 | 1990-10-02 | Kureha Kagaku Kogho K.K. | Poly (arylene thioether) block copolymer fibers and production process thereof |
| US4975479A (en) * | 1988-10-25 | 1990-12-04 | Kureha Kagaku Kogyo K.K. | Heat-resistant thermoplastic resin composition |
| US5008370A (en) * | 1988-11-11 | 1991-04-16 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether-ketones) improved in melt stability and preparation process thereof |
| US5045630A (en) * | 1988-11-11 | 1991-09-03 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether-ketones) improved in melt stability and preparation process thereof |
| US5110681A (en) * | 1987-10-30 | 1992-05-05 | Kureha Kagaku Kogyo K. K. | Melt-stable poly(arylene thioether-ketone) prepregs and molded or formed products thereof |
| US5120808A (en) * | 1988-10-25 | 1992-06-09 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether) block copolymer and production process thereof |
| US5153264A (en) * | 1988-10-25 | 1992-10-06 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether) block copolymer and production process thereof |
| US5153278A (en) * | 1988-10-25 | 1992-10-06 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether) block copolymer and production process thereof |
| US5153279A (en) * | 1988-10-25 | 1992-10-06 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether) block copolymer and production process thereof |
| US5250636A (en) * | 1990-04-25 | 1993-10-05 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether-ketone-ketone) copolymer and production process thereof |
| US5258440A (en) * | 1991-05-10 | 1993-11-02 | Kureha Kagaku Kogyo K. K. | Resin compositions of high heat resistance |
| US5391646A (en) * | 1990-04-25 | 1995-02-21 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether-ketone) copolymer and production process thereof |
-
1983
- 1983-11-10 JP JP21152983A patent/JPS60104126A/en active Granted
Cited By (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61138627A (en) * | 1984-12-11 | 1986-06-26 | Mitsubishi Chem Ind Ltd | Production of aromatic polyketone |
| JPS62119230A (en) * | 1985-11-20 | 1987-05-30 | Mitsubishi Chem Ind Ltd | Production of aromatic poly(thio)ether ketone |
| JPS62241922A (en) * | 1986-04-14 | 1987-10-22 | Mitsubishi Chem Ind Ltd | Production of aromatic poly(thio)ether ketone |
| US4886871A (en) * | 1987-05-15 | 1989-12-12 | Kureha Kagaku Kogyo K. K. | Melt-stable poly(arylene thioetherketone) and production process thereof |
| US4895912A (en) * | 1987-05-15 | 1990-01-23 | Kureha Kagaku Kogyo K.K. | Stretched poly(arylene thioether-ketone) films and production process thereof |
| EP0293118A2 (en) | 1987-05-15 | 1988-11-30 | Kureha Kagaku Kogyo Kabushiki Kaisha | Molded or formed poly(arylene thioether-ketone) articles |
| EP0293117A2 (en) | 1987-05-15 | 1988-11-30 | Kureha Kagaku Kogyo Kabushiki Kaisha | Heat-resistant molded or formed articles and production process thereof |
| US4873283A (en) * | 1987-05-15 | 1989-10-10 | Kureha Kagaku Kogyo K.K. | Molded or formed poly(arylene thioether-ketone) articles |
| US4897238A (en) * | 1987-05-15 | 1990-01-30 | Kureha Kagaku Kogyo K.K. | Stretched poly(arylene thioether-ketone) films and production process thereof |
| US4895924A (en) * | 1987-05-15 | 1990-01-23 | Kureha Kagaku Kogyo K. K. | Poly(arylene thioether-ketone) fibers and production process thereof |
| EP0293113A2 (en) | 1987-05-15 | 1988-11-30 | Kureha Kagaku Kogyo Kabushiki Kaisha | Stretched poly(arylene thioether-ketone) films and production process thereof |
| US4895892A (en) * | 1987-05-15 | 1990-01-23 | Kureha Kagaku Kogyo K.K. | Melt-stable poly(arylene thioether-ketone) compositions |
| US4895691A (en) * | 1987-05-15 | 1990-01-23 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether-ketone) fibers and production process thereof |
| US4895893A (en) * | 1987-05-15 | 1990-01-23 | Kureha Kagaku Kogyo K.K. | Heat-resistant resin compositions, and heat-resistant molded or formed articles and production process thereof |
| US4895925A (en) * | 1987-05-15 | 1990-01-23 | Kureha Kagaku Kogyo K.K. | Melt-stable poly(arylene thioether-ketone) and production process thereof |
| US4826906A (en) * | 1987-06-22 | 1989-05-02 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether-ketone) compositions improved in both melt stability and crystallinity |
| US5110681A (en) * | 1987-10-30 | 1992-05-05 | Kureha Kagaku Kogyo K. K. | Melt-stable poly(arylene thioether-ketone) prepregs and molded or formed products thereof |
| US4910086A (en) * | 1987-12-25 | 1990-03-20 | Kureha Kagaku Kogyo K.K. | Resin coated metal body |
| US5153278A (en) * | 1988-10-25 | 1992-10-06 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether) block copolymer and production process thereof |
| US4962143A (en) * | 1988-10-25 | 1990-10-09 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether) block copolymer fibers and production process thereof |
| US4975479A (en) * | 1988-10-25 | 1990-12-04 | Kureha Kagaku Kogyo K.K. | Heat-resistant thermoplastic resin composition |
| US5153279A (en) * | 1988-10-25 | 1992-10-06 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether) block copolymer and production process thereof |
| US4960555A (en) * | 1988-10-25 | 1990-10-02 | Kureha Kagaku Kogho K.K. | Poly (arylene thioether) block copolymer fibers and production process thereof |
| US4960806A (en) * | 1988-10-25 | 1990-10-02 | Kureha Kagaku Kagyo K.K. | Stretched poly(arylene thioether) block copolymer films and production process thereof |
| US5120808A (en) * | 1988-10-25 | 1992-06-09 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether) block copolymer and production process thereof |
| US5153264A (en) * | 1988-10-25 | 1992-10-06 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether) block copolymer and production process thereof |
| US5045630A (en) * | 1988-11-11 | 1991-09-03 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether-ketones) improved in melt stability and preparation process thereof |
| US5008370A (en) * | 1988-11-11 | 1991-04-16 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether-ketones) improved in melt stability and preparation process thereof |
| US5250636A (en) * | 1990-04-25 | 1993-10-05 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether-ketone-ketone) copolymer and production process thereof |
| US5374692A (en) * | 1990-04-25 | 1994-12-20 | Kureha Kagaku Kogyo K.K. | Poly (arylene thioether-ketone-ketone) copolymer and production process thereof |
| US5378770A (en) * | 1990-04-25 | 1995-01-03 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether-ketone-ketone) copolymer and production process thereof |
| US5391646A (en) * | 1990-04-25 | 1995-02-21 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether-ketone) copolymer and production process thereof |
| US5391645A (en) * | 1990-04-25 | 1995-02-21 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether-ketone) copolymer and production process thereof |
| US5258440A (en) * | 1991-05-10 | 1993-11-02 | Kureha Kagaku Kogyo K. K. | Resin compositions of high heat resistance |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0460137B2 (en) | 1992-09-25 |
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