JPH01129023A - Polycyanocarboxylaryl ether - Google Patents
Polycyanocarboxylaryl etherInfo
- Publication number
- JPH01129023A JPH01129023A JP28540487A JP28540487A JPH01129023A JP H01129023 A JPH01129023 A JP H01129023A JP 28540487 A JP28540487 A JP 28540487A JP 28540487 A JP28540487 A JP 28540487A JP H01129023 A JPH01129023 A JP H01129023A
- Authority
- JP
- Japan
- Prior art keywords
- ether
- polycyanocarboxylaryl
- aromatic ring
- solution
- reduced viscosity
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title abstract description 36
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 239000000243 solution Substances 0.000 abstract description 12
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 abstract description 7
- -1 alkali metal salt Chemical class 0.000 abstract description 6
- 229920013730 reactive polymer Polymers 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 5
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 229920000090 poly(aryl ether) Polymers 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000008378 aryl ethers Chemical class 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、高分子改質剤、イオン交換樹脂１反応性高分
子等の分野に応用可能な優れた耐熱性を有する新規ポリ
シアノカルボキシルアリールエーテルに関する。Detailed Description of the Invention [Field of Industrial Application] The present invention provides a novel polycyanocarboxylaryl compound having excellent heat resistance that can be applied to the fields of polymer modifiers, ion exchange resins, and reactive polymers. Concerning ether.
［従来の技術］
カルボキシル基は反応性の高い基で多様な反応が知られ
ているが、高分子についたカルボキシル基も高い反応性
を示すため、高分子カルボン酸は、反応性高分子として
重要な分野をなしている。[Prior art] Carboxyl groups are highly reactive groups and are known to be involved in a variety of reactions, but since carboxyl groups attached to polymers also exhibit high reactivity, polymeric carboxylic acids are important as reactive polymers. It is a major field.
このような高分子カルボン酸としては、ポリアクリル酸
、ポリメタクリル酸などが広く用いられ、それらの単独
重合体のほかに、多くの共重合体が知られている。（た
とえば、岩倉義勇、栗田恵輔著、反応性高分子、１７０
ページ、講談社、１９７７年）
一方、ポリシアノアリールエーテルは優れた耐熱性を有
するポリマーであり、種々の構造のものが既に報告され
ている（たとえば、特開昭４７−１４２７０号公報、特
開昭５９−２０６４３３号公報など）。Polyacrylic acid, polymethacrylic acid, and the like are widely used as such polymeric carboxylic acids, and in addition to their homopolymers, many copolymers are known. (For example, Yoshiyu Iwakura, Keisuke Kurita, Reactive Polymers, 170
Page, Kodansha, 1977) On the other hand, polycyanoaryl ether is a polymer with excellent heat resistance, and various structures have already been reported (for example, JP-A-47-14270, JP-A-Sho. 59-206433, etc.).
しかしながら高耐熱性のポリカルボン酸はこれまでほと
んど例がなく、またシアノ基とカルボキシル基の両方を
有するポリシアノカルボキシルエーテルは現在まで報告
されていない。However, there have been few examples of highly heat-resistant polycarboxylic acids, and no polycyanocarboxyl ethers having both a cyano group and a carboxyl group have been reported to date.
［発明が解決しようとする問題点］
高分子カルボン酸は、カルボキシル基の反応性のため反
応性高分子として種々の用途があるが、従来の高分子カ
ルボン酸は、耐熱性が低く高分子改質剤をはじめ耐熱性
が要求される分野ではその使用が限定されていた。[Problems to be Solved by the Invention] Polymeric carboxylic acids have various uses as reactive polymers due to the reactivity of their carboxyl groups, but conventional polymeric carboxylic acids have low heat resistance and are not suitable for polymer modification. Its use has been limited in fields where heat resistance is required, such as in quality agents.
［問題点を解決するための手段］
本発明者らは、上記問題点を解決するために、鋭意努力
し、
式（Ｉ）
Ｎ
（Ａｒは、芳香族環を表わす）
で示される繰り返し単位をに個
式（ｎ）
（Ａｒは、芳香族環を表わす）
で示される繰り返し単位１個を有しに／（ｋ＋β）の値
が０．２０〜０．８０であり、かつＰ−クロロフェノー
ルを溶媒とする濃度０．５ｔ／ｄｌ溶液の６０℃におけ
る還元粘度［η ／Ｃ］が ｐ
Ｏ，３ｄ１／を以上であるポリシアノカルボキシルアリ
ールエーテルが耐熱性の優れたポリカルボン酸であるこ
とを見いだし本発明を完成するに至った。[Means for Solving the Problems] In order to solve the above problems, the present inventors have made earnest efforts to solve the above problems, and the repeating unit represented by the formula (I) N (Ar represents an aromatic ring) has one repeating unit represented by the formula (n) (Ar represents an aromatic ring), has a value of /(k+β) of 0.20 to 0.80, and contains P-chlorophenol. It was discovered that polycyanocarboxyl aryl ether whose reduced viscosity [η /C] at 60°C of a solution with a concentration of 0.5 t/dl as a solvent is p O,3d1/ or more is a polycarboxylic acid with excellent heat resistance. The present invention has now been completed.
本発明のポリシアノカルボキシルアリールエーテルにあ
っては、式（Ｉ）の繰り返し単位を１個またはこの単位
が複数個適宜に直鎖状に連結してなる連結体と、式（Ｉ
Ｉ）の繰り返し単位１個又はこの単位が複数個適宜に直
鎖上に連結して成る連結体とが、互いに無秩序に又は秩
序立って直鎖状に連結して構成されている。In the polycyanocarboxylaryl ether of the present invention, a linkage formed by connecting one repeating unit of the formula (I) or a plurality of repeating units of the formula (I) in a linear chain as appropriate;
One repeating unit of I) or a linkage formed by appropriately connecting a plurality of repeating units in a linear chain are connected to each other in a linear chain in a disordered or ordered manner.
このポリシアノカルボキシルアリールエーテルにおいて
、各繰り返し単位の総数ｋｌ！は、０．２０≦に／に＋
β≦０．８０の関係を満足することが必要である。０．
２０未溝の場合には機械的性質および耐熱性が悪くなる
。Ｏ，ＳＯを超える場合にはポリカルボン酸の特徴が十
分に発揮されない。In this polycyanocarboxylaryl ether, the total number of each repeating unit kl! is 0.20≦/to+
It is necessary to satisfy the relationship β≦0.80. 0.
If there are no 20 grooves, the mechanical properties and heat resistance will be poor. If it exceeds O, SO, the characteristics of polycarboxylic acid will not be fully exhibited.
本発明のポリシアノカルボキシルアリールエーテルは、
このポリマーをＰ−クロロフェノールに溶解して、その
濃度を０．５ｔ／ｄｉにしなとき、この溶液の６０℃に
おける還元粘度［η ／Ｃ］ Ｐ
が０゜３ｄβ／ｇ以上であるような分子量を有するポリ
マーである。還元粘度が０．３ｄβ／ｇ未満であるよう
な重合度の場合にはポリマーの機械的強度が劣り、実用
性に乏しくなる。The polycyanocarboxylaryl ether of the present invention is
When this polymer is dissolved in P-chlorophenol to a concentration of 0.5 t/di, the molecular weight is such that the reduced viscosity [η /C] P of this solution at 60°C is 0°3dβ/g or more. It is a polymer with If the degree of polymerization is such that the reduced viscosity is less than 0.3 dβ/g, the mechanical strength of the polymer will be poor, making it impractical.
本発明のポリシアノカルボキシルアリールエーテルの製
造方法としては、一般式＜１）（Ａｒは、芳香族環を表
わす）
で示されるＰ−クロロフェノールを溶媒とする濃度０．
５ｇ／ｄｊ２溶液の６０℃における還元粘度［ηｓｐ／
Ｃ］が０．３ｄＩｌ／ｇ以上であるポリシアノアリール
エーテルを有機溶媒に溶解した液にアルカリ金属塩の水
溶液を加え、０〜２００℃で数十分から数時間反応させ
ることにより、製造する方法、あるいはアルカリ金属塩
のかわりに無機酸を使用する方法を例示することができ
る。The method for producing polycyanocarboxylaryl ether of the present invention involves using P-chlorophenol represented by the general formula <1) (Ar represents an aromatic ring) as a solvent at a concentration of 0.
Reduced viscosity at 60°C of 5g/dj2 solution [ηsp/
A method of manufacturing by adding an aqueous solution of an alkali metal salt to a solution of a polycyanoaryl ether having C] of 0.3 dIl/g or more dissolved in an organic solvent and reacting at 0 to 200°C for several tens of minutes to several hours. Alternatively, a method using an inorganic acid instead of an alkali metal salt can be exemplified.
などが挙げられる。Examples include.
この方法に使用されるポリシアノアリールエーテルは、
たとえば２．６−ジハロゲン化ベンゾニトリルと各種の
芳香族ビスフェノールのアルカリ金属塩とを有機溶媒中
で反応させて製造する方法を例示することができる。The polycyanoaryl ether used in this method is
For example, a method can be exemplified in which 2,6-dihalogenated benzonitrile and alkali metal salts of various aromatic bisphenols are reacted in an organic solvent.
また、２種類以上のビスフェノールを使用してもよい。Furthermore, two or more types of bisphenols may be used.
有機溶媒としては、テトラヒドロフラン、Ｎ−メチルピ
ロリドン、ジメチルスルホキシド、ジメチルホルムアミ
ド、ジメチルアセトアミド等を例示することができる。Examples of the organic solvent include tetrahydrofuran, N-methylpyrrolidone, dimethylsulfoxide, dimethylformamide, and dimethylacetamide.
アルカリ金属塩としては、水酸化ナトリウム、水酸化カ
リウム等のアルカリ金属の水酸化物を例示することがで
きる。また無機酸としては硫酸、塩酸等を例示すること
ができる。Examples of the alkali metal salt include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. Examples of inorganic acids include sulfuric acid and hydrochloric acid.
［作用］
本発明の式（Ｉ＞および（ｎ）で表わされるポリシアノ
カルボキシルアリールエーテルは、耐熱性に優れたボリ
アリールエーテルを１頷骨格とするため、耐熱性に優れ
ており、ｌＰＩ鎖のカルボキシル基の高い反応性のため
、種々の化学反応を起こすことができ耐熱性の優れた反
応性樹脂として耐熱性高分子改質剤、耐熱性イオン交換
樹脂等の耐熱性の優れた反応性高分子として種々の分野
に使用することが可能である。[Function] The polycyanocarboxyl aryl ether represented by the formulas (I> and (n) of the present invention has a polyaryl ether skeleton with excellent heat resistance, so it has excellent heat resistance and Due to the high reactivity of carboxyl groups, various chemical reactions can occur, and reactive resins with excellent heat resistance are used as heat-resistant polymer modifiers, heat-resistant ion exchange resins, etc. It can be used as a molecule in various fields.
［実施例］
以下に本発明の方法を実施例によって示すがこれらによ
って本発明が限定されるものではない。[Examples] The method of the present invention will be illustrated below by examples, but the present invention is not limited to these.
実施例１
ポリシアノカルボキシルアリールエーテルの製造は、以
下の様に行った。Example 1 Polycyanocarboxylaryl ether was produced as follows.
ディーンースターク（Ｄｅａｎ−３ｔａｒｋ） トラッ
プおよび凝縮器、撹拌機、窒素ガス導入管および温度計
を有する３ ００ ｍｌのセパラブルフラスコ中に、２
．６−シクロロペンゾニトリル１７．０２ｔｒ （０゜
１０モル）、ビスフェノールＡ２２．８３ｔ （０，１
０モル）、炭酸カリウム１６、５９ｔ （０，１２モル
）、スルホラン１００ｍ１．）ルエン５０ｍ１を入れ１
６０℃において１．５時間反応させ、水およびトルエン
を共沸蒸留により除去した。次いで１９０℃に昇温して
２時間反応させた０重合反応の終了後生成物をメタノー
ル中に投入して重合体を析出させ、水およびメタノール
で数回づつ洗浄し、１００℃において８時間真空乾燥し
た。ポリシアノアリールエーテルの収量は、３６．２５
ｇ （収率１００％）であった。In a 300 ml separable flask with a Dean-3tark trap and condenser, stirrer, nitrogen gas inlet tube and thermometer, 2
．． 6-cyclopenzonitrile 17.02 tr (0°10 mol), bisphenol A 22.83 t (0,1
0 mol), potassium carbonate 16.59 t (0.12 mol), sulfolane 100 ml. ) Add 50ml of luene and 1
The reaction was carried out at 60° C. for 1.5 hours, and water and toluene were removed by azeotropic distillation. The temperature was then raised to 190°C and the reaction was carried out for 2 hours. After completion of the polymerization reaction, the product was poured into methanol to precipitate a polymer, washed several times with water and methanol, and then heated at 100°C for 8 hours under vacuum. Dry. The yield of polycyanoaryl ether is 36.25
g (yield 100%).
このポリシアノアリールエーテルのＰ−クロロフェノー
ルを溶媒とする０、２ｇ／ｄβ溶液の６０℃における還
元粘度［η ／ＣＩは、 ｐ
０．４６ｄＪ２／ｇであった。The reduced viscosity [η /CI at 60° C. of a 0.2 g/dβ solution of this polycyanoaryl ether in P-chlorophenol as a solvent was p 0.46 dJ2/g.
２００ｍ１のフラスコに撹拌機をとりつけ、上記にて合
成したポリシアノアリールエーテル４．９０ｒ （０，
０１５当量）のテトラヒドロフラン３０ａ＋ｌの溶液を
調製した。続いて４８％水酸化ナトリウム水溶液を加え
、室温で２時間反応させた０反応後、反応液を大量の水
に加えることにより沈澱物を得た。沈澱物を水、メタノ
ールで数回洗浄後８０℃で１０時間真空乾燥した。ポリ
シアノカルボキシルアリールエーテルの収量は５．０４
ｇ、（収率９９％）
このポリシアノカルボキシルアリールエーテルのＰ−ク
ロロフェノールを溶媒とする０、５ｇ／ｄｉ溶液の６０
℃における還元粘度［η５ｐ／Ｃコは０．３７ｄｌ／ｇ
であった。A 200 ml flask was equipped with a stirrer, and 4.90 r (0,
A solution of 30a+l of tetrahydrofuran (015 equivalents) was prepared. Subsequently, a 48% aqueous sodium hydroxide solution was added, and after 0 reaction, the mixture was allowed to react at room temperature for 2 hours, and the reaction solution was added to a large amount of water to obtain a precipitate. The precipitate was washed several times with water and methanol, and then vacuum-dried at 80° C. for 10 hours. The yield of polycyanocarboxylaryl ether is 5.04
g, (yield 99%) 60 of a 0.5 g/di solution of this polycyanocarboxylaryl ether in P-chlorophenol as a solvent.
Reduced viscosity at °C [η5p/C is 0.37 dl/g
Met.
また赤外線吸収スペクトル分析を行った結果３０３０ｃ
ｍ＋−’と８３０ａｍ−１の位置にベンゼン環のＣ−Ｈ
結合、１５９０ａｍ“１の位置にベンゼン環のｃ−ｃ結
合、１２４０ａａ−１の位置に芳香族エーテル結合、１
６６０ａｏ−’にカルボキシル基の存在に基づく特性吸
収また、２２２０ａａ−’にシアノ基に基づく吸収が見
られた。In addition, the result of infrared absorption spectrum analysis was 3030c.
C-H of benzene ring at position m+-' and 830am-1
Bond, c-c bond of benzene ring at position 1590am"1, aromatic ether bond at position 1240aa-1, 1
A characteristic absorption based on the presence of a carboxyl group was observed at 660ao-', and an absorption based on a cyano group was observed at 2220aa-'.
赤外線吸収スペクトルのピークよりシアノ基□とカルボ
キシル基の割合に／（ｋ＋！）は０．４であった。From the peak of the infrared absorption spectrum, the ratio of cyano groups to carboxyl groups /(k+!) was 0.4.
また、このポリマーを熱分析した結果、ガラス転移温度
（Ｔｇ）が１３６℃、熱分解温度（Ｔｄ）が４２１℃の
耐熱性の優れた樹脂であった。Further, as a result of thermal analysis of this polymer, it was found to be a resin with excellent heat resistance, having a glass transition temperature (Tg) of 136°C and a thermal decomposition temperature (Td) of 421°C.
［発明の効果］
以上の説明で明らかなように、本発明のポリシアノカル
ボキシルアリールエーテルは、強い極性基であるシアノ
基と反応性基であるカルボキシル基の両方を有し、かつ
高い耐熱性を有するため、高分子改質剤をはじめ反応性
高分子として種々の用途に有用である。[Effects of the Invention] As is clear from the above explanation, the polycyanocarboxyl aryl ether of the present invention has both a cyano group, which is a strong polar group, and a carboxyl group, which is a reactive group, and has high heat resistance. Therefore, it is useful for various purposes as a reactive polymer including a polymer modifier.
Claims (1)
が０．２０〜０．８０であり、かつＰ−クロロフェノー
ルを溶媒とする濃度 ０．５を／ｄｌ溶液の６０℃における還元粘度［η＿ｓ
＿ｐ／Ｃ］が０．３ｄｌ／ｇ以上であるポリシアノカル
ボキシルアリールエーテル。[Claims] 1) Formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼…(I) (Ar represents an aromatic ring) k repeating units represented by formula (II) ▲Mathical formula , chemical formulas, tables, etc. ▼...(II) (Ar represents an aromatic ring) It has l repeating units and the value of k/(k+l) is 0.20 to 0.80, and the reduced viscosity [η_s
_p/C] is 0.3 dl/g or more.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28540487A JPH0826146B2 (en) | 1987-11-13 | 1987-11-13 | Polycyanocarboxyl aryl ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28540487A JPH0826146B2 (en) | 1987-11-13 | 1987-11-13 | Polycyanocarboxyl aryl ether |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01129023A true JPH01129023A (en) | 1989-05-22 |
| JPH0826146B2 JPH0826146B2 (en) | 1996-03-13 |
Family
ID=17691083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28540487A Expired - Fee Related JPH0826146B2 (en) | 1987-11-13 | 1987-11-13 | Polycyanocarboxyl aryl ether |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0826146B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005013399A1 (en) * | 2003-07-31 | 2005-02-10 | Toyo Boseki Kabushiki Kaisha | Electrolyte membrane-electrode assembly, fuel cell using same, and method for producing electrolyte membrane-electrode assembly |
| JP2005232240A (en) * | 2004-02-18 | 2005-09-02 | Toyobo Co Ltd | Manufacturing method of polymer solid electrolyte membrane |
-
1987
- 1987-11-13 JP JP28540487A patent/JPH0826146B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005013399A1 (en) * | 2003-07-31 | 2005-02-10 | Toyo Boseki Kabushiki Kaisha | Electrolyte membrane-electrode assembly, fuel cell using same, and method for producing electrolyte membrane-electrode assembly |
| JP2005232240A (en) * | 2004-02-18 | 2005-09-02 | Toyobo Co Ltd | Manufacturing method of polymer solid electrolyte membrane |
| JP4534126B2 (en) * | 2004-02-18 | 2010-09-01 | 東洋紡績株式会社 | Method for producing solid polymer electrolyte membrane |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0826146B2 (en) | 1996-03-13 |
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