JPH0791383B2 - Polychenylene or its methyl derivative film - Google Patents
Polychenylene or its methyl derivative filmInfo
- Publication number
- JPH0791383B2 JPH0791383B2 JP1283257A JP28325789A JPH0791383B2 JP H0791383 B2 JPH0791383 B2 JP H0791383B2 JP 1283257 A JP1283257 A JP 1283257A JP 28325789 A JP28325789 A JP 28325789A JP H0791383 B2 JPH0791383 B2 JP H0791383B2
- Authority
- JP
- Japan
- Prior art keywords
- film
- polyphenylene
- polychenylene
- heat treatment
- present
- 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.)
- Expired - Lifetime
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims description 4
- 229920000265 Polyparaphenylene Polymers 0.000 claims description 19
- -1 polyphenylene Polymers 0.000 claims description 19
- 229920000642 polymer Polymers 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000010408 film Substances 0.000 description 36
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 8
- 229930192474 thiophene Natural products 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 4
- 238000005162 X-ray Laue diffraction Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000003115 supporting electrolyte Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
Landscapes
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は、電子デバイスの分野に利用される高分子フィ
ルムに関する。TECHNICAL FIELD OF THE INVENTION The present invention relates to a polymer film used in the field of electronic devices.
従来の技術 従来、ポリチェニレンは触媒としてニッケル化合物を用
いて、ジハロゲン化チオフェンを有機合成法により重合
することによって粉末状で得られ、その重合度は14〜30
であることを知られている（特開昭56−47421号公報並
びに特開昭58−96626号公報）。2. Description of the Related Art Conventionally, polyphenylene has been obtained in a powder form by polymerizing a dihalogenated thiophene by an organic synthesis method using a nickel compound as a catalyst, and its polymerization degree is 14 to 30.
Is known (Japanese Patent Laid-Open Nos. 56-47421 and 58-96626).
更に本発明者らは、先に特願昭57−80895号においてチ
オフェンの電解酸化重合に関し、ポリチェニレンのフィ
ルム化に成功している。Furthermore, the present inventors have succeeded in forming a film of polychenylene in connection with electrolytic oxidation polymerization of thiophene in Japanese Patent Application No. 57-80895.
発明が解決しようとする課題 しかしながら、上記の有機合成法による提案では、ポリ
チェニレンは重合度が低く粉末状であるため、機械的特
性の優れた強靱なフィルムとはならない課題であった。However, in the proposal by the above-mentioned organic synthesis method, since polyphenylene has a low degree of polymerization and is in the form of powder, it is a problem that a tough film having excellent mechanical properties cannot be obtained.
また従来の電解酸化重合法だけで重合したフィルムで
は、フィルムの膜質が弱く引っ張り強度に劣る課題があ
った。Further, a film polymerized only by the conventional electrolytic oxidation polymerization method has a problem that the film quality of the film is weak and the tensile strength is poor.
本発明の目的はこの欠点を解消して、機械的特性の優れ
た強靱なアモルファス化ポリチェニレンフィルムを提供
することである。It is an object of the present invention to overcome this drawback and to provide a tough amorphized polychenylene film with excellent mechanical properties.
ここでアモルファス（無定形）化とは、高分子フィルム
中で高分子鎖が規則性を持たないようにさせることと定
義する。また、このアモルファス化状態はＸ線回折によ
る測定方法で、回折像がはっきりとしたパターンを示さ
ないことによって確認される。Here, the term "amorphous (amorphous)" means that the polymer chains in the polymer film do not have regularity. This amorphized state is confirmed by the X-ray diffraction measurement method, in which the diffraction pattern does not show a clear pattern.
課題を解決するための手段 高分子鎖が無定形状態で、引っ張り強度が1200〜3300kg
/cm2である、反復単量体が下記化学式ＡまたはＢの何れ
かで示されるポリチェニレンもしくはそのメチル誘導体
フィルムである。Means for solving the problem Polymer chains are in an amorphous state and tensile strength is 1200 to 3300 kg
The repeating monomer, which is / cm 2 , is a polyphenylene or its methyl derivative film represented by the following chemical formula A or B.
作用 例えば電解酸化重合法等の手法により、重合度を高くす
ることによりポリチェニレンはフィルム状で得らる。こ
のようなポリチェニレンフィルムは結晶性であり、ポリ
チェニレンの高分子鎖を無定形状態にすることにより、
高分子鎖はばらばらになり、規則性を失い、ランダムに
絡み合うようになる。その結果、ポリチェニレンフィル
ムが強靱になると考えられる。 Action Polychenylene can be obtained in the form of a film by increasing the degree of polymerization by a method such as electrolytic oxidation polymerization. Such a polyphenylene film is crystalline, and by making the polymer chain of polyphenylene amorphous,
The polymer chains fall apart, lose their regularity, and become entangled randomly. As a result, it is considered that the polychenylene film becomes tough.
実施例 本発明のアモルファス化ポリチェニレンの基本骨格と
は、チオフェン環の２位と５位とを結合させた重合体で
あり、本発明で言うポリチェニレン誘導体とは、３位に
メチル基が結合したチオフェン環の２位と５位とを結合
させた重合体である。Example The basic skeleton of the amorphous polyphenylene of the present invention is a polymer in which the 2- and 5-positions of the thiophene ring are bonded together, and the polyphenylene derivative referred to in the present invention is thiophene in which a methyl group is bonded in the 3-position. It is a polymer in which the 2- and 5-positions of the ring are bonded.
本発明のアモルファス化ポリチェニレンもしくはその誘
導体フィルムの製造法は、例えばチオフェンもしくはそ
の誘導体を支持電解質の存在下で電解酸化重合して、陽
極上にポリチェニレンもしくはその誘導体フィルムを形
成し、引き続いて電極を反転し、電解還元する手法が挙
げられる。The method for producing an amorphized polyphenylene or its derivative film of the present invention includes, for example, electrolytically oxidatively polymerizing thiophene or its derivative in the presence of a supporting electrolyte to form a polyphenylene or its derivative film on an anode, and subsequently invert the electrode. Then, a method of electrolytic reduction may be used.
このフィルムを不活性雰囲気下で熱処理することによっ
て、フィルムがアモルファス化され強靱化される。By heat-treating this film in an inert atmosphere, the film is made amorphous and toughened.
一般に高分子をアモルファス化する場合には、高分子を
溶融させた後急令する手法、もしくは溶剤に溶解させた
後溶剤を揮発させる手法等がある。しかし本発明のポリ
チェニレンフィルムもしくはポリチェニレン誘導体フィ
ルムは、融点を持たないため溶融状態に出来ず、また今
のところ溶解する溶剤も見受けられない。従って本発明
のポリチェニレンフィルムもしくはポリチェニレン誘導
体フィルムをアモルファス化するためには、熱処理を行
うのが最も簡便で着実な手法である。Generally, when a polymer is made amorphous, there is a method of melting the polymer and then carrying out a rapid method, or a method of dissolving the polymer in a solvent and then volatilizing the solvent. However, since the polyphenylene film or the polyphenylene derivative film of the present invention does not have a melting point, it cannot be made into a molten state, and at present, no solvent that dissolves is found. Therefore, in order to make the polyphenylene film or the polyphenylene derivative film of the present invention amorphous, heat treatment is the simplest and most consistent method.
なおここで、熱処理は不活性雰囲気で行なうのがよい。Here, the heat treatment is preferably performed in an inert atmosphere.
この不活性雰囲気とは、ポリチェニレンフィルムを数百
度に加熱しても、酸化あるいは熱分解しない雰囲気のこ
とである。The inert atmosphere is an atmosphere that does not oxidize or thermally decompose even when the polyphenylene film is heated to several hundred degrees.
不活性雰囲気の例としては、窒素ガス中、ヘリウムガス
中、ネオンガス中、アルゴンガス中等の不活性ガス中あ
るいは、空気圧が10mmHg以下の減圧状態などがあげられ
る。Examples of the inert atmosphere include an inert gas such as nitrogen gas, helium gas, neon gas, and argon gas, or a depressurized state where the air pressure is 10 mmHg or less.
空気圧が数十mmHgになると、酸素の影響を受け易くな
る。そのため、減圧の場合は、10mmHg以下が望ましい。When the air pressure reaches several tens of mmHg, it is easily affected by oxygen. Therefore, in the case of reduced pressure, 10 mmHg or less is desirable.
熱処理温度は、熱処理時間と深い関係があり、例えば、
400℃なら20分、600℃なら１分、800℃なら30秒程度で
ある。熱処理温度が低いほど、熱処理時間を長くする必
要がある。熱処理温度としては、100〜1000℃が有効
で、望ましくは400〜800℃である。The heat treatment temperature has a deep relationship with the heat treatment time.
It is 20 minutes at 400 ℃, 1 minute at 600 ℃, and 30 seconds at 800 ℃. The lower the heat treatment temperature, the longer the heat treatment time must be. The heat treatment temperature is effectively 100 to 1000 ° C, preferably 400 to 800 ° C.
次に具体的な実施例を用いて本発明を説明する。The present invention will be described with reference to specific examples.
実施例１ チオフェン5.05g、支持電解質としてのテトラ−ｎ−ブ
チルアンモニウムパークロレート2.05gを300mlのニトロ
ベンゼンに溶解する。陰極として白金板を用い、陽極と
してスズをドープした酸化インジウム薄膜を備えたガラ
ス電極を用い、電解酸化重合を行ない、緑黒色のフィル
ム状の重合体を陽極上に得た。電流密度は2mA/cm2，反
応温度は５℃、反応時間は10分とした。その後、引き続
いて、２つの電極を反転し、電解還元を行なった。電流
密度は4mA/cm2、反応時間は３分とした。反応後、フィ
ルムを電極から剥離し、メタノールで洗浄後、一昼夜真
空乾燥し、ポリチェニレンフィルムを得た。Example 1 5.05 g of thiophene and 2.05 g of tetra-n-butylammonium perchlorate as a supporting electrolyte are dissolved in 300 ml of nitrobenzene. Using a platinum plate as a cathode and a glass electrode provided with a tin-doped indium oxide thin film as an anode, electrolytic oxidation polymerization was performed to obtain a green-black film-like polymer on the anode. The current density was 2 mA / cm 2 , the reaction temperature was 5 ° C., and the reaction time was 10 minutes. Then, subsequently, the two electrodes were inverted and electrolytic reduction was performed. The current density was 4 mA / cm 2 , and the reaction time was 3 minutes. After the reaction, the film was peeled from the electrode, washed with methanol, and vacuum dried for a whole day and night to obtain a polychenylene film.
このフィルムを、石英ガラス製の密封管に入れて脱気し
た後、窒素ガスを封入し、電気炉で600℃の温度で１分
間加熱した。熱処理後、封管の温度が室温に下がってか
ら、ポリチェニレンフィルムを取り出した。緑赤色のフ
ィルムを得た。This film was placed in a quartz glass sealed tube and deaerated, then nitrogen gas was sealed therein, and the film was heated in an electric furnace at a temperature of 600 ° C. for 1 minute. After the heat treatment, the temperature of the sealed tube dropped to room temperature, and then the polyphenylene film was taken out. A green-red film was obtained.
実施例２ 実施例１において、ポリチェニレンフィルムを、1mmHg
に減圧した密封管中で、同じ条件で熱処理し、緑黒色の
ポリチェニレンフィルムを得た。Example 2 In Example 1, the polyphenylene film was replaced with 1 mmHg.
Heat treatment was performed under the same conditions in a sealed tube depressurized to obtain a green-black polychenylene film.
実施例３ 実施例１において、チオフェン5.05gを３−メチルチオ
フェン5.89gにかえて同様の実験を行い、黄赤色のフィ
ルムを得た。Example 3 The same experiment as in Example 1 was performed except that 5.05 g of thiophene was replaced with 5.89 g of 3-methylthiophene to obtain a yellow-red film.
実施例４ 実施例１において、チオフェン5.05gを３−メチルチオ
フェン5.89gにかえ、また熱処理を1mmHgに減圧した密封
管で、同じ条件で熱処理し、黄赤色のフィルムを得た。Example 4 In Example 1, 5.05 g of thiophene was replaced with 5.89 g of 3-methylthiophene, and the heat treatment was performed under the same conditions with a sealed tube whose pressure was reduced to 1 mmHg to obtain a yellow-red film.
比較例 実施例１および４において、熱処理工程を省いて緑赤色
のフィルムを得た。Comparative Example In Examples 1 and 4, the heat treatment step was omitted to obtain a green-red film.
実施例１及び４と比較例で得られたフィルムの機械的強
度を、引っ張り試験機（オートグラフAG500（島津製作
所製）で、室温で測定した結果を表に示す。The results of measuring the mechanical strength of the films obtained in Examples 1 and 4 and Comparative Example at room temperature with a tensile tester (Autograph AG500 (manufactured by Shimadzu Corporation) are shown in the table.
表から明白なように本発明の熱処理したフィルムはいず
れも、比較例の未処理のフィルムに比べて数倍大きな値
を示した。 As is apparent from the table, all of the heat-treated films of the present invention showed a value several times higher than that of the untreated film of Comparative Example.
また、理学電機FR−Ｂ、Ｘ線発生器とArndt−Wanacott
オッシレーションカメラを用いて0.1×0.1mmのCuKα放
射線をフィルム面に垂直に入射させてこれらのフィルム
のラウエ写真を撮った。いずれの写真も、回折像は熱処
理無しのものに比べて、はっきりとしたパターンが見え
ずアモルファス化状態を示していた。Also, Rigaku Denki FR-B, X-ray generator and Arndt-Wanacott
Laue photographs of these films were taken using an oscillation camera with 0.1 × 0.1 mm CuKα radiation incident perpendicular to the film plane. In all the photographs, the diffraction pattern showed an amorphized state without showing a clear pattern as compared with that without heat treatment.
その１例として、ポリ（３−メチル）チェニレンのラウ
エ写真を第１図と第２図に示す。As one example thereof, Laue photographs of poly (3-methyl) chenylene are shown in FIGS. 1 and 2.
第１図は実施例４のラウエ写真で、第２図は実施例４の
比較例（熱処理前）のラウエ写真である。FIG. 1 is a Laue photograph of Example 4, and FIG. 2 is a Laue photograph of Comparative Example (before heat treatment) of Example 4.
比較例では結晶状態を示す輪状の回折パターン１が見ら
れたが、実施例では見られなくなっている。このことか
ら本発明のポリチェニレンもしくはその誘導体は、アモ
ルファス状態であることを確認した。Although the ring-shaped diffraction pattern 1 showing a crystalline state was seen in the comparative example, it is not seen in the example. From this, it was confirmed that the polyphenylene or its derivative of the present invention was in an amorphous state.
発明の効果 以上の説明から明らかなように、本発明は電解重合によ
り得られるアモルファス化ポリチェニレンもしくはその
誘導体であるため、機械的特性の優れた強靱なフィルム
を提供する効果があり、工業的価値は高い。EFFECTS OF THE INVENTION As is clear from the above description, the present invention is an amorphous polyphenylene obtained by electrolytic polymerization or a derivative thereof, and thus has an effect of providing a tough film having excellent mechanical properties, and has an industrial value. high.
第１図は本発明のアモルファス化ポリ（３−メチル）チ
ェニレンのＸ線回折像を示す図、第２図は従来のポリ
（３−メチル）チェニレンのＸ線回折像を示す図であ
る。 １…回折パターンFIG. 1 is a diagram showing an X-ray diffraction image of amorphized poly (3-methyl) chenylene of the present invention, and FIG. 2 is a diagram showing an X-ray diffraction image of a conventional poly (3-methyl) chenylene. 1 ... Diffraction pattern
フロントページの続き (72)発明者 保阪 富治 大阪府門真市大字門真1006番地 松下電器 産業株式会社内 (72)発明者 下間 亘 大阪府門真市大字門真1006番地 松下電器 産業株式会社内 (56)参考文献 特開 昭59−221330（ＪＰ，Ａ) 特公 昭58−24446（ＪＰ，Ｂ２)Front Page Continuation (72) Inventor Fumiharu Hosaka 1006 Kadoma, Kadoma, Osaka Prefecture Matsushita Electric Industrial Co., Ltd. (72) Inventor Wataru Shimama 1006, Kadoma, Kadoma City, Osaka (56) References JP-A-59-221330 (JP, A) JP-B-58-24446 (JP, B2)
Claims (1)
1200〜3300kg/cm2であることを特徴とする、反復単量体
が下記化学式ＡまたはＢの何れかで示されることを特徴
とするポリチェニレンもしくはそのメチル誘導体フィル
ム。 1. A polymer chain is in an amorphous state and has a tensile strength.
A polyphenylene or methyl derivative film thereof, wherein the repeating monomer is represented by one of the following chemical formulas A and B, which is 1200 to 3300 kg / cm 2 .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1283257A JPH0791383B2 (en) | 1989-10-30 | 1989-10-30 | Polychenylene or its methyl derivative film |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1283257A JPH0791383B2 (en) | 1989-10-30 | 1989-10-30 | Polychenylene or its methyl derivative film |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58175331A Division JPS6067534A (en) | 1983-09-22 | 1983-09-22 | Polythienylene or film thereof and its manufacture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02167336A JPH02167336A (en) | 1990-06-27 |
| JPH0791383B2 true JPH0791383B2 (en) | 1995-10-04 |
Family
ID=17663113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1283257A Expired - Lifetime JPH0791383B2 (en) | 1989-10-30 | 1989-10-30 | Polychenylene or its methyl derivative film |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0791383B2 (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4400442A (en) * | 1981-07-13 | 1983-08-23 | Rockwell International Corporation | Fiber reinforced electroformed superplastic nickel-cobalt matrices |
| JPS59221330A (en) * | 1983-06-01 | 1984-12-12 | Showa Denko Kk | Crystalline 2,5-thienylene polymer and its production |
-
1989
- 1989-10-30 JP JP1283257A patent/JPH0791383B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02167336A (en) | 1990-06-27 |
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