JPH01313811A - Manufacture of conductive high molecular composite film - Google Patents
Manufacture of conductive high molecular composite filmInfo
- Publication number
- JPH01313811A JPH01313811A JP63144294A JP14429488A JPH01313811A JP H01313811 A JPH01313811 A JP H01313811A JP 63144294 A JP63144294 A JP 63144294A JP 14429488 A JP14429488 A JP 14429488A JP H01313811 A JPH01313811 A JP H01313811A
- Authority
- JP
- Japan
- Prior art keywords
- film
- oxidization
- composite film
- compound
- conductive polymer
- 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
- 239000002131 composite material Substances 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000007800 oxidant agent Substances 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 12
- 230000001590 oxidative effect Effects 0.000 claims abstract description 8
- 239000002120 nanofilm Substances 0.000 claims abstract 2
- 229920001940 conductive polymer Polymers 0.000 claims description 24
- 229920006254 polymer film Polymers 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 5
- 230000006866 deterioration Effects 0.000 abstract description 5
- 150000001491 aromatic compounds Chemical class 0.000 abstract description 3
- 230000032683 aging Effects 0.000 abstract 2
- 239000010408 film Substances 0.000 description 37
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 20
- 239000011230 binding agent Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000011810 insulating material Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- -1 polyethylene Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920000128 polypyrrole Polymers 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Laminated Bodies (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Non-Insulated Conductors (AREA)
- Manufacturing Of Electric Cables (AREA)
Abstract
Description
【発明の詳細な説明】
（イ）産業上の利用分野
この発明は、導電性を有する高分子複合フィルムの製造
方法に関する。DETAILED DESCRIPTION OF THE INVENTION (a) Industrial Application Field The present invention relates to a method for producing a conductive polymer composite film.
（ロ）従来の技術
従来、導電性高分子フィルムを製造するには、ポリエチ
レン、塩化ビニル、ナイロン等のマトリクス高分子に、
金属の粉末または繊維、もしくはカーボンブラックの粉
末等を分散複合したものを膜状に成形する方法や、電極
、例えばガラス板表面に金・白金等の導電性蒸着膜を形
成したものを、ある種の酸化重合性化合物（ビロール類
、チオフェン類等）が溶解されると共に電解質が添加さ
れた溶剤中に浸漬し、電解重合により前記電極上に導電
性高分子フィルムを形成する方法が知られている。(b) Conventional technology Conventionally, in order to manufacture conductive polymer films, matrix polymers such as polyethylene, vinyl chloride, nylon, etc.
There are some methods of forming metal powders or fibers, carbon black powder, etc. into a film shape, and forming electrodes, such as conductive vapor-deposited films of gold, platinum, etc., on the surface of glass plates. A known method is to form a conductive polymer film on the electrode by electrolytic polymerization by immersing the electrode in a solvent in which an oxidatively polymerizable compound (viroles, thiophenes, etc.) is dissolved and an electrolyte is added. .
（ハ）発明が解決しようとする課題
上記方法の内、前者の方法では、マトリクス高分子中に
分散する粉末、繊維の大きさが０．１〜１μｍ程度であ
るので、薄い導電性高分子フィルムを得る。のが困難で
ある。また、後者の方法では、大面積の導電性高分子フ
ィルムを得るには、大面積の電極上で電解重合を行わね
ばならず、膜厚が均一にならない問題点があった。(c) Problems to be Solved by the Invention Among the above methods, in the former method, the size of the powder and fibers dispersed in the matrix polymer is about 0.1 to 1 μm, so a thin conductive polymer film is used. get. It is difficult to Furthermore, in the latter method, in order to obtain a large-area conductive polymer film, electrolytic polymerization must be carried out on a large-area electrode, which has the problem that the film thickness is not uniform.
そこで、本願発明者らは、上記問題点を解決するため、
高分子化合物を酸化剤と共に溶解した溶液を、適当な材
料上にコーティングして樹脂膜を形成し、この樹脂膜に
酸化重合性化合物、例えばピロールのガスを接触させ、
固気界面重合を行って導電性高分子複合フィルムを作製
することに成功した。しかしながら、この場合には、導
電性高分子複合フィルム中に酸化剤が残存するので、こ
の導電性高分子複合フィルムが経時的に劣化する問題点
を有している。Therefore, in order to solve the above problems, the inventors of the present application
A solution in which a polymer compound is dissolved together with an oxidizing agent is coated on a suitable material to form a resin film, and an oxidatively polymerizable compound such as pyrrole gas is brought into contact with this resin film.
We succeeded in fabricating a conductive polymer composite film by solid-gas interfacial polymerization. However, in this case, since the oxidizing agent remains in the conductive polymer composite film, there is a problem that the conductive polymer composite film deteriorates over time.
この発明は上記に鑑みなされたものであり、薄膜化が容
易で、かつ膜厚が均一で大面積の導電性高分子複合フィ
ルムの形成が容易な経時劣化の少ない導電性高分子複合
フィルムを製造する方法の提供を目的としている。This invention was made in view of the above, and aims to produce a conductive polymer composite film that is easily thinned, has a uniform thickness, is easy to form a large area conductive polymer composite film, and has little deterioration over time. The purpose is to provide a method to do so.
（ニ）課題を解決するための手段及び作用上記課題を解
決するため、この発明の導電性高分子複合フィルムの製
造方法は、絶縁性高分子フィルムに、酸化重合性化合物
（酸化重合性芳香族化合物又は酸化重合性複素環式化合
物）を含浸付着させ、この絶縁性高分子フィルムを酸化
ポテンシャルを適切に制御した酸化剤溶液に浸漬し、前
記酸化重合性化合物を前記絶縁性高分子フィルム内及び
表面で酸化重合させるものである。(d) Means and action for solving the problems In order to solve the above problems, the method for producing a conductive polymer composite film of the present invention includes adding an oxidatively polymerizable compound (an oxidatively polymerizable aromatic compound) to an insulating polymeric film. This insulating polymer film is immersed in an oxidizing agent solution with an appropriately controlled oxidation potential, and the oxidative polymerizable compound is deposited within the insulating polymer film. It causes oxidative polymerization on the surface.
この発明の導電性高分子複合フィルムの製造方法では、
金属粉末等を高分子中に分散する必要がないので薄膜化
が容易となり、また電解重合ではなく酸化重合を適用し
ているから電極が不要で、大面積化が容易となる。In the method for producing a conductive polymer composite film of this invention,
Since there is no need to disperse metal powder or the like in the polymer, it is easy to form a thin film, and since oxidative polymerization is applied instead of electrolytic polymerization, electrodes are not required, making it easy to increase the area.
この発明に類似した方法は、特開昭６２−１６７３２９
号公報、特開昭６２−１６７３３０号公報及び化繊講演
集第４３集（１９８６年１２月、Ｐ５１−５７）に記載
されてはいるが、酸化ポテンシャルが制御されていない
ため、製造された導電性高分子フィルムの導電率は低い
。A method similar to this invention is disclosed in Japanese Patent Application Laid-open No. 62-167329.
Although the oxidation potential is not controlled, the manufactured conductivity is Polymer films have low conductivity.
これに対し、この発明の導電性高分子複合フィルムの製
造方法は酸化ポテンシャルを適切に制御した酸化剤溶液
中で、酸化重合性化合物を酸化重合するものであるから
、導電性高分子複合フィルムの導電性を高くできると共
に、導電性高分子複合フィルム中に残留する酸化剤が極
めて少なく、導電性高分子複合フィルムの経時劣化を防
止することができる。In contrast, the method for producing a conductive polymer composite film of the present invention involves oxidatively polymerizing an oxidatively polymerizable compound in an oxidizing agent solution with an appropriately controlled oxidation potential. In addition to increasing the conductivity, the amount of oxidizing agent remaining in the conductive polymer composite film is extremely small, and deterioration of the conductive polymer composite film over time can be prevented.
（ホ）実施例 この発明の一実施例を図面に基づいて以下に説明する。(e) Examples An embodiment of the present invention will be described below based on the drawings.
まず、基材としてのポリエチレンテレフタート（以下Ｐ
ＥＴという）フィルム２（厚さ１００μ）上に、メタク
リル樹脂（以下ＰＭＭＡという）よりなるバインダーポ
リマー膜３を形成する（第１図参照）。ＰＥＴフィルム
２上にバインダーポリマー膜３が形成されたものを以下
フィルムＡと呼ぶ。First, polyethylene tereftate (hereinafter P
A binder polymer film 3 made of methacrylic resin (hereinafter referred to as PMMA) is formed on a film 2 (100 μm thick) (referred to as ET) (see FIG. 1). A film in which a binder polymer film 3 is formed on a PET film 2 is hereinafter referred to as film A.
バインダーポリマー膜３は、この実施例では、ＰＭＭＡ
２０ ｇを、メチルエチルケトン１００ｃｃに溶解した
液を、ＰＥＴフィルム２上に塗布し、４０°Ｃのオーブ
ン中に２４時間以上放置することにより形成される。こ
の他に、デイツプにより、バインダーポリマー膜３を形
成することができる。The binder polymer film 3 is, in this example, PMMA.
It is formed by dissolving 20 g of methyl ethyl ketone in 100 cc of methyl ethyl ketone and applying the solution onto the PET film 2 and leaving it in an oven at 40° C. for 24 hours or more. In addition to this, the binder polymer film 3 can be formed by a dip.
なお、上記基材には、他の高分子フィルムやガラスなど
の絶縁材質を使用してもよい。また、バインダーポリマ
ー膜３には、ポリスチレン樹脂やポリ酢酸ビニル樹脂等
の酸化重合性化合物に溶解もしくは膨潤するような樹脂
はすべて使用することができる。Note that other insulating materials such as polymer films and glass may be used for the base material. Further, for the binder polymer film 3, any resin that dissolves or swells in an oxidatively polymerizable compound, such as polystyrene resin or polyvinyl acetate resin, can be used.
次に１ｍｏｊ２／ｊ！の塩化鉄（Ｉｌｌ）水溶液に、１
１当り、Ｏ，ＯＯＯｌｍｏ ｌの塩化鉄（ＩＩ）を添加
することによって、酸化ポテンシャルを６３０〜６６０
ｍ Ｖとなる酸化剤溶液０（０°Ｃ）を調製する。Next 1moj2/j! In an aqueous solution of iron chloride (Ill), 1
The oxidation potential was increased from 630 to 660 by adding 0,001 mol of iron(II) chloride per
Prepare an oxidizing agent solution with mV at 0 (0°C).
一方、前記フィルムＡのバインダーポリマー膜３は、ピ
ロールＰ（０℃）に約５秒間デイツプしく第２図参照）
、バインダーポリマー膜３にピロール４を含浸・付着さ
せる。フィルムＡは、ピロールＰより取出して直ちに、
前記酸化剤溶：ａ、Ｏに５分間浸漬しく第３図参照）、
ピロール４を酸化重合し、ポリピロール薄膜４ｐとする
。On the other hand, the binder polymer film 3 of the film A is immersed in pyrrole P (0°C) for about 5 seconds (see Figure 2).
, pyrrole 4 is impregnated and adhered to the binder polymer film 3. Immediately after taking out the film A from the pyrrole P,
The oxidizing agent solution: a, immersed in O for 5 minutes (see Figure 3),
Pyrrole 4 is oxidized and polymerized to form a polypyrrole thin film 4p.
ポリピロール薄膜４ｐが形成されたフィルムＡは、撹拌
された蒸留水及びメタノール中にそれぞれ約２分間ずつ
浸漬され、表面に付着する酸化剤溶液や残留ピロールモ
ノマーを除去し、４０°Ｃ真空下で乾燥されて、導電性
高分子複合フィルムＢとなる（第４図参照）。この導電
性高分子複合フィルムＢの比電気伝導度はＩＱ６Ｓ／ｃ
ｍであった。Film A, on which the polypyrrole thin film 4p was formed, was immersed in stirred distilled water and methanol for about 2 minutes each to remove the oxidizing agent solution and residual pyrrole monomer adhering to the surface, and then dried at 40°C under vacuum. As a result, a conductive polymer composite film B is obtained (see FIG. 4). The specific electrical conductivity of this conductive polymer composite film B is IQ6S/c
It was m.
なお、ピロールに代えて、チオフエン等の他の酸化重合
性芳香族化合物を使用することができ、また、その含浸
・付着方法もデイツプの他に、蕩気暴露等の方法を使用
してもよい。In addition, instead of pyrrole, other oxidatively polymerizable aromatic compounds such as thiophene can be used, and the method of impregnating and adhering them may also be a method such as exposure to vapor in addition to dip. .
さらに、上記実施例では、基材を用いているかバインダ
ーポリマーそのものをフィルムとしてもよく適宜変更可
能である。Furthermore, in the above embodiments, the base material may be used or the binder polymer itself may be used as a film, and changes can be made as appropriate.
（へ）発明の詳細
な説明したように、この発明の導電性高分子複合フィル
ムの製造方法は、薄くかつ膜厚が均一で大面積の導電性
高分子複合フィルムを簡単な操作で容易に得ることがで
きる七共に、得られた導電性高分子複合フィルム内に酸
化剤が残留しにくいから、その経時劣化を抑えることが
できる利点を有している。(f) As described in detail of the invention, the method for producing a conductive polymer composite film of the present invention allows a conductive polymer composite film that is thin, has a uniform thickness, and has a large area to be easily obtained by a simple operation. Since the oxidizing agent is less likely to remain in the conductive polymer composite film obtained, it has the advantage that its deterioration over time can be suppressed.
また、種々の絶縁物上に導電性高分子複合フィルムを形
成できるから、これら絶縁物に容易に導電性を付与でき
る利点も有している。Furthermore, since a conductive polymer composite film can be formed on various insulating materials, it also has the advantage that conductivity can be easily imparted to these insulating materials.
さらに、短い時間で導電性高分子複合フィルムを製造で
きる利点をも有している。Furthermore, it has the advantage that a conductive polymer composite film can be produced in a short time.
図面は何れもこの発明の一実施例を示し、第１図は、ポ
リエチレンテレフタートフィルム上にバインダーポリマ
ー膜を形成した状態を示す図、第２図は、このバインダ
ーポリマー膜にピロールを付着含浸する状態を示す図、
第３図は、付着含浸されたピロールを酸化重合する状態
を示す図、第４図は、作製された導電性高分子複合フィ
ルムを示す図である。
３：バインダーポリマー膜、
Ｐ・４：ピロール、４ｐ：ポリピロール薄膜、Ｏ：酸化
剤溶液。
特許出願人 宮 １）清 藏（ほか１名）
代理人 弁理士 中 村 茂 信第１図
第３図
ム
第４図Each of the drawings shows an embodiment of the present invention; Fig. 1 shows a state in which a binder polymer film is formed on a polyethylene tereft film, and Fig. 2 shows a state in which pyrrole is adhered and impregnated into this binder polymer film. A diagram showing the state,
FIG. 3 is a diagram showing the state in which the adhered and impregnated pyrrole is oxidized and polymerized, and FIG. 4 is a diagram showing the produced conductive polymer composite film. 3: binder polymer film, P.4: pyrrole, 4p: polypyrrole thin film, O: oxidizing agent solution. Patent Applicant Miya 1) Kiyoshi Kura (and 1 other person) Agent Patent Attorney Shigeru Nakamura Figure 1 Figure 3 Figure 4
Claims (1)
浸付着させ、この絶縁性高分子フィルムを酸化ポテンシ
ャルを適切に制御した酸化剤溶液に浸漬し、前記酸化重
合性化合物を前記絶縁性高分子フィルム内及び表面で酸
化重合させる導電性高分子複合フィルムの製造方法。(1) An oxidative polymerizable compound is impregnated onto an insulating polymer film, and the insulating polymer film is immersed in an oxidizing agent solution with an appropriately controlled oxidation potential. A method for producing a conductive polymer composite film that undergoes oxidative polymerization within and on the surface of the molecular film.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63144294A JP2674783B2 (en) | 1988-06-10 | 1988-06-10 | Method for producing conductive polymer composite film |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63144294A JP2674783B2 (en) | 1988-06-10 | 1988-06-10 | Method for producing conductive polymer composite film |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01313811A true JPH01313811A (en) | 1989-12-19 |
| JP2674783B2 JP2674783B2 (en) | 1997-11-12 |
Family
ID=15358725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63144294A Expired - Lifetime JP2674783B2 (en) | 1988-06-10 | 1988-06-10 | Method for producing conductive polymer composite film |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2674783B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000239361A (en) * | 1998-07-06 | 2000-09-05 | Showa Denko Kk | Conductive polymer, solid electrolytic capacitor and production thereof |
| JP2005116301A (en) * | 2003-10-07 | 2005-04-28 | Sony Corp | Photoelectric conversion element, its manufacturing method, electronic equipment, its manufacturing method, electrode, and its manufacturing method |
| JP2006215104A (en) * | 2005-02-01 | 2006-08-17 | Nitto Denko Corp | Adhesive optical film and image display unit |
| JP2009239296A (en) * | 1998-07-06 | 2009-10-15 | Showa Denko Kk | Solid electrolytic capacitor and method of producing same |
-
1988
- 1988-06-10 JP JP63144294A patent/JP2674783B2/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000239361A (en) * | 1998-07-06 | 2000-09-05 | Showa Denko Kk | Conductive polymer, solid electrolytic capacitor and production thereof |
| JP2009239296A (en) * | 1998-07-06 | 2009-10-15 | Showa Denko Kk | Solid electrolytic capacitor and method of producing same |
| JP2005116301A (en) * | 2003-10-07 | 2005-04-28 | Sony Corp | Photoelectric conversion element, its manufacturing method, electronic equipment, its manufacturing method, electrode, and its manufacturing method |
| JP2006215104A (en) * | 2005-02-01 | 2006-08-17 | Nitto Denko Corp | Adhesive optical film and image display unit |
| JP4582704B2 (en) * | 2005-02-01 | 2010-11-17 | 日東電工株式会社 | Adhesive optical film and image display device |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2674783B2 (en) | 1997-11-12 |
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