JPH0348933B2 - - Google Patents
Info
- Publication number
- JPH0348933B2 JPH0348933B2 JP17143084A JP17143084A JPH0348933B2 JP H0348933 B2 JPH0348933 B2 JP H0348933B2 JP 17143084 A JP17143084 A JP 17143084A JP 17143084 A JP17143084 A JP 17143084A JP H0348933 B2 JPH0348933 B2 JP H0348933B2
- Authority
- JP
- Japan
- Prior art keywords
- thin film
- membered heterocyclic
- oxidizing agent
- heterocyclic compound
- 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.)
- Expired
Links
- 239000007800 oxidant agent Substances 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 18
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 10
- 150000000565 5-membered heterocyclic compounds Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000007792 gaseous phase Substances 0.000 claims 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 10
- 239000010409 thin film Substances 0.000 description 10
- 239000011521 glass Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- 239000005297 pyrex Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical class C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000414 polyfuran Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Description
（産業上の利用分野）
本発明は複素５員環式化合物の薄膜状重合体の
製造方法に関するものである。
（従来の技術）
複素５員環式化合物は酸や酸化剤により樹脂化
することが知られている。たとえば、ピロール及
びその誘導体は無機酸、塩化鉄、ベンゾキノン、
オゾンなどによりピロール黒、ピロール赤などの
重合体となることが知られている〔G.P.Gardini、
Adv.Heterocycl.Chem.、15、67（1973）など〕。
また、フランやチオフエン及びそれらの誘導体も
酸などにより重合体が生成することが知られてい
る。
しかしながら、このようにして得られる複素５
員環式化合物の重合体は、不溶不融の粉末または
塊状であつて、そのまま利用できる用途がなかつ
た。
一方、最近、これらの複素５員環式化合物を有
機溶媒中、電解質の存在下で電解酸化することに
より薄膜状の重合体が得られることが報告されて
いる（J.C.S.Chem.Comm.1979854、J.
Electroanal.Chem.135173（1982）など）がこの
ような方法では白金板や導電性ガラスなどの特殊
な電極や電解質を用いる必要があり、また電解装
置を必要とするなどの問題があつた。
〔発明が解決しようとする問題点〕
本発明の目的は複素５員環式化合物の薄膜状重
合体の容易な製造方法を提供することである。
〔問題点を解決するための手段〕
本発明者らは、複雑な電解装置を使用すること
なく、複素５員環式化合物の薄膜状重合体を製造
する方法を検討したところ、特定の条件でこれら
の化合物を重合することにより容易に薄膜状重合
体が得られることを見い出し、本発明を完成し
た。
すなわち、本発明は、複素５員環式化合物を酸
および／または酸化剤を用いて重合する際に、酸
および／または酸化剤を実質的に液相とし、複素
５員環式化合物を気相として、接触させることを
特徴とする薄膜状の複素５員環式化合物重合体を
製造する方法である。
本発明において使用される酸および／または酸
化剤（以下、単に酸化剤と表わす。）としては、
無機酸、金属化合物などが有効であり、無機酸と
しては硫酸、塩酸、硝酸、クロルスルホン酸など
が挙げられる。また、金属化合物はルイス酸とし
て知られるもので液状または、本発明に使用され
る溶媒に可溶なものである。特に好ましいものと
しては、アルミニウム、錫、チタン、ジルコニウ
ム、クロム、マンガン、鉄、銅、モリブデン、タ
ングステン、ルテニウム、パラジウム、白金等の
塩化物、硫酸塩、硝酸塩、アセチルアセトナート
化合物等があげられる。
その他にはベンゾキノン、ジアゾニウム塩など
の有機化合物も有効である。これらの酸化剤は１
種あるいは２種以上混合して用いても差しつかえ
ない。
本発明に使用する酸化剤は実質的に液状にする
ことが必要であり、硫酸のように液状のものを除
いては酸化剤を溶解するための溶媒が必要であ
る。
これに使用する溶媒としては、水の他、アルコ
ール、ベンゼン、トルエン、ヘキサン、テトラヒ
ドロフラン、ジオキサン、クロルベンゼン、エチ
レングリコール誘導体などの有機溶媒などが適宜
用いられる。
本発明において使用する複素環式化合物として
は、ピロール、フラン、チオフエン及びそれらの
誘導体である。
本発明における重合方法は、実質的に液相にあ
る酸化剤と気体状の複素５員環式化合物を接触さ
せれば良く、その界面に褐色〜黒色の薄膜状の重
合体が得られる。従つて、ガラスやプラスチツク
などの表面を酸化剤溶液でぬらしておくことによ
り、その表面に複素５員環化合物の薄膜状重合体
を生成させることも容易にできる。また、繊維な
どに酸化剤溶液を含浸しておくことにより、薄膜
状重合体に覆われた繊維を得ることも可能であ
る。
これらの重合体から余分な酸化剤を除去する方
法としては、酸化剤溶液を除いたあと、酸化剤が
溶解する溶媒で洗浄すれば良く、その操作は容易
である。
〔実施例〕
以下、実施例によりさらに本発明を説明する。
実施例 １
内容量200mlのパイレツクスガラス製セパラブ
ルフラスコに硫酸第二鉄１ｇを1N硫酸水溶液50
mlに溶解した溶液を入れ、窒素ガスで置換後ピロ
ールを飽和した窒素ガスを導入した。重合は界面
で起こり、黒色の薄膜が生成した。30分後に再び
窒素ガスで置換したのち、薄膜を取り出し、水洗
後メタノールで洗浄し、減圧下で乾燥した。生成
した薄膜の厚さは8μｍであり、電気伝導度を測
定したところ1.7Scm-1であつた。第１図に得られ
た重合体のIRスペクトルを示す。
実施例 ２
酸化剤溶液として、塩化第二鉄１ｇを蒸留水50
mlに溶解した溶液を用意して、清浄な顕微鏡用ス
ライドグラスを溶液中に浸したのち取り出して余
分の溶液を除いたのち、パイレツクス製ガラス管
中に水平になるように置いた。
ガラス管の一方からピロールを飽和した窒素ガ
スを導入したところ、すぐに重合が始まり、１時
間後には薄膜が生成していた。スライドグラスを
取り出し、水、メタノールで洗浄した後、減圧下
に乾燥した。
重合物はガラス上に密着した薄膜となつてい
た。膜厚は5μｍであり、電気伝導度を測定した
ところ1.2S・cm-1であつた。
実施例 ３〜９
酸化剤溶液として表１に示した種々の酸化剤溶
液を用いた他は、実施例２と同様にして、スライ
ドガラス上に薄膜を生成させた。
結果を表１に示した。
(Industrial Application Field) The present invention relates to a method for producing a thin film-like polymer of a five-membered heterocyclic compound. (Prior Art) It is known that a five-membered heterocyclic compound can be turned into a resin by using an acid or an oxidizing agent. For example, pyrrole and its derivatives can be used in inorganic acids, iron chloride, benzoquinone,
It is known that ozone etc. can form polymers such as pyrrole black and pyrrole red [GPGardini,
Adv.Heterocycl.Chem., 15 , 67 (1973), etc.].
Furthermore, it is known that furan, thiophene, and their derivatives also form polymers when exposed to acids. However, the complex 5 obtained in this way
Polymers of membered cyclic compounds are in the form of insoluble and infusible powders or lumps, and there is no use for them as they are. On the other hand, it has recently been reported that thin film-like polymers can be obtained by electrolytically oxidizing these five-membered heterocyclic compounds in an organic solvent in the presence of an electrolyte (JCSChem.Comm. 1979 854, J .
Electroanal.Chem. 135 173 (1982), etc.) However, this method required the use of special electrodes and electrolytes such as platinum plates and conductive glass, and also required an electrolytic device. [Problems to be Solved by the Invention] An object of the present invention is to provide an easy method for producing a thin film-like polymer of a five-membered heterocyclic compound. [Means for Solving the Problems] The present inventors investigated a method for producing a thin film-like polymer of a five-membered heterocyclic compound without using a complicated electrolytic device, and found that under specific conditions. The inventors have discovered that a thin film-like polymer can be easily obtained by polymerizing these compounds, and have completed the present invention. That is, in the present invention, when a 5-membered heterocyclic compound is polymerized using an acid and/or an oxidizing agent, the acid and/or oxidizing agent is substantially in a liquid phase, and the 5-membered heterocyclic compound is in a gas phase. This is a method for producing a thin film-like 5-membered heterocyclic compound polymer, which is characterized by contacting the polymer with the 5-membered heterocyclic compound. The acids and/or oxidizing agents (hereinafter simply referred to as oxidizing agents) used in the present invention include:
Inorganic acids, metal compounds, and the like are effective, and examples of the inorganic acids include sulfuric acid, hydrochloric acid, nitric acid, and chlorosulfonic acid. Further, the metal compound is known as a Lewis acid and is liquid or soluble in the solvent used in the present invention. Particularly preferred are chlorides, sulfates, nitrates, and acetylacetonate compounds of aluminum, tin, titanium, zirconium, chromium, manganese, iron, copper, molybdenum, tungsten, ruthenium, palladium, platinum, and the like. In addition, organic compounds such as benzoquinone and diazonium salts are also effective. These oxidants are 1
There is no problem in using seeds or a mixture of two or more kinds. It is necessary that the oxidizing agent used in the present invention be substantially liquid, and a solvent is required to dissolve the oxidizing agent, except for liquid oxidizing agents such as sulfuric acid. As the solvent used for this purpose, in addition to water, organic solvents such as alcohol, benzene, toluene, hexane, tetrahydrofuran, dioxane, chlorobenzene, and ethylene glycol derivatives are appropriately used. Heterocyclic compounds used in the present invention include pyrrole, furan, thiophene and derivatives thereof. In the polymerization method of the present invention, an oxidizing agent substantially in a liquid phase and a gaseous five-membered heterocyclic compound are brought into contact with each other, and a brown to black thin film-like polymer is obtained at the interface. Therefore, by wetting the surface of glass or plastic with an oxidizing agent solution, a thin film-like polymer of a five-membered heterocyclic compound can be easily formed on the surface. It is also possible to obtain fibers covered with a thin film-like polymer by impregnating the fibers with an oxidizing agent solution. The method for removing excess oxidizing agent from these polymers is to remove the oxidizing agent solution and then washing with a solvent in which the oxidizing agent is dissolved, which is an easy operation. [Example] The present invention will be further described below with reference to Examples. Example 1 In a Pyrex glass separable flask with a capacity of 200 ml, 1 g of ferric sulfate was added to 50% of a 1N sulfuric acid aqueous solution.
ml of the solution was added, and after purging with nitrogen gas, nitrogen gas saturated with pyrrole was introduced. Polymerization occurred at the interface and a black thin film was formed. After 30 minutes, the air was replaced with nitrogen gas again, and then the thin film was taken out, washed with water, methanol, and dried under reduced pressure. The thickness of the produced thin film was 8 μm, and the electrical conductivity was 1.7 Scm −1 when measured. Figure 1 shows the IR spectrum of the obtained polymer. Example 2 As an oxidizing agent solution, 1 g of ferric chloride was added to 50 ml of distilled water.
A clean microscope slide glass was immersed in the solution, removed to remove excess solution, and placed horizontally in a Pyrex glass tube. When nitrogen gas saturated with pyrrole was introduced from one side of the glass tube, polymerization started immediately, and a thin film was formed after one hour. The slide glass was taken out, washed with water and methanol, and then dried under reduced pressure. The polymer formed a thin film that adhered to the glass. The film thickness was 5 μm, and the electrical conductivity was 1.2 S·cm −1 when measured. Examples 3 to 9 Thin films were produced on glass slides in the same manner as in Example 2, except that various oxidizing agent solutions shown in Table 1 were used as oxidizing agent solutions. The results are shown in Table 1.
【表】【table】
本発明により得られる複素５員環化合物の薄膜
状重合体は電気伝導性又は半伝導性を有するもの
が多く、エレクロトニクス分野などで、電気伝導
性又は半伝導性部品として利用できる。たとえば
有機発熱体、ヒユーズ、表示用素子、電池用素
子、光起電力変換用素子、電磁放射保護膜などに
使用することができる。
Many of the thin film polymers of five-membered heterocyclic compounds obtained by the present invention have electrical conductivity or semi-conductivity, and can be used as electrically conductive or semi-conductive parts in the field of electronics and the like. For example, it can be used for organic heating elements, fuses, display elements, battery elements, photovoltaic power conversion elements, electromagnetic radiation protection films, and the like.
第１図、第２図、第３図はそれぞれ本発明の実
施例１、実施例10、実施例11で得られたポリピロ
ール薄膜、ポリフラン薄膜、ポリチオフエン薄膜
のIRスペクトルである。
FIG. 1, FIG. 2, and FIG. 3 are IR spectra of the polypyrrole thin film, polyfuran thin film, and polythiophene thin film obtained in Example 1, Example 10, and Example 11 of the present invention, respectively.
Claims (1)
剤を用いて重合する際に、酸および／または酸化
剤を実質的に液相とし、複素５員環式化合物を気
相として、接触させることを特徴とする薄膜状の
複素５員環式化合物重合体を製造する方法。1. When polymerizing a 5-membered heterocyclic compound using an acid and/or an oxidizing agent, contact the 5-membered heterocyclic compound with the acid and/or oxidizing agent in a substantially liquid phase and the 5-membered heterocyclic compound in a gaseous phase. A method for producing a thin film-like five-membered heterocyclic compound polymer characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17143084A JPS6151026A (en) | 1984-08-20 | 1984-08-20 | Production of five-membered heterocyclic compound polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17143084A JPS6151026A (en) | 1984-08-20 | 1984-08-20 | Production of five-membered heterocyclic compound polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6151026A JPS6151026A (en) | 1986-03-13 |
| JPH0348933B2 true JPH0348933B2 (en) | 1991-07-26 |
Family
ID=15922979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17143084A Granted JPS6151026A (en) | 1984-08-20 | 1984-08-20 | Production of five-membered heterocyclic compound polymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6151026A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62201924A (en) * | 1986-02-28 | 1987-09-05 | Nitto Electric Ind Co Ltd | Production of thin electroconductive organic film |
| JPH0618863B2 (en) * | 1986-03-28 | 1994-03-16 | 三菱化成株式会社 | Organic semiconductor |
| JPH02279720A (en) * | 1989-04-20 | 1990-11-15 | Sanyo Electric Co Ltd | Production of thin conductive polymer film |
| TW586131B (en) * | 1998-07-06 | 2004-05-01 | Showa Denko Kk | Electroconducting polymer, solid electrolytic capacitor and method for producing the same |
| JP4507297B2 (en) * | 1998-07-06 | 2010-07-21 | 株式会社村田製作所 | Conductive polymer, solid electrolytic capacitor and manufacturing method thereof |
-
1984
- 1984-08-20 JP JP17143084A patent/JPS6151026A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6151026A (en) | 1986-03-13 |
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