JPH0386763A - Conductive polymeric material composite - Google Patents
Conductive polymeric material compositeInfo
- Publication number
- JPH0386763A JPH0386763A JP22308289A JP22308289A JPH0386763A JP H0386763 A JPH0386763 A JP H0386763A JP 22308289 A JP22308289 A JP 22308289A JP 22308289 A JP22308289 A JP 22308289A JP H0386763 A JPH0386763 A JP H0386763A
- Authority
- JP
- Japan
- Prior art keywords
- dopant
- polymeric material
- conductive polymeric
- conductive polymer
- polymer material
- 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.)
- Pending
Links
- 239000002131 composite material Substances 0.000 title claims abstract description 15
- 239000000463 material Substances 0.000 title abstract description 11
- 239000002019 doping agent Substances 0.000 claims abstract description 20
- 239000000696 magnetic material Substances 0.000 claims abstract description 4
- 229920001940 conductive polymer Polymers 0.000 claims description 19
- 239000002861 polymer material Substances 0.000 claims description 18
- 229910044991 metal oxide Inorganic materials 0.000 claims description 9
- 150000004706 metal oxides Chemical class 0.000 claims description 9
- 150000002736 metal compounds Chemical class 0.000 claims description 7
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 3
- 150000004692 metal hydroxides Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 11
- 229920000128 polypyrrole Polymers 0.000 abstract description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract description 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 2
- 229910000765 intermetallic Inorganic materials 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000002841 Lewis acid Substances 0.000 description 5
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000005389 magnetism Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- -1 polyparaphenylene Polymers 0.000 description 3
- 229920000123 polythiophene Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- FDRNXKXKFNHNCA-UHFFFAOYSA-N 4-(4-anilinophenyl)-n-phenylaniline Chemical compound C=1C=C(C=2C=CC(NC=3C=CC=CC=3)=CC=2)C=CC=1NC1=CC=CC=C1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 description 1
- 229910017048 AsF6 Inorganic materials 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 229910019891 RuCl3 Inorganic materials 0.000 description 1
- 229910009973 Ti2O3 Inorganic materials 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910001914 chlorine tetroxide Inorganic materials 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 239000006247 magnetic powder Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000323 polyazulene Polymers 0.000 description 1
- 229920001088 polycarbazole Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- GQUJEMVIKWQAEH-UHFFFAOYSA-N titanium(III) oxide Chemical compound O=[Ti]O[Ti]=O GQUJEMVIKWQAEH-UHFFFAOYSA-N 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、磁性材料、電磁波シールド材料、磁性トナー
等の画像記録媒体に有用な導電性高分子材料と金属化合
物との複合体に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a composite of a conductive polymer material and a metal compound useful for image recording media such as magnetic materials, electromagnetic shielding materials, and magnetic toners.
［従来の技術］
ポリピロール、ポリチオフェンなどのπ電子系の発達し
た高分子材料はルイス酸ｔｌどの不純物をドーピングす
ることにより導電性を発現せしめること゛ができる。電
気化学的にはこのドーピングが可逆に行なわれるために
機能材料として注目されている。一方、この高分子の機
能とさらに他の材料を複合化せしめる試みがある。例え
ば導電性高分子と他のポリマー（ＰＶＡ１ポリカーボネ
ート、塩ビ、ナフィオン、ＰＭＭＡなと）との複合化に
よる力学的性質、熱的性質、加工性の向上、Ｆｅｄ、Ｆ
ｅ５０＜、ＭｎＯ２等との複合化による磁性、誘電性の
付与などがある。[Prior Art] Polymer materials with a developed π-electron system, such as polypyrrole and polythiophene, can be made to exhibit electrical conductivity by doping them with impurities such as Lewis acid Tl. Electrochemically, this doping is reversible, so it is attracting attention as a functional material. On the other hand, there are attempts to combine the functions of this polymer with other materials. For example, improving mechanical properties, thermal properties, and processability by combining conductive polymers with other polymers (PVA1 polycarbonate, PVC, Nafion, PMMA, etc.), Fed, F
Examples include e50<, imparting magnetism and dielectricity by combining with MnO2, etc.
例えばＪＡＰＡＮＥＳＥ ＪＯＵＲＮＡＬ ＯＦ ＡＰ
ＰＬＩＥＤＰＨＹＳＩＣ８Ｖｏｌ、２４．Ｎｏ、９（１
９８５）Ｌ ８８７−８８８ではポリピロールの電解重
合系に磁性粉体（ＦｅＯ５Ｆｅ３０４粉末）を添加する
ことにより電解重合膜内に磁性体を取り込ませ磁性を発
現せしめている。また、電解重合と同時に金属酸化物を
析出せしめる方法なども知られている。いずれも注目さ
れる機能性付与の方法であるが次のような欠点をもって
いる。For example, JAPANESE JOURNAL OF AP
PLIEDPHYSIC8Vol, 24. No, 9 (1
985) L 887-888, by adding magnetic powder (FeO5Fe304 powder) to the electrolytic polymerization system of polypyrrole, the magnetic substance is incorporated into the electrolytic polymerized film to develop magnetism. Also known is a method in which a metal oxide is precipitated simultaneously with electrolytic polymerization. All of these methods are attracting attention, but they have the following drawbacks.
１〉これらの場合いずれも電解重合法に限定され、しか
も成膜することが条件となる。1> In all of these cases, the method is limited to the electrolytic polymerization method, and the condition is that it is necessary to form a film.
２）電解重合のためのモノマーの酸化電位と金属酸化物
の析出電位が異るためいずれかの生成物を印加電界で破
壊してしまうことがある。2) Since the oxidation potential of the monomer for electrolytic polymerization and the deposition potential of the metal oxide are different, either product may be destroyed by the applied electric field.
［発明が解決しようとする課題］
本発明は、こうした従来の欠点に鑑み、導電性高分子材
料の製法に依存せず、かつ、安定した複合体を提供する
ことを目的とするものである。[Problems to be Solved by the Invention] In view of these conventional drawbacks, the present invention aims to provide a stable composite that does not depend on the manufacturing method of the conductive polymer material.
［課題を解決するための手段］
本発明者らは、前記した課題を解決するため、鋭意検討
した結果、導電性高分子材料中に含まれている金属化合
物ドーパントを出発材料として利用し、これを脱活性化
せしめ、さらにこれを酸化物または水酸化物として導電
性高分子材料中に形成せしめることが有効であることを
知見し、本発明に至った。[Means for Solving the Problems] In order to solve the above-mentioned problems, the present inventors, as a result of intensive studies, utilized a metal compound dopant contained in a conductive polymer material as a starting material. It has been found that it is effective to deactivate and further form the oxide or hydroxide in a conductive polymer material, leading to the present invention.
すなわち、本発明は金属化合物をドーパントとして含有
する導電性高分子材料において、該ドーパントの活性を
失わせるとともに、該ドーパントを出発物質として金属
酸化物又は金属水酸化物を導電性高分子材料内部に複合
化せしめてなる導電性高分子材料複合体である。脱ドー
プの方法としては電気化学的脱ドープ、光、熱などの物
理作用による脱ドープの他、アンモニア、ヒドラジン等
の還元剤による化学処理が挙げられる。更にドーパント
の活性を失わせる方法としては、ドーパントの分解ある
いは中性塩に変化させるなどの方法がある。この場合、
アンモニアによる処理はドーパントを脱ドープせしめる
と同時にアンモニウム塩にして活性を失わせることがで
きるため、ひとつの工程でドーパントを失活させること
ができる。That is, in a conductive polymer material containing a metal compound as a dopant, the present invention eliminates the activity of the dopant and also introduces a metal oxide or metal hydroxide into the conductive polymer material using the dopant as a starting material. It is a conductive polymer material composite made of composite materials. Dedoping methods include electrochemical dedoping, dedoping by physical action such as light and heat, and chemical treatment using a reducing agent such as ammonia and hydrazine. Furthermore, as a method for losing the activity of the dopant, there are methods such as decomposing the dopant or changing it into a neutral salt. in this case,
Treatment with ammonia can dedope the dopant and at the same time turn it into an ammonium salt and deactivate it, so the dopant can be deactivated in one step.
本発明はドーピングという分子レベルの反応を出発とし
ているため複合体は分子レベルで均一に複合されると考
えられる。従って複合化によって得られた材料の機能も
均一であり、微粒子化による機能の不均一化（機能を持
ったものと持っていないものの混在）フィルムにおける
機能の局在化を防ぐことができる。Since the present invention starts with a reaction at the molecular level called doping, it is thought that the complex is formed uniformly at the molecular level. Therefore, the functions of the material obtained by compounding are uniform, and it is possible to prevent non-uniformity of functions (mixture of functional and non-functional materials) caused by microparticulation and localization of functions in the film.
本発明において使用する導電性高分子材料としては、た
とえば、ポリアセチレン、ポリパラフェニレン、ポリピ
ロール、ポリＮ−メチルピロール、ポリチオフェン、ポ
リ−３−アルキルチオフェン、ポリ−３，４−ジアルキ
ルチオフェン、ポリアニリン、ポリジフェニルベンジジ
ン、ポリカルバゾール、ポリアズレン、ポリフェニレン
ビニレン、ポリチェニレンビニレンなどが挙げられる。The conductive polymer materials used in the present invention include, for example, polyacetylene, polyparaphenylene, polypyrrole, polyN-methylpyrrole, polythiophene, poly-3-alkylthiophene, poly-3,4-dialkylthiophene, polyaniline, poly Examples include diphenylbenzidine, polycarbazole, polyazulene, polyphenylene vinylene, and polythenylene vinylene.
これらは電解重合法、あるいは化学重合法によって得ら
れたものでよく、製法にとくに制限を受けるものではな
いが、下記に示すように本発明においては金属化合物を
ドーパントとして利用するので、この観点からルイス酸
触媒によって得る方法が好ましい。These may be obtained by an electrolytic polymerization method or a chemical polymerization method, and there are no particular restrictions on the manufacturing method, but from this point of view, since a metal compound is used as a dopant in the present invention as shown below. Preferred is the method using Lewis acid catalysts.
また、これらの導電性高分子材料にドーピングされるド
ーパントとしてはＣＩ”−ＢｒＢＦ４″″ ＣｌＯ４″
″ ＰＦｉ’″ ＳｂＦ＆ＡｓＦ６″″などが代表的な
例として挙げられるが、本発明に用いられるドーパント
としては金属化合物で゛あることが要求される。特に好
ましくはＦｅＣｌ３、ＲｕＣｌ３などのルイス酸である
。これらのルイス酸はＡｌＣ１３ＴｉＣ１３−ＦｅＣｌ
３− ＲｕＣｌ３−などの形でドープされていること
が、予想され、それ自身酸化剤として導電性高分子材料
の重合反応に用いることができる。In addition, CI"-BrBF4""ClO4" is used as a dopant to be doped into these conductive polymer materials.
Typical examples include "PFi'", "SbF &AsF6"", but the dopant used in the present invention is required to be a metal compound. Particularly preferred are Lewis acids such as FeCl3 and RuCl3. These Lewis acids are AlC13TiC13-FeCl
It is expected that it will be doped in the form of 3-RuCl3- or the like, and itself can be used as an oxidizing agent in the polymerization reaction of conductive polymer materials.
本発明はこれらの金属化合物であるルイス酸のドーパン
トとしての活性を失わせるとともに、これを金属酸化物
または水酸化物に還元せしめることによって実現する。The present invention is achieved by deactivating these metal compounds, Lewis acids, as dopants and reducing them to metal oxides or hydroxides.
これらのルイス酸から得られる金属酸化物としてはＦｅ
ｚｅｓ、Ｆ ｅ ３０４ 、Ａ １２０３、Ｔｉ２Ｏ３
などが挙げられ水酸化物としてはＦｅｏＯＨ％Ｎｉ０Ｏ
Ｈなどが得られる。Metal oxides obtained from these Lewis acids include Fe.
zes, Fe 304, A 1203, Ti2O3
etc., and the hydroxide is FeoOH%Ni0O
H etc. can be obtained.
本発明の導電性高分子材料複合体は、本来の導電性に加
え、複合化する金属酸化物、または水酸化物の有する特
性をも保持することができる。たとえば、Ｆｅ３Ｏ４と
複合化された導電性高分子は、磁性材料となる。The conductive polymer material composite of the present invention can maintain not only the original conductivity but also the properties of the metal oxide or hydroxide used in the composite. For example, a conductive polymer compounded with Fe3O4 becomes a magnetic material.
［実施例］
以下に本発明の実施例を挙げて本発明をさらに詳細に説
明する。[Example] The present invention will be explained in further detail by giving examples of the present invention below.
実施例１
水、メタノールがｌ：１の比率の混合液１こＦｅＣｌ３
８Ｈ２０を０．１Ｍ溶解せしめて樗た酸化浴中に撹拌
しながらビロール０．５Ｍを滴下し、約２時間反応せし
めた。Example 1 1 volume of a mixed solution of water and methanol in a ratio of 1:1 FeCl3
8H20 was dissolved in 0.1M, and 0.5M of virol was added dropwise to the oxidation bath with stirring, and the mixture was allowed to react for about 2 hours.
反応終了後生成したポリピロールを濾過するとともにメ
タノールで十分に洗浄し８０℃の温度で真空乾燥した。After the reaction was completed, the polypyrrole produced was filtered, thoroughly washed with methanol, and dried under vacuum at a temperature of 80°C.
次にアセトニトリル中に十分に乾燥した無水のＦｅＣｌ
２を０．０１Ｍ溶解せしめこの中にポリピロール０．５
Ｍを分散せしめた。Then thoroughly dry anhydrous FeCl in acetonitrile
2 was dissolved at 0.01M, and 0.5% of polypyrrole was dissolved in it.
M was dispersed.
その後５０％のアンモニア水を撹拌しながら滴下し、約
１時間反応させ、ポリピロール中のドーパントを脱活性
化した。この時脱活性化したドーパントはＦｅＣ１ｚ及
びアンモニアと反応してマグネタイトが複合化される。Thereafter, 50% ammonia water was added dropwise with stirring, and the mixture was reacted for about 1 hour to deactivate the dopant in the polypyrrole. At this time, the deactivated dopant reacts with FeC1z and ammonia to form a composite of magnetite.
その後、ポリピロールのみを分離し、メタノールで十分
に洗浄した後二６０℃の温度で再び真空乾燥した。Thereafter, only the polypyrrole was separated, thoroughly washed with methanol, and then vacuum-dried again at a temperature of 260°C.
得られたポリピロールはＦｅ３Ｏ４を含む複合体であり
磁性を示した。The obtained polypyrrole was a composite containing Fe3O4 and exhibited magnetism.
実施例２
メタノールにＦｅＣｌ３を０．１Ｍ溶解せしめた酸化洛
中でチオフェン０，５Ｍを反応させた以外は実施例１と
同様にしてポリチオフェンを得た。これを用いて実施例
１と同様にして磁性を示す複合体を得た。Example 2 Polythiophene was obtained in the same manner as in Example 1, except that 0.5 M of thiophene was reacted in an oxidizing solution containing 0.1 M of FeCl3 dissolved in methanol. Using this, a magnetic composite was obtained in the same manner as in Example 1.
実施例３
実施例１で得られたポリピロールに再びＩ２ガス雰囲気
にさらし、！２をドーピングした。Example 3 The polypyrrole obtained in Example 1 was exposed to an I2 gas atmosphere again, and! 2 was doped.
これによって導電性及び磁性の両者の機能を持たせるこ
とができた。（導電性は１Ｏ−ｓＳ／ｃｍから０、ＩＳ
／ｃ−へと向上した）
［発明の効果］
以上説明したように、本発明によれば導電性高分子材料
の製法に制限されることなく、導電性高分子材料と金属
酸化物又は水酸化物との複合体とすることができ、該材
料に導電性に加えて他の機能も付与することができる。This made it possible to provide both conductive and magnetic functions. (Conductivity is from 1O-sS/cm to 0, IS
/c-) [Effects of the Invention] As explained above, according to the present invention, without being limited to the manufacturing method of the conductive polymer material, the method of manufacturing the conductive polymer material and the metal oxide or hydroxide It can be made into a composite with an object, and the material can be given other functions in addition to electrical conductivity.
しかも、その複合化は分子レベル又は超微粒子レベルで
均一に実現できる。Moreover, the compositing can be uniformly realized at the molecular level or ultrafine particle level.
Claims (2)
分子材料において、該ドーパントの活性を失わせるとと
もに、該ドーパントを出発物質として金属酸化物又は金
属水酸化物を導電性高分子材料内部に複合化せしめてな
ることを特徴とする導電性高分子材料複合体。(1) In a conductive polymer material containing a metal compound as a dopant, the activity of the dopant is lost, and a metal oxide or metal hydroxide is composited inside the conductive polymer material using the dopant as a starting material. A conductive polymer material composite characterized by:
電性高分子材料複合体。(2) The conductive polymer material composite according to claim (1), wherein the metal oxide is a magnetic material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22308289A JPH0386763A (en) | 1989-08-31 | 1989-08-31 | Conductive polymeric material composite |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22308289A JPH0386763A (en) | 1989-08-31 | 1989-08-31 | Conductive polymeric material composite |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0386763A true JPH0386763A (en) | 1991-04-11 |
Family
ID=16792559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22308289A Pending JPH0386763A (en) | 1989-08-31 | 1989-08-31 | Conductive polymeric material composite |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0386763A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0992548A2 (en) * | 1998-10-09 | 2000-04-12 | Toyo Boseki Kabushiki Kaisha | Anticorrosive primer composition |
| EP1209530A1 (en) * | 2000-11-28 | 2002-05-29 | Xerox Corporation | Toner compositions comprising polypyrroles |
| US6439711B1 (en) | 2000-11-28 | 2002-08-27 | Xerox Corporation | Ballistic aerosol marking process employing marking material comprising polyester resin and poly (3,4-ethylenedioxythiophene) |
| US6467871B1 (en) | 2000-11-28 | 2002-10-22 | Xerox Corporation | Ballistic aerosol marking process employing marking material comprising vinyl resin and poly (3,4-ethylenedioxypyrrole) |
| US6485874B1 (en) | 2000-11-28 | 2002-11-26 | Xerox Corporation | Toner compositions comprising vinyl resin and poly(3,4-ethylenedioxypyrrole) |
| US6673501B1 (en) | 2000-11-28 | 2004-01-06 | Xerox Corporation | Toner compositions comprising polyester resin and polypyrrole |
| US6686111B1 (en) | 2000-11-28 | 2004-02-03 | Xerox Corporation | Toner compositions comprising vinyl resin and poly (3,4-ethylenedioxythiophene) |
| US6699633B2 (en) | 2000-11-28 | 2004-03-02 | Xerox Corporation | Toner compositions comprising polyester resin and poly(3,4-ethylenedioxythiophene) |
| CN102660222A (en) * | 2012-05-16 | 2012-09-12 | 南昌航空大学 | Graphite-doped poly-schiff base/ferrite composite stealth material |
| CN103555270A (en) * | 2013-11-07 | 2014-02-05 | 南昌航空大学 | Chiral poly-schiff alkali salt/ferrite wave-adsorbing material and preparation method thereof |
-
1989
- 1989-08-31 JP JP22308289A patent/JPH0386763A/en active Pending
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0992548A2 (en) * | 1998-10-09 | 2000-04-12 | Toyo Boseki Kabushiki Kaisha | Anticorrosive primer composition |
| EP0992548A3 (en) * | 1998-10-09 | 2001-09-12 | Toyo Boseki Kabushiki Kaisha | Anticorrosive primer composition |
| EP1209530A1 (en) * | 2000-11-28 | 2002-05-29 | Xerox Corporation | Toner compositions comprising polypyrroles |
| US6439711B1 (en) | 2000-11-28 | 2002-08-27 | Xerox Corporation | Ballistic aerosol marking process employing marking material comprising polyester resin and poly (3,4-ethylenedioxythiophene) |
| US6467871B1 (en) | 2000-11-28 | 2002-10-22 | Xerox Corporation | Ballistic aerosol marking process employing marking material comprising vinyl resin and poly (3,4-ethylenedioxypyrrole) |
| US6485874B1 (en) | 2000-11-28 | 2002-11-26 | Xerox Corporation | Toner compositions comprising vinyl resin and poly(3,4-ethylenedioxypyrrole) |
| US6589702B1 (en) | 2000-11-28 | 2003-07-08 | Xerox Corporation | Toner compositions comprising polypyrroles |
| US6673501B1 (en) | 2000-11-28 | 2004-01-06 | Xerox Corporation | Toner compositions comprising polyester resin and polypyrrole |
| US6686111B1 (en) | 2000-11-28 | 2004-02-03 | Xerox Corporation | Toner compositions comprising vinyl resin and poly (3,4-ethylenedioxythiophene) |
| US6689527B2 (en) | 2000-11-28 | 2004-02-10 | Xerox Corporation | Toner compositions comprising vinyl resin and poly (3,4-ethylenedioxythiophene) |
| US6699633B2 (en) | 2000-11-28 | 2004-03-02 | Xerox Corporation | Toner compositions comprising polyester resin and poly(3,4-ethylenedioxythiophene) |
| US6730450B1 (en) | 2000-11-28 | 2004-05-04 | Xerox Corporation | Toner compositions comprising polyester resin and poly (3,4-ethylenedioxythiophene) |
| US6743559B2 (en) * | 2000-11-28 | 2004-06-01 | Xerox Corporation | Toner compositions comprising polyester resin and polypyrrole |
| CN102660222A (en) * | 2012-05-16 | 2012-09-12 | 南昌航空大学 | Graphite-doped poly-schiff base/ferrite composite stealth material |
| CN103555270A (en) * | 2013-11-07 | 2014-02-05 | 南昌航空大学 | Chiral poly-schiff alkali salt/ferrite wave-adsorbing material and preparation method thereof |
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