JPS6346377B2 - - Google Patents
Info
- Publication number
- JPS6346377B2 JPS6346377B2 JP55145156A JP14515680A JPS6346377B2 JP S6346377 B2 JPS6346377 B2 JP S6346377B2 JP 55145156 A JP55145156 A JP 55145156A JP 14515680 A JP14515680 A JP 14515680A JP S6346377 B2 JPS6346377 B2 JP S6346377B2
- Authority
- JP
- Japan
- Prior art keywords
- electrode
- enzyme
- tcnq
- oxidase
- immobilized
- 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
- 102000004190 Enzymes Human genes 0.000 claims description 14
- 108090000790 Enzymes Proteins 0.000 claims description 14
- VWWQXMAJTJZDQX-UYBVJOGSSA-N flavin adenine dinucleotide Chemical compound C1=NC2=C(N)N=CN=C2N1[C@@H]([C@H](O)[C@@H]1O)O[C@@H]1CO[P@](O)(=O)O[P@@](O)(=O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C2=NC(=O)NC(=O)C2=NC2=C1C=C(C)C(C)=C2 VWWQXMAJTJZDQX-UYBVJOGSSA-N 0.000 claims description 4
- 235000019162 flavin adenine dinucleotide Nutrition 0.000 claims description 4
- 239000011714 flavin adenine dinucleotide Substances 0.000 claims description 4
- 229940093632 flavin-adenine dinucleotide Drugs 0.000 claims description 4
- 108090000854 Oxidoreductases Proteins 0.000 claims description 2
- 102000004316 Oxidoreductases Human genes 0.000 claims description 2
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 claims description 2
- 229940088598 enzyme Drugs 0.000 description 13
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 108091006149 Electron carriers Proteins 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 108010015776 Glucose oxidase Proteins 0.000 description 2
- 239000004366 Glucose oxidase Substances 0.000 description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229940116332 glucose oxidase Drugs 0.000 description 2
- 235000019420 glucose oxidase Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- -1 potassium ferricyanide Chemical compound 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- CCBICDLNWJRFPO-UHFFFAOYSA-N 2,6-dichloroindophenol Chemical compound C1=CC(O)=CC=C1N=C1C=C(Cl)C(=O)C(Cl)=C1 CCBICDLNWJRFPO-UHFFFAOYSA-N 0.000 description 1
- JMEVHYCNAPFOAB-UHFFFAOYSA-L 2-(3-hydroxy-5-sulfonato-1H-indol-2-yl)-3-oxoindole-5-sulfonate Chemical compound [O-]c1c([nH]c2ccc(cc12)S([O-])(=O)=O)C1=[NH+]c2ccc(cc2C1=O)S([O-])(=O)=O JMEVHYCNAPFOAB-UHFFFAOYSA-L 0.000 description 1
- RXGJTUSBYWCRBK-UHFFFAOYSA-M 5-methylphenazinium methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC=C2[N+](C)=C(C=CC=C3)C3=NC2=C1 RXGJTUSBYWCRBK-UHFFFAOYSA-M 0.000 description 1
- 108010025188 Alcohol oxidase Proteins 0.000 description 1
- 108091023020 Aldehyde Oxidase Proteins 0.000 description 1
- 241001480748 Argas Species 0.000 description 1
- 102000004674 D-amino-acid oxidase Human genes 0.000 description 1
- 108010003989 D-amino-acid oxidase Proteins 0.000 description 1
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 1
- 108010093096 Immobilized Enzymes Proteins 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 108010093894 Xanthine oxidase Proteins 0.000 description 1
- 102100033220 Xanthine oxidase Human genes 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000005842 biochemical reaction Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 230000009088 enzymatic function Effects 0.000 description 1
- 235000012209 glucono delta-lactone Nutrition 0.000 description 1
- 229960003681 gluconolactone Drugs 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
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 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
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000005373 porous glass Substances 0.000 description 1
- SOUHUMACVWVDME-UHFFFAOYSA-N safranin O Chemical compound [Cl-].C12=CC(N)=CC=C2N=C2C=CC(N)=CC2=[N+]1C1=CC=CC=C1 SOUHUMACVWVDME-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/86—Inert electrodes with catalytic activity, e.g. for fuel cells
- H01M4/90—Selection of catalytic material
- H01M4/9008—Organic or organo-metallic compounds
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/001—Enzyme electrodes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
Description
本発明は、新規な電子伝達体を有する酵素電極
に関する。
酵素は、特定物質（基質）に対してある一定反
応のみを起こさせる基質特異性および反応特異性
をもつことが知られている。このような酵素の生
化学的反応を電気化学的反応に関連させると対象
物質の有無の検知や、酵素を固定化した電極と対
極との組み合わせによる電池の構成等に応用でき
る。
生体内におけるエネルギー変換には、酸化還元
酵素が主に関与している。一般に酸化還元によつ
て基質の酸化還元を行う場合、電子伝達体を必要
とする。例えば、酵素としてグルコースオキシダ
ーゼ（以下、GODで表す）を用い、グリコース
の酸化反応を行わせる場合には、以下の反応式に
示すように酸素O2が電子伝達体、特に電子受容
体としての働きをしている。
グルコース＋O2GOD
――――→
グルコノラクトン＋
H2O2
この酸素のように電子伝達体として知られてい
るレドツクス化合物としては、メチレンブルー、
２，６―ジクロロインドフエノール、インジゴジ
サルホネート、フエノサフラニン、フエナジンメ
トサルフエート、フエリシアン化カリ、ベンゾキ
ノン、クロラニル等がある。
本発明は、この電子伝達体として特性の優れた
新規な化合物、すなわち７，７，８，８―テトラ
シアノキノジメタン（以下、TCNQで表す）を
見出したものである。TCNQの構造式は次の通
りである。
The present invention relates to an enzyme electrode having a novel electron carrier. Enzymes are known to have substrate specificity and reaction specificity that cause only certain reactions to occur with respect to specific substances (substrates). When the biochemical reaction of such an enzyme is related to an electrochemical reaction, it can be applied to detecting the presence or absence of a target substance, and to construct a battery by combining an electrode with an immobilized enzyme and a counter electrode. Redox enzymes are mainly involved in energy conversion in living organisms. Generally, when redoxing a substrate by redox, an electron carrier is required. For example, when performing a glycose oxidation reaction using glucose oxidase (hereinafter referred to as GOD) as an enzyme, oxygen O 2 acts as an electron carrier, especially an electron acceptor, as shown in the reaction formula below. doing. Glucose + O 2 GOD ――――→ Gluconolactone +
H 2 O 2 Redox compounds known as electron carriers like oxygen include methylene blue,
Examples include 2,6-dichloroindophenol, indigo disulfonate, phenosafranin, phenazine methosulfate, potassium ferricyanide, benzoquinone, and chloranil. The present invention has discovered a novel compound with excellent properties as an electron carrier, namely 7,7,8,8-tetracyanoquinodimethane (hereinafter referred to as TCNQ). The structural formula of TCNQ is as follows.
【式】
TCNQが電子伝達体として働く酸化還元酵素
としては、フラヴインアデニンジヌクレオチド
（FAD）を有する酵素が有効であつた。例えば、
グルコースオキシダーゼ、キサンチンオキシダー
ゼ、アミノ酸オキシダーゼ、アルデヒドオキシダ
ーゼ、コレステロールオキシダーゼ、アルコール
オキシダーゼ等である。
レドツクス化合物は、TCNQを単体で用いて
もよいが、他のレドツクス化合物、例えばクロラ
ニル等と共存して用いてもよい。また、ゴム、高
分子等の種々のバインダー等ともちろん共存して
用いてもよいものである。
電子集電体とは、導電性材料である。例えば、
カーボン（グラフアイトを含む）、白金、金、銀、
イリジウム、パラジウム等の良導電材料、酸化ス
ズ、酸化インジムウ、酸化チタン等の半導体材料
がある。
以下、本発明を実施例により説明する。
実施例 １
TCNQとグラフアイト粉末を重量比で１：１
の割合に混合した後、プレス成形して厚さ約１mm
の円板状電極にした。この電極の片面にGODを
グルタルアルデヒドによる架橋法で固定化した。
このGOD固定化電極を第１図に示した測定系に
セツトした。
第１図において、１はアルゴンガスの導入口、
２は導出口、３は白金よりなる対極、４はガラス
の多孔体からなるセパレータ、５は酵素電極、６
は緩衝液、７は塩橋、８は飽和カロメル電極、９
はKClの飽和水溶液である。
GODを固定化した酵素電極５を飽和カロメル
電極８に対し＋0.4Vの定電位に設定する。一方、
緩衝液を十分アルガスでハブリングした後、グル
コースを５×10-4モル／ｌ注入したところ、第２
図に示すように、4μAのアノード電流増加が認め
られた。
実施例 ２
実施例１と同様にTCNQとグラフアイト粉末
からプレス成形した平板電極を作製した。この電
極の片面にＤ―アミノ酸オキシダーゼをグルタル
アルデヒドで固定化した。この固定電極を第１図
に示した測定系に組み込んだ。固定化電極を飽和
カロメル電極に対し、＋0.35Vの定電位に設定し
た。緩衝液を十分アルゴンガスでバブリング後、
Ｄ―ａ―アラニンを３×10-4モル／ｌ注入したと
ころ、0.1μAのアノード電流増加が認められた。
以上の実施例では、基質濃度測定について述べ
たが、本発明による酵素電極は、例えば実施例１
に述べたグルコースオキシダーゼ固定化酵素電極
の場合、対極として酸素電極を用いると、グルコ
ースを燃料とする燃料電池を構成することができ
る。
また、レドツクス化合物として従来公知の化合
物の多くは水に溶解しやすいが、TCNQは水に
ほとんど溶解しない難溶性化合物である。従つ
て、特に、集電体、レドツクス化合物、酵素を一
体化した電極を構成した場合、TCNQは溶出し
にくいため長寿命、安定な酵素電極を作製するこ
とが可能である。
以上のように、本発明は、新規なレドツクス化
合物を用いることにより、有効に酵素機能を利用
できるものである。[Formula] As an oxidoreductase in which TCNQ acts as an electron carrier, an enzyme containing flavin adenine dinucleotide (FAD) was effective. for example,
These include glucose oxidase, xanthine oxidase, amino acid oxidase, aldehyde oxidase, cholesterol oxidase, and alcohol oxidase. As for the redox compound, TCNQ may be used alone, but it may also be used in combination with other redox compounds such as chloranil. Furthermore, it may of course be used in combination with various binders such as rubber and polymers. An electron current collector is an electrically conductive material. for example,
Carbon (including graphite), platinum, gold, silver,
There are good conductive materials such as iridium and palladium, and semiconductor materials such as tin oxide, indium oxide, and titanium oxide. The present invention will be explained below using examples. Example 1 TCNQ and graphite powder in a weight ratio of 1:1
After mixing in the proportion of
It was made into a disc-shaped electrode. GOD was immobilized on one side of this electrode using a crosslinking method using glutaraldehyde.
This GOD-immobilized electrode was set in the measurement system shown in FIG. In Fig. 1, 1 is an argon gas inlet;
2 is an outlet, 3 is a counter electrode made of platinum, 4 is a separator made of a porous glass material, 5 is an enzyme electrode, 6
is a buffer solution, 7 is a salt bridge, 8 is a saturated calomel electrode, 9
is a saturated aqueous solution of KCl. The enzyme electrode 5 on which GOD is immobilized is set at a constant potential of +0.4 V with respect to the saturated calomel electrode 8. on the other hand,
After sufficiently hubbing the buffer solution with Argas, glucose was injected at 5 x 10 -4 mol/l.
As shown in the figure, an increase in anode current of 4 μA was observed. Example 2 In the same manner as in Example 1, a press-molded flat plate electrode was produced from TCNQ and graphite powder. D-amino acid oxidase was immobilized on one side of this electrode with glutaraldehyde. This fixed electrode was incorporated into the measurement system shown in FIG. The immobilized electrode was set at a constant potential of +0.35 V with respect to the saturated calomel electrode. After bubbling the buffer solution with argon gas,
When D-a-alanine was injected at 3×10 −4 mol/l, an increase in anode current of 0.1 μA was observed. In the above examples, substrate concentration measurement was described, but the enzyme electrode according to the present invention can be used, for example, in Example 1.
In the case of the glucose oxidase-immobilized enzyme electrode described in , if an oxygen electrode is used as the counter electrode, a fuel cell using glucose as fuel can be constructed. Additionally, many of the conventionally known redox compounds are easily soluble in water, but TCNQ is a sparingly soluble compound that hardly dissolves in water. Therefore, especially when an electrode is constructed in which a current collector, a redox compound, and an enzyme are integrated, it is possible to produce a long-life and stable enzyme electrode because TCNQ is difficult to elute. As described above, the present invention makes it possible to effectively utilize enzyme functions by using a novel redox compound.
第１図は酵素電極を用いた測定系の構成を示す
図、第２図はグリコース添加によるアノード電流
の変化を示す図である。
FIG. 1 is a diagram showing the configuration of a measurement system using an enzyme electrode, and FIG. 2 is a diagram showing changes in anode current due to glycose addition.
Claims (1)
を有する酸化還元酵素と、この酵素の電子伝達体
となるレドツクス化合物と、電子集電体からな
り、前記レドツクス化合物として少なくとも７，
７，８，８―テトラシアノキノジメタンを含有す
ることを特徴とする酵素電極。1 Flavin adenine dinucleotide (FAD)
an oxidoreductase with
An enzyme electrode characterized by containing 7,8,8-tetracyanoquinodimethane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55145156A JPS5769668A (en) | 1980-10-16 | 1980-10-16 | Enzyme electrode |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55145156A JPS5769668A (en) | 1980-10-16 | 1980-10-16 | Enzyme electrode |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5769668A JPS5769668A (en) | 1982-04-28 |
| JPS6346377B2 true JPS6346377B2 (en) | 1988-09-14 |
Family
ID=15378714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55145156A Granted JPS5769668A (en) | 1980-10-16 | 1980-10-16 | Enzyme electrode |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5769668A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2168815A (en) * | 1984-11-13 | 1986-06-25 | Genetics Int Inc | Bioelectrochemical assay electrode |
| FR2835655B1 (en) * | 2002-02-07 | 2004-03-12 | Commissariat Energie Atomique | FUEL CELL USING ENZYMES AS CATALYSTS OF CATHODIC AND / OR ANODIC REACTIONS |
| GB0500289D0 (en) * | 2005-01-07 | 2005-02-16 | Imp College Innovations Ltd | Electrodes |
-
1980
- 1980-10-16 JP JP55145156A patent/JPS5769668A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5769668A (en) | 1982-04-28 |
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