JPH0130832B2 - - Google Patents
Info
- Publication number
- JPH0130832B2 JPH0130832B2 JP4936686A JP4936686A JPH0130832B2 JP H0130832 B2 JPH0130832 B2 JP H0130832B2 JP 4936686 A JP4936686 A JP 4936686A JP 4936686 A JP4936686 A JP 4936686A JP H0130832 B2 JPH0130832 B2 JP H0130832B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon disulfide
- dithiolane
- reaction
- thione
- 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
Links
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 11
- XCWPBWWTGHQKDR-UHFFFAOYSA-N 1,3-dithiolane-2-thione Chemical class S=C1SCCS1 XCWPBWWTGHQKDR-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 238000000262 chemical ionisation mass spectrometry Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- CXYRUNPLKGGUJF-OZVSTBQFSA-M pamine Chemical compound [Br-].C1([C@@H](CO)C(=O)OC2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)C)=CC=CC=C1 CXYRUNPLKGGUJF-OZVSTBQFSA-M 0.000 description 3
- QMQSSUMAIXESIR-UHFFFAOYSA-N 4,4-dimethyl-1,3-dithiolane-2-thione Chemical compound CC1(C)CSC(=S)S1 QMQSSUMAIXESIR-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical compound S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- KGUJXUWJUOETGS-UHFFFAOYSA-N 1-sulfanylidenedithiolane Chemical class S=S1CCCS1 KGUJXUWJUOETGS-UHFFFAOYSA-N 0.000 description 1
- XRWMHJJHPQTTLQ-UHFFFAOYSA-N 2-(chloromethyl)thiirane Chemical compound ClCC1CS1 XRWMHJJHPQTTLQ-UHFFFAOYSA-N 0.000 description 1
- MBNVSWHUJDDZRH-UHFFFAOYSA-N 2-methylthiirane Chemical compound CC1CS1 MBNVSWHUJDDZRH-UHFFFAOYSA-N 0.000 description 1
- OQOIYECUXDNABI-UHFFFAOYSA-N 2-phenylthiirane Chemical compound C1SC1C1=CC=CC=C1 OQOIYECUXDNABI-UHFFFAOYSA-N 0.000 description 1
- XJCWNDPNURTXMH-UHFFFAOYSA-N 4-(chloromethyl)-1,3-dithiolane-2-thione Chemical compound ClCC1CSC(=S)S1 XJCWNDPNURTXMH-UHFFFAOYSA-N 0.000 description 1
- OVMVMMNHNMZUAS-UHFFFAOYSA-N 4-methyl-1,3-dithiolane-2-thione Chemical compound CC1CSC(=S)S1 OVMVMMNHNMZUAS-UHFFFAOYSA-N 0.000 description 1
- UNAVLWYSWPISLX-UHFFFAOYSA-N 4-phenyl-1,3-dithiolane-2-thione Chemical compound S1C(=S)SCC1C1=CC=CC=C1 UNAVLWYSWPISLX-UHFFFAOYSA-N 0.000 description 1
- PQWJNIJNYRPOAA-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]heptane Chemical compound C1CCCC2SC21 PQWJNIJNYRPOAA-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical compound [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 1
- 239000012989 trithiocarbonate Substances 0.000 description 1
Landscapes
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Description
【発明の詳細な説明】
本発明は１，３−ジチオラン−２−チオン誘導
体の製造法に関するもので、より詳細にはこれら
の化合物を、チイラン化合物と二硫化炭素とを塩
基の存在下に高圧で反応させることにより簡単に
かつ収率よく製造する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 1,3-dithiolane-2-thione derivatives, and more specifically, the present invention relates to a method for producing 1,3-dithiolane-2-thione derivatives. The present invention relates to a method for producing easily and with good yield by reacting with
（産業上の利用分野）
従来、１，３−ジチオラン−２−チオンの誘導
体には、電荷移動錯体であるTTF（テトラチアフ
ルバレンの合成中間体としての利用が多数知られ
ており、また近年では生理活性物質の中間材料と
しての利用も多数報告されている。（U.
S.4131683、Berg.876202、U.S.4172941、U.
S.4206119）。(Industrial Application Field) Traditionally, derivatives of 1,3-dithiolane-2-thione include TTF, a charge transfer complex, which is known to be used as a synthetic intermediate for tetrathiafulvalene, and in recent years, Many reports have also been made of its use as an intermediate material for physiologically active substances. (U.
S.4131683, Berg.876202, US4172941, U.
S.4206119).
（発明が解決しようとする問題点）
このように１，３−ジチオラン−２−チオンの
誘導体は有用な化合物であるが、現在は１，２−
ジチオールのナトリウム塩とチオホスゲンとの反
応、トリチオ炭酸のナトリウム塩と１，２−ジハ
ロゲノ化合物との反応などにより合成されている
が、操作が複雑であり、精製が困難な場合もあ
る。塩基を用いたチイランと二硫化炭素との反応
はエチレンスルフイド以外のチイランを用た場合
は収率が低く実用的ではなかつた。(Problems to be Solved by the Invention) As described above, 1,3-dithiolane-2-thione derivatives are useful compounds, but currently 1,2-dithiolane-2-thione derivatives are useful compounds.
It is synthesized by the reaction of the sodium salt of dithiol with thiophosgene, the reaction of the sodium salt of trithiocarbonate with a 1,2-dihalogeno compound, etc., but the operations are complicated and purification may be difficult. The reaction between thiirane and carbon disulfide using a base was impractical due to low yields when thiirane other than ethylene sulfide was used.
したがつて、本発明の目的は１，３−ジチオラ
ン−２−チオン誘導体の効率的な製造方法を開発
することである。 Therefore, an object of the present invention is to develop an efficient method for producing 1,3-dithiolane-2-thione derivatives.
（問題点を解決するための手段）
本発明者らは高圧条件下にチイラン１と二硫化
炭素とを塩基の存在下反応させることにより１，
３−ジチオラン−２−チオン誘導体２を高収率で
製造できることを見出し、本発明を完成するに至
つた。(Means for solving the problem) The present inventors reacted thiirane 1 and carbon disulfide under high pressure conditions in the presence of a base.
It was discovered that 3-dithiolane-2-thione derivative 2 can be produced in high yield, and the present invention was completed.
すなわち本発明は
一般式
（式中R1はアルキル基、アリール基、又は水素
原子であり、R2、R3はアルキル基又は水素原子
を表わす。）
で示されるチイランと二硫化炭素とを塩基の存在
下、高圧をかけて反応させることを特徴とする
一般式
（式中R1、R2及びR3は前記と同じ意味を持つ。）
で示される１，３−ジチオラン−２−チオン誘導
体の製造方法を提供するものである。 That is, the present invention has the general formula (In the formula, R 1 is an alkyl group, an aryl group, or a hydrogen atom, and R 2 and R 3 are an alkyl group or a hydrogen atom.) Thiirane and carbon disulfide are heated under high pressure in the presence of a base. general formula characterized by the reaction (In the formula, R 1 , R 2 and R 3 have the same meanings as above.)
The present invention provides a method for producing a 1,3-dithiolane-2-thione derivative shown in the following.
本発明の出発原料であるチイラン化合物１は相
当するエポキシドよりチオ尿素またはチオシアン
酸カリウムを用いて容易に合成でき、二硫化炭素
も安価に市販されている。したがつて化合物１を
適宜に選択することによりR1、R2及びR3にいて
所望の置換基を導入した任意の１，３−チオラン
−２−チオン誘導体を製造することができる。な
お本発明においてR1〜R3は反応に不活性な置換
基でさらに置換されている場合も包含する。 Thiirane compound 1, which is the starting material of the present invention, can be easily synthesized from the corresponding epoxide using thiourea or potassium thiocyanate, and carbon disulfide is also commercially available at low cost. Therefore, by appropriately selecting Compound 1, any 1,3-thiolane-2-thione derivative having desired substituents introduced at R 1 , R 2 and R 3 can be produced. In the present invention, R 1 to R 3 also include cases where they are further substituted with a substituent inert to the reaction.
次に本発明における目的化合物２の生成経路を
塩基としてトリエチルアミンを用いたイソブチレ
ンスルフイドと二硫化炭素との反応を例にとれば
下記の式(3)のように表現できる。 Next, if we take as an example the reaction between isobutylene sulfide and carbon disulfide using triethylamine as a base, the production route of the target compound 2 in the present invention can be expressed as shown in the following formula (3).
本発明の反応は通常、第三級アミン触媒の存在
下にて高圧条件下で行なわれる。例えばトリエチ
ルアミン、ピリジン等が触媒として用いられた。
圧力は高圧ほど好ましいが、一般には500〜9000
Kg／cm2の範囲で選択される。反応温度は特に制約
されないが、副反応の進行を抑制する意味では室
温〜100℃の温度の採用が好ましい。反応時間は
圧力、温度等に左右されるが、通常５〜50時間で
十分である。 The reaction of the present invention is typically carried out under high pressure conditions in the presence of a tertiary amine catalyst. For example, triethylamine, pyridine, etc. were used as catalysts.
The higher the pressure, the better, but generally 500 to 9000
Selected in the range of Kg/ cm2 . Although the reaction temperature is not particularly limited, it is preferable to use a temperature between room temperature and 100°C in order to suppress the progress of side reactions. The reaction time depends on pressure, temperature, etc., but usually 5 to 50 hours is sufficient.
反応混合物から過剰の二硫化炭素を留去したの
ち減圧蒸留もしくは再結晶することにより本発明
の目的化合物が純度よく得られる。かくして得ら
れた目的化合物は、IR、NMS、MSを分析する
ことによりその構造を確認できる。 The target compound of the present invention can be obtained with high purity by distilling off excess carbon disulfide from the reaction mixture and then distilling it under reduced pressure or recrystallizing it. The structure of the target compound thus obtained can be confirmed by analyzing IR, NMS, and MS.
（発明の効果）
本発明によれば１，３−ジチオラン−２−チオ
ン類を高収率つ効率的に製造することができる。(Effects of the Invention) According to the present invention, 1,3-dithiolane-2-thiones can be produced efficiently with high yield.
（実施例）
次に本発明を実施例に基づきさらに詳細に説明
する。(Examples) Next, the present invention will be described in more detail based on Examples.
実施例 １
テフロンチユーブにイソブチレンスルフイド
0.88ｇ、トリエチルアミン0.10ｇ、及び二硫化炭
素38.0ｇを封入し、高圧反応装置に入れて8000
Kg／cm2に加圧し40℃で20時間反応した。圧を常圧
に戻したのち反応物をとり出し、過剰の二硫化炭
素を留去した。残留物を減圧蒸留することにより
４，４−ジメチル−１，３−ジチオラン−２−チ
オンを収率87.8％で得た。Example 1 Isobutylene sulfide in Teflon tube
0.88 g, triethylamine 0.10 g, and carbon disulfide 38.0 g were sealed and placed in a high pressure reactor and heated to 8000 g.
The pressure was increased to Kg/cm 2 and the reaction was carried out at 40°C for 20 hours. After the pressure was returned to normal pressure, the reactant was taken out, and excess carbon disulfide was distilled off. The residue was distilled under reduced pressure to obtain 4,4-dimethyl-1,3-dithiolane-2-thione in a yield of 87.8%.
IR；1089cm-1、1054cm-1
CI−MSによるQM+；165
NMR；1.74（Ｓ、6H、2CH3）、3.76（Ｓ、2H、
CH2）
実施例 ２
前記と同様にしてイソブチレンスルフイド0.88
ｇ、トリエチルアミン0.10ｇ、及び二硫化炭素
3.80ｇを2000Kg／cm2、70℃で20時間反応させた。
前記と同様の処理により４，４−ジメチル−１，
３−ジチオラン−２−チオンを収率96％で得た。 IR; 1089 cm -1 , 1054 cm -1 QM + by CI-MS; 165 NMR; 1.74 (S, 6H, 2CH 3 ), 3.76 (S, 2H,
CH 2 ) Example 2 Isobutylene sulfide 0.88 in the same manner as above
g, triethylamine 0.10 g, and carbon disulfide
3.80g was reacted at 2000Kg/cm 2 at 70°C for 20 hours.
By the same treatment as above, 4,4-dimethyl-1,
3-dithiolane-2-thione was obtained in a yield of 96%.
実施例 ３
前記と同様にしてシクロヘキセンスルフイド
0.98ｇ、トリエチルアミン0.10ｇ、及び二硫化炭
素3.80ｇを8000Kg／cm2、40℃で20時間反応させ
た。反応物は過剰の二硫化炭素を留去したのちエ
タノールで再結晶することにより４，５−テトラ
メチレン−１，３−ジチオラン−２−チオンを収
率97％で得た。Example 3 Cyclohexene sulfide was prepared in the same manner as above.
0.98g of triethylamine, 0.10g of triethylamine, and 3.80g of carbon disulfide were reacted at 8000Kg/cm 2 at 40°C for 20 hours. After distilling off excess carbon disulfide, the reaction product was recrystallized from ethanol to obtain 4,5-tetramethylene-1,3-dithiolane-2-thione in a yield of 97%.
IR；1058cm-1、1033cm-1
CI−MSによるQM+；191
NMR；1.00〜2.40（ｍ、8H、CH2）、3.90〜4.35
（ｍ、2H、2CH）
実施例 ４
前記と同様にしてスチレンスルフイド1.36ｇ、
トリエチルアミン0.10ｇ及び二硫化炭素3.80ｇを
8000Kg／cm2、100℃で20時間反応させた。反応物
は過剰の二硫化炭素を留去したのちエタノールで
再結晶することにより４−フエニル−１，３−ジ
チオラン−２−チオンを収率91％で得た。 IR; 1058 cm -1 , 1033 cm -1 QM + by CI-MS; 191 NMR; 1.00-2.40 (m, 8H, CH 2 ), 3.90-4.35
(m, 2H, 2CH) Example 4 1.36g of styrene sulfide in the same manner as above,
0.10g of triethylamine and 3.80g of carbon disulfide
The reaction was carried out at 8000Kg/cm 2 and 100°C for 20 hours. After distilling off excess carbon disulfide, the reaction product was recrystallized from ethanol to obtain 4-phenyl-1,3-dithiolane-2-thione in a yield of 91%.
IR；1047cm-1
CI−MSによるQM+、213
NMR；3.90〜4.40（ｍ、2H、CH2）、5.55〜5.80
（dd、1H、CH）、7.25〜7.70（ｍ、5H、
C6H5）
実施例 ５
前記と同様にして３−クロルプロピレンスルフ
イド1.08ｇ、トリエチルアミン0.30ｇ及び二硫化
炭素3.80ｇを5000Kg／cm2、100℃で20時間反応さ
せた。反応物は過剰の二硫化炭素を留去したのち
減圧蒸留より４−クロロメチル−１，３−ジチオ
ラン−２−チオンを収率32％で得た。 IR; 1047 cm -1 QM + by CI-MS, 213 NMR; 3.90-4.40 (m, 2H, CH 2 ), 5.55-5.80
(dd, 1H, CH), 7.25-7.70 (m, 5H,
C 6 H 5 ) Example 5 In the same manner as above, 1.08 g of 3-chloropropylene sulfide, 0.30 g of triethylamine and 3.80 g of carbon disulfide were reacted at 5000 Kg/cm 2 at 100° C. for 20 hours. After removing excess carbon disulfide, the reaction product was distilled under reduced pressure to obtain 4-chloromethyl-1,3-dithiolane-2-thione in a yield of 32%.
IR；1067cm-1、1039cm-1、
CI−MSによるQM+；185
NMR；3.55〜4.05（ｍ、2H、CH2）、4.05〜4.30
（ｍ、2H、CH2）、4.30〜4.65（ｍ、1H、
CH）
実施例 ６
前記と同様にしてプロピレンスルフイド0.74
ｇ、トリエチルアミン0.10ｇ及び二硫化炭素3.80
ｇを8000Kg／cm2、40℃で20時間反応させた。反応
物は過剰の二硫化炭素を留去したのち減圧蒸留に
より４−メチル−１，３−ジチオラン−２−チオ
ンを収率97％で得た。 IR; 1067 cm -1 , 1039 cm -1 , QM + by CI-MS; 185 NMR; 3.55-4.05 (m, 2H, CH 2 ), 4.05-4.30
(m, 2H, CH 2 ), 4.30~4.65 (m, 1H,
CH) Example 6 Propylene sulfide 0.74 in the same manner as above
g, triethylamine 0.10 g and carbon disulfide 3.80 g
8000Kg/cm 2 and 40°C for 20 hours. After removing excess carbon disulfide, the reaction product was distilled under reduced pressure to obtain 4-methyl-1,3-dithiolane-2-thione in a yield of 97%.
IR：1076cm-1、1050cm-1、1033cm-1
CI−MSよるQM+；151
NMR；1.64（ｄ、3H、CH3）、3.55〜3.85（ｄ、
2H、CH2の1H）、3.95〜4.20（ｄ、1H、
CH2の1H）、4.35〜4.75（ｍ、1H、CH） IR: 1076 cm -1 , 1050 cm -1 , 1033 cm -1 QM + by CI-MS; 151 NMR; 1.64 (d, 3H, CH 3 ), 3.55-3.85 (d,
2H, 1H of CH 2 ), 3.95-4.20 (d, 1H,
CH 2 1H), 4.35-4.75 (m, 1H, CH)
Claims (1)
原子であり、R2、R3はアルキル基又は水素原子
を表わす。） で示されるチイランと二硫化炭素とを塩基の存在
下、高圧をかけて反応させることを特徴とする 一般式 （式中R1、R2、及びR3は前記と同じ意味を持
つ。） で示される１，３ジチオラン−２−チオン誘導体
の製造方法。[Claims] 1. General formula (In the formula, R 1 is an alkyl group, an aryl group, or a hydrogen atom, and R 2 and R 3 are an alkyl group or a hydrogen atom.) Thiirane and carbon disulfide are heated under high pressure in the presence of a base. general formula characterized by the reaction (In the formula, R 1 , R 2 and R 3 have the same meanings as above.) A method for producing a 1,3 dithiolane-2-thione derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4936686A JPS62207268A (en) | 1986-03-06 | 1986-03-06 | Production of 1,3-dithiolane-2-thione derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4936686A JPS62207268A (en) | 1986-03-06 | 1986-03-06 | Production of 1,3-dithiolane-2-thione derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62207268A JPS62207268A (en) | 1987-09-11 |
| JPH0130832B2 true JPH0130832B2 (en) | 1989-06-22 |
Family
ID=12829018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4936686A Granted JPS62207268A (en) | 1986-03-06 | 1986-03-06 | Production of 1,3-dithiolane-2-thione derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62207268A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7541319B2 (en) * | 2004-10-26 | 2009-06-02 | Chemtura Corporation | 1,3-dithiolane-2-thione additives for lubricants and fuels |
| KR100832128B1 (en) | 2007-04-20 | 2008-05-27 | 경희대학교 산학협력단 | Method for producing alkylene trithiocarbonate |
| KR100898319B1 (en) | 2007-05-29 | 2009-05-20 | 경희대학교 산학협력단 | Method for preparing alkylene trithiocarbonate using imidazolium halide |
| JP5858212B2 (en) * | 2011-03-31 | 2016-02-10 | 和光純薬工業株式会社 | Method for producing cyclic trithiocarbonate |
-
1986
- 1986-03-06 JP JP4936686A patent/JPS62207268A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62207268A (en) | 1987-09-11 |
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