JPS6130650B2 - - Google Patents
Info
- Publication number
- JPS6130650B2 JPS6130650B2 JP4799079A JP4799079A JPS6130650B2 JP S6130650 B2 JPS6130650 B2 JP S6130650B2 JP 4799079 A JP4799079 A JP 4799079A JP 4799079 A JP4799079 A JP 4799079A JP S6130650 B2 JPS6130650 B2 JP S6130650B2
- Authority
- JP
- Japan
- Prior art keywords
- aluminum
- aspirin
- heavy
- present
- alumina gel
- 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
- GKJRJGXKDYCFNF-UHFFFAOYSA-K aluminum;2-acetyloxybenzoate Chemical compound [Al+3].CC(=O)OC1=CC=CC=C1C([O-])=O.CC(=O)OC1=CC=CC=C1C([O-])=O.CC(=O)OC1=CC=CC=C1C([O-])=O GKJRJGXKDYCFNF-UHFFFAOYSA-K 0.000 claims description 27
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 17
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 claims description 7
- 239000000017 hydrogel Substances 0.000 claims description 6
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 5
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910001388 sodium aluminate Inorganic materials 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000908 ammonium hydroxide Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 14
- 239000000499 gel Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 9
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000000428 dust Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 102100026123 Pirin Human genes 0.000 description 1
- 101710176373 Pirin Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は医薬品製剤の原料として使用するに際
して取扱いの容易な流動性の良い重質１塩基性ア
ルミニウムアセチルサリチレートの製造方法に関
する。
近年、ピリン系解熱鎮痛薬の使用が制限された
ことに伴ない、アセチルサリチル酸（以下アスピ
リンと称する）やそのアルミニウム塩である１−
塩基性アルミニウムアセチルサリチレート（以下
アスピリンアルミニウムと称する）の使用の頻度
が高くなつてきた。
殊にアスピリンアルミニウムはアスピリンに比
べて胃腸障害が少ない為に特に繁用される様にな
つて来た。
しかるに従来知られ、もしくは使用されている
アスピリンアルミニウムはその粒子が極めて微細
で粉塵化し易く、かつ、嵩高で、付着性が強く、
流動性の悪いものである為、製剤用原流として使
用するに際して作業者の健康を害したり、他の製
剤への混入を起し易く、又製剤の体積を所望の範
囲内に抑え難く、更に製剤に当つて混合、篩過、
練合、造粒、乾燥、打錠時の作業能率が悪い等製
剤上極めて欠点の多いものであつた。
本発明者らは、嵩が低く、粉塵化し難く、流動
性の良いアスピリンアルミニウムをうる為に鋭意
研究を重ねたところ、本発明の方法により前述し
た従来のアスピリンアルミニウムに見られる如き
諸々の欠点のない重質アスピリンアルミニウムを
うることに成功した。したがつて、本発明は、流
動性の良い重質アスピリンアルミニウムの製法を
提供するものである。
即ち、本発明は水酸化ナトリウム、アルミン酸
ナトリウム及び水酸化アンモニウムから選ばれた
１種もしくは２種以上のアルカリと硫酸アルミニ
ウムとを反応させることにより得られる生成物を
水洗して得た活性な水酸化アルミニウムヒドロゲ
ル（以下アルミナゲルと称する）とアスピリンと
を45〜65℃で、PH2.8〜3.5で反応させることを特
徴とする流動性の良い重質アスピリンアルミニウ
ムの製造方法を提供するものである。
以下に本発明を詳細に説明する。本発明方法に
おいては、水酸化アルミニウムヒドロゲルは水酸
化ナトリウム、アルミン酸ナトリウム及び水酸化
アンモニウムから選ばれた１種もしくは２種以上
のアルカリと硫酸アルミニウムとを反応させて調
製されるものであるが、この場合に生成した水酸
化アルミニウムヒドロゲル（以下アルミナゲルと
記す）は、その中に含まれている、硫酸ナトリウ
ム及び又は硫酸アンモニウムを除去するため、例
えば洗浄式圧過機（フイルタープレス）、流下
過式洗浄機（フイルターウオツシヤー）、連続
向流シツクナー及び洗浄式円筒真空過機などで
洗浄される。この水酸化アルミニウムヒドロゲル
の調製にあたつては、硫酸アルミニウムと上記の
アルカリとを等モル近辺で連続的に少量ずつ添加
すると、得られたアルミナゲルが最も過性及び
通水性の良いことが見い出された。
アルミナゲルとアスピリンとの反応に際しての
反応液の濃度はアスピリンアルミニウムとして15
W/V%前後となる様にアルミナゲル及びアスピ
リンを仕込むが、その際のモル比はアスピリン２
に対してアルミニウム１〜1.1である。
この場合の反応温度は45〜65℃に保つが、65℃
を越える温度にすると原料アスピリン及び生成し
たアスピリンアルミニウムが共に加水分解を受け
易くなり好ましくない。又45℃より低い温度では
反応が進行しにくくなる。
本発明方法の目的を達成するには反応を緩徐に
起こさせ、反応時間をかけて生成するアスピリン
アルミニウムの結晶を大きく均一に成長させる必
要がある。従つて溶存アスピリンが加水分解を受
けにくく、アルミナゲルが重合しないようにする
ことは長時間の反応を可能とするための必須な要
件となる。本発明方法におけるアルミナゲルとア
スピリンとの反応液のPHは2.8〜3.5であるが、そ
の範囲では溶存アスピリン（pKa＝3.5）の50％
以上が分子型なので比較的加水分解も受けにく
く、かつまた、アルミナゲルも更に重合して不活
性化されることもない。一方、アルミナゲルを水
洗しないでアスピリン末と反応させようとする
と、共存塩類である硫酸ナトリウム及び又は硫酸
アンモニウムの緩衝作用によりその懸濁液PHは約
4.3となり、このPHではアスピリンの殆んどがイ
オン型で分解しやすくなり、またアルミナゲル
は、より高度に重合して不活性化するため目的と
する重質アスピリンアルミニウムは得られないこ
ととなる。
撹拌の操作は反応液中に気泡を巻き込むことな
く、かつ、沈積物が生じない状態に保ちうる様な
速度で行なう。
反応時間は通常６〜10時間である。
生成した重質アスピリンアルミニウムの沈澱は
水洗した後、過し、乾燥して粉末とする。本発
明方法によつて得られる重質アスピリンアルミニ
ウムは過性が極めて良好で、又ケーキ状沈澱と
して得られる際にも容易にほぐれてしかも付着性
が少ない。これらの性質は製造作業上において
も、著しい利点となる。
かくして得られた重質アスピリンアルミニウム
の粉末は、嵩が低く、粉塵化し難く、付着性が少
なく、又流動性に富んでいるので作業性が良く、
製剤用原料として使用する際に従来のアスピリン
アルミニウムに見られない利点を有するものであ
る。
次に本発明を実施例を挙げて具体的に説明す
る。
実施例 １
硫酸アルミニウム溶液（Al2O37.8％含有）180
とアルミン酸ナトリウム溶液（Na2O／Al2O3＝
1.7、Al2O310.2％含有）180とを、温度30℃、
生成液PHを７〜８に保持しつつ、撹拌しながら
200の水に同時に滴下する。通水型フイルター
プレスにより生成物を洗浄、ロ過したのち再び水
に懸濁する。
得られたアルミナゲル懸濁液（Al2O39.5％含
有）100に水300を加えたのち撹拌しながらア
スピリン62.2Kgを加えて分散させ、次いで50℃で
８時間撹拌を継続し、生成物を遠心分離機により
洗浄、脱水し、奈良式パドルドライヤーにより乾
燥したのち粉砕して見掛け比容積2.0ml/ｇの重質
アスピリンアルミニウム粉末67Kgを得た。
実施例 ２
25％硫酸アルミニウム溶液と９％水酸化アンモ
ニウム溶液とを用い、実施例１と同様に処理して
得たアルミナゲル懸濁液（Al2O35％含有）150
に水250を注加してからアスピリン53.6Kgを添
加し、60℃６時間撹拌後、以下実施例１と同様に
処理して見掛け比容積2.1ml/ｇの重質アスピリン
アルミニウム粉末54Kgを得た。
実施例 ３
水酸化ナトリウム12Kgとアルミン酸ナトリウム
（Na2O／Al2O3＝1.7、Al2O319％含有）50Kgを含
む溶液180と45％硫酸アルミニウム溶液180と
を用い、実施例１と同様に処理して得たアルミナ
ゲル懸濁液（Al2O36.8％含有）140に水260を
注加してからアスピリン62.2Kgを添加し、50℃８
時間撹拌後、以下実施例１と同様に処理して見掛
け比容積2.1ml/ｇの重質アスピリンアルミニウム
粉末67.5Kgを得た。
本発明方法により得られた重質アスピリンアル
ミニウムの物性値を市販のアスピリンアルミニウ
ムと比較した結果を第１表に示す。この表から、
本発明方法により得られる製品が重質でかつ、流
動の良いものであることがわかる。特に比容積に
ついて見ると市販のアスピリンアルミニウムは30
ml/ｇ前後であるのに対して、本発明方法により
得られた重質アスピリンアルミニウムでは2.0ml/
ｇ前後である。このような性質を有する本発明製
品は製剤作業に際して、特に大量の材料を取扱う
場合に極めて大きな利点をもたらすものである。
The present invention relates to a method for producing heavy monobasic aluminum acetylsalicylate, which is easy to handle and has good fluidity when used as a raw material for pharmaceutical preparations. In recent years, as the use of pirin antipyretic analgesics has been restricted, acetylsalicylic acid (hereinafter referred to as aspirin) and its aluminum salt 1-
Basic aluminum acetylsalicylate (hereinafter referred to as aspirin aluminum) has been used with increasing frequency. In particular, aspirin aluminum has become particularly popular because it causes fewer gastrointestinal disorders than aspirin. However, the conventionally known or used aspirin aluminum has extremely fine particles and easily becomes dust, is bulky, and has strong adhesive properties.
Because it has poor fluidity, when used as a raw material for pharmaceutical preparations, it may harm the health of workers, easily cause contamination with other preparations, and make it difficult to keep the volume of the preparation within the desired range. Mixing, sieving,
It had many drawbacks in terms of formulation, such as poor working efficiency during kneading, granulation, drying, and tableting. The present inventors have conducted extensive research to obtain aspirin aluminum that is low in bulk, difficult to turn into dust, and has good fluidity, and has found that the method of the present invention overcomes the various drawbacks of conventional aspirin aluminum described above. succeeded in obtaining heavy aspirin aluminum. Therefore, the present invention provides a method for producing heavy aspirin aluminum with good fluidity. That is, the present invention provides activated water obtained by washing with water a product obtained by reacting one or more alkalis selected from sodium hydroxide, sodium aluminate, and ammonium hydroxide with aluminum sulfate. Provided is a method for producing heavy aspirin aluminum with good fluidity, which is characterized by reacting aluminum oxide hydrogel (hereinafter referred to as alumina gel) and aspirin at 45 to 65°C and pH 2.8 to 3.5. . The present invention will be explained in detail below. In the method of the present invention, aluminum hydroxide hydrogel is prepared by reacting aluminum sulfate with one or more alkalis selected from sodium hydroxide, sodium aluminate, and ammonium hydroxide. In order to remove the sodium sulfate and/or ammonium sulfate contained in the aluminum hydroxide hydrogel (hereinafter referred to as alumina gel) produced in this case, the aluminum hydroxide hydrogel (hereinafter referred to as alumina gel) is processed using, for example, a washing-type pressure press (filter press) or a flowing-through type. It is cleaned using a washer (filter washer), a continuous countercurrent thickener, a cleaning cylindrical vacuum filtration machine, etc. In preparing this aluminum hydroxide hydrogel, it has been found that when aluminum sulfate and the above-mentioned alkali are continuously added in small amounts in equimolar amounts, the resulting alumina gel has the best permeability and water permeability. It was. When reacting alumina gel with aspirin, the concentration of the reaction solution is 15% as aspirin aluminum.
Alumina gel and aspirin are prepared so that the W/V% is around 2.
aluminum to 1 to 1.1. The reaction temperature in this case is kept at 45-65℃, but 65℃
If the temperature exceeds 100%, both the raw material aspirin and the produced aspirin aluminum are susceptible to hydrolysis, which is not preferable. Furthermore, at temperatures lower than 45°C, the reaction will be difficult to proceed. In order to achieve the purpose of the method of the present invention, it is necessary to cause the reaction to occur slowly and to grow large and uniform crystals of aspirin aluminum over the reaction time. Therefore, it is essential to ensure that dissolved aspirin is not susceptible to hydrolysis and that alumina gel is not polymerized in order to enable a long reaction time. In the method of the present invention, the pH of the reaction solution of alumina gel and aspirin is 2.8 to 3.5, and within this range, 50% of the dissolved aspirin (pKa = 3.5)
Since the above is a molecular type, it is relatively resistant to hydrolysis, and furthermore, the alumina gel is not further polymerized and inactivated. On the other hand, if you attempt to react alumina gel with aspirin powder without washing it with water, the pH of the suspension will be approximately
At this pH, most of the aspirin becomes ionic and easily decomposes, and the alumina gel polymerizes to a higher degree and becomes inactive, making it impossible to obtain the desired heavy aspirin aluminum. . Stirring is performed at a speed that does not introduce bubbles into the reaction solution and keeps the reaction solution free from deposits. The reaction time is usually 6 to 10 hours. The produced heavy aspirin aluminum precipitate is washed with water, filtered, and dried to form a powder. The heavy aspirin aluminum obtained by the method of the present invention has extremely good permeability, and even when obtained as a cake-like precipitate, it is easily loosened and has little adhesion. These properties also provide significant advantages in manufacturing operations. The thus obtained heavy aspirin aluminum powder has a low bulk, is difficult to turn into dust, has little adhesion, and is highly fluid, so it has good workability.
When used as a raw material for pharmaceutical preparations, it has advantages not found in conventional aspirin aluminum. Next, the present invention will be specifically described with reference to Examples. Example 1 Aluminum sulfate solution (containing 7.8% Al 2 O 3 ) 180
and sodium aluminate solution (Na 2 O/Al 2 O 3 =
1.7, containing 10.2% Al 2 O 3 ) 180, temperature 30℃,
While stirring while maintaining the pH of the product liquid at 7 to 8.
200 drops into water at the same time. The product is washed and filtered using a water filter press and then resuspended in water. After adding 300 g of water to 100 g of the obtained alumina gel suspension (containing 9.5% Al 2 O 3 ), 62.2 kg of aspirin was added and dispersed with stirring, and stirring was continued at 50°C for 8 hours to form a product. The product was washed and dehydrated using a centrifuge, dried using a Nara paddle dryer, and pulverized to obtain 67 kg of heavy aspirin aluminum powder with an apparent specific volume of 2.0 ml/g. Example 2 Alumina gel suspension (containing 5% Al 2 O 3 ) obtained by the same treatment as in Example 1 using 25% aluminum sulfate solution and 9% ammonium hydroxide solution 150
After adding 250 g of water, 53.6 kg of aspirin was added, and after stirring at 60°C for 6 hours, the following treatment was carried out in the same manner as in Example 1 to obtain 54 kg of heavy aspirin aluminum powder with an apparent specific volume of 2.1 ml/g. . Example 3 Using a solution 180 containing 12 kg of sodium hydroxide and 50 kg of sodium aluminate (Na 2 O / Al 2 O 3 = 1.7, containing 19% Al 2 O 3 ) and 180 45% aluminum sulfate solution, Example 1 After adding 260 g of water to 140 g of alumina gel suspension (containing 6.8% Al 2 O 3 ) obtained by the same treatment as above, 62.2 kg of aspirin was added, and the mixture was heated at 50℃8.
After stirring for an hour, the mixture was treated in the same manner as in Example 1 to obtain 67.5 kg of heavy aspirin aluminum powder with an apparent specific volume of 2.1 ml/g. Table 1 shows the results of comparing the physical properties of heavy aspirin aluminum obtained by the method of the present invention with commercially available aspirin aluminum. From this table,
It can be seen that the product obtained by the method of the present invention is heavy and has good fluidity. Especially when looking at the specific volume, commercially available aspirin aluminum is 30
ml/g, whereas for heavy aspirin aluminum obtained by the method of the present invention, it is 2.0ml/g.
It is around g. The product of the present invention having such properties brings extremely great advantages during formulation operations, particularly when handling large quantities of materials.
【表】
更に本発明方法により得られる重質アスピリン
アルミニウムを用いた場合の製剤上の利点を例示
的に説明する。[Table] Furthermore, the advantages in formulation when using heavy aspirin aluminum obtained by the method of the present invention will be exemplified.
【表】【table】
【表】
ルロース
[Table] Lurose
Claims (1)
び水酸化アンモニウムの内から選ばれた１種もし
くは２種以上のアルカリと硫酸アルミニウムとを
反応させて得られる生成物を水洗して得た活性な
水酸化アルミニウムヒドロゲルとアセチルサリチ
ル酸とを45〜65℃でPH2.8〜3.5で反応させること
を特徴とする流動性の良い重質１塩基性アルミニ
ウムアセチルサリチレートの製造方法。1 Active aluminum hydroxide hydrogel obtained by washing the product obtained by reacting one or more alkalis selected from sodium hydroxide, sodium aluminate, and ammonium hydroxide with aluminum sulfate with water. A method for producing heavy monobasic aluminum acetylsalicylate with good fluidity, which comprises reacting acetylsalicylic acid and acetylsalicylic acid at 45 to 65°C and pH 2.8 to 3.5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4799079A JPS55141438A (en) | 1979-04-20 | 1979-04-20 | Preparation of ground mono-basic aluminum acetylsalicylate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4799079A JPS55141438A (en) | 1979-04-20 | 1979-04-20 | Preparation of ground mono-basic aluminum acetylsalicylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55141438A JPS55141438A (en) | 1980-11-05 |
| JPS6130650B2 true JPS6130650B2 (en) | 1986-07-15 |
Family
ID=12790750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4799079A Granted JPS55141438A (en) | 1979-04-20 | 1979-04-20 | Preparation of ground mono-basic aluminum acetylsalicylate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55141438A (en) |
-
1979
- 1979-04-20 JP JP4799079A patent/JPS55141438A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55141438A (en) | 1980-11-05 |
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