JPH0149349B2 - - Google Patents
Info
- Publication number
- JPH0149349B2 JPH0149349B2 JP5432184A JP5432184A JPH0149349B2 JP H0149349 B2 JPH0149349 B2 JP H0149349B2 JP 5432184 A JP5432184 A JP 5432184A JP 5432184 A JP5432184 A JP 5432184A JP H0149349 B2 JPH0149349 B2 JP H0149349B2
- Authority
- JP
- Japan
- Prior art keywords
- caprolactam
- sulfuric acid
- acid
- distilled
- solution
- 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
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 88
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 10
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 10
- 239000012071 phase Substances 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- YKHZGLKQBYTRHO-UHFFFAOYSA-N 11-cyanoundecanoic acid Chemical compound OC(=O)CCCCCCCCCCC#N YKHZGLKQBYTRHO-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000012535 impurity Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- -1 cyclic lactams Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は、12―ナイロンモノマーである12―ア
ミノドデカン酸（以下ADAという）の製造方法
において、1.1―パーオキシジシクロヘキシルア
ミン（以下PXAという）の熱分解により11―シ
アノウンデカン酸（以下CUAという）を製造す
る際に副生するε―カプロラクタム水溶液から高
純度のε―カプロラクタムを回収する方法に関す
る。Detailed Description of the Invention The present invention provides a method for producing 12-aminododecanoic acid (hereinafter referred to as ADA), which is a 12-nylon monomer, by thermally decomposing 1,1-peroxydicyclohexylamine (hereinafter referred to as PXA). This invention relates to a method for recovering highly purified ε-caprolactam from an aqueous ε-caprolactam solution that is produced as a by-product during the production of undecanoic acid (hereinafter referred to as CUA).
PXAの熱分解で生成したCUA溶液よりCUAと
シクロヘキサノンおよびε―カプロラクタムに分
離する方法が提案されている（特公昭57−25029
号公報参照）。しかし、この方法で得られたε―
カプロラクタムは数wt％のε―カプロラクタム
希薄溶液で、しかも硫安などの無機物の他に熱分
解時に生成する炭素数５〜12を中心としたアミド
やカルボン酸などの鎖状および環状の従来のラク
タム製造方法とは違つた多種類の不純物を含有し
ている。このため、このε―カプロラクタムの希
薄溶液から繊維用ナイロン原料として使用可能な
高純度のε―カプロラクタムを効率よく回収する
ことは、これまで困難であつた。 A method has been proposed to separate CUA, cyclohexanone, and ε-caprolactam from a CUA solution generated by thermal decomposition of PXA (Japanese Patent Publication No. 57-25029
(see publication). However, the ε− obtained using this method
Caprolactam is a dilute solution of several wt% ε-caprolactam, and in addition to inorganic substances such as ammonium sulfate, chain and cyclic lactams such as amides and carboxylic acids mainly having 5 to 12 carbon atoms are produced during thermal decomposition. Contains many types of impurities that differ from the method used. For this reason, it has hitherto been difficult to efficiently recover high-purity ε-caprolactam that can be used as a raw material for nylon for textiles from this dilute solution of ε-caprolactam.
本発明者は、さらに検討した結課、このε―カ
プロラクタム水溶液から高収率で高純度なε―カ
プロラクタムを回収する方法を見出すことができ
た。 As a result of further investigation, the present inventor was able to discover a method for recovering high-yield, highly pure ε-caprolactam from this ε-caprolactam aqueous solution.
すなわち、本発明は、PXAの熱分解により
CUAを製造する際に副生するε―カプロラクタ
ム水溶液から、高純度のε―カプロラクタムを回
収する方法において、第１工程において該ε―カ
プロラクタム水溶液を濃縮によりε―カプロラク
タム油相と硫安水相に分離し、第２工程において
該ε―カプロラクタム油相を有機溶剤で抽出し、
第３工程において該抽出液の蒸溜により溶剤と粗
製ε―カプロラクタムを留出させ、第４工程にお
いて該粗製ε―カプロラクタムに硫酸または発煙
硫酸を混合液中の硫酸換算酸濃度が50〜65wt％
になるように添加して90〜150℃に温度を保ち、
第５工程において安水で中和したのち、第６工程
において有機溶媒で抽出し、第７工程で該抽出液
を蒸溜して高純度のε―カプロラクタムを留出さ
せることを特徴とするε―カプロラクタムの回収
方法に関するものである。 In other words, the present invention enables the thermal decomposition of PXA to
In a method for recovering high-purity ε-caprolactam from an aqueous ε-caprolactam solution produced as a by-product during the production of CUA, in the first step, the ε-caprolactam aqueous solution is separated into an ε-caprolactam oil phase and an ammonium sulfate aqueous phase by concentration. In the second step, the ε-caprolactam oil phase is extracted with an organic solvent,
In the third step, the solvent and crude ε-caprolactam are distilled out by distillation of the extract, and in the fourth step, sulfuric acid or fuming sulfuric acid is added to the crude ε-caprolactam so that the acid concentration in terms of sulfuric acid in the mixed solution is 50 to 65 wt%.
Add it so that the temperature is between 90 and 150℃,
After neutralizing with ammonium water in the fifth step, extraction is carried out with an organic solvent in the sixth step, and in the seventh step, the extract is distilled to distill out highly pure ε-caprolactam. This invention relates to a method for recovering caprolactam.
本発明の方法に使用するε―カプロラクタムは
PXAの熱分解において主生成物であるCUAと共
に得られ、PXA1Kgにつき0.10〜0.20Kg副生する。
この副生ε―カプロラクタムは数wt％のε―カ
プロラクタム水溶液として得られ、硫安の他に、
熱分解時に生成する炭素数５から12を中心とした
アミドやカルボン酸などの鎖状および環状の従来
の製造方法と違つた多種類の不純物を含有してい
る。 The ε-caprolactam used in the method of the present invention is
It is obtained together with CUA, which is the main product, during the thermal decomposition of PXA, and 0.10 to 0.20 kg of it is produced as a by-product for every 1 kg of PXA.
This by-product ε-caprolactam is obtained as a several wt% ε-caprolactam aqueous solution, and in addition to ammonium sulfate,
It contains many types of impurities that are different from conventional production methods, such as amide and carboxylic acid with mainly carbon atoms of 5 to 12, which are produced during thermal decomposition.
次に本発明の方法を各工程について説明する。 Next, each step of the method of the present invention will be explained.
（第１工程）
ε―カプロラクタム水溶液の濃縮においては油
相へのε―カプロラクタムの収率をよくするため
に、水相中の硫安濃度が20〜40wt％、好ましく
は30〜40wt％になるように濃縮度を調節する。
この時、濃縮度を容易にするために、分離水相の
一部を再循環してもよい。また抜き出した水相か
ら晶析により硫安を回収できる。(First step) In concentrating the ε-caprolactam aqueous solution, in order to improve the yield of ε-caprolactam to the oil phase, the ammonium sulfate concentration in the aqueous phase is adjusted to 20 to 40 wt%, preferably 30 to 40 wt%. Adjust the concentration accordingly.
At this time, a portion of the separated aqueous phase may be recycled to facilitate concentration. Furthermore, ammonium sulfate can be recovered from the extracted aqueous phase by crystallization.
（第２工程）
ε―カプロラクタム油相をトルエンやベンゼン
などの有機溶剤で抽出することにより、不純物を
抽出残分として除去する。この時、油相のPHをア
ンモニア等の塩基で７以上にすると、抽出効率が
向上する。(Second step) Impurities are removed as an extraction residue by extracting the ε-caprolactam oil phase with an organic solvent such as toluene or benzene. At this time, if the pH of the oil phase is adjusted to 7 or higher using a base such as ammonia, the extraction efficiency will be improved.
（第３工程）
ε―カプロラクタム抽出液を蒸溜して溶剤を回
収すると共に粗製ε―カプロラクタムを留出させ
て、高沸点不純物は蒸溜釜残として除去する。(Third step) The ε-caprolactam extract is distilled to recover the solvent and crude ε-caprolactam is distilled off, and high-boiling impurities are removed as distillation residue.
（第４工程）
この粗製ε―カプロラクタムに混合液中の硫酸
換算濃度で50〜65wt％、好ましくは55〜60wt％
になるように、硫酸もしくは発煙硫酸を加えて、
90〜150℃、好ましくは120〜140℃に温度を保ち
不純物を分解する。硫酸換算濃度50wt％以下で
は不純物の分解が不充分になる。また65wt％以
上ではε―カプロラクタムの分解がおこる。分解
温度90℃以下では不純物の分解が不充分で精製効
果がおとる。また150℃以上ではε―カプロラク
タムの分解がおこり収率の低下をきたす。(Fourth step) The concentration of this crude ε-caprolactam in terms of sulfuric acid in the mixed solution is 50 to 65 wt%, preferably 55 to 60 wt%.
Add sulfuric acid or fuming sulfuric acid so that
The temperature is maintained at 90-150°C, preferably 120-140°C to decompose impurities. If the sulfuric acid equivalent concentration is less than 50 wt%, the decomposition of impurities will be insufficient. In addition, above 65wt%, decomposition of ε-caprolactam occurs. If the decomposition temperature is below 90°C, the decomposition of impurities will be insufficient and the purification effect will be poor. Furthermore, at temperatures above 150°C, decomposition of ε-caprolactam occurs, resulting in a decrease in yield.
（第５工程）
この酸性溶液に安水を加えて中和する。安水濃
度は10〜14wt％が好ましい。(Fifth step) Ammonium water is added to this acidic solution to neutralize it. The concentration of ammonium water is preferably 10 to 14 wt%.
（第６工程）
この中和溶液をベンゼンやトルエンなどの有機
溶媒で抽出し、分解した不純物を硫安水と共に除
去する。この硫安水からも晶析により硫安が回収
される。(Sixth step) This neutralized solution is extracted with an organic solvent such as benzene or toluene, and decomposed impurities are removed together with ammonium sulfate water. Ammonium sulfate is also recovered from this ammonium sulfate solution by crystallization.
（第７工程）
この抽出液を蒸溜して溶剤を除去すると共に高
純度のε―カプロラクタムを留出させる。得られ
た高純度ε―カプロラクタムの過マンガン酸価は
21600秒以上で、10wt％水溶液の290nmにおける
透過率は95％以上である。(Seventh step) This extract is distilled to remove the solvent and distill high purity ε-caprolactam. The permanganate value of the obtained high purity ε-caprolactam is
The transmittance of a 10wt% aqueous solution at 290nm is more than 95% for more than 21600 seconds.
なお、過マンガン酸価とは試料１ｇをPH7.0に
調整した蒸溜水100mlに溶解して20℃に保ち100分
の１規定の渦マンガン酸溶液を加えて、比較液と
同じ色になるまでに要する秒数を測定したもであ
る。 In addition, the permanganic acid value is defined by dissolving 1 g of a sample in 100 ml of distilled water adjusted to pH 7.0, keeping it at 20°C, adding 1/100 normal vortex manganese acid solution until it becomes the same color as the comparison solution. This is a measurement of the number of seconds required for
比較液は塩化コバルト六水塩0.3ｇと硫酸銅0.2
ｇを蒸溜水に溶解して100mlとしたものを使用し
た。 The comparison liquid is cobalt chloride hexahydrate 0.3g and copper sulfate 0.2g.
g was dissolved in distilled water to make 100 ml.
実施例 １
第１工程で常圧、100℃で１％のε―カプロラ
クタム水溶液を濃縮して、水相中の硫安濃度が
35wt％になるように濃縮度を調節した。第２工
程で分離した油相をアンモニアガスで中和してPH
８に調節した上で、抽出塔を使用して対油相3.1
重量倍のトルエンによつて抽出した。第３工程で
この抽出液に少量のカセイソーダを加えて蒸溜
し、トルエンを留出除去したのちに粗製ε―カプ
ロラクタムを留出させる。第４工程ではこの粗製
ε―カプロラクタムに発煙硫酸を加えて混合液中
の硫酸換算酸濃度を57wt％として、２時間130℃
にたもつた。第５工程ではこの酸混合液を安水で
中和し、第６工程ではこの中和液を２容積倍のベ
ンゼンで２回抽出した。第７工程ではこの抽出液
のベンゼンを除去したのち、カセイソーダを
0.2wt％添加して単蒸溜にかけ、初留として5wt
％留出除去した後に主留分として精製ε―カプロ
ラクタムを留出させ高沸点物として10wt％残し
た。得られた主留分の品質は、過マンガン酸価が
21600秒以上で、290nmにおける透過率は98％で
あつた。Example 1 In the first step, a 1% ε-caprolactam aqueous solution was concentrated at normal pressure and 100°C to reduce the ammonium sulfate concentration in the aqueous phase.
The concentration was adjusted to 35wt%. The oil phase separated in the second step is neutralized with ammonia gas to pH
After adjusting the oil phase to 3.1 to
Extracted with twice the weight of toluene. In the third step, a small amount of caustic soda is added to this extract and distilled, toluene is removed by distillation, and then crude ε-caprolactam is distilled out. In the fourth step, fuming sulfuric acid was added to this crude ε-caprolactam to make the acid concentration in terms of sulfuric acid in the mixture 57 wt%, and the temperature was kept at 130°C for 2 hours.
I was bored. In the fifth step, this acid mixture was neutralized with ammonium water, and in the sixth step, this neutralized solution was extracted twice with twice the volume of benzene. In the seventh step, after removing the benzene from this extract, caustic soda is added.
Add 0.2wt% and apply simple distillation to 5wt as the first distillation.
After distilling off the purified ε-caprolactam as the main fraction, 10 wt% of the high boiling point product remained. The quality of the main distillate obtained is determined by the permanganate value.
The transmittance at 290 nm was 98% over 21,600 seconds.
実施例 ２
上記操作の第４工程で混合液中の硫酸換算濃度
を53wt％としたところ、得られた主留分の品質
は過マンガン酸価が21600秒以上で、290nmにお
ける透過率は98％であつた。Example 2 In the fourth step of the above operation, the concentration of sulfuric acid in the mixed solution was set to 53 wt%, and the quality of the main distillate obtained was such that the permanganate value was 21600 seconds or more, and the transmittance at 290 nm was 98%. It was hot.
実施例 ３
実施例１の操作の第４工程で温度を100℃にし
たところ、得られた主留分の品質は、過マンガン
酸価が21600秒以上で、290nmにおける透過率は
98％であつた。Example 3 When the temperature was raised to 100°C in the fourth step of the operation of Example 1, the quality of the main fraction obtained was such that the permanganate value was 21600 seconds or more, and the transmittance at 290 nm was
It was 98%.
Claims (1)
分解により11―シアノウンデカン酸を製造する際
に副生するε―カプロラクタム水溶液から、高純
度のε―カプロラクタムを回収する方法におい
て、第１工程において該ε―カプロラクタム水溶
液を濃縮してε―カプロラクタム油相と硫安水相
に分離し、第２工程において該ε―カプロラクタ
ム油相を有機溶剤で抽出し、第３工程において該
抽液の蒸溜により溶剤と粗製ε―カプロラクタム
を留出させ、第４工程において該粗製ε―カプロ
ラクタムに硫酸または発煙硫酸を混合液中の硫酸
換算酸濃度が50〜65wt％になるように添加して
90〜150℃に温度を保ち、第５工程において安水
で中和したのち、第６工程において有機溶媒で抽
出し、第７工程で該抽出液を蒸溜して高純度のε
―カプロラクタムを留出させることを特徴とする
ε―カプロラクタムの回収方法。1. A method for recovering high-purity ε-caprolactam from an aqueous ε-caprolactam solution produced as a by-product during the production of 11-cyanoundecanoic acid by thermal decomposition of 1-peroxydicyclohexylamine, in which the ε-caprolactam is recovered in the first step. The aqueous solution is concentrated and separated into an ε-caprolactam oil phase and an ammonium sulfate aqueous phase. In the second step, the ε-caprolactam oil phase is extracted with an organic solvent. In the third step, the extracted liquid is distilled to remove the solvent and the crude ε- Caprolactam is distilled off, and in the fourth step, sulfuric acid or fuming sulfuric acid is added to the crude ε-caprolactam so that the acid concentration in terms of sulfuric acid in the mixture becomes 50 to 65 wt%.
After maintaining the temperature at 90-150℃ and neutralizing with ammonium water in the 5th step, extraction with an organic solvent in the 6th step, and distilling the extract in the 7th step to obtain highly pure ε.
- A method for recovering ε-caprolactam, which comprises distilling caprolactam.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5432184A JPS60199873A (en) | 1984-03-23 | 1984-03-23 | Recovery of epsilon-caprolactam |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5432184A JPS60199873A (en) | 1984-03-23 | 1984-03-23 | Recovery of epsilon-caprolactam |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60199873A JPS60199873A (en) | 1985-10-09 |
| JPH0149349B2 true JPH0149349B2 (en) | 1989-10-24 |
Family
ID=12967321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5432184A Granted JPS60199873A (en) | 1984-03-23 | 1984-03-23 | Recovery of epsilon-caprolactam |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60199873A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2601945B2 (en) * | 1990-11-21 | 1997-04-23 | 宇部興産株式会社 | Lactam oil refining method |
| TW420662B (en) * | 1996-02-17 | 2001-02-01 | Du Pont | Recovery of <epsilon>-caprolactam |
| EP0826665A1 (en) * | 1996-09-02 | 1998-03-04 | Dsm N.V. | Recovery of epsilon-caprolactam from aqueous mixtures |
| JP2003507294A (en) * | 1999-08-17 | 2003-02-25 | ディーエスエム エヌ．ブイ． | Method for treating a mixture comprising an ammonium sulfate solution phase and an aqueous lactam phase |
| CN109678754B (en) * | 2017-10-19 | 2021-09-07 | 万华化学集团股份有限公司 | Preparation method of 11-cyanoundecanoic acid |
-
1984
- 1984-03-23 JP JP5432184A patent/JPS60199873A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60199873A (en) | 1985-10-09 |
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