JP2802654B2 - A method for recovering oligosaccharide-bound sialic acids from alkaline washing waste liquid of anion exchange resin generated during desalting of whey - Google Patents
A method for recovering oligosaccharide-bound sialic acids from alkaline washing waste liquid of anion exchange resin generated during desalting of wheyInfo
- Publication number
- JP2802654B2 JP2802654B2 JP1282729A JP28272989A JP2802654B2 JP 2802654 B2 JP2802654 B2 JP 2802654B2 JP 1282729 A JP1282729 A JP 1282729A JP 28272989 A JP28272989 A JP 28272989A JP 2802654 B2 JP2802654 B2 JP 2802654B2
- Authority
- JP
- Japan
- Prior art keywords
- exchange resin
- oligosaccharide
- anion exchange
- whey
- sialic acid
- 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 - Lifetime
Links
Classifications
-
- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A20/00—Water conservation; Efficient water supply; Efficient water use
- Y02A20/124—Water desalination
- Y02A20/131—Reverse-osmosis
Landscapes
- Treatment Of Liquids With Adsorbents In General (AREA)
- Dairy Products (AREA)
- Saccharide Compounds (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は、ホエーを脱塩する際して生ずるイオン交換
樹脂の洗浄廃液から、シアル酸類、特にオリゴ糖結合型
シアル酸を回収する方法に関する。Description: TECHNICAL FIELD The present invention relates to a method for recovering sialic acids, particularly oligosaccharide-bound sialic acid, from a washing waste liquid of an ion exchange resin generated when desalting whey.
技術的背景 従来、チーズやカゼインを製造する際に、原料乳を凝
乳酵素や酸で処理して蛋白質を凝固させた後、大量のホ
エーが生成する。TECHNICAL BACKGROUND Conventionally, when producing cheese or casein, a large amount of whey is produced after coagulating protein by treating raw milk with a milk-clotting enzyme or acid.
このホエーがそのまま廃棄され、排水の汚染源となる
ことを防止し、更に、乳成分の有効利用という観点か
ら、色々な提案がなされている。そのひとつとして、ホ
エーを脱塩した後、育児用粉乳や製菓原料などとして利
用されている。ところで、ホエーを脱塩する目的は、無
機塩類を除去してホエー中の灰分含有量を低下させるこ
とにある。Various proposals have been made from the viewpoint of preventing this whey from being discarded as it is and becoming a polluting source of wastewater, and from the viewpoint of effective utilization of milk components. As one of them, after desalting whey, it is used as powdered milk for childcare and as a raw material for confectionery. Meanwhile, the purpose of desalting whey is to reduce the ash content in whey by removing inorganic salts.
近年、ホエーの脱塩は電気透析法で行われるようにな
ってきているが、従来から行われているイオン交換樹脂
を用いる方法も依然として行われている現状にある。イ
オン交換樹脂法は、主に荷電に基づいて物質を吸着する
ものであり、無機塩類ばかりでなく、電荷を持つ有機物
質も、その選択係数に依存するものの、若干、吸着され
ることは避けられない。その有機物質中にペプチドやオ
リゴ糖、その他の複合糖質など、微量成分が含まれてい
ることが十分考えられる。従って、この有機物質中の微
量成分は、ホエーの脱塩のためのイオン交換樹脂処理の
際に樹脂に吸着され、ホエーのイオン交換樹脂処理に用
いた樹脂を再生する際に溶出され、そのまま、廃棄され
ることとなる。In recent years, whey has been desalted by electrodialysis, but the conventional method using an ion exchange resin is still being carried out. In the ion exchange resin method, substances are mainly adsorbed on the basis of charge, and not only inorganic salts, but also organic substances having electric charge, although depending on their selectivity, can be avoided from being slightly adsorbed. Absent. It is fully conceivable that the organic substance contains trace components such as peptides, oligosaccharides and other complex carbohydrates. Therefore, the trace components in this organic substance are adsorbed on the resin during the ion exchange resin treatment for the desalination of whey, eluted when regenerating the resin used for the ion exchange resin treatment of the whey, It will be discarded.
一方、シアル酸及びその誘導体は、通常、糖タンパク
室や糖脂質など複合糖質の糖鎖に結合した状態で動物界
に広く分布している。近年、シアル酸を含む複合糖質の
生理活性について、次々に報告されると共に、シアル酸
自身の担う役割や意義についても、次第に明らかにされ
つつある。例えば、シアル酸を含む複合糖質の寿命制
御、ウィルスのレセプター活性の付与、プロテアーゼ消
化への抵抗性や保水性の付与などである。従って、遊離
型シアル酸を精製し、それを基にシアル酸結合物質を合
成することは、非常に意義のあることである。また、シ
アル酸に限らず、一般に糖質を用いた有機化合物の合成
は、その多官能性の故に困難さを持つことが知られてい
ることから、天然に存在するシアル酸結合型の複合糖質
をそのまま精製して利用することも非常に重要な意味を
持つものと考えられる。On the other hand, sialic acid and its derivatives are generally widely distributed in the animal kingdom in a state of being bound to sugar chains of complex carbohydrates such as glycoprotein chambers and glycolipids. In recent years, the physiological activities of conjugated saccharides containing sialic acid have been reported one after another, and the role and significance of sialic acid itself have been gradually clarified. For example, the control of the life span of glycoconjugates containing sialic acid, the provision of viral receptor activity, the provision of resistance to protease digestion and the provision of water retention. Therefore, it is very significant to purify free sialic acid and synthesize a sialic acid binding substance based on the purified sialic acid. In addition, it is known that synthesis of organic compounds using not only sialic acid but also saccharides is generally difficult due to its polyfunctionality. It is considered that the purification and utilization of the quality as it is has a very important meaning.
ところで、オリゴ糖結合型シアル酸類、糖ペプチド或
いは糖タンパク質結合型シアル酸、及び糖脂質結合型シ
アル酸は、先に述べたホエー中に存在することが知られ
ており、ホエーからシアル酸類を抽出する方法も提案さ
れている。しかしながら、これらのシアル酸は比較的強
い陰性の荷電を持つ為、ホエーをイオン交換樹脂で脱塩
する際、その一部がイオン交換樹脂に吸着され、樹脂を
再生する際に溶出され、そのまま、廃棄されているとい
う問題がある。By the way, oligosaccharide-bound sialic acids, glycopeptide or glycoprotein-bound sialic acids, and glycolipid-bound sialic acids are known to be present in whey as described above, and sialic acids are extracted from whey. A method of doing so has also been proposed. However, since these sialic acids have a relatively strong negative charge, when desalting whey with an ion-exchange resin, a part of it is adsorbed on the ion-exchange resin and eluted when regenerating the resin. There is a problem of being discarded.
発明が解決しようとする課題 本発明は、上述した状況に鑑みなされたものであつ
て、従来、廃棄されていた、ホエーの脱塩時に生ずる陰
イオン交換樹脂のアルカリ洗浄廃液から簡便な方法でシ
アル酸誘導体であるオリゴ糖結合型シアル酸類を極めて
高純度で効率よく回収するための方法を提供することを
課題とする。DISCLOSURE OF THE INVENTION The present invention has been made in view of the above-described circumstances, and is directed to a method for sializing an alkaline washing waste liquid of an anion-exchange resin which has been conventionally discarded and which is generated at the time of desalting whey, by a simple method. An object of the present invention is to provide a method for efficiently recovering oligosaccharide-bound sialic acids which are acid derivatives with extremely high purity.
以下本発明を詳しく説明する。 Hereinafter, the present invention will be described in detail.
課題を解決するための手段 本発明は、レンネツトカゼイン或は酸カゼインなどを
製造する際に副生されるホエーを、イオン交換樹脂方式
で処理して脱塩する際に用いた陰イオン交換樹脂を水洗
し、次いで水酸化ナトリウムのようなアルカリの水溶液
を通液し、さらに水を通液して得られる陰イオン交換樹
脂カラムのアルカリ洗浄廃液からオリゴ糖結合型シアル
酸類を回収する方法に係る。Means for Solving the Problems The present invention provides an anion exchange resin which is used when desalting by treating the whey by-produced in producing rennet casein or acid casein by an ion exchange resin method. And then passing an aqueous solution of an alkali such as sodium hydroxide, and further recovering oligosaccharide-bound sialic acids from the alkaline washing waste liquid of the anion exchange resin column obtained by passing water. .
本発明では、上記陰イオン交換樹脂のアルカリ洗浄廃
液を塩酸などの酸で中和した後、限外濾過処理を行って
透過液を得、次いでこの透過液を逆浸透膜処理して濃縮
と同時に脱塩する。得られた濃縮透過液は強塩基型陰イ
オン交換樹脂を通液してシアル酸類を吸着させ、次いで
このシアル酸類を溶出する。この溶出にあたっては、シ
アル酸類の吸着カラムを脱イオン水で洗浄した後、０−
2Mのギ酸濃度勾配によって行うとよい。In the present invention, the alkali washing waste liquid of the anion exchange resin is neutralized with an acid such as hydrochloric acid, and then subjected to ultrafiltration to obtain a permeate. Desalting. The resulting concentrated permeate is passed through a strong base type anion exchange resin to adsorb sialic acids and then elute the sialic acids. In this elution, the sialic acid adsorption column was washed with deionized water,
It is preferable to use a 2M formic acid concentration gradient.
上記溶出液は、一定量づつ分画し、エーリッヒ法によ
って発色する画分を集め、減圧濃縮してギ酸を除去した
後、凍結乾燥などにより乾燥してオリゴ糖結合型シアル
酸類の粉末を得る。The eluate is fractionated by a predetermined amount, and the color-developing fractions are collected by the Erich method, concentrated under reduced pressure to remove formic acid, and dried by freeze-drying or the like to obtain a powder of oligosaccharide-bound sialic acids.
次に、上述のごとくして得られたオリゴ糖結合型シア
ル酸類におけるオリゴ糖の鉄号状態を下記により調べた
結果を示す。Next, the results obtained by examining the iron-state of the oligosaccharide in the oligosaccharide-bound sialic acids obtained as described above are described below.
オリゴ糖結合型シアル酸類の粉末を脱イオン水に溶解
した溶液を陰イオン交換樹脂ギ酸型に通液して目的物質
を吸着させ、次いで上記樹脂を脱イオン水で十分洗浄し
た後、０−2Mのギ酸濃度勾配によって溶出し、各溶出画
分を高速液体クロマトグラフィーで分析の結果、α−２
→３結合型シアリルラクトース及びα−２→６結合型シ
アリルラクトースを高純度で含む二つの画分が得られ
た。A solution obtained by dissolving the oligosaccharide-bound sialic acid powder in deionized water is passed through an anion exchange resin formic acid type to adsorb the target substance, and then the resin is sufficiently washed with deionized water, and then subjected to 0-2M. And elution fractions were analyzed by high performance liquid chromatography.
Two fractions containing the → 3-linked sialyl lactose and α-2 → 6-linked sialyl lactose in high purity were obtained.
以下実施例により本発明を具体的に説明する。 Hereinafter, the present invention will be described specifically with reference to examples.
実施例 まず、アンバーライト410A型陰イオン交換樹脂OH型
（オルガノ社製）を充填した1,000容量のカラムに、
チーズホエー10tを通液して脱塩を行い、次いで上記カ
ラムを十分水洗した後、４重量％の水酸化ナトリウム水
溶液1,000を通液し、さらに、水2,000を通液して陰
イオン交換樹脂カラムのアルカリ洗浄廃液3,000を得
た。Example First, a 1,000-volume column packed with Amberlite 410A type anion exchange resin OH type (manufactured by Organo Corporation)
After passing through 10 tons of cheese whey to desalinate, then thoroughly washing the above column with water, passing 1,000% of a 4% by weight aqueous sodium hydroxide solution, and then passing water 2,000, an anion exchange resin column Of 3,000 was obtained.
このアルカリ洗浄廃液3,000に塩酸約2.2を加えて
中和し、この中和液を、分子量20,000でカット・オフす
る膜（ローヌプーラン社製）を用いて限外濾過法で濾過
し、透過液3,200を得た。The alkaline washing waste liquid 3,000 is neutralized by adding about 2.2 hydrochloric acid, and the neutralized liquid is filtered by an ultrafiltration method using a membrane cut off with a molecular weight of 20,000 (manufactured by Rhone Poulin Co.), and the permeated liquid 3,200 I got
次に、この透過液を、HC−50膜（DDS社製）を用い
て、逆浸透膜法で濃縮と同時に脱塩し、更に水洗して、
濃縮液100を得た。Next, using a HC-50 membrane (manufactured by DDS), the permeate was concentrated and desalted simultaneously with a reverse osmosis membrane method, and further washed with water.
A concentrate 100 was obtained.
最後に、１×４型陰イオン交換樹脂ギ酸型（ダウエッ
クス社製）を充填した30容量のカラムに、上記濃縮液
を通液して目的物質を吸着させ、ついでカラムを脱イオ
ン水で十分洗浄した後、０−2Mのギ酸濃度勾配によって
溶出した。この溶出液を500mlずつ分画し、エーリッヒ
法によって発色する画分を集めて、35℃以下で減圧濃縮
しギ酸を除去した後、凍結乾燥して、オリゴ糖結合型シ
アル酸類の粉末124gを得た。Finally, the above-mentioned concentrated solution is passed through a 30-volume column filled with a 1 × 4 type anion exchange resin formic acid type (manufactured by Dowex) to adsorb the target substance, and then the column is sufficiently filled with deionized water. After washing, elution was carried out with a formic acid concentration gradient of 0-2M. The eluate was fractionated by 500 ml, and the color-developing fractions were collected by the Erich method, concentrated at 35 ° C. or lower under reduced pressure to remove formic acid, and lyophilized to obtain 124 g of oligosaccharide-bound sialic acid powder. Was.
上記のようにして得られたオリゴ糖結合型シアル酸類
は、TBA法による測定の結果、シアリルラクトース換算
で、純度95.6％であった。The oligosaccharide-bound sialic acids obtained as described above had a purity of 95.6% in terms of sialyllactose as a result of measurement by the TBA method.
このようにして得られたオリゴ糖結合型シアル酸類に
おけるオリゴ糖の結合様式を下記により測定した。The oligosaccharide binding mode in the oligosaccharide-linked sialic acids thus obtained was measured as follows.
１×４型陰イオン交換樹脂ギ酸型（ダウエックス社
製）を充填した500ml容量のカラムに、上記実施例で得
られたオリゴ糖結合型シアル酸粉末10gを脱イオン水で
溶解した水溶液を通液して目的物質を吸着させ、ついで
カラムを脱イオン水で十分洗浄した後、０−2Mのギ酸濃
度勾配によって溶出した。そして、各溶出画分を高速液
体クロマトグラフィー〔HPX−87H型カラム（バイオラッ
ド社製）、移動層:0.1N−H2SO4、流速:0.7ml/min.、検
出波長:206nm〕で分析し、α−２→３結合型シアリルラ
クトース及びα−２→６結合型シアリルリクトースを高
純度で含む二つの画分を得た。An aqueous solution obtained by dissolving 10 g of the oligosaccharide-bound sialic acid powder obtained in the above example in deionized water was passed through a column of 500 ml capacity packed with a 1 × 4 type anion exchange resin formic acid type (manufactured by Dowex). The mixture was liquefied to adsorb the target substance, and then the column was sufficiently washed with deionized water, and then eluted with a formic acid concentration gradient of 0-2M. Each eluted fraction is analyzed by high performance liquid chromatography (HPX-87H type column (manufactured by Bio-Rad), moving bed: 0.1 N-H 2 SO 4 , flow rate: 0.7 ml / min., Detection wavelength: 206 nm). Then, two fractions containing α-2 → 3 linked sialyl lactose and α-2 → 6 linked sialyl lactose with high purity were obtained.
この二つの画分をそれぞれ減圧濃縮して、シアリルラ
クトースＡの粉末7.8g及びシアリルラクトースＢの粉末
1.2gを得た。The two fractions were concentrated under reduced pressure, respectively, to obtain 7.8 g of sialyl lactose A powder and sialyl lactose B powder.
1.2 g were obtained.
なお、シアリルラクトースＡは、上記、高速液体クロ
マトグラフィー分析の結果、α−２→３結合型シアリル
ラクトース99.5％、α−２→６結合型シリアルラクトー
ス０％であり、シアリルラクトースＢは、同様の分析の
結果、α−２→３結合型シアリルラクトース0.2％、α
−２→６結合型シアリルラクトース99.4％であった。As a result of the above-mentioned high performance liquid chromatography analysis, sialyl lactose A was 99.5% of α-2 → 3 bond type sialyl lactose and 0% of α-2 → 6 bond cereal lactose. As a result of the analysis, α-2 → 3-linked sialyl lactose 0.2%, α
The ratio of -2 → 6 linked sialyl lactose was 99.4%.
発明の効果 叙上のとおり、本発明によると、従来、廃棄されてい
た、脱塩ホエーの製造時に生ずる陰イオン交換樹脂のア
ルカリ洗浄廃液から、生理活性物質として有用とされる
オリゴ糖結合型シアル酸類を簡便な方法で極めて高純度
で回収し得るので、本発明は、有用物質の生産のみなら
ず、未利用資源活用の観点からも有益であると言うこと
ができる。Effect of the Invention As described above, according to the present invention, an oligosaccharide-bound sialic acid useful as a physiologically active substance is obtained from an alkaline washing waste liquid of an anion exchange resin which is conventionally discarded and produced during the production of desalted whey. The present invention can be said to be useful not only from the production of useful substances but also from the viewpoint of utilization of unused resources, because acids can be recovered in a very simple manner and with extremely high purity.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭51−91358（ＪＰ，Ａ) 特開 昭51−105015（ＪＰ，Ａ) 特開 昭59−184197（ＪＰ，Ａ) 特開 平１−168693（ＪＰ，Ａ) 特開 平２−261343（ＪＰ，Ａ) 特公 昭40−21234（ＪＰ，Ｂ１) (58)調査した分野(Int.Cl.6，ＤＢ名) A23C 21/00──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-51-91358 (JP, A) JP-A-51-105015 (JP, A) JP-A-59-184197 (JP, A) JP-A-1- 168693 (JP, A) JP-A-2-261343 (JP, A) JP 40-21234 (JP, B1) (58) Fields investigated (Int. Cl. 6 , DB name) A23C 21/00
Claims (2)
塩する際に用いた陰イオン交換樹脂にアルカリ水溶液を
通液して、陰イオン交換樹脂カラムのアルカリ洗浄液を
得、該アルカリ洗浄廃液を中和処理した後、限外濾過に
付して透過液を得、次いで該透過液を逆浸透膜処理して
濃縮するとともに脱塩し、得られた濃縮透過液を強塩基
型陰イオン交換樹脂に通液してシアル酸を吸着させ、次
いでこのシアル酸を溶出して脱塩、乾燥することを特徴
とするオリゴ糖結合型シアル酸類の回収方法。An alkaline aqueous solution is passed through an anion exchange resin used in treating and desalinating whey with an ion exchange resin method to obtain an alkaline washing liquid for an anion exchange resin column. After neutralization, the filtrate is subjected to ultrafiltration to obtain a permeate. Then, the permeate is subjected to reverse osmosis membrane treatment, concentrated and desalted, and the obtained concentrated permeate is subjected to strong base type anion exchange. A method for recovering oligosaccharide-bound sialic acids, comprising passing sialic acid through a resin to adsorb the sialic acid, then eluting the sialic acid, desalting, and drying.
を脱イオン水で洗浄した後、０−2Mのギ酸濃度勾配を用
いて行う請求項（１）に記載のオリゴ糖結合型シアル酸
類の回収方法。2. The oligosaccharide-bound sialic acid according to claim 1, wherein the sialic acid is eluted by washing the sialic acid adsorption column with deionized water and then using a formic acid concentration gradient of 0-2M. Collection method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1282729A JP2802654B2 (en) | 1989-10-30 | 1989-10-30 | A method for recovering oligosaccharide-bound sialic acids from alkaline washing waste liquid of anion exchange resin generated during desalting of whey |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1282729A JP2802654B2 (en) | 1989-10-30 | 1989-10-30 | A method for recovering oligosaccharide-bound sialic acids from alkaline washing waste liquid of anion exchange resin generated during desalting of whey |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03143351A JPH03143351A (en) | 1991-06-18 |
| JP2802654B2 true JP2802654B2 (en) | 1998-09-24 |
Family
ID=17656285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1282729A Expired - Lifetime JP2802654B2 (en) | 1989-10-30 | 1989-10-30 | A method for recovering oligosaccharide-bound sialic acids from alkaline washing waste liquid of anion exchange resin generated during desalting of whey |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2802654B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL2001377C2 (en) * | 2008-03-14 | 2009-09-15 | Friesland Brands Bv | Process for isolating sialic acid-containing oligosaccharides, as well as the compositions containing sialic acid-containing oligosaccharides. |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3035833B2 (en) * | 1991-01-21 | 2000-04-24 | 雪印乳業株式会社 | Method for producing sialic acids-containing composition |
| HUP0001634A2 (en) * | 1996-10-10 | 2000-09-28 | Cytel Corporation | Carbohydrate purification using ultrafiltration, reverse osmosis and nanofiltration |
| US6288222B1 (en) * | 2000-02-16 | 2001-09-11 | Neose Technologies, Inc. | Method of filtration of a dairy stream |
| JP2001240599A (en) * | 2000-02-29 | 2001-09-04 | Snow Brand Milk Prod Co Ltd | Lactic oligosaccharide fraction |
| DK1951060T3 (en) * | 2005-11-04 | 2018-01-29 | Arla Foods Amba | CONCENTRATE derived from a milk product enriched with naturally occurring sialyl lactose and a process for its preparation |
| JP5261732B2 (en) * | 2007-07-18 | 2013-08-14 | ニュテックス株式会社 | Method for producing oligosaccharide containing sialic acid |
| US9055752B2 (en) | 2008-11-06 | 2015-06-16 | Intercontinental Great Brands Llc | Shelf-stable concentrated dairy liquids and methods of forming thereof |
| UA112972C2 (en) | 2010-09-08 | 2016-11-25 | Інтерконтінентал Грейт Брендс ЛЛС | LIQUID DAIRY CONCENTRATE WITH A HIGH CONTENT OF DRY SUBSTANCES |
| CN106365251B (en) * | 2016-08-25 | 2019-06-21 | 山东省鲁洲食品集团有限公司 | A kind of starch syrup ion-exchange binder water recovery method |
-
1989
- 1989-10-30 JP JP1282729A patent/JP2802654B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL2001377C2 (en) * | 2008-03-14 | 2009-09-15 | Friesland Brands Bv | Process for isolating sialic acid-containing oligosaccharides, as well as the compositions containing sialic acid-containing oligosaccharides. |
| WO2009113861A3 (en) * | 2008-03-14 | 2009-11-19 | Friesland Brands B.V. | Process for isolating sialic acid containing oligosaccharides, and the compositions containing sialic acid containing oligosaccharides obtainable thereby |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03143351A (en) | 1991-06-18 |
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