JP3174855B2 - Method for producing emulsion having antioxidant ability - Google Patents
Method for producing emulsion having antioxidant abilityInfo
- Publication number
- JP3174855B2 JP3174855B2 JP27651191A JP27651191A JP3174855B2 JP 3174855 B2 JP3174855 B2 JP 3174855B2 JP 27651191 A JP27651191 A JP 27651191A JP 27651191 A JP27651191 A JP 27651191A JP 3174855 B2 JP3174855 B2 JP 3174855B2
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- JP
- Japan
- Prior art keywords
- emulsion
- antioxidant
- parts
- glycine
- tocopherol
- Prior art date
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Description
【０００１】[0001]
【産業上の利用分野】本発明は、油脂や色素等食品ない
し一部成分で空気中の酸素により酸化され変質する成分
の酸化防止剤の製造法に関するものであり、食品，医薬
品，化粧品に広く利用できる可能性がある。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing an antioxidant for a food such as oils and fats or pigments or a component which is oxidized and degraded by oxygen in the air, and is widely used in foods, pharmaceuticals and cosmetics. May be available.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】近年、
酸化防止剤は安全性の点から合成品より天然品が多く使
用されるようになってきている。特にトコフェロールは
その代表であるが、抗酸化力の点で合成品に比べ劣るた
め従来より他の抗酸化物質やシネルギストを併用して使
用する方法は公知である。例えば、アミン類やアミンオ
キサイド，アミノ酸類やアミノ酸エステルとトコフェロ
ールの併用が知られている。しかしながらその抗酸化力
は未だ十分でない。2. Description of the Related Art In recent years,
Antioxidants are used more naturally than synthetic products in terms of safety. In particular, tocopherol is a typical example, but since it is inferior to a synthetic product in antioxidant power, a method of using another antioxidant or synergist in combination is conventionally known. For example, it is known to use tocopherol in combination with amines, amine oxides, amino acids and amino acid esters. However, its antioxidant power is not yet sufficient.
【０００３】アミノ酸のトコフェロールとの相乗効果に
関する研究は、活性酸素または重量法などの方法で豚
脂，メンヘイデン油及びトリリノレインなどを基質とし
て非水系で行われる場合が多く基質や抗酸化剤の種類に
よって異なった効果が報告されている。Studies on the synergistic effect of amino acids with tocopherol have been carried out in non-aqueous systems using lactose, menhaden oil, trilinolein, etc. as substrates by active oxygen or gravimetric methods in many cases. Different effects have been reported by type.
【０００４】湯木らは、ＡＯＭおよび Weighing Method
（重量法）による非水系の試験及びワールブルグ検圧計
を使用するエマルジョン（Ｏ／Ｗ）系の試験を行い試験
条件の違いと抗酸化効果の関係を検討した。ＡＯＭの条
件でラードを基質としたエマルジョン（Ｏ／Ｗ）系での
試験の結果は、アミノ酸及びアミノ酸エステル単独での
抗酸化効果は非常に小さくグリシン，メチオニン，トリ
プトファン及びリジンの場合に微かに認められる程度で
ある。一方、トコフェロールと共存する場合は、アミノ
酸及びそのエチルエステルは相乗効果を示した。しか
し、その抗酸化力は、トコフェロール単独の僅かな相乗
効果にすぎない。（New Food Industry, vol.27,12,74
(1985) ）[0004] Yugi et al. Disclose AOM and Weighing Method.
A non-aqueous system test (by gravimetric method) and an emulsion (O / W) system test using a Warburg manometer were conducted to examine the relationship between the difference in test conditions and the antioxidant effect. The results of a test in an emulsion (O / W) system using lard as a substrate under AOM conditions show that the antioxidant effect of amino acids and amino acid esters alone is extremely small and is slightly observed in the case of glycine, methionine, tryptophan and lysine. To the extent that it is possible. On the other hand, when coexisting with tocopherol, the amino acid and its ethyl ester showed a synergistic effect. However, its antioxidant power is only a slight synergistic effect of tocopherol alone. (New Food Industry, vol.27,12,74
(1985))
【０００５】[0005]
【課題を解決するための手段】本発明者等は、鋭意研究
を重ねた結果アミノ酸の一種であるグリシンと抗酸化剤
を乳化してＷ／Ｏ型またはＯ／Ｗ／Ｏ型エマルジョンを
製造し食品に加えること、あるいはグリシンを乳化し
て、Ｗ／Ｏ型またはＯ／Ｗ／Ｏ型エマルジョンを製造し
食品に加える際に抗酸化剤を併用することにより食品の
酸化を長期にわたり防ぐことを見いだした。Means for Solving the Problems As a result of intensive studies, the present inventors have emulsified glycine, which is a kind of amino acid, and an antioxidant to produce a W / O or O / W / O emulsion. Addition to food or emulsifying glycine to produce a W / O or O / W / O emulsion and use it together with antioxidants to prevent oxidation of food for a long time. Was.
【０００６】具体的には、水50重量部以上、油脂 500重
量部以下、グリシン0.01重量部以上、乳化剤0.01重量部
以上、抗酸化剤0.01重量部以上からなる原料を乳化して
得たＷ／Ｏ型またはＯ／Ｗ／Ｏ型エマルジョンが従来か
ら使用されている合成の抗酸化剤ＢＨＴと比較して、非
常に高い抗酸化活性を有すること、及び水50重量部以
上、油脂 500重量部以下、グリシン0.01重量部以上、乳
化剤0.01重量部以上からなる原料を乳化して得たＷ／Ｏ
型またはＯ／Ｗ／Ｏ型エマルジョン使用時に抗酸化剤を
加え用いると非常に高い抗酸化活性を有することを見い
だした。この結果より、Ｗ／Ｏ型またはＯ／Ｗ／Ｏ型エ
マルジョン系でグリシンがシネルギストとして非常に優
れた効果を有することを見いだすことができた。Specifically, W / E obtained by emulsifying a raw material comprising 50 parts by weight or more of water, 500 parts by weight or less of fats and oils, 0.01 parts by weight or more of glycine, 0.01 parts by weight or more of an emulsifier, and 0.01 parts by weight or more of an antioxidant. The O-type or O / W / O-type emulsion has a very high antioxidant activity as compared with the conventionally used synthetic antioxidant BHT, and at least 50 parts by weight of water and 500 parts by weight of fats and oils W / O obtained by emulsifying a raw material comprising 0.01 parts by weight or more of glycine and 0.01 parts by weight or more of an emulsifier
It has been found that the use of an antioxidant when the emulsion of the type or O / W / O type is used has a very high antioxidant activity. From these results, it was found that glycine had a very excellent effect as a synergist in a W / O type or O / W / O type emulsion system.
【０００７】[0007]
【作用】本発明はＷ／Ｏ型またはＯ／Ｗ／Ｏ型エマルジ
ョンで特に優れた効果を示す。本発明に使用する油脂は
各種動物脂，植物油およびエイコサペンタエン酸（ＥＰ
Ａ），ドコサヘキサエン酸（ＤＨＡ）を含有する油脂を
使用することができる。According to the present invention, a W / O type or O / W / O type emulsion exhibits particularly excellent effects. The oils and fats used in the present invention are various animal fats, vegetable oils and eicosapentaenoic acid (EP
A) Oils and fats containing docosahexaenoic acid (DHA) can be used.
【０００８】本発明における抗酸化剤として、トコフェ
ロール，リン脂質，ビタミンＣ，香辛料抽出物，カテキ
ン，ひまわり抽出物等があげられる。The antioxidants in the present invention include tocopherol, phospholipid, vitamin C, spice extract, catechin, sunflower extract and the like.
【０００９】乳化剤としては、プロピレングリコール脂
肪酸エステル，レシチン，ソルビタン脂肪酸エステル，
グリセリン脂肪酸エステル，グリセリン脂肪酸有機酸エ
ステル，ポリグリセリン脂肪酸エステル，ポリグリセリ
ンポリリシノール酸エステル，ショ糖脂肪酸エステルの
いずれを使用しても高い抗酸化力が得られる。As emulsifiers, propylene glycol fatty acid esters, lecithin, sorbitan fatty acid esters,
High antioxidant power can be obtained by using any of glycerin fatty acid ester, glycerin fatty acid organic acid ester, polyglycerin fatty acid ester, polyglycerin polyricinoleate, and sucrose fatty acid ester.
【００１０】[0010]
（実施例１）ラードを基質としたときの抗酸化活性 ナタネ油60部，水20部，トリグリセリンテトラリシノー
ル酸エステル（ＰＧＰＲ）10部，グリシン10部，トコフ
ェロール 0.2部を原料として混合後、乳化ミキサーを用
い1000回転10分間乳化を行い、試験区−１のＷ／Ｏエマ
ルジョンを得た。(Example 1) Antioxidant activity using lard as a substrate 60 parts of rapeseed oil, 20 parts of water, 10 parts of triglycerin tetraricinoleate (PGPR), 10 parts of glycine, and 0.2 part of tocopherol were mixed, and emulsified. Emulsification was performed at 1000 rpm for 10 minutes using a mixer to obtain a W / O emulsion in Test Section-1.
【００１１】抗酸化能の評価方法として抗酸化剤無添加
のラード90部に、試験区−１のＷ／Ｏエマルジョン10部
添加し抗酸化活性を測定した。抗酸化活性はＡＯＭ（強
制酸化法）により測定を行い、ＰＯＶ（過酸化物価）１
００到達時間で比較を行った（表１）。As a method for evaluating the antioxidant ability, 10 parts of the W / O emulsion of Test Section-1 was added to 90 parts of lard without the addition of an antioxidant, and the antioxidant activity was measured. The antioxidant activity is measured by AOM (forced oxidation method), and POV (peroxide value) 1
The comparison was made with the arrival time at 00 (Table 1).
【００１２】比較試験として ・試験区−２：グリシン及びトコフェロール無添加 ・ 〃 −３：グリシン無添加 ・ 〃 −４：トコフェロール無添加 ・ 〃 −５：グリシン無添加でトコフェロールの代わ
りにＢＨＴを 0.2部添加 により試験区−１と同様にエマルジョンを製造して抗酸
化能を測定した。As a comparative test: Test group-2: no glycine and tocopherol added 〃-3: no glycine added 〃-4: no tocopherol added 〃-5: 0.2 gram of BHT instead of tocopherol without glycine added Emulsions were prepared in the same manner as in Test Section-1 by the addition, and the antioxidant capacity was measured.
【００１３】対照区はラードのみのＰＯＶ１００到達時
間を測定した。In the control group, the arrival time of POV100 of only lard was measured.
【００１４】その結果、試験区−１のナタネ油，水，Ｐ
ＧＰＲ，グリシン，トコフェロールからなる原料を乳化
して得たＷ／Ｏ型エマルジョンは 509時間の活性が認め
られ、試験区−２（グリシン及びトコフェロール無添
加）、試験区−３（グリシン無添加）及び試験区−４
（トコフェロール無添加）より約20倍の活性が認めら
れ、抗酸化活性を増大させるためには、エマルジョンを
作製する際、トコフェロールとグリシン両方を添加しな
ければならないことを見いだした。また、ＢＨＴを添加
したエマルジョン（試験区−５）と比較しても優れた抗
酸化能を示した。As a result, rapeseed oil, water, P
The W / O emulsion obtained by emulsifying the raw material consisting of GPR, glycine, and tocopherol showed an activity of 509 hours, and the test plot-2 (without glycine and tocopherol), the test plot-3 (without glycine) and Test plot-4
The activity was about 20 times higher than (without addition of tocopherol), and it was found that both tocopherol and glycine had to be added when preparing an emulsion in order to increase the antioxidant activity. In addition, it showed excellent antioxidant ability as compared with the emulsion to which BHT was added (test group-5).
【００１５】また、ラード90部に表１の試験区−４のＷ
／Ｏエマルジョン10部及びトコフェロール0.02部を添加
して抗酸化活性を調べた結果、ＰＯＶ１００到達時間 4
90時間が得られ、トコフェロールをＷ／Ｏエマルジョン
使用時に添加しても同等の効果が認められた。In addition, 90 parts of Lard had W in Test Section-4 in Table 1.
As a result of adding 10 parts of / O emulsion and 0.02 parts of tocopherol and examining the antioxidant activity, the time to reach POV100 was 4
90 hours were obtained, and the same effect was observed even when tocopherol was added when using the W / O emulsion.
【００１６】試験区−６では、ナタネ油20部，水65部，
グリセリンモノステアレート５部，グリシン10部，トコ
フェロール 0.2部を原料として混合後、乳化ミキサーを
用いて 10000回転10分間乳化を行いＯ／Ｗエマルジョン
を得、上記と同様の方法にて抗酸化能を測定したところ
試験区−１と同様にグリシン，トコフェロールを添加し
ているにもかかわらず試験区−１の様な高い抗酸化能は
得られなかった。In the test section-6, 20 parts of rapeseed oil, 65 parts of water,
After mixing 5 parts of glycerin monostearate, 10 parts of glycine, and 0.2 parts of tocopherol as raw materials, emulsification was performed at 10,000 rpm for 10 minutes using an emulsification mixer to obtain an O / W emulsion. As a result of the measurement, as in the case of the test group-1, the high antioxidant ability as in the test group-1 could not be obtained despite the addition of glycine and tocopherol.
【００１７】[0017]
【表１】 [Table 1]
【００１８】（実施例２）大豆白紋油、ナタネ油を基質
としたときの抗酸化活性 実施例１と同様にしてＷ／Ｏエマルジョンを作製し抗酸
化活性を測定するための基質を大豆白紋油、ナタネ油を
用いて抗酸化活性の測定を行った。その際、大豆白紋
油、ナタネ油にはトコフェロールが含まれているためエ
マルジョンにトコフェロールの添加を行わなかった。そ
の結果、本製法によって得られたエマルジョンに高い抗
酸化活性が認められ、動物油だけでなく、植物油にも効
果が認められた。（表２及び表３）Example 2 Antioxidant Activity Using Soybean White Crest Oil and Rapeseed Oil as Substrates A W / O emulsion was prepared in the same manner as in Example 1 and the substrate for measuring antioxidant activity was soybean white. The antioxidant activity was measured using crest oil and rapeseed oil. At that time, tocopherol was not added to the emulsion because soybean white-mark oil and rapeseed oil contained tocopherol. As a result, a high antioxidant activity was observed in the emulsion obtained by this production method, and an effect was observed not only in animal oil but also in vegetable oil. (Tables 2 and 3)
【００１９】[0019]
【表２】 [Table 2]
【００２０】[0020]
【表３】 [Table 3]
【００２１】（実施例３）グリシン以外のアミノ酸のシ
ネルギストとしての効果 グリシン以外のアミノ酸について同等の抗酸化力の効果
があるかどうか検討を行った。アミノ酸として、アラニ
ン，グルタミン酸，ヒスチジン，チロシン，トリプトフ
ァンを用いた。エマルジョンの作製は実施例１の試験区
−１と同様に作製した。ラードを基質としてＡＯＭによ
り抗酸化活性を測定した結果、グリシンは他のアミノ酸
と比較して高い活性を有しシネルギストとして優れてい
た。（表４）(Example 3) Effect of amino acids other than glycine as synergist It was examined whether amino acids other than glycine have the same antioxidative effect. Alanine, glutamic acid, histidine, tyrosine, and tryptophan were used as amino acids. The emulsion was prepared in the same manner as in Test Section-1 of Example 1. As a result of measuring antioxidant activity by AOM using lard as a substrate, glycine had higher activity than other amino acids and was excellent as a synergist. (Table 4)
【００２２】[0022]
【表４】 [Table 4]
【００２３】（実施例４）ＥＰＡ（エイコサペンタエン
酸）、ＤＨＡ（ドコサヘキサエン酸）の安定化試験 実施例１と同様にしてＷ／Ｏエマルジョンを作製し、抗
酸化活性を測定するための基質をＥＰＡ，ＤＨＡを含有
する油を用いて試験を行った。ＥＰＡ、及びＤＨＡはラ
ードにそれぞれ20％ずつ添加し試験を行った。ＡＯＭに
より抗酸化活性を測定した結果、本製法によって得られ
たエマルジョン（試験区−11及び13）はＢＨＴ（試験区
−12及び14）と比較して高い抗酸化活性が認められ、Ｅ
ＰＡ及びＤＨＡの安定化を行うことができる。（表５及
び表６）(Example 4) Stability test of EPA (eicosapentaenoic acid) and DHA (docosahexaenoic acid) A W / O emulsion was prepared in the same manner as in Example 1 and the substrate for measuring the antioxidant activity was EPA. , DHA were tested. EPA and DHA were each added to lard at 20% and tested. As a result of measuring the antioxidant activity by AOM, the emulsion obtained by this production method (test groups -11 and 13) showed higher antioxidant activity than BHT (test groups -12 and 14).
PA and DHA can be stabilized. (Tables 5 and 6)
【００２４】[0024]
【表５】 [Table 5]
【００２５】[0025]
【表６】 [Table 6]
【００２６】（実施例５）油溶性色素の退色防止試験 本製法で作製したエマルジョンについて、油脂の抗酸化
性だけでなく油溶性色素の退色防止効果についても試験
を行った。Example 5 Test for Preventing Discoloration of Oil-Soluble Dye The emulsion prepared by this method was tested not only for the antioxidant property of fats and oils but also for the effect of preventing the discoloration of oil-soluble dyes.
【００２７】Ｗ／Ｏエマルジョンは表７の様に示す配合
で作製した。砂糖に１％の油溶性色素（アナトー色素、
パプリカ色素）及びＷ／Ｏエマルジョンを３％添加し、
プラスチックシャーレに入れ 8000LUXの蛍光灯存在下で
退色試験を行った。退色度は色差計を用いａ値を測定し
残存率を求め判定した。その結果、油溶性色素について
も、トコフェロールとグリシンを両者添加したＷ／Ｏエ
マルジョンが最も退色防止効果を示し、本エマルジョン
は油脂に対する抗酸化作用だけでなく、油溶性色素の光
酸化に対しても有効であった。（図１及び図２）The W / O emulsion was prepared with the composition shown in Table 7. 1% oil-soluble dye in sugar (anato dye,
Paprika dye) and 3% W / O emulsion,
A discoloration test was performed in a plastic petri dish in the presence of 8000 LUX fluorescent light. The degree of fading was determined by measuring the a value using a color difference meter to determine the residual ratio. As a result, as for the oil-soluble dye, the W / O emulsion to which both tocopherol and glycine were added exhibited the most anti-fading effect. This emulsion not only has an antioxidant effect on fats and oils, but also has a photo-oxidation effect on the oil-soluble dye. Was effective. (FIGS. 1 and 2)
【００２８】[0028]
【表７】 [Table 7]
【００２９】（実施例６）Ｏ／Ｗ／Ｏエマルジョンでの
抗酸化試験 水を65℃まで加温し、グリシン及びデカグリセリンモノ
ラウレートを溶解後これに65℃のビタミンＣパルミテー
トを添加したラードを徐々に添加して、乳化ミキサーで
10000回転、10分間攪拌後15℃まで急冷しＯ／Ｗエマル
ジョンを作製した。次に、トコフェロールを添加したコ
ーンサラダ油を50℃まで加温しグリセリンモノステアレ
ートを充分に溶解した後、15℃まで冷却し、さきに調製
したＯ／Ｗエマルジョンを攪拌しながら徐々に添加し、
Ｏ／Ｗ／Ｏエマルジョンを調製した。(Example 6) Antioxidant test with O / W / O emulsion Water was heated to 65 ° C, glycine and decaglycerin monolaurate were dissolved, and then added with vitamin C palmitate at 65 ° C. And gradually add
After stirring at 10,000 rpm for 10 minutes, the mixture was rapidly cooled to 15 ° C. to prepare an O / W emulsion. Next, the corn salad oil to which tocopherol was added was heated to 50 ° C. to sufficiently dissolve glycerin monostearate, cooled to 15 ° C., and the O / W emulsion prepared earlier was gradually added while stirring.
An O / W / O emulsion was prepared.
【００３０】このＯ／Ｗ／Ｏエマルジョンについて、実
施例１と同様にして抗酸化活性の測定を行った結果、Ｗ
／Ｏエマルジョンと同様に高い活性が認められた。（表
８）The antioxidant activity of this O / W / O emulsion was measured in the same manner as in Example 1.
High activity was observed as in the / O emulsion. (Table 8)
【００３１】[0031]
【表８】 [Table 8]
【図１】本発明法に係るエマルジョンによる油溶性色素
（アナトー色素）の退色防止試験の結果を示す実測図で
ある。FIG. 1 is an actual measurement diagram showing the results of a test for preventing the dissolution of an oil-soluble dye (annatto dye) using an emulsion according to the present invention.
【図２】本発明法に係るエマルジョンによる油溶性色素
（パプリカ色素）の退色防止試験の結果を示す実測図で
ある。FIG. 2 is an actual measurement diagram showing the results of a test for preventing fading of an oil-soluble dye (paprika dye) using the emulsion according to the method of the present invention.
15，16，17はいずれも試験区の番号 15, 16, and 17 are the numbers of test plots
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ Ｃ０９Ｋ 15/34 Ｃ０９Ｋ 15/34 (58)調査した分野(Int.Cl.7，ＤＢ名) B01J 13/00 ────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. 7 identification symbol FI C09K 15/34 C09K 15/34 (58) Fields investigated (Int.Cl. 7 , DB name) B01J 13/00
Claims (2)
グリシン0.01重量部以上、乳化剤0.01重量部以上、抗酸
化剤0.01重量部以上からなる原料を乳化することを特徴
とする抗酸化能を有するＷ／Ｏ型またはＯ／Ｗ／Ｏ型エ
マルジョンの製造法。(1) at least 50 parts by weight of water, at most 500 parts by weight of fats and oils,
A method for producing a W / O or O / W / O emulsion having antioxidant activity, comprising emulsifying a raw material comprising at least 0.01 part by weight of glycine, at least 0.01 part by weight of an emulsifier, and at least 0.01 part by weight of an antioxidant. .
グリシン0.01重量部以上、乳化剤0.01重量部以上からな
る原料を乳化して使用時に抗酸化剤を加えることを特徴
とするＷ／Ｏ型またはＯ／Ｗ／Ｏ型エマルジョンの製造
法。2. Water 50 parts by weight or more, fats and oils 500 parts by weight or less,
A method for producing a W / O or O / W / O emulsion, comprising emulsifying a raw material comprising at least 0.01 part by weight of glycine and at least 0.01 part by weight of an emulsifier and adding an antioxidant at the time of use.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27651191A JP3174855B2 (en) | 1991-09-27 | 1991-09-27 | Method for producing emulsion having antioxidant ability |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27651191A JP3174855B2 (en) | 1991-09-27 | 1991-09-27 | Method for producing emulsion having antioxidant ability |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0584436A JPH0584436A (en) | 1993-04-06 |
| JP3174855B2 true JP3174855B2 (en) | 2001-06-11 |
Family
ID=17570490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27651191A Expired - Fee Related JP3174855B2 (en) | 1991-09-27 | 1991-09-27 | Method for producing emulsion having antioxidant ability |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3174855B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2957782C (en) * | 2014-09-02 | 2022-07-26 | Loders Croklaan B.V. | Glyceride composition |
| JP2016186002A (en) * | 2015-03-27 | 2016-10-27 | 不二製油株式会社 | Antioxidant |
| US11957135B2 (en) | 2016-03-02 | 2024-04-16 | Fuji Oil Holdings Inc. | Chocolate-like food containing polyunsaturated fatty acid |
| WO2017149701A1 (en) * | 2016-03-02 | 2017-09-08 | 不二製油グループ本社株式会社 | Fat or oil composition |
| BR112018016998B1 (en) * | 2016-03-02 | 2023-10-24 | Fuji Oil Holdings Inc | OIL AND FAT ANTIOXIDANT COMPOSITION AND METHODS FOR PRODUCING THE SAME |
-
1991
- 1991-09-27 JP JP27651191A patent/JP3174855B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0584436A (en) | 1993-04-06 |
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