JP2597122B2 - Curing agent for epoxy resin - Google Patents
Curing agent for epoxy resinInfo
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- JP2597122B2 JP2597122B2 JP62332564A JP33256487A JP2597122B2 JP 2597122 B2 JP2597122 B2 JP 2597122B2 JP 62332564 A JP62332564 A JP 62332564A JP 33256487 A JP33256487 A JP 33256487A JP 2597122 B2 JP2597122 B2 JP 2597122B2
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- curing agent
- epoxy resin
- ethyl
- curing
- carbon atoms
- Prior art date
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Description
【発明の詳細な説明】 ＜産業上の利用分野＞ 本発明はエポキシ樹脂用液状硬化剤に関するものであ
る。Description: TECHNICAL FIELD The present invention relates to a liquid curing agent for epoxy resins.
＜従来の技術及び本発明が解決しようとする問題点＞ ２−エチル−４−メチルイミダゾールはエポキシ樹脂
の硬化剤、硬化促進剤として広範囲に使用されている有
用なイミダゾール化合物である。<Prior Art and Problems to be Solved by the Present Invention> 2-Ethyl-4-methylimidazole is a useful imidazole compound widely used as a curing agent and curing accelerator for epoxy resins.
２−エチル−４メチルイミダゾールは、通常室温では
過冷却状態にあり、液状を保っているが、粘度が非常に
高く取扱いが容易でなく、また本来、融点45℃の固体で
あるため、何らかの原因により容易に固化する性質を有
しており液状維持が困難である。一旦固化したものは加
熱融解し、液状となして使用しているが、それは甚だ煩
雑な作業となっている。2-Ethyl-4-methylimidazole is usually in a supercooled state at room temperature and remains in a liquid state, but has a very high viscosity and is not easy to handle, and is originally a solid having a melting point of 45 ° C. It has the property of solidifying more easily, and it is difficult to maintain the liquid state. Once solidified, it is heated and melted and used in the form of a liquid, which is a very complicated operation.
エポキシ樹脂が室温で液状の場合には、硬化剤、硬化
促進剤が室温で液状であれば、両者の均一混合は容易と
なり、反対に硬化剤、硬化促進剤が固体である場合に
は、両者の混合は困難となり、硬化剤、硬化促進剤は室
温で液状であることが望ましい。以上は多くの使用者の
願望である。When the epoxy resin is liquid at room temperature, if the curing agent and the curing accelerator are liquid at room temperature, uniform mixing of both becomes easy, and conversely, if the curing agent and the curing accelerator are solid, Becomes difficult, and the curing agent and the curing accelerator are desirably liquid at room temperature. These are the wishes of many users.
＜問題を解決するための手段＞ 本発明者等は、このような欠点を解消すべく克明な試
験研究を重ねた結果、一般式［Ｉ］ （式中、R1は炭素数２〜６のアルキル基を示す。R2は炭
素数１〜６のアルキル基、又は一般式［II］ で表わされる置換基（R3は水素原子又は炭素数１〜４の
アルキル基を示す。）を示す。ただし、R1が炭素数３〜
６のアルキル基であってR2がメチル基又はエチル基であ
る場合は除く。）で表わされる室温で液状の１−置換イ
ミダゾール化合物を２−エチル−４−メチルイミダゾー
ルに配合したものは、室温で長期間低粘度の液状を示す
ことを見出した。一方、一般式［Ｉ］で表わされる１−
置換イミダゾール化合物を通常硬化剤として良く使用さ
れ、２−エチル−４−メチルイミダゾールの同族体であ
る２−メチルイミダゾール又は２−フェニルイミダゾー
ルなどに配合したものは前記配合物とは逆に室温で均一
な液状を示しがたいことが判明した。従って、一般式
［Ｉ］で表わされる１−置換イミダゾール化合物と２−
エチル−４−メチルイミダゾールとの配合物における前
述の知見は極めて意外なものである。<Means for Solving the Problem> The inventors of the present invention have conducted intensive studies and studies in order to solve such a drawback, and as a result, the general formula [I] (In the formula, R 1 represents an alkyl group having 2 to 6 carbon atoms. R 2 represents an alkyl group having 1 to 6 carbon atoms or a general formula [II] Wherein R 3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Provided that R 1 has 3 to 3 carbon atoms
Except when the alkyl group is 6 and R 2 is a methyl group or an ethyl group. It has been found that a compound obtained by mixing a 1-substituted imidazole compound which is liquid at room temperature represented by the formula (2) with 2-ethyl-4-methylimidazole exhibits a low-viscosity liquid at room temperature for a long period of time. On the other hand, 1- represented by the general formula [I]
Substituted imidazole compounds are commonly used as curing agents, and those mixed with 2-methylimidazole or 2-phenylimidazole, which is a homologue of 2-ethyl-4-methylimidazole, are uniform at room temperature, contrary to the above compound. It turned out that it was difficult to show a good liquid. Therefore, the 1-substituted imidazole compound represented by the general formula [I] and 2-
The foregoing findings in blends with ethyl-4-methylimidazole are quite surprising.
又、一般式［Ｉ］で表わされるＩ−置換イミダゾール
化合物と２−エチル−４−メチルイミダゾールとの配合
物はエポキシ樹脂との相溶性、配合性に優れており、さ
らに、この配合物を含有するエポキシ樹脂組成物を硬化
させてえられる硬化生成物は、２−エチル−４−メチル
イミダゾールと同様に良好な硬化物性を示す事も見出し
本発明を完成するに至った。Further, a blend of the I-substituted imidazole compound represented by the general formula [I] and 2-ethyl-4-methylimidazole has excellent compatibility with an epoxy resin and blendability, and further contains this blend. The cured product obtained by curing the epoxy resin composition described above has also been found to exhibit good cured physical properties in the same manner as 2-ethyl-4-methylimidazole, thereby completing the present invention.
すなわち、本発明は一般式［Ｉ］ （式中、R1は炭素数２〜６のアルキル基を示す。R2は炭
素数１〜６のアルキル基、又は一般式［II］ で表わされる置換基（R3は水素原子又は炭素数１〜４の
アルキル基を示す。）を示す。ただし、R1が炭素数３〜
６のアルキル基であってR2がメチル基又はエチル基であ
る場合は除く。）で表わされる１−置換イミダゾール化
合物（以下、１−置換イミダゾール（Ｉ）という）と２
−エチル−４−メチルイミダゾールからなるエポキシ樹
脂溶液状硬化剤に関する。That is, the present invention provides a compound represented by the general formula [I]: (In the formula, R 1 represents an alkyl group having 2 to 6 carbon atoms. R 2 represents an alkyl group having 1 to 6 carbon atoms or a general formula [II] Wherein R 3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Provided that R 1 has 3 to 3 carbon atoms
Except when the alkyl group is 6 and R 2 is a methyl group or an ethyl group. 1) -substituted imidazole compound (hereinafter referred to as 1-substituted imidazole (I))
An epoxy resin solution curing agent comprising -ethyl-4-methylimidazole.
一般式［Ｉ］中、R1は炭素数２〜６のアルキル基、例
えばエチル、プロピル、イソプロピル、ブチル、イソブ
チル、第２ブチル、第３ブチル、ペンチル、イソペンチ
ル、ネオペンチル、ヘキシル等である。In the general formula [I], R 1 is an alkyl group having 2 to 6 carbon atoms, for example, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl and the like.
一般式［Ｉ］中、R2は炭素数１〜６のアルキル基、例
えばメチル、エチル、プロピル、イソプロピル、ブチ
ル、イソブチル、第２ブチル、第３ブチル、ペンチル、
イソペンチル、ネオペンチル、ヘキシル等である。In the general formula [I], R 2 is an alkyl group having 1 to 6 carbon atoms, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl,
Isopentyl, neopentyl, hexyl and the like.
一般式［II］中、R3は水素原子、あるいは炭素数１〜
４のアルキル基、例えばメチル、エチル、プロピル、イ
ソプロピル、ブチル、イソブチル、第２ブチル、第３ブ
チル等である。また、R3はアルキル基である場合、フェ
ニル基のオルト、メタ、バラ何れの位置にあってもよ
い。In the general formula [II], R 3 is a hydrogen atom or a group having 1 to 1 carbon atoms.
And 4 alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl and the like. When R 3 is an alkyl group, it may be located at any of ortho, meta and rose positions of the phenyl group.
本発明において使用される、１−置換イミダゾール
（Ｉ）の具体例としては、１−エチル−２−メチルイミ
ダゾール、１−エチル−２−フェニルイミダゾール、１
−プロピル−２−フェニルイミダゾール、１−ブチル−
２−フェニルイミダゾール、１−イソブチル−２−フェ
ニルイミダゾール、１−エチル−２−（ｐ−メチルフェ
ニル）イミダゾール、１−エチル−２−（ｐ−メチルフ
ェニル）イミダゾールなどが挙げられるが、これらに限
定されるものではない。Specific examples of the 1-substituted imidazole (I) used in the present invention include 1-ethyl-2-methylimidazole, 1-ethyl-2-phenylimidazole,
-Propyl-2-phenylimidazole, 1-butyl-
Examples include, but are not limited to, 2-phenylimidazole, 1-isobutyl-2-phenylimidazole, 1-ethyl-2- (p-methylphenyl) imidazole, 1-ethyl-2- (p-methylphenyl) imidazole It is not something to be done.
本発明の硬化剤を利用しうるエポキシ樹脂としては一
分子当たり平均一個以上のエポキシ基を有する化合物、
例えば、ビスフェノールＡ型エポキシ樹脂、フェノール
ノボラック型エポキシ樹脂、クレゾールノボラック型エ
ポキシ樹脂、脂肪族グリシジルエーテル型エポキシ樹
脂、脂環式エポキシ樹脂、複素環型エポキシ樹脂等が挙
げられるが、これらに限定されるものではない。また上
記エポキシ化合物とフェニルグリシジルエーテル、ブチ
ルグリシジルエーテル、フェノキシエーテル系モノエポ
キサイドなどのモノエポキシ化合物を適宜併用したもの
であってもさしつかえはない。Epoxy resins that can utilize the curing agent of the present invention include compounds having an average of one or more epoxy groups per molecule,
Examples include, but are not limited to, bisphenol A type epoxy resin, phenol novolak type epoxy resin, cresol novolak type epoxy resin, aliphatic glycidyl ether type epoxy resin, alicyclic epoxy resin, and heterocyclic type epoxy resin. Not something. In addition, there may be no problem even if the above epoxy compound and a monoepoxy compound such as phenyl glycidyl ether, butyl glycidyl ether, and phenoxy ether monoepoxide are appropriately used in combination.
本発明の硬化剤は、１−置換イミダゾール（Ｉ）と２
−エチル−４−メチルイミダゾールとの広範囲にわたる
配合比で室温で長期間低粘度を示し、その配合比は特に
限定されるものではないが、２−エチル−４−メチルイ
ミダゾールと同等の硬化特性、硬化物性を得ようとする
場合なら１−置換イミダゾール（Ｉ）の配合比を40重量
％以下にするのが好ましい。The curing agent of the present invention comprises 1-substituted imidazole (I) and 2
It exhibits low viscosity at room temperature for a long time at a wide range of compounding ratio with -ethyl-4-methylimidazole, and the compounding ratio is not particularly limited, but has the same curing properties as 2-ethyl-4-methylimidazole, When it is desired to obtain cured physical properties, it is preferable that the compounding ratio of the 1-substituted imidazole (I) is 40% by weight or less.
本発明の硬化剤の使用量は通常エポキシ樹脂100重量
部に対して0.1〜20重量部である。即ち0.1重量部以下で
は硬化に長時間を要し20重量部以上では耐湿性が低下す
るためである。本発明の硬化剤を含有するエポキシ樹脂
組成物の硬化温度は60〜200℃であり、好ましくは100〜
180℃の範囲である。The amount of the curing agent of the present invention is usually 0.1 to 20 parts by weight based on 100 parts by weight of the epoxy resin. That is, when it is 0.1 part by weight or less, it takes a long time for curing, and when it is 20 parts by weight or more, the moisture resistance decreases. The curing temperature of the epoxy resin composition containing the curing agent of the present invention is 60 to 200 ° C, preferably 100 to 200 ° C.
180 ° C range.
本発明の硬化剤は他の硬化成分、例えばフタル酸無水
物、テトラヒドロフタル酸無水物、メチル−3.6−エン
ドメチレン−４−テトラヒドロフタル酸無水物、ピロメ
リット酸無水物、トリメリット酸無水物などのポリカル
ボン酸無水物、メタフェニレンヂアミン、ジアミノジフ
ェニルメタンなどの芳香族アミン、ジシアンジアミド、
フェノール樹脂、ノボラック樹脂などの多価フェノー
ル、トリフェニルホスファイトフェノールメルカプタ
ン、第４級アンモニウムなどと併用しても使用できる。
この場合、本発明の硬化剤の使用量は、エポキシ樹脂10
0重量部に対して0.1〜10重量部である。The curing agent of the present invention contains other curing components such as phthalic anhydride, tetrahydrophthalic anhydride, methyl-3.6-endomethylene-4-tetrahydrophthalic anhydride, pyromellitic anhydride, trimellitic anhydride and the like. Polycarboxylic anhydride, metaphenylene diamine, aromatic amines such as diaminodiphenylmethane, dicyandiamide,
It can also be used in combination with polyhydric phenols such as phenolic resins and novolak resins, triphenyl phosphite phenol mercaptan, quaternary ammonium and the like.
In this case, the used amount of the curing agent of the present invention is
0.1 to 10 parts by weight with respect to 0 parts by weight.
本発明の１−置換イミダゾール（Ｉ）は、特開昭59−
8487や、特願昭61−37646の明細書記載の方法により容
易にえられる。The 1-substituted imidazole (I) of the present invention is disclosed in
8487 or the method described in the specification of Japanese Patent Application No. 61-37646.
本発明の硬化剤を含有するエポキシ樹脂組成物は顔
料、可塑剤、充填剤、あるいはモノエポキシドのごとき
稀釈剤と併用しても使用できる。The epoxy resin composition containing the curing agent of the present invention can be used in combination with a pigment, a plasticizer, a filler, or a diluent such as a monoepoxide.
また本エポキシ樹脂組成物は抵抗器、コンデンサ、ダ
イオード、トランジスタ、などの絶縁封止用塗料、接着
剤、注型材料や、本エポキシ樹脂組成物を適当な繊維物
質に含浸させて得られる積層物（含浸エポキシ）の製造
等に使用することができる。In addition, the epoxy resin composition is used for insulating sealing paints such as resistors, capacitors, diodes, transistors, etc., adhesives, casting materials, and laminates obtained by impregnating the epoxy resin composition with an appropriate fiber substance. (Impregnated epoxy).
以下、本発明を実施例及び比較例に基づいて説明す
る。Hereinafter, the present invention will be described based on examples and comparative examples.
実施例１、２及び比較例１ （粘度及び液状の保存安定性） 比較例１としての２−エチル−４−メチルイミダゾー
ル（以下2E4MImと略す）そのもの、実施例１としての2E
4MImに１−エチル−２−メチルイミダゾール（以下1E2M
Imと略す）を配合してなる硬化剤、実施例２としての2E
4MImに１−エチル−２−フェニルイミダゾール（以下1E
2PhImと略す）を配合してなる硬化剤について、25℃に
おける粘度を測定し、さらに０℃における保存安定性テ
ストを行なった。その結果を表−１に示した。Examples 1 and 2 and Comparative Example 1 (Viscosity and storage stability of liquid) 2-Ethyl-4-methylimidazole (hereinafter abbreviated as 2E4MIm) itself as Comparative Example 1, 2E as Example 1
1-ethyl-2-methylimidazole (hereinafter referred to as 1E2M
Im), 2E as Example 2
1-Ethyl-2-phenylimidazole (hereinafter referred to as 1E)
2PhIm), the viscosity at 25 ° C. was measured, and a storage stability test was performed at 0 ° C. The results are shown in Table 1.
表−１から明らかなように実施例１、２の硬化剤の粘
度は、比較例１の2E4MImより大幅に低下している。又、
液状の安定性は、実施例１、２の硬化剤は、０℃で３か
月以上液状を示した。As is clear from Table 1, the viscosities of the curing agents of Examples 1 and 2 are significantly lower than 2E4MIm of Comparative Example 1. or,
As for the stability of the liquid, the curing agents of Examples 1 and 2 were liquid at 0 ° C. for 3 months or more.
比較例１の2E4MImは０℃で１か月後には融点45℃の結
晶となった。2E4MIm of Comparative Example 1 was a crystal having a melting point of 45 ° C. after one month at 0 ° C.
実施例３、４及び比較例２ （配合性） エピコート828（２、２−ビス（４−オキシフェニ
ル）プロパンのジグリシジルエーテル）10重量部と各種
硬化剤0.5重量部を室温で３分間撹拌混合し、エポキシ
樹脂との配合の容易さを検討した。 Examples 3 and 4 and Comparative Example 2 (Compoundability) 10 parts by weight of Epikote 828 (diglycidyl ether of 2,2-bis (4-oxyphenyl) propane) and 0.5 part by weight of various curing agents were stirred and mixed at room temperature for 3 minutes. Then, the ease of blending with the epoxy resin was examined.
硬化剤としては、比較例２に2E4MIm、実施例３に2E4M
Imに1E2MImを配合してなる硬化剤、実施例４に2E4MImに
1E2PhImを配合してなる硬化剤を用いた。As the curing agent, 2E4MIm in Comparative Example 2 and 2E4M in Example 3
A curing agent obtained by mixing 1E2MIm with Im, and 2E4MIm in Example 4.
A curing agent containing 1E2PhIm was used.
その結果を表−２に示した。表−２から明らかなよう
に、実施例３の2E4MImに1E2MImを配合してなる硬化剤、
実施例４の2E4MImに1E2PhImを配合してなる硬化剤は、
比較例２の2E4MImに比べ、速やかに溶解し配合が容易で
あった。The results are shown in Table-2. As is clear from Table 2, a curing agent obtained by blending 1E2MIm with 2E4MIm of Example 3,
The curing agent obtained by blending 1E2PhIm with 2E4MIm in Example 4 is as follows:
Compared to 2E4MIm of Comparative Example 2, it was dissolved more quickly and was easier to mix.
実施例５、６及び比較例３ （硬化特性及び硬化物性） エポキシ樹脂としてエピコート828の100重量部、各種
硬化剤の４重量部を室温で30分間撹拌混合して得られた
エポキシ樹脂組成物の可使時間、発熱特性を評価し、更
に該組成物を60℃で６時間、150℃で２時間硬化させて
得られた硬化物の熱変形温度、曲げ特性、煮沸吸水率を
評価した。 Examples 5 and 6 and Comparative Example 3 (Curing Properties and Cured Physical Properties) An epoxy resin composition obtained by stirring and mixing 100 parts by weight of Epicoat 828 and 4 parts by weight of various curing agents as an epoxy resin at room temperature for 30 minutes. The pot life and exothermic characteristics were evaluated, and the cured product obtained by curing the composition at 60 ° C. for 6 hours and 150 ° C. for 2 hours was evaluated for the heat distortion temperature, bending characteristics, and boiling water absorption.
実施例５は2E4MImに１−置換イミダゾール（１）とし
て1E2MImを配合したもの、実施例６は1E2PhImを配合し
たもの、比較例３は2E4MImを硬化剤として使用した。Example 5 used 1E2MIm as 1-substituted imidazole (1) in 2E4MIm, Example 6 used 1E2PhIm, and Comparative Example 3 used 2E4MIm as a curing agent.
その結果を表−３に示した。表−３から明らかなよう
に、実施例５の硬化剤は比較例３の2E4MImと比較すると
ほぼ同様な硬化物性であるが、1E2MImの配合比が増える
と硬化が速くなる。即ち、硬化物性を変えずに硬化をは
やめることができる。The results are shown in Table-3. As is clear from Table 3, the curing agent of Example 5 has almost the same curing physical properties as 2E4MIm of Comparative Example 3, but the curing speed increases as the mixing ratio of 1E2MIm increases. That is, curing can be stopped without changing the cured physical properties.
実施例６の硬化剤は比較例３の2E4MImと比較して、1E
2PhImの配合比を増やすことにより硬化を遅らせること
ができる。又、硬化物性は比較例３の2E4MImと比較する
と、熱変形温度、曲げ特性はほぼ同等ないし、同等以上
であった。The curing agent of Example 6 was 1E in comparison with 2E4MIm of Comparative Example 3.
Curing can be delayed by increasing the blending ratio of 2PhIm. Also, as compared with the 2E4MIm of Comparative Example 3, the cured materials had almost the same or higher heat deformation temperature and bending characteristics than the 2E4MIm.
＜発明の効果＞ 本発明のエポキシ樹脂硬化剤は、室温で長期間低粘度
の液状を示し、またエポキシ樹脂との配合が非常に容易
である。 <Effect of the Invention> The epoxy resin curing agent of the present invention shows a liquid having a low viscosity at room temperature for a long period of time, and is very easy to mix with an epoxy resin.
又、本発明の硬化剤は、配合する１−置換イミダゾー
ル（Ｉ）の種類により、本硬化剤を含有するエポキシ樹
脂組成物の硬化速度の増減、硬化物性の向上など、種々
の特性を付与することができる。Further, the curing agent of the present invention imparts various properties, such as an increase or a decrease in curing speed of an epoxy resin composition containing the present curing agent, and an improvement in cured properties, depending on the type of the 1-substituted imidazole (I) to be blended. be able to.
Claims (1)
素数１〜６のアルキル基、又は一般式［II］ で表わされる置換基（R3は水素原子又は炭素数１〜４の
アルキル基を示す。）を示す。ただし、R1が炭素数３〜
６のアルキル基であってR2がメチル基又はエチル基であ
る場合は除く。）で表わされる１−置換イミダゾール化
合物と２−エチル−４−メチルイミダゾールからなるエ
ポキシ樹脂用液状硬化剤。1. A compound of the general formula [I] (In the formula, R 1 represents an alkyl group having 2 to 6 carbon atoms. R 2 represents an alkyl group having 1 to 6 carbon atoms or a general formula [II] Wherein R 3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Provided that R 1 has 3 to 3 carbon atoms
Except when the alkyl group is 6 and R 2 is a methyl group or an ethyl group. A liquid curing agent for an epoxy resin comprising a 1-substituted imidazole compound represented by the formula) and 2-ethyl-4-methylimidazole.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62332564A JP2597122B2 (en) | 1987-12-29 | 1987-12-29 | Curing agent for epoxy resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62332564A JP2597122B2 (en) | 1987-12-29 | 1987-12-29 | Curing agent for epoxy resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01174520A JPH01174520A (en) | 1989-07-11 |
| JP2597122B2 true JP2597122B2 (en) | 1997-04-02 |
Family
ID=18256333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62332564A Expired - Fee Related JP2597122B2 (en) | 1987-12-29 | 1987-12-29 | Curing agent for epoxy resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2597122B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7113758B2 (en) * | 2016-12-15 | 2022-08-05 | 広栄化学株式会社 | Epoxy compound polymerization catalyst containing amidate compound |
| CN113121794B (en) * | 2019-12-31 | 2022-05-20 | 惠州盛世达科技有限公司 | Dimethyl imidazole liquefaction method |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2533781B2 (en) * | 1987-10-30 | 1996-09-11 | 油化シエルエポキシ株式会社 | Amorphous imidazole derivative composition that is liquid at room temperature |
-
1987
- 1987-12-29 JP JP62332564A patent/JP2597122B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01174520A (en) | 1989-07-11 |
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