JPS63105024A - Production of resin composition for flame-retardant laminated sheet - Google Patents
Production of resin composition for flame-retardant laminated sheetInfo
- Publication number
- JPS63105024A JPS63105024A JP25049386A JP25049386A JPS63105024A JP S63105024 A JPS63105024 A JP S63105024A JP 25049386 A JP25049386 A JP 25049386A JP 25049386 A JP25049386 A JP 25049386A JP S63105024 A JPS63105024 A JP S63105024A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- bisphenol
- epoxy resin
- parts
- weight
- 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.)
- Granted
Links
- 239000011342 resin composition Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims description 3
- 239000003063 flame retardant Substances 0.000 title claims description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000003822 epoxy resin Substances 0.000 claims abstract description 22
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 22
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 15
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 abstract description 6
- 229930185605 Bisphenol Natural products 0.000 abstract 2
- 239000004593 Epoxy Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 239000004843 novolac epoxy resin Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000218691 Cupressaceae Species 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229920006015 heat resistant resin Polymers 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Landscapes
- Reinforced Plastic Materials (AREA)
- Laminated Bodies (AREA)
- Epoxy Resins (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は、耐熱性に優れた難燃性ｌｆＩ層板由四脂組成
物の製造法に関するものである。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a method for producing a flame-retardant lfI-laminated four-fat composition having excellent heat resistance.
従来の技術
電子機器の小型軽量化Ｃ二伴なって、積層板を用いた絶
縁基板に搭載下る部品として、チップ部品及びフラット
パッケージＬｓＴが多用されてきている。これに対応下
る為、クレゾールノボラック樹脂エポキシ、フェ／−ル
ツボラック樹脂エポキシ、或はその他の多官能エポキシ
樹脂などをビスフェノールＡ系エポキシ樹脂に冷加した
樹脂１５ｅ噴層板の製造に用いる事により耐熱性を同上
させてさた。BACKGROUND OF THE INVENTION As electronic devices become smaller and lighter, chip components and flat packages LsT are increasingly used as components mounted on insulating substrates using laminates. In order to cope with this, heat-resistant resin 15e is used in the manufacture of resin 15e spray plates, which are made by cooling cresol novolac resin epoxy, ferro-crucible resin epoxy, or other multifunctional epoxy resins into bisphenol A-based epoxy resin. Same with gender.
発明が解決しようとＴる問題点
しかしながら、ビスフェノールＡ系エポキシ樹脂と多官
能エポキシ樹脂とは硬化速度が異なる為、積層板の＃熱
性の向上が小さく、耐薬品性が悪くなると同時Ｃ二未反
応エポキシ情脂が多く残り、スミアの発生が生じや丁く
なる。Problems that the invention seeks to solve However, since the curing speeds of bisphenol A-based epoxy resins and multifunctional epoxy resins are different, the improvement in thermal properties of the laminate is small, and chemical resistance deteriorates, resulting in simultaneous C2 non-reaction. A large amount of epoxy oil remains, causing smear and dryness.
本発明は、上記の点に鑑み、耐熱性、耐薬品性が良好で
、スミアの発生が少ない積層板を製造でさる＃、燃牲指
層板用街脂組成物な提供するものである。In view of the above points, the present invention provides a street grease composition for use in flammable finger laminates, which can be used to produce laminates that have good heat resistance and chemical resistance and are less likely to cause smear.
問題点を解決下るための手段
上記目的を達成するためＣ二、本発明は、平均分子量４
５０以下の２官能エポキシ樹脂と下記の一般式で示され
る２１１ｆｔｉフエノール類（化合物■）とビスフェノ
ールＡおよび下記の一般式で示すｆｌ−６ビスフエノー
ルＡ多官能エポキシ樹脂（化合物ＩＩ）を有機或は無機
の塩基性触媒下で反応させるものである。Means for Solving the Problems In order to achieve the above objects, the present invention provides an average molecular weight of 4.
50 or less bifunctional epoxy resin, 211fti phenols represented by the following general formula (Compound ■), bisphenol A, and fl-6 bisphenol A polyfunctional epoxy resin represented by the following general formula (Compound II) are combined with organic or The reaction is carried out under an inorganic basic catalyst.
（イ８．Ｌ、Ｒ凰、Ｒｓ−ばＨ，Ｏ＋〜Ｃ１のアルキル
基またはアルケニル基を示し、Ｘは）馬ロゲンを水下）
化合物■
（但し、Ｒｓ Ｒｓ ｔｓ ｌｏｔ″−Ｏｓのアルキル
基また１１アルグニル基ン示し、ｎ：１〜３を示す）
そじて、前記２官能エポキシ樹脂と化合物ＩＩを合せた
配合量】００＊量部に対し化合物ＩとビスフェノールＡ
の合計配合量ｖｘｏ〜５０ｇ賃部とし、２官能エポキシ
８＋脂と化合物ＩおよびビスフェノールＡを合せた配合
−５１１００重重部に対し化合物■の配合量を５〜６０
重量部として反応させるものである。(I8. L, R 凰, Rs- represents H, O+ ~ C1 alkyl group or alkenyl group, 11 Argunyl group, n: 1 to 3) Then, the combined amount of the bifunctional epoxy resin and Compound II] 00* parts Compound I and Bisphenol A
The total blending amount of vxo is ~50 g parts, and the blending amount of compound ■ is 5 to 60 parts by weight to -51,100 parts by weight of the combination of bifunctional epoxy 8+ fat, compound I, and bisphenol A.
The reaction is carried out in parts by weight.
作用
一般に、耐熱性を向上させるために、フェノールノボラ
ック型エポキシｍ Ｉ′！Ｉ￥、クレゾールノボラック
型エポキシ樹脂或はビスフェノールＡ多官能エポキシ明
ハ゛百など化臭素化ビスフェノールＡ系エポキシ情脂（
二冷加Ｔると、硬化速度が異なる為、積層板の耐熱性の
同上が小さく、耐薬品性か悪くなると（ロ）時に未反応
エポキシ樹脂が多く伐すスミ丁の発生が生じや丁くなる
。そこで、予め一平均分千重４５０以下の２官能エポキ
シ樹脂、化合物Ｉ、ビスフェノールＡ、化合物ＩＩを有
機或は無機の塩基性触媒下に反応させておく事にエリ上
記欠点が克服され、大幅に耐熱性が向上した。Action Generally, in order to improve heat resistance, phenol novolac type epoxy m I'! I￥, cresol novolak type epoxy resin or bisphenol A multifunctional epoxy resin, brominated bisphenol A type epoxy resin (
When two cooling temperatures are used, the curing speed is different, so the heat resistance of the laminate is lower, and the chemical resistance is worse. Become. Therefore, by reacting a bifunctional epoxy resin, Compound I, Bisphenol A, and Compound II with an average weight of 450 parts per minute or less under an organic or inorganic basic catalyst, the above drawbacks can be overcome and greatly improved. Improved heat resistance.
化合物ｌの配合割合は、希望下る臭素含率を得るためＣ
二自由に変えられ、特に限定されない。The blending ratio of compound l is C to obtain the desired lower bromine content.
It can be changed freely and is not particularly limited.
しかし、平均分子量４５０以下の２官能エボキ７樹脂と
化合物１１を合せたｌ （＋ （ｌ Ｎ虜謳に対して、
化合物ＩとビスフェノールＡの合計配合量は、１０〜５
０１（霊部に規制するのが望ましい。However, when combining bifunctional EBOKI 7 resin with an average molecular weight of 450 or less and Compound 11,
The total amount of compound I and bisphenol A is 10 to 5
01 (It is desirable to restrict it to the spiritual part.
配合１が１０重ｆ都未満であると一本発明（二より得ら
れ７Ｓ：樹脂組成物の硬化反工６後に、未反応エポキシ
か残留し、ｔｄ層板の耐薬品性が惑くスミアも多くなる
。配合量が５０３（音部を越えると、 ｔｕ層板製造（
二際して、樹脂組成物の全林への含浸性が悪くなる。If Formulation 1 is less than 10%, unreacted epoxy may remain after the resin composition is cured and smear may occur, which may impair the chemical resistance of the TD laminate. If the compounding amount exceeds 503 (tone part), tu layer plate manufacturing (
As a result, the impregnation of the resin composition into the entire forest becomes poor.
ｆ、ｙｚ、平均分子！４５０以下の２官能エポキシ樹脂
と化合物ＩおよびビスフェノールＡを合せた１ＵＯｉｋ
都に対して、化合物Ｕの配合量１μ５〜６０ｉ童部（＝
規制するのが望ましい。配合量が５重量部未満であると
檜ｊ−板の耐熱性が向上せず、配合量か６０１拉部を越
えると２反応時にゲル化が生じてしまい樹脂として使用
できない。f, yz, average molecule! 1UOik consisting of a bifunctional epoxy resin of 450 or less, compound I and bisphenol A
For the amount of compound U, 1 μ5 to 60 i Dobe (=
It is desirable to regulate it. If the blending amount is less than 5 parts by weight, the heat resistance of the cypress j-board will not be improved, and if the blending amount exceeds 601 parts by weight, gelation will occur during the second reaction and it cannot be used as a resin.
２官罷エポキシ樹脂の平均分子量は、４５０を越えると
、反応系の粘度の増大が大き丁ぎ−かつ反応も良好でな
かった。When the average molecular weight of the 2-functional epoxy resin exceeded 450, the viscosity of the reaction system increased significantly and the reaction was not good.
実施例 次に本発明の実施ｆｆ１Ｊ ’＆説明する。Example Next, implementation ff1J'& of the present invention will be explained.
実施例１−比較例１〜３
２官能エポキシ樹脂（分子量３７０、エポキシ当量１８
６．商品名Ｋｐ−８２７，油化シェル製）、化合物１と
してテトラブロモビスフェノールＡ、ビスフェノールＡ
、化合物■としてビスフェノールＡノボラックエボキ７
樹脂（エポキシ当量２０５、大日本インキ製）を、第１
表に示Ｔ配合割合（重電部）で、ナトリウムエトキシド
ｌ触媒として８０〜１６０℃で７時間反応させ樹脂組成
物を得た。Example 1 - Comparative Examples 1 to 3 Bifunctional epoxy resin (molecular weight 370, epoxy equivalent weight 18
6. (Product name Kp-827, manufactured by Yuka Shell), compound 1 is tetrabromobisphenol A, bisphenol A
, Bisphenol A novolac EBOKI 7 as compound ■
A resin (epoxy equivalent: 205, manufactured by Dainippon Ink) was added to the first
A resin composition was obtained by reacting at 80 to 160° C. for 7 hours using sodium ethoxide as a catalyst at the T compounding ratio (heavy electric section) shown in the table.
この組成物に、硬化剤としてジシアンジアミド、２−エ
チル−４メチルイミダゾールを刃口え。To this composition, dicyandiamide and 2-ethyl-4-methylimidazole were added as a curing agent.
ガラスクロス基材Ｃ二含浸乾燥して樹脂−３１４１重量
。％のプリプレグを得た。該プリプレグを用いて、両面
粗化銅箔を内層に２層介在させ１画表ＩｆＩζ二も銅箔
を配置した４＠回路板用の１．６３厚積層板な加熱カロ
圧成形で得た。その特性を第１表に併せて示す。Glass cloth base material C2 impregnated and dried resin - 3141 weight. % prepreg was obtained. Using the prepreg, a 1.63-thick laminate for a 4@ circuit board with two layers of double-sided roughened copper foil interposed in the inner layer and two copper foils arranged on one scale was obtained by hot calopress molding. Its characteristics are also shown in Table 1.
比較例４
Ｅｐ−８２８を７７重量部、ビスフェノールＡノボラッ
クエポキシ樹脂２ａｉｉ部、ジシアンシアはド３ｔｔｉ
、２−エチル−４−メチルイミダゾール０．１５′Ｎ童
部を加えた樹脂組成物を用いて、実施例と［Ｕ１様にプ
リプレグ？作製し。Comparative Example 4 77 parts by weight of Ep-828, 2aii parts of bisphenol A novolac epoxy resin, and 3tti of dicyancia
, 2-ethyl-4-methylimidazole 0.15'N Dobe was added to the resin composition in Example and [Prepreg like U1? Created.
１．６ｓｏｗ厚の４層回路板用ｆｒｉ層根な得た。その
特性を第２表に示す。A 4-layer circuit board with a thickness of 1.6 sow was obtained. Its properties are shown in Table 2.
比較例５
２官能エポキシ倒脂（分子量］ ０５０、エポキシ当量
５２５１曲品名ｐｐ−１００１，油化シェル’Ａ ）
７０ Ｍ ｉＪ： Ｆｆ１５．テトラブロモビスフェノ
ールＡ２５重１部、ビスフェノールＡ５重量部、ビスフ
ェノールＡノボラックエポキシ樹脂ヲナトリウムエトキ
シドを触媒として１６０℃で反応系 １ 表
第１表、第２表Ｃ二示し心持性で、スミア率は、ドリル
の回転数６０００ Ｏｒｐｍ、 送り速＋ｔｉ ５０
”４７で測定した。ｆ、た、耐薬品性は、トリクレン
蒸気中で１時間処理後（二評価しにものである。Comparative Example 5 Bifunctional epoxy fallen fat (molecular weight: 050, epoxy equivalent: 5251, product name pp-1001, Yuka Shell 'A)
70 M iJ: Ff15. 1 part by weight of 25 tetrabromobisphenol A, 5 parts by weight of bisphenol A, bisphenol A novolac epoxy resin, reacted at 160°C using sodium ethoxide as a catalyst. Drill rotation speed 6000 orpm, feed speed +ti 50
Chemical resistance was measured after 1 hour of treatment in trichlene vapor (secondary evaluation).
Ｏ：異常なし
Δ：若干の肌荒ＩＬ
×：著しい肌荒ＩＬ
発明の効果
第１表、第２表から明らかなように１本発明（二よれば
、耐熱性、１耐薬品性が良好で、ス＜ −ｙの発生が少
ない積層板を提供でさるー燻往積層板用樹崩組酸物ｙ！
−裂造でさる点、工業的側堰が大である。O: No abnormality Δ: Slightly rough skin IL By providing laminates with less occurrence of , s < -y, we offer dendritic acid y for smoked laminates!
-The industrial side dam is large in its construction.
Claims (1)
般式で示される２価フェノール類（化合物 I ）とビス
フェノールＡおよび下記の一般式で示されるビスフェノ
ールＡ多官能エポキシ樹脂（化合物II）を有機或は無機
の塩基性触媒下で反応させる方法であって、前記２官能
エポキシ樹脂と化合物IIを合せた配合量１００重量部に
対し化合物 I とビスフェノールＡの合計配合量を１０
〜５０重量部とし、２官能エポキシ樹脂と化合物 I お
よびビスフェノールＡを合せた配合量１００重量部に対
し化合物IIの配合量を５〜６０重量部とする難燃性積層
板用樹脂組成物の製造法。 化合物 I ▲数式、化学式、表等があります▼ （但し、Ｒ＿１、Ｒ＿２はＨ、Ｃ＿１〜Ｃ＿３のアルキ
ル基またはアルケニル基を示し、ｘはハロゲンを示す） 化合物II ▲数式、化学式、表等があります▼ （但し、Ｒ＿１、Ｒ＿２はＣ＿１〜Ｃ＿３のアルキル基
またはアルケニル基を示し、ｎ＝１〜３を示す）[Scope of Claims] A bifunctional epoxy resin having an average molecular weight of 450 or less, a dihydric phenol (compound I) represented by the following general formula, bisphenol A, and a bisphenol A polyfunctional epoxy resin (compound I) represented by the following general formula. II) under an organic or inorganic basic catalyst, the total amount of compound I and bisphenol A is 10 parts by weight per 100 parts by weight of the bifunctional epoxy resin and compound II.
Production of a resin composition for flame-retardant laminates, in which the amount of Compound II is 5 to 60 parts by weight based on 100 parts by weight of the bifunctional epoxy resin, Compound I, and Bisphenol A. Law. Compound I ▲ Contains mathematical formulas, chemical formulas, tables, etc. ▼ (However, R_1 and R_2 represent H, an alkyl group or alkenyl group of C_1 to C_3, and x represents a halogen.) Compound II ▲ Contains mathematical formulas, chemical formulas, tables, etc. ▼ (However, R_1 and R_2 represent an alkyl group or an alkenyl group of C_1 to C_3, and n = 1 to 3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25049386A JPS63105024A (en) | 1986-10-21 | 1986-10-21 | Production of resin composition for flame-retardant laminated sheet |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25049386A JPS63105024A (en) | 1986-10-21 | 1986-10-21 | Production of resin composition for flame-retardant laminated sheet |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63105024A true JPS63105024A (en) | 1988-05-10 |
| JPH0316368B2 JPH0316368B2 (en) | 1991-03-05 |
Family
ID=17208688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25049386A Granted JPS63105024A (en) | 1986-10-21 | 1986-10-21 | Production of resin composition for flame-retardant laminated sheet |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63105024A (en) |
-
1986
- 1986-10-21 JP JP25049386A patent/JPS63105024A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0316368B2 (en) | 1991-03-05 |
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