JPH0228601B2 - TAINETSUSEIKYOKASEIKEIYOSOSEIBUTSU - Google Patents
TAINETSUSEIKYOKASEIKEIYOSOSEIBUTSUInfo
- Publication number
- JPH0228601B2 JPH0228601B2 JP11090986A JP11090986A JPH0228601B2 JP H0228601 B2 JPH0228601 B2 JP H0228601B2 JP 11090986 A JP11090986 A JP 11090986A JP 11090986 A JP11090986 A JP 11090986A JP H0228601 B2 JPH0228601 B2 JP H0228601B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- bond
- heat resistance
- molded
- group
- 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
- 239000000203 mixture Substances 0.000 claims description 9
- 238000000465 moulding Methods 0.000 claims description 6
- 239000012763 reinforcing filler Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- -1 diacetylene compound Chemical class 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 8
- 238000002411 thermogravimetry Methods 0.000 description 6
- 230000004580 weight loss Effects 0.000 description 6
- 238000005452 bending Methods 0.000 description 5
- 239000004642 Polyimide Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 229920000049 Carbon (fiber) Polymers 0.000 description 3
- 239000004917 carbon fiber Substances 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- 239000000057 synthetic resin Substances 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 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 1
- 125000005462 imide group Chemical group 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 230000007847 structural defect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
〔産業上の利用分野〕
本発明は低温、短時間で容易に成形できる耐熱
性強化成形用組成物に関するものである。
〔従来技術〕
無機物質、炭素繊維、ガラス繊維等の強化性を
有する基材を合成樹脂に混入し成形して得られた
成形体は強度等の物性をより向上させることにつ
いてはよく知られた事実であり、用いられる合成
樹脂も多種にわたつている。
この様な強化成形品は、低温、短時間で容易に
成形でき、又、エレクトロニクス等の分野におい
ては、高度の耐熱性を要求されているが、まだ十
分開発されていないため、尚種々の検討がなされ
てきた。
〔発明が解決しようとする問題点〕
ところがこれまでに開発されている合成樹脂を
用いる強化成形品では、成形性と耐熱性とが満足
されるものは得られていないのが現状である。現
在一般的にはエポキシ樹脂が多く使用されている
が、価格が安く、成形条件にバリエーシヨンがあ
るものの耐熱性が不十分である。一方、耐熱性の
高いものとしてポリイミドが知られているが、成
形が極めて困難であり、一般に強化剤を混入する
場合、ポリイミドの前駆体の溶液を強化剤に含浸
させた後加熱し脱溶媒とキユアを行つて強化成形
体とする方法がとられている。しかしポリイミド
前駆体を素材とするものは加熱時に起こるイミド
環形成による縮合水によつてふくれとか分子量の
低下、更には完全な脱溶媒ができないなど充分に
満足できるようなものではなかつた。一方、付加
反応によつて硬化するタイプのポリイミド化合
物、例えば、PMR（NASA商標）、ケルイミド
（Rhone Poulenc商標）が開発され市販されてい
るが、硬化成形性と耐熱性のバランスがまだ充分
に満足されておらず、特に耐熱性の面で充分でな
いのが現状である。
又、近年アセチレン結合を架橋反応に利用した
化合物、たとえばThermid（Golfoil商標）が研究
開発されているが、この場合には硬化温度が高
く、かつ硬化時間が長いなどの問題がある。本発
明者らは、低温でかつ短時間に成形でき、更に耐
熱性の高い強化成形体製造のための素材について
種々検討した結果、低温で容易に硬化する素材を
見い出し、この素材を用い強化性充填物とを組み
合わせた物が極めて高い耐熱性を持つ事を見い出
し本発明に到達した。
〔問題点を解決するための手段〕
すなわち、本発明は下記の一般構造式又は
で表わされる。
（式中R1及びR2は
[Industrial Application Field] The present invention relates to a heat-resistant reinforced molding composition that can be easily molded at low temperatures and in a short time. [Prior art] It is well known that molded products obtained by mixing reinforcing base materials such as inorganic substances, carbon fibers, and glass fibers into synthetic resins have improved physical properties such as strength. This is true, and there are a wide variety of synthetic resins used. Such reinforced molded products can be easily molded at low temperatures in a short time, and in fields such as electronics, a high degree of heat resistance is required, but since they have not been sufficiently developed, various studies are still needed. has been done. [Problems to be Solved by the Invention] However, the current situation is that none of the reinforced molded products developed so far using synthetic resins have satisfactory moldability and heat resistance. Currently, epoxy resins are commonly used, but although they are cheap and have variations in molding conditions, they have insufficient heat resistance. On the other hand, polyimide is known to have high heat resistance, but it is extremely difficult to mold, and generally when a reinforcing agent is mixed in, a solution of a polyimide precursor is impregnated with the reinforcing agent and then heated to remove the solvent. A method of curing is used to form a reinforced molded body. However, those made from polyimide precursors were not completely satisfactory, as they suffered from blistering and a decrease in molecular weight due to condensed water due to the formation of imide rings during heating, as well as the inability to completely remove the solvent. On the other hand, polyimide compounds that harden through addition reactions, such as PMR (NASA trademark) and Kelimide (Rhone Poulenc trademark), have been developed and are commercially available, but the balance between curing moldability and heat resistance is still insufficient. Currently, the heat resistance is insufficient. Furthermore, in recent years, compounds that utilize acetylene bonds for crosslinking reactions, such as Thermid (Golfoil trademark), have been researched and developed, but in this case there are problems such as high curing temperatures and long curing times. As a result of various studies on materials for manufacturing reinforced molded bodies that can be molded at low temperatures and in a short time and have high heat resistance, the present inventors discovered a material that hardens easily at low temperatures, and used this material to The present invention was achieved by discovering that a product in combination with a filler has extremely high heat resistance. [Means for Solving the Problems] That is, the present invention is represented by the following general structural formula. (In the formula, R 1 and R 2 are
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】
で表わされる二価の基であり、−X1−、及び−X2
−は炭素数１〜12の二価の炭化水素基、又は、エ
ーテル結合、ウレタン結合、エステル結合、アミ
ド結合により連結された炭化水素基であり、−Y1
及び−Y2はアルキル基、アリール基、シクロア
ルキル基である。）
末端二重結合を有するジアセチレン化合物およ
び強化性充填物とからなる耐熱性強化成形用組成
物である。
一般式及びにおいて、R1，R2は特定
の二重結合を有する二価の基であり、
[Formula] A divalent group represented by -X 1 - and -X 2
- is a divalent hydrocarbon group having 1 to 12 carbon atoms, or a hydrocarbon group connected by an ether bond, urethane bond, ester bond, or amide bond, and -Y 1
and -Y2 is an alkyl group, an aryl group, or a cycloalkyl group. ) A heat-resistant reinforced molding composition comprising a diacetylene compound having a terminal double bond and a reinforcing filler. In the general formula and, R 1 and R 2 are divalent groups having a specific double bond,
【式】【formula】
【式】【formula】
【式】【formula】
【式】
で表わされる。
成形物の耐熱性の点で好ましくは
Represented by [Formula]. Preferably in terms of heat resistance of the molded product
【式】【formula】
【式】【formula】
【式】であり、特に好ましいのは[Formula], particularly preferred is
【式】である。これらの好ましい二重結合
を有する二価の基は、ジエノフイルであるマレイ
ン酸誘導体と共役二重結合を有する化合物とのデ
イールスアルダー（Diels−Alder）反応によつて
得られる二価の基である。
−X1−及び−X2−は、ジアセチレンとイミド
結合、アミド結合とを連結する基であり、特に限
定はないが、炭素数１〜12の二価の炭化水素基で
あり、エーテル結合、ウレタン結合、アミド結
合、エステル結合により連結された炭化水素基も
含まれる。例えば、−CH2−，[Formula]. These preferred divalent groups having a double bond are divalent groups obtained by a Diels-Alder reaction between a dienophilic maleic acid derivative and a compound having a conjugated double bond. . -X 1 - and -X 2 - are groups that connect diacetylene with an imide bond or an amide bond, and are divalent hydrocarbon groups having 1 to 12 carbon atoms, although there are no particular limitations, and ether bonds , hydrocarbon groups connected by urethane bonds, amide bonds, and ester bonds. For example, −CH 2 −,
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】などである。好ま しくは成形性の点から−CH2−、[Formula] etc. Preferably -CH 2 - from the viewpoint of moldability,
【式】【formula】
以上の様に、式又はで示す化合物は、強化
性充填物に対して良好な浸透性、接着性を有し、
かつ低温で硬化する。又、強化性充填物を入れる
事により硬化成形時の亀裂等の構造欠陥が生じ難
く、シート状物、板状物、繊維状物、棒状物、管
状物等種々の形状の成形体を得る事ができる。得
られた成形体は、空気中で熱重量分析を行なうと
400℃以上においてもほとんど減量しないばかり
でなく、加熱による機械的強度の低下も少なく極
めて良好な耐熱性を示し、耐熱性の要求される分
野、たとえば電機、エレクトロニクス等の分野に
極めて有用である。
〔実施例〕
次に実施例を挙げて本発明を具体的に説明する
が本発明はこれらに限定されるものではない。
実施例 １
一般構造式において、X1，X2が−CH2−，
R1，R2が
As mentioned above, the compound represented by the formula or has good permeability and adhesion to reinforcing fillers,
and hardens at low temperatures. In addition, by adding a reinforcing filler, structural defects such as cracks are less likely to occur during hardening and molding, making it possible to obtain molded objects of various shapes such as sheet-like objects, plate-like objects, fibrous objects, rod-like objects, and tubular objects. Can be done. The obtained compact was subjected to thermogravimetric analysis in air.
It not only shows almost no weight loss even at temperatures above 400°C, but also exhibits extremely good heat resistance with little decrease in mechanical strength due to heating, making it extremely useful in fields that require heat resistance, such as electrical machinery and electronics. [Example] Next, the present invention will be specifically explained with reference to Examples, but the present invention is not limited thereto. Example 1 In the general structural formula, X 1 and X 2 are -CH 2 -,
R 1 , R 2
【式】である化合物の30％メチル
エチルケトン溶液をPAN系カーボンフアイバー
のクロス（旭シユエーベル製）４cm×10cmに含浸
させ、10枚かさねて風乾させた後、300℃にて200
Kg／cm2の圧力で30分間の成形を行なつた。得られ
た成形体の樹脂含量は22％であつた。この物の熱
重量分析を空気中で行なつたところ、450℃でも
わずかに1.2％の減量であり、耐熱性が非常に良
好であつた。
又、熱変形温度（18.6Kg／cm2荷重）は350℃以
上であり、曲げ強度及び曲げ弾性率の高温での保
持率も良好であつた。
実施例 ２
一般構造式において、X1，X2が−CH2−，
R1，R2がA 4 cm x 10 cm PAN carbon fiber cloth (manufactured by Asahi Schwebel) was impregnated with a 30% methyl ethyl ketone solution of the compound [formula], stacked on top of 10 sheets, air-dried, and heated to 300℃ for 200 minutes.
Molding was carried out for 30 minutes at a pressure of Kg/cm 2 . The resin content of the molded article obtained was 22%. Thermogravimetric analysis of this product in air revealed that the weight loss was only 1.2% even at 450°C, indicating that it had very good heat resistance. Further, the thermal deformation temperature (18.6 Kg/cm 2 load) was 350° C. or higher, and the retention of bending strength and bending elastic modulus at high temperatures was also good. Example 2 In the general structural formula, X 1 and X 2 are -CH 2 -,
R 1 , R 2
【式】である化合物の30％メチル
エチルケトン溶液に、ガラスチヨツプドストラン
ド（旭フアイバーグラス製03MA429）を浸漬し、
その後、ロータリーエバポレーターでメチルエチ
ルケトンを除去し、樹脂量が35％の混合物を得
た。
その混合物を250℃にて200Kg／cm2の圧力で10分
間の圧縮成形を行ない、厚さ1.3mmの板状物を得
た。この板状物の熱重量分析を空気中で行なつた
ところ、450℃でもわずかに0.6％の減量であり耐
熱性が非常に良好であつた。
実施例 ３
一般構造式においてX1，X2が−CH2−，R1，
R2がA glass chopped strand (03MA429 manufactured by Asahi Fiber Glass) is immersed in a 30% methyl ethyl ketone solution of the compound of [formula],
Thereafter, methyl ethyl ketone was removed using a rotary evaporator to obtain a mixture containing 35% resin. The mixture was compression molded at 250° C. and a pressure of 200 kg/cm 2 for 10 minutes to obtain a plate with a thickness of 1.3 mm. Thermogravimetric analysis of this plate in air revealed that the weight loss was only 0.6% even at 450°C, indicating very good heat resistance. Example 3 In the general structural formula, X 1 and X 2 are -CH 2 -, R 1 ,
R 2 is
【式】である化合物40部と、チタン酸カ
リウム繊維（大塚化学薬品製、TISMO）60部と
を小型ミルにて混合した物を300℃にて200Kg／cm2
の圧力で20分間の圧縮成形を行ない、厚さ1.4mm
の成形体を得た。この成形体の熱重量分析を空気
中で行なつたところ、450℃でもわずかに0.5％の
減量であり、耐熱性が非常に良好であつた。
実施例 ４
一般構造式においてX1，X2が−CH2−，R1，
R2がA mixture of 40 parts of the compound [formula] and 60 parts of potassium titanate fiber (manufactured by Otsuka Chemicals, TISMO) in a small mill was heated to 200 kg/cm 2 at 300°C.
Compression molded for 20 minutes at a pressure of 1.4mm thick.
A molded body was obtained. Thermogravimetric analysis of this molded body in air revealed that the weight loss was only 0.5% even at 450°C, indicating that it had very good heat resistance. Example 4 In the general structural formula, X 1 and X 2 are -CH 2 -, R 1 ,
R 2 is
【式】である化合物40部と、ガラスフレ
ーク（日本硝子繊維製CEF−150）60部とを小型
ミルにて混合した物を、300℃にて200Kg／cm2の圧
力で20分間の圧縮成形を行ない、厚さ1.5mmの板
状物を得た。この板状物の熱重量分析を空気中で
行なつたところ、450℃でもわずかに１％の減量
であり、耐熱性が非常に良好であつた。
比較例 １
エポキシ樹脂（DOWケミカル製DER383）25
部を100部のメチルエチルケトンに溶解し、更に
硬化剤としてトリエチレンテトラミン（油化シエ
ル製エピキユアTETA）をエポキシ樹脂に対し
て13.5部になる様に加えた。この溶液を実施例−
１と同様のカーボンフアイバーのクロスに樹脂が
30％になる様に塗布し、80℃で20分乾燥してプリ
プレグを得た。このプリプレグを10枚重ねて180
℃×50Kg／cm2の条件で10分間プレスし成形体を得
た。
この成形体の熱重量分析を空気中で行なつたと
ころ、300℃で10％の減量が起こつた。
又熱変形温度（18.6Kg／cm2荷重）は198℃であ
り、曲げ強度及び曲げ弾性率の高温での保持率は
200℃でそれぞれ25％、66％であつた。A mixture of 40 parts of the compound of [formula] and 60 parts of glass flakes (CEF-150 manufactured by Nippon Glass Fiber) in a small mill was compression molded at 300°C and a pressure of 200 kg/cm 2 for 20 minutes. A plate-like product with a thickness of 1.5 mm was obtained. Thermogravimetric analysis of this plate in air revealed that the weight loss was only 1% even at 450°C, indicating very good heat resistance. Comparative example 1 Epoxy resin (DOW Chemical DER383) 25
1 part was dissolved in 100 parts of methyl ethyl ketone, and triethylenetetramine (Epiquure TETA manufactured by Yuka Shell Co., Ltd.) was added as a curing agent in an amount of 13.5 parts to the epoxy resin. Example of this solution
Resin is applied to the same carbon fiber cloth as in 1.
It was applied to a concentration of 30% and dried at 80°C for 20 minutes to obtain a prepreg. Layer 10 sheets of this prepreg to 180
A molded product was obtained by pressing for 10 minutes at 50 Kg/cm 2 at ℃. When thermogravimetric analysis of this molded body was performed in air, a weight loss of 10% occurred at 300°C. In addition, the thermal deformation temperature (18.6Kg/cm 2 load) is 198℃, and the retention rate of bending strength and bending elastic modulus at high temperatures is
At 200°C, they were 25% and 66%, respectively.
第１図は、本発明による組成物の熱安定性を、
比較例と比較して測定の温度に対して曲げ強度の
保持率で示した図である。第２図は、本発明によ
る組成物の熱安定性を、比較例と比較して、測定
の温度に対して曲げ弾性率の保持率で示した図で
ある。
その中で１は実施例−１，２は比較例−１を示
す。
FIG. 1 shows the thermal stability of the composition according to the invention.
FIG. 3 is a diagram showing the retention rate of bending strength against the measurement temperature in comparison with a comparative example. FIG. 2 is a diagram showing the thermal stability of the composition according to the present invention in terms of retention of flexural modulus versus measurement temperature, in comparison with a comparative example. Among them, 1 indicates Example-1, and 2 indicates Comparative Example-1.
Claims (1)
−は炭素数１〜12の二価の炭化水素基、又は、エ
ーテル結合、ウレタン結合、エステル結合、アミ
ド結合により連結された炭化水素基であり、−Y1
及び−Y2は水素、アルキル基、アリール基、シ
クロアルキル基である。） 末端二重結合を有するジアセチレン化合物およ
び強化性充填物とからなる耐熱性強化成形用組成
物。[Claims] 1. Represented by the following general structural formula or. (In the formula, R 1 and R 2 are divalent groups represented by [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula] [formula], and - X 1 −, and −X 2
- is a divalent hydrocarbon group having 1 to 12 carbon atoms, or a hydrocarbon group connected by an ether bond, urethane bond, ester bond, or amide bond, and -Y 1
and -Y2 is hydrogen, an alkyl group, an aryl group, or a cycloalkyl group. ) A heat-resistant reinforced molding composition comprising a diacetylene compound having a terminal double bond and a reinforcing filler.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11090986A JPH0228601B2 (en) | 1986-05-16 | 1986-05-16 | TAINETSUSEIKYOKASEIKEIYOSOSEIBUTSU |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11090986A JPH0228601B2 (en) | 1986-05-16 | 1986-05-16 | TAINETSUSEIKYOKASEIKEIYOSOSEIBUTSU |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62267308A JPS62267308A (en) | 1987-11-20 |
| JPH0228601B2 true JPH0228601B2 (en) | 1990-06-25 |
Family
ID=14547721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11090986A Expired - Lifetime JPH0228601B2 (en) | 1986-05-16 | 1986-05-16 | TAINETSUSEIKYOKASEIKEIYOSOSEIBUTSU |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0228601B2 (en) |
-
1986
- 1986-05-16 JP JP11090986A patent/JPH0228601B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62267308A (en) | 1987-11-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |