JPH0340052B2 - - Google Patents
Info
- Publication number
- JPH0340052B2 JPH0340052B2 JP61250300A JP25030086A JPH0340052B2 JP H0340052 B2 JPH0340052 B2 JP H0340052B2 JP 61250300 A JP61250300 A JP 61250300A JP 25030086 A JP25030086 A JP 25030086A JP H0340052 B2 JPH0340052 B2 JP H0340052B2
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- epoxy
- curing
- present
- curing agent
- 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
- 239000003822 epoxy resin Substances 0.000 claims description 27
- 229920000647 polyepoxide Polymers 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 10
- 239000005011 phenolic resin Substances 0.000 claims description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 description 17
- 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 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000008358 core component Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- -1 heterocyclic amines Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Description
〔産業上の利用分野〕
本発明は、耐熱性、耐水性、可撓性及び絶縁性
に優れたエポキシ樹脂組成物に関するものであ
る。
〔従来の技術および発明が解決すべき問題点〕
現在、エポキシ樹脂の硬化剤としては、芳香族
ポリアミン、ジシアンジアミド、酸無水物、BF3
錯体が使われている。しかしながら、このような
硬化剤が配合されているエポキシ樹脂組生物は、
それぞれ次のような問題を有している。すなわち
芳香族ポリアミンを用いたものは貯蔵安定性に欠
け、しかもその硬化物の耐湿性が悪い。また、ジ
シアンジアミドを用いたものは、優れた貯蔵安定
性を示すが、その硬化物が耐熱性に欠け、しかも
硬化速度が遅い。酸無水物を用いたものは、耐熱
性に比較的優れた硬化物を生成するが、吸湿しや
すく貯蔵安定性に欠ける。BF3錯体を用いたもの
は、貯蔵安定性に優れ、速硬性を有するが、生成
硬化物が吸湿するとその電気特性が劣化する。こ
のように従来の硬化剤を用いた場合、耐熱性、耐
水性に富む硬化物を生成でき、かつ貯蔵安定性に
優れている組成物を得ることは困難であつた。
〔問題点を解決するための手段〕
本発明者らは、耐熱性、耐水性可撓性に富む硬
化物を生成でき、かつ貯蔵安定性の優れたエポキ
シ樹脂組成物を得るために鋭意検討の結果、硬化
剤としてジシクロペンタジエン変性フエノール樹
脂を使用することにより目的が達成できることを
見いだし、本発明に至つたものである。
すなわち本発明は、下記一般式［］
（式中ｎは０〜15の整数を示す。）
で示されるジシクロペンタジエン変性フエノール
樹脂を硬化剤とするエポキシ樹脂組成物を提供し
たものである。
〔作用〕
上記一般式［］で示されるジシクロペンタジ
エン変性フエノール樹脂は、ジシクロペンタジエ
ンとフエノールをルイス酸触媒中で重合すること
によつて得られる。
例えばフエノール類を加熱溶融させ、そこへ
AlCl3、BF3、ZnCl2、H2SO4、TiCl4、H3PO4な
どのルイス触媒を添加し均一に溶解した後、50〜
180℃でジシクロペンタジエンを１〜10時間かけ
て滴下し、その後数時間反応させて得られる。
トリシクロデカン環を含有することは樹脂の化
学構造からみてもわかるように水酸基の間隔が拡
がり、エポキシ基との反応率が上がるため、架橋
密度を適度にコントロールできる。このため弾性
的が低下し、トリシクロデカン環の疎水性により
給水率を下げることができる。
従来のノボラツク型樹脂はメチレン基でフエノ
ール類と結合している。このため、硬化剤がエポ
キシ樹脂中のグリシジル基と反応した際に、隣接
のグリシジル基が立体障害によつて反応を妨げら
れ、エポキシ樹脂の硬化特性が低下する要因に働
く。この結果、硬化物の耐熱性、耐湿性などを低
下させる原因となつている。
本発明の硬化剤ではジシクロペンタジエン変性
フエノール樹脂中のトリシクロデカン環が疎水基
として働くため、エポキシ樹脂組成物として用い
た場合、従来のノボラツク型硬化剤に比べ、耐水
性を大きく向上させることができる。また得られ
たエポキシ樹脂の硬化体に可撓性を付与すること
もできる。成形材料に適用する場合、流動特性が
重要であり、本発明の硬化剤によれば、ノボラツ
ク型樹脂を使用した場合に比較して低温で流動性
を示す。またフエニル核成分としてフエノールを
用いることにより、エポキシ当量が小さくなり、
耐熱性をさらに向上させることができる。
本発明で用いるこの樹脂は、アセトン、メチル
エチルケトン、テトラヒドロフラン、クロロホル
ム、メタノール、エタノール等の有機溶剤に溶解
し、種々のエポキシ樹脂、トリフエニルフオスフ
エート、トリクレジルフオスフエート可塑化剤等
と相溶する。
本発明の適用を受けるエポキシ樹脂は、公知の
ものが用いられる。これらのエポキシ樹脂は、一
分子当り少なくとも２個のエポキシ基を有し、多
価アルコール、多価フエノール、多価カルボン酸
あるいは多価アミンなどのグリシジル化合物であ
るグリシジル型エポキシ樹脂や非グリシジル型エ
ポキシ樹脂が挙げられる。
本発明の硬化剤とエポキシ樹脂との配合比は、
本発明の硬化剤の活性水素当量とエポキシ樹脂の
エポキシ当量ととの比率で決定するのが通常であ
るが、多少当量比がずれても所期の性能は十分発
揮されるので、特に配合比を限定する必要はな
い。
このエポキシ樹脂組成物には、硬化剤の他に必
要に応じてカーボンフアイバー、グラスフアイバ
ー、可塑剤、有機溶剤、反応性希釈剤、増量剤、
充填剤、補強剤、顔料、難燃化剤、増粘剤、促進
剤及び可撓性付与剤等の種々の添加剤を配合する
ことができる。エポキシ樹脂の硬化促進剤として
は、一般的に用いられる複素環式アミン類、三フ
ツ化ホウ素等のルイス酸及びそれらの塩類、有機
酸類、有機酸無水物類、尿素若しくはそれらの誘
導体を単一あるいは混合して使用することができ
る。
本発明のエポキシ樹脂組成物は、エポキシ樹脂
と硬化剤の相溶性がよく、このエポキシ樹脂組成
物を硬化させることにより得られるエポキシ樹脂
は、可撓性に富み接着性が強力で剥離強度が高
く、衝撃に耐え、耐水性が高く、高い絶縁性を示
し、耐薬品性が良好である等、種々のすぐれた性
能を発揮する。
〔実施例および発明の効果〕
以下に本発明の硬化剤の特徴を一層明確にする
ために、実施例によつて具体的に説明する。ただ
し、本発明はこれらの実施令に限定されるもので
はない。以下に単に部とあるのはいずれも重量部
を示す。
実施例 １
第１表に示すエポキシ樹脂に一般式［］で示
されるジシクロペンタジエン変性フエノール樹脂
を化学量論的に添加し、硬化促進剤として２−メ
チルイミダゾール（２−MI）0.8部を配合し、
160℃で13時間、ついで230℃で２時間加熱し硬化
させた。硬化体の物性を第１表に示す。
比較例 １
実施例１で用いたジシクロペンジエン変性フエ
ノールル樹脂に代えて、フエノールノボラツク樹
脂を使用した以外同様な処理を行なつた。得られ
た硬化体の物性を第１表に併記した。
[Industrial Application Field] The present invention relates to an epoxy resin composition that has excellent heat resistance, water resistance, flexibility, and insulation properties. [Prior art and problems to be solved by the invention] Currently, aromatic polyamines, dicyandiamide, acid anhydrides, and BF 3 are used as curing agents for epoxy resins.
complexes are used. However, epoxy resin compositions containing such curing agents,
Each has the following problems. That is, products using aromatic polyamines lack storage stability, and their cured products have poor moisture resistance. Further, those using dicyandiamide exhibit excellent storage stability, but the cured products thereof lack heat resistance and have a slow curing speed. Those using acid anhydrides produce cured products with relatively excellent heat resistance, but tend to absorb moisture and lack storage stability. Products using the BF 3 complex have excellent storage stability and quick curing properties, but when the resulting cured product absorbs moisture, its electrical properties deteriorate. As described above, when conventional curing agents are used, it is difficult to obtain a composition that can produce a cured product with high heat resistance and water resistance and has excellent storage stability. [Means for Solving the Problems] The present inventors have carried out extensive studies in order to obtain an epoxy resin composition that can produce a cured product that is highly heat resistant, water resistant and flexible, and has excellent storage stability. As a result, it was discovered that the object could be achieved by using a dicyclopentadiene-modified phenolic resin as a curing agent, leading to the present invention. That is, the present invention is based on the following general formula [] (In the formula, n represents an integer of 0 to 15.) An epoxy resin composition using a dicyclopentadiene-modified phenolic resin as a curing agent is provided. [Function] The dicyclopentadiene-modified phenolic resin represented by the above general formula [] can be obtained by polymerizing dicyclopentadiene and phenol in a Lewis acid catalyst. For example, by heating and melting phenols,
After adding and uniformly dissolving Lewis catalysts such as AlCl3 , BF3 , ZnCl2 , H2SO4 , TiCl4 , H3PO4 , 50 ~
It is obtained by adding dicyclopentadiene dropwise over 1 to 10 hours at 180°C and then reacting for several hours. As can be seen from the chemical structure of the resin, the inclusion of tricyclodecane rings widens the spacing between hydroxyl groups and increases the reaction rate with epoxy groups, making it possible to appropriately control the crosslinking density. Therefore, the elasticity decreases, and the water supply rate can be lowered due to the hydrophobicity of the tricyclodecane ring. Conventional novolac type resins are bonded to phenols through methylene groups. Therefore, when the curing agent reacts with the glycidyl groups in the epoxy resin, the reaction is hindered by the steric hindrance of the adjacent glycidyl groups, which acts as a factor in deteriorating the curing properties of the epoxy resin. As a result, this causes a decrease in heat resistance, moisture resistance, etc. of the cured product. In the curing agent of the present invention, the tricyclodecane ring in the dicyclopentadiene-modified phenolic resin acts as a hydrophobic group, so when used in an epoxy resin composition, water resistance can be greatly improved compared to conventional novolac type curing agents. Can be done. It is also possible to impart flexibility to the obtained cured epoxy resin. When applied to molding materials, flow properties are important, and the curing agent of the present invention exhibits flowability at lower temperatures than when novolac type resins are used. In addition, by using phenol as the phenyl core component, the epoxy equivalent becomes smaller,
Heat resistance can be further improved. This resin used in the present invention is dissolved in organic solvents such as acetone, methyl ethyl ketone, tetrahydrofuran, chloroform, methanol, and ethanol, and is compatible with various epoxy resins, triphenyl phosphate, tricresyl phosphate plasticizers, etc. dissolve As the epoxy resin to which the present invention is applied, publicly known epoxy resins are used. These epoxy resins have at least two epoxy groups per molecule, and include glycidyl-type epoxy resins, which are glycidyl compounds such as polyhydric alcohols, polyhydric phenols, polyhydric carboxylic acids, or polyhydric amines, and non-glycidyl-type epoxy resins. Examples include resin. The compounding ratio of the curing agent and epoxy resin of the present invention is:
It is usually determined by the ratio between the active hydrogen equivalent of the curing agent of the present invention and the epoxy equivalent of the epoxy resin. There is no need to limit. In addition to the curing agent, this epoxy resin composition also contains carbon fibers, glass fibers, plasticizers, organic solvents, reactive diluents, extenders,
Various additives such as fillers, reinforcing agents, pigments, flame retardants, thickeners, accelerators and flexibilizing agents can be incorporated. As curing accelerators for epoxy resins, commonly used heterocyclic amines, Lewis acids such as boron trifluoride and their salts, organic acids, organic acid anhydrides, urea or their derivatives can be used as a single agent. Alternatively, they can be used in combination. The epoxy resin composition of the present invention has good compatibility between the epoxy resin and the curing agent, and the epoxy resin obtained by curing this epoxy resin composition has high flexibility, strong adhesiveness, and high peel strength. It exhibits a variety of excellent properties, including shock resistance, high water resistance, high insulation properties, and good chemical resistance. [Examples and Effects of the Invention] In order to further clarify the characteristics of the curing agent of the present invention, Examples will be specifically described below. However, the present invention is not limited to these implementation orders. All parts hereinafter simply indicate parts by weight. Example 1 A dicyclopentadiene-modified phenol resin represented by the general formula [] was added stoichiometrically to the epoxy resin shown in Table 1, and 0.8 parts of 2-methylimidazole (2-MI) was added as a curing accelerator. death,
It was cured by heating at 160°C for 13 hours and then at 230°C for 2 hours. Table 1 shows the physical properties of the cured product. Comparative Example 1 The same treatment was carried out except that a phenol novolac resin was used in place of the dicyclopendiene-modified phenol resin used in Example 1. The physical properties of the obtained cured product are also listed in Table 1.
【表】
以上の記載および第１表から明らかなように、
本発明の樹脂組成物はエポキシ樹脂硬化剤として
ジシクロペンタジエン変性フエノール樹脂を用い
ることによつて絶縁性、可撓性、耐水性、耐薬品
性に優れたエポキシ樹脂硬化物を得ることができ
た。この硬化物は積層板やIC封止剤用樹脂など
の民生用電子部品の進歩に十分対応できる非常に
有利なものである。[Table] As is clear from the above description and Table 1,
By using a dicyclopentadiene-modified phenol resin as an epoxy resin curing agent, the resin composition of the present invention was able to obtain a cured epoxy resin product with excellent insulation, flexibility, water resistance, and chemical resistance. . This cured product is extremely advantageous as it can fully respond to advances in consumer electronic components such as resins for laminates and IC sealants.
Claims (1)
を必須成分とする電子部品用エポキシ樹脂組成
物。[Claims] 1. The following general formula [] (In the formula, n represents an integer of 0 to 15.) An epoxy resin composition for electronic components containing a dicyclopentadiene phenol resin represented by the following formula as an essential component.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60-244769 | 1985-10-31 | ||
| JP60244769 | 1985-10-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62201922A JPS62201922A (en) | 1987-09-05 |
| JPH0340052B2 true JPH0340052B2 (en) | 1991-06-17 |
Family
ID=17123631
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25030186A Granted JPS62201923A (en) | 1985-10-31 | 1986-10-21 | Epoxy resin composition |
| JP25030086A Granted JPS62201922A (en) | 1985-10-31 | 1986-10-21 | Epoxy resin composition |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25030186A Granted JPS62201923A (en) | 1985-10-31 | 1986-10-21 | Epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (2) | JPS62201923A (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01105562A (en) * | 1987-10-19 | 1989-04-24 | Sumitomo Bakelite Co Ltd | Resin-sealed semiconductor device |
| JPH0689112B2 (en) * | 1989-11-25 | 1994-11-09 | 松下電工株式会社 | Epoxy resin composition for semiconductor encapsulation |
| JPH0689113B2 (en) * | 1989-11-27 | 1994-11-09 | 松下電工株式会社 | Epoxy resin composition for semiconductor encapsulation |
| JPH0597970A (en) * | 1991-10-07 | 1993-04-20 | Shin Etsu Chem Co Ltd | Thermosetting resin composition and semiconductor device |
| JP2643706B2 (en) * | 1991-11-26 | 1997-08-20 | 信越化学工業株式会社 | Thermosetting resin composition and semiconductor device |
| EP0705856A2 (en) | 1994-10-07 | 1996-04-10 | Shell Internationale Researchmaatschappij B.V. | Epoxy resin composition for semiconductor encapsulation |
| JPH10245473A (en) * | 1997-03-03 | 1998-09-14 | Yuka Shell Epoxy Kk | Epoxy resin composition |
| KR100421927B1 (en) * | 2001-08-21 | 2004-03-12 | 제일모직주식회사 | Epoxy Resin Compound for Sealing Semiconductive Device |
| KR100480945B1 (en) * | 2001-12-28 | 2005-04-06 | 제일모직주식회사 | Epoxy Resin Composition for Sealing Semiconductor Device |
| ATE551389T1 (en) | 2009-08-07 | 2012-04-15 | Ticona Llc | POLYACETAL COMPOSITION WITH LOW FORMALDEYD EMISSION |
| CN103946294B (en) | 2011-09-29 | 2017-10-03 | 提克纳有限责任公司 | Polymer composition for manufacturing the product with metal appearance |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5499160A (en) * | 1978-01-20 | 1979-08-04 | Nippon Oil Co Ltd | Epoxy resin composition |
-
1986
- 1986-10-21 JP JP25030186A patent/JPS62201923A/en active Granted
- 1986-10-21 JP JP25030086A patent/JPS62201922A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5499160A (en) * | 1978-01-20 | 1979-08-04 | Nippon Oil Co Ltd | Epoxy resin composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62201922A (en) | 1987-09-05 |
| JPS62201923A (en) | 1987-09-05 |
| JPH0340053B2 (en) | 1991-06-17 |
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| LAPS | Cancellation because of no payment of annual fees |