JPS6258618B2 - - Google Patents
Info
- Publication number
- JPS6258618B2 JPS6258618B2 JP20489483A JP20489483A JPS6258618B2 JP S6258618 B2 JPS6258618 B2 JP S6258618B2 JP 20489483 A JP20489483 A JP 20489483A JP 20489483 A JP20489483 A JP 20489483A JP S6258618 B2 JPS6258618 B2 JP S6258618B2
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- phenol
- parts
- novolak type
- type epoxy
- 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
Links
- 239000003822 epoxy resin Substances 0.000 claims description 30
- 229920000647 polyepoxide Polymers 0.000 claims description 30
- 229920003986 novolac Polymers 0.000 claims description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 18
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 6
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
- 101150065749 Churc1 gene Proteins 0.000 claims description 2
- 102100038239 Protein Churchill Human genes 0.000 claims description 2
- 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
- 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 5
- 239000004593 Epoxy Substances 0.000 description 5
- 229930003836 cresol Natural products 0.000 description 5
- 239000012778 molding material Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000006082 mold release agent Substances 0.000 description 3
- -1 that is Chemical class 0.000 description 3
- 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 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229920001342 Bakelite® Polymers 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 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 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Description
本発明は、耐湿性に優れる速硬化性エポキシ樹
脂組成物に係わり、その特徴は疎水性の高いフエ
ノールノボラツク型エポキシ樹脂を用いるところ
にある。
近年、金属部品やセラミツク部品類のプラスチ
ツク化は驚異的な速さで進行していることは衆知
の事実である。プラスチツクとしてはフエノール
樹脂、ポリエステル樹脂、エポキシ樹脂等が使わ
れており、用途としては家電、自動車分野で多量
に用いられている。これら分野での最近の動きと
してはVTRの小型化、自動車の軽量化といつた
動きである。又日本の製品が世界中で使用される
確率がますます高まつてきている。このためこれ
ら用途で使われる部品類は、小型、軽量化や環境
の変化に対する強さが要求されている。又、汎用
化のために低コスト化も要求されている。このた
めプラスチツク素材そのものの耐湿性、耐熱性の
向上並びに低コスト化が必要となつてきている。
とりわけ、プラスチツクの中でも絶縁性、耐熱
性、耐湿性に優れるエポキシ樹脂に対する要求が
強い。
本発明はこれら要求を満足させる耐湿性、耐熱
性、さらには、速硬化性を兼ねそろえたエポキシ
樹脂組成物を提供するものである。本発明はフエ
ノールと炭化水素置換アルデヒド（ブチルアルデ
ヒド、ベンズアルデヒド、アクロレイン等）との
共縮合フエノールノボラツクのエポキシ化物、即
ち、フエノール核間の結合炭素が疎水性を有する
炭化水素で置換されているフエノールノボラツク
型エポキシ樹脂を配合してなるエポキシ樹脂組成
物を提供するものである。
本発明は、フエノールとブチルアルデヒド、ベ
ンズアルデヒドまたはアクロレインの炭化水素置
換アルデヒドとの共縮合フエノールノボラツクを
エポキシ化した下記の一般式で示されるエポキシ
樹脂を配合してなるエポキシ樹脂組成物である。
Ｒ：CH3CH2CH2CH2―、（CH3）2CHCH2―、
CH3CH2CH（CH3）―、CH2＝CH―、
The present invention relates to a fast-curing epoxy resin composition with excellent moisture resistance, and its feature lies in the use of a highly hydrophobic phenol novolak type epoxy resin. It is a well-known fact that metal parts and ceramic parts are being replaced with plastic at an astonishing rate in recent years. Phenol resin, polyester resin, epoxy resin, etc. are used as plastics, and they are used in large quantities in the fields of home appliances and automobiles. Recent trends in these fields include the miniaturization of VCRs and the reduction in weight of automobiles. Furthermore, the probability that Japanese products will be used all over the world is increasing. For this reason, parts used in these applications are required to be smaller, lighter, and more resistant to environmental changes. Furthermore, cost reduction is also required for general use. For this reason, it has become necessary to improve the moisture resistance and heat resistance of the plastic material itself, and to reduce the cost. In particular, there is a strong demand for epoxy resin, which has excellent insulation, heat resistance, and moisture resistance among plastics. The present invention provides an epoxy resin composition that satisfies these requirements and has moisture resistance, heat resistance, and rapid curing properties. The present invention is directed to epoxidized phenol novolaks co-condensed with phenol and hydrocarbon-substituted aldehydes (butyraldehyde, benzaldehyde, acrolein, etc.), that is, phenols in which the bonding carbon between the phenol nuclei is substituted with a hydrophobic hydrocarbon. The present invention provides an epoxy resin composition containing a novolak type epoxy resin. The present invention is an epoxy resin composition containing an epoxy resin represented by the following general formula, which is obtained by epoxidizing a phenol novolac co-condensed with a hydrocarbon-substituted aldehyde of phenol and butyraldehyde, benzaldehyde, or acrolein. R: CH 3 CH 2 CH 2 CH 2 -, (CH 3 ) 2 CHCH 2 -, CH 3 CH 2 CH (CH 3 ) -, CH 2 = CH -,
【式】
ｎ：０〜６の整数
上記樹脂でｎが７以上になると軟化点が高くな
り充填材などとの混練がしにくくなり、また成形
材料になつても低圧では封止できなくなり、半導
体用には適さなくなる。
通常、エポキシ樹脂としては、ビスフエノール
型エポキシ樹脂、フエノールノボラツク型エポキ
シ樹脂、クレゾールノボラツク型エポキシ樹脂が
知られているが、耐熱性の用途にはノボラツク型
エポキシ樹脂が使われる。これはエポキシ当量が
小さく架橋密度が高くなる理由によるものであ
る。しかし、ノボラツク型エポキシ樹脂といつて
も、フエノールノボラツク型とクレゾールノボラ
ツク型とは互いに一長一短であり、速硬化性と耐
湿性とは両立しなかつた。即ち、クレゾールノボ
ラツク型は、耐湿性に特長はあるが、速硬化性に
難がある。又、フエノールノボラツク型は逆の特
徴をもつ。
クレゾールノボラツク型は、疎水性のメチル基
を持つゆえ撥水効果を持つが、このメチル基がフ
エノール核に置換しているため、反応性を低下さ
せる原因にもなつている。
本発明者らは、フエノール核に疎水基を置換さ
せるのではなくフエノール核の結合炭素に疎水基
を置換させることにより、速硬化性と耐湿性が両
立できることを見い出したものである。
本発明でいうところのエポキシ樹脂組成物とは
フエノール核間の結合炭素が炭化水素で置換され
ているフエノールノボラツク型エポキシ樹脂を配
合してなるもの全般をいうが、一般的にはエポキ
シ樹脂、硬化剤、硬化促進剤、充填材、その他添
加剤を混合しているものである。
エポキシ樹脂として本発明で用いるエポキシ樹
脂と従来のエポキシ樹脂を併用しても良いが、こ
の場合従来のエポキシ樹脂の併用比率は50％以下
とするのが望ましい。あまり多くすると本来の効
果が薄らぎ、特長が出なくなる場合がある。
以下、半導体封止用低圧封入成形材料への実施
例で説明する。実施例で用いる部は全て重量部で
ある。
又、実施例で用いた原料は次の通りである。
エポキシ樹脂 大日本インキ(株)製
エピクロンＮ―670
（クレゾールノボラツク型エポキシ）
エポキシ樹脂 日本化薬(株)製 EPPN―201
（フエノールノボラツク型エポキシ）
エポキシ樹脂フエノール／ベンズアルデヒド
共縮合 フエノールノボラツク型エポキシ
（本発明でのエポキシ、軟化点70℃）
硬化剤 住友ベークライト(株)製 フエノールノ
ボラツク
硬化促進剤 住友化学工業(株) スミキユアーＤ
充填材 東芝セラミツク(株) 溶融シリカ
カツプリング剤 日本ユニカー(株) Ａ―186
顔 料 三菱化成(株) カーボン
離型剤 ヘキストジヤパン(株) ヘキストワツク
スOP
難燃剤 住友金属鉱山(株) 三酸化アンチモン
実施例
エポキシ樹脂20部、硬化剤10部、硬化促進剤
0.2部、充填材70部、カツプリング剤0.3部、顔料
0.2部、離型剤0.4部、難燃剤３部を混合し、コニ
ーダーで混練し、成形材料にした。この時エポキ
シ樹脂として，，，／＝4/6、／
＝7/3、／＝4/6、／＝7/3なる７水準を
取り７種の成形材料を得た。この成形材料の硬化
性・電気特性・強度・吸水性及びIC封止品の特
性を調べた結果表―１のように、エポキシ樹脂と
してを配合した５種が優れていた。又、この中
でもを1/2以上用いたものが特に優れている。[Formula] n: An integer from 0 to 6 If n is 7 or more in the above resin, the softening point will be high and it will be difficult to knead with fillers, etc. Even if it is used as a molding material, it will not be possible to seal it at low pressure, and it will not be possible to seal semiconductors. It becomes unsuitable for use. Generally, as epoxy resins, bisphenol type epoxy resins, phenol novolak type epoxy resins, and cresol novolak type epoxy resins are known, but novolak type epoxy resins are used for heat-resistant applications. This is due to the fact that the epoxy equivalent is small and the crosslinking density is high. However, when it comes to novolac type epoxy resins, the phenol novolac type and the cresol novolak type have advantages and disadvantages, and fast curing properties and moisture resistance are not compatible with each other. That is, although the cresol novolak type has the advantage of moisture resistance, it has difficulty in fast curing. Moreover, the phenol novolak type has the opposite characteristics. Cresol novolac type has a water-repellent effect because it has a hydrophobic methyl group, but this methyl group is substituted with a phenol nucleus, which causes a decrease in reactivity. The present inventors have discovered that by substituting a hydrophobic group not on the phenol nucleus but on the bonded carbon of the phenol nucleus, both rapid curing properties and moisture resistance can be achieved. In the present invention, the epoxy resin composition refers to any compound containing a phenol novolak type epoxy resin in which the bonding carbon between phenol nuclei is replaced with a hydrocarbon, but generally, epoxy resins, It contains a curing agent, curing accelerator, filler, and other additives. As the epoxy resin, the epoxy resin used in the present invention and a conventional epoxy resin may be used in combination, but in this case, it is desirable that the ratio of the conventional epoxy resin used in combination is 50% or less. If too much is used, the original effect may be weakened and the features may not be apparent. Examples of low-pressure encapsulation molding materials for semiconductor encapsulation will be described below. All parts used in the examples are parts by weight. Further, the raw materials used in the examples are as follows. Epoxy resin Manufactured by Dainippon Ink Co., Ltd. Epicron N-670 (Cresol novolac type epoxy) Epoxy resin Manufactured by Nippon Kayaku Co., Ltd. EPPN-201 (Phenol novolac type epoxy) Epoxy resin Phenol/benzaldehyde co-condensation Phenol novolac type Epoxy (Epoxy in the present invention, softening point 70°C) Curing agent Phenol Novolac manufactured by Sumitomo Bakelite Co., Ltd. Curing accelerator Sumitomo Chemical Co., Ltd. Sumikure D Filler Toshiba Ceramics Co., Ltd. Fused silica Coupling agent Nippon Unicar Co., Ltd. ) A-186 Pigment Mitsubishi Kasei Co., Ltd. Carbon Mold release agent Hoechst Japan Co., Ltd. Hoechstwax OP Flame retardant Sumitomo Metal Mining Co., Ltd. Antimony trioxide Example 20 parts of epoxy resin, 10 parts of hardening agent, hardening accelerator
0.2 parts, filler 70 parts, coupling agent 0.3 parts, pigment
0.2 parts of mold release agent, 0.4 parts of mold release agent, and 3 parts of flame retardant were mixed and kneaded in a co-kneader to obtain a molding material. At this time, as epoxy resin,,,/=4/6,/
Seven types of molding materials were obtained by taking seven levels: =7/3, /=4/6, and /=7/3. The curability, electrical properties, strength, water absorption, and characteristics of IC-sealed products of this molding material were investigated, and as shown in Table 1, five types containing epoxy resin were superior. Also, among these, those using 1/2 or more are particularly excellent.
Claims (1)
デヒドまたはアクロレインの炭化水素置換アルデ
ヒドとの共縮合フエノールノボラツクをエポキシ
化した下記の一般式で示されるエポキシ樹脂を配
合してなるエポキシ樹脂組成物。 Ｒ：CH3CH2CH2CH2―、（CH3）2CHCH2―、 CH3CH2CH（CH3）―、CH2＝CH―、 【式】 ｎ：０〜６の整数[Scope of Claims] 1. An epoxy resin composition comprising an epoxy resin represented by the following general formula, which is obtained by epoxidizing a co-condensed phenol novolak of phenol and a hydrocarbon-substituted aldehyde of butyraldehyde, benzaldehyde or acrolein. R: CH 3 CH 2 CH 2 CH 2 -, (CH 3 ) 2 CHCH 2 -, CH 3 CH 2 CH (CH 3 ) -, CH 2 = CH -, [Formula] n: Integer from 0 to 6
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20489483A JPS6099125A (en) | 1983-11-02 | 1983-11-02 | Epoxy resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20489483A JPS6099125A (en) | 1983-11-02 | 1983-11-02 | Epoxy resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6099125A JPS6099125A (en) | 1985-06-03 |
| JPS6258618B2 true JPS6258618B2 (en) | 1987-12-07 |
Family
ID=16498156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20489483A Granted JPS6099125A (en) | 1983-11-02 | 1983-11-02 | Epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6099125A (en) |
-
1983
- 1983-11-02 JP JP20489483A patent/JPS6099125A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6099125A (en) | 1985-06-03 |
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