JPH09143287A - Prepreg sheet and laminated product - Google Patents
Prepreg sheet and laminated productInfo
- Publication number
- JPH09143287A JPH09143287A JP7344653A JP34465395A JPH09143287A JP H09143287 A JPH09143287 A JP H09143287A JP 7344653 A JP7344653 A JP 7344653A JP 34465395 A JP34465395 A JP 34465395A JP H09143287 A JPH09143287 A JP H09143287A
- Authority
- JP
- Japan
- Prior art keywords
- prepreg sheet
- epoxy resin
- resin
- heat resistance
- softening point
- 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
Landscapes
- Reinforced Plastic Materials (AREA)
- Moulding By Coating Moulds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】この発明は耐熱性と耐湿性に優れ
るプリプレグシート及び積層品に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a prepreg sheet and a laminate having excellent heat resistance and moisture resistance.
【０００２】[0002]
【従来技術及びその問題点】エポキシ樹脂は、接着力、
耐熱性、耐湿性といった性能とコストとのバランスが良
く、積層板・棒・管等の積層品あるいはプリント配線板
材料等に広く利用されている。最近になって、信頼性向
上や長寿命化の要求がこれらの分野において強くなって
きており、そのため耐熱性を向上する必要が生じてき
た。耐熱性を向上させるには、エポキシ樹脂と硬化剤と
の組合せにおいて、耐熱性に優れるものを選択すること
であるが、耐熱性と引きかえに、エポキシ樹脂本来の特
質である接着力や耐湿性を失ってしまうと云うのが大半
であった。エポキシ樹脂としては、ビスフェノールＡ型
エポキシを用いるのが一般的であるが、耐熱性で不十分
であるため、ノボラックエポキシやその他の多官能エポ
キシが用いられている。しかし、これらの耐熱性エポキ
シも耐熱性と引き換えに接着力や耐湿性が低下すると云
う欠点を有している。硬化剤は、プリプレグシートの用
途では室温における保存安定性が良好である必要があ
り、使用できるものは限られ、ジシアンジアミドやジア
ミノジフェニルスルホンのようなアミン、フェノールノ
ボラック樹脂やポリフェノールと云ったフェノール樹脂
がありそれぞれ一長一短を有している。ジシアンジアミ
ドは耐熱性と耐湿性の点で不十分であり、ジアミノジフ
ェニルスルホンは耐熱性は向上するが耐湿性に劣る。フ
エノール樹脂は耐湿性は良好であるものの接着力に劣る
と云う欠点があり、耐熱性でも満足するものではない。
耐熱性の高いエポキシ樹脂と耐熱性の高い硬化剤を組み
合わせると、ポリイミドにも匹敵するほどの高い耐熱性
を得ることができるものの、接着力や耐湿性がそれに応
じてより一層の低下を生じてしまう。そこで、この発明
の目的は、プリプレグとしての保存安定性に優れ、高い
耐熱性を有しながら、高い耐湿性、高い接着力を有する
プリプレグシート及びその積層品を提供することにあ
る。2. Description of the Related Art Epoxy resin is used for adhesive strength,
It has a good balance between performance such as heat resistance and humidity resistance and cost, and is widely used for laminated products such as laminated plates, rods and tubes, and printed wiring board materials. Recently, demands for improved reliability and longer life have become stronger in these fields, and therefore, it has become necessary to improve heat resistance. In order to improve heat resistance, it is necessary to select a combination of epoxy resin and curing agent that has excellent heat resistance. However, in exchange for heat resistance, the original characteristics of epoxy resin, such as adhesive strength and moisture resistance Most of them said that they would lose. As the epoxy resin, bisphenol A type epoxy is generally used, but novolac epoxy and other polyfunctional epoxies are used because of insufficient heat resistance. However, these heat-resistant epoxies also have the drawback of lowering the adhesive strength and moisture resistance in exchange for heat resistance. The curing agent is required to have good storage stability at room temperature in the application of the prepreg sheet, and the usable ones are limited. Yes, each has advantages and disadvantages. Dicyandiamide is insufficient in heat resistance and moisture resistance, and diaminodiphenyl sulfone is improved in heat resistance but inferior in moisture resistance. Although the phenol resin has good moisture resistance, it has a drawback that it is inferior in adhesive strength, and the heat resistance is not satisfactory.
By combining a highly heat-resistant epoxy resin and a highly heat-resistant curing agent, it is possible to obtain heat resistance that is comparable to that of polyimide, but the adhesive strength and moisture resistance will be further reduced accordingly. I will end up. Therefore, an object of the present invention is to provide a prepreg sheet having excellent storage stability as a prepreg, high heat resistance, high moisture resistance, and high adhesive strength, and a laminated product thereof.
【０００３】[0003]
【課題を解決するための手段】請求項１に係る発明のプ
リプレグシートは、ジシクロペンタジエン・フェノール
類変性エポキシ樹脂をエポキシ樹脂の総量に対し２０〜
１００重量％、軟化点１５０℃以上のクレゾールノボラ
ック樹脂、架橋ニトリルゴム、及び硬化促進剤を必須成
分とした樹脂組成物を補強基材に含浸し、予備乾燥した
のである。請求項２に係る発明の積層品は、請求項１に
係るプリプレグシート適数枚を加熱加圧して積層成形す
るようにしたのである。A prepreg sheet of the invention according to claim 1 comprises a dicyclopentadiene / phenol-modified epoxy resin in an amount of 20 to 20 relative to the total amount of the epoxy resin.
A resin composition containing 100 wt% of a cresol novolac resin having a softening point of 150 ° C. or higher, a crosslinked nitrile rubber, and a curing accelerator as essential components was impregnated into a reinforcing base material and preliminarily dried. In the laminated product of the invention according to claim 2, a proper number of prepreg sheets according to claim 1 are heat-pressed and laminated.
【０００４】本発明で使用するジシクロペンタジエン骨
格エポキシ樹脂（ａ）は、分子中に非常にバルキーなジ
シクロペンタジエンと云う脂肪族環状骨格を有してお
り、その剛直性と架橋網目鎖内での分子運動を束縛する
立体障害のため、フェノールノボラックエポキシやクレ
ゾールノボラックエポキシと同等の耐熱性を持ちなが
ら、吸水率を低くすることができる。従って、一般に多
用されているビスフェノールＡ型エポキシ樹脂よりも耐
湿性が良好であり、さらに耐熱エポキシ樹脂の代表とさ
れるノボラックエポキシとほぼ同等の耐熱特性を有して
いる上に、接着力が優れている。本願発明の目的を達成
するには少なくとも２０重量％を配合することが必要で
ある。ジシクロペンタジエン骨格エポキシ樹脂（ａ）以
外のエポキシ樹脂（ｂ）は、特にその種類を限定するも
のではなく、耐熱性の調整あるいは難燃性の付与等の目
的に適宜に選択して配合することができ、例えばビスフ
ェノールＡエポキシ樹脂、ノボラック型エポキシ樹脂、
三官能エポキシ樹脂、四官能エポキシ樹脂、ビフェニル
型エポキシ樹脂、等やそれらの変性エポキシ樹脂又は臭
素化エポキシ樹脂、などを例示することができる。The dicyclopentadiene skeleton epoxy resin (a) used in the present invention has a very bulky aliphatic cyclic skeleton called dicyclopentadiene in the molecule, and its rigidity and crosslinked network chain Due to the steric hindrance that constrains the molecular motion of, the water absorption rate can be reduced while having the same heat resistance as phenol novolac epoxy and cresol novolac epoxy. Therefore, it has better moisture resistance than the commonly used bisphenol A type epoxy resin, and has heat resistance characteristics almost equal to those of novolac epoxy, which is a typical heat resistant epoxy resin, and has excellent adhesive strength. ing. To achieve the object of the present invention, it is necessary to add at least 20% by weight. The epoxy resin (b) other than the dicyclopentadiene skeleton epoxy resin (a) is not particularly limited in type, and may be appropriately selected and blended for the purpose of adjusting heat resistance or imparting flame retardancy. For example, bisphenol A epoxy resin, novolac type epoxy resin,
Examples thereof include a trifunctional epoxy resin, a tetrafunctional epoxy resin, a biphenyl type epoxy resin, and the like, and modified epoxy resins or brominated epoxy resins thereof.
【０００５】本発明で使用する軟化点１５０℃以上のク
レゾールノボラック樹脂（ｃ）は、エポキシ樹脂
（ａ），（ｂ）の硬化剤であり、耐熱性と耐湿性を付与
する成分である。軟化点が１５０℃未満だと耐熱性の向
上効果が少ないため、軟化点が１５０℃以上のものを使
用する。クレゾールノボラック樹脂は、軟化点が高いほ
ど高温での安定性に優れていて、熱分解を起こし難いの
であるが、高い軟化点とするためには、分子量を上げる
必要があり、その場合には合成時にゲル化物が発生して
溶剤への溶解性が低下するため、一般には軟化点が１５
０℃以下のものである。軟化点１５０℃以上のクレゾー
ルノボラック樹脂（ｃ）はゲル化物を発生させることな
く軟化点の高い線状高分子化した樹脂であり、溶剤への
溶解性つまりワニス化が容易であり、積層板用途に用い
ることができる。The cresol novolac resin (c) having a softening point of 150 ° C. or higher used in the present invention is a curing agent for the epoxy resins (a) and (b) and is a component which imparts heat resistance and moisture resistance. If the softening point is lower than 150 ° C, the effect of improving the heat resistance is small, so a softening point of 150 ° C or higher is used. The cresol novolac resin has a higher softening point, which is more stable at high temperatures and is less likely to cause thermal decomposition.However, in order to obtain a high softening point, it is necessary to increase the molecular weight, and in that case, it is necessary to synthesize it. Since a gelled product is sometimes generated and the solubility in a solvent is lowered, the softening point is generally 15
It is below 0 ° C. The cresol novolac resin (c) having a softening point of 150 ° C. or higher is a linear polymerized resin having a high softening point without generating a gelled product, and is easily soluble in a solvent, that is, varnished, and used for laminated plates. Can be used for.
【０００６】本発明で用いる架橋ニトリルゴム（ｄ）
は、末端にカルボキシル基を持っていて、中央部には架
橋された三次元の立体的ゴム部分を有しているため、エ
ポキシ樹脂硬化物中に少量点在させて靭性を付与し接着
力を向上させるのに役立ち、エポキシ樹脂の耐熱性と耐
湿性を損しない。この架橋ニトリルゴムは予めエポキシ
樹脂と反応させておいて用いても差し支えない。Crosslinked nitrile rubber (d) used in the present invention
Has a carboxyl group at the terminal and has a cross-linked three-dimensional three-dimensional rubber part in the center part, so a small amount is scattered in the epoxy resin cured product to give toughness and adhesive strength. Helps improve and does not impair the heat and moisture resistance of epoxy resin. This crosslinked nitrile rubber may be used after being reacted with an epoxy resin in advance.
【０００７】本発明で用いる硬化促進剤（ｅ）は、特に
限定するものではなく、例えばイミダゾール、三級アミ
ン、三フッ化ホウソ錯体、有機ホスフィン類などを使用
することができる。The curing accelerator (e) used in the present invention is not particularly limited and, for example, imidazole, tertiary amine, boron trifluoride complex, organic phosphine and the like can be used.
【０００８】本発明は使用する樹脂組成物の目的に反し
ない範囲で着色剤、難燃剤、カップリング剤、界面活性
剤、あるいは滑剤などを配合しても良い。In the present invention, a colorant, a flame retardant, a coupling agent, a surfactant, a lubricant or the like may be blended within a range not deviating from the purpose of the resin composition used.
【０００９】補強基材は、特に限定するものではなく、
例えば紙やガラス布、ガラス不織布、アラミド紙、アラ
ミド布、ガラスマット、ガラスロービング布などを使用
することができる。以下、本発明を実施例・比較例を用
いて説明する。The reinforcing base material is not particularly limited,
For example, paper, glass cloth, glass non-woven fabric, aramid paper, aramid cloth, glass mat, glass roving cloth and the like can be used. Hereinafter, the present invention will be described using examples and comparative examples.
【００１０】[0010]
【実施例１】 ジシクロペンタジエン・フェノール類変性エポキシ樹脂（ａ）として、大日 本インキ化学工 業（株）製ＥＸＡ−７２００Ｈ（ａ１） …５０重量部 他のエポキシ樹脂（ｂ）として、東都化成（株）製ＹＤＢ−４００（ｂ１） …５０重量部 軟化点１５０℃以上のクレゾールノボラック樹脂（ｃ）として、油化電子（ 株）製レジンＸ−Ｈ，Ｍｎ＝２４００，軟化点１６５℃（ｃ１） …５０重量部 架橋ニトリルゴム（ｄ）として、日本合成ゴム（株）製ＸＥＲ−９１（ｄ１ ） …５重量部 硬化促進剤（ｅ）として、２Ｅ４ＭＺ（ｅ１） …０．１重量部 これら〜の樹脂組成物をＭＥＫ，メチルセロソル
ブ、ＤＭＦ等の溶剤に溶解してワニスとし、ガラス布に
含浸した後、予備乾燥してプリプレグシートを得た。更
に、このプリプレグシートの複数枚とその上に銅箔を重
ねて、加熱加圧成形して１．６ｍｍ厚の銅張積層板とし
て測定評価した。測定結果を表１に示す。Example 1 As a dicyclopentadiene / phenol modified epoxy resin (a), EXA-7200H (a 1 ) manufactured by Dainichi Ink & Chemicals Co., Ltd. 50 parts by weight As another epoxy resin (b), YDB-400 (b 1 ) manufactured by Tohto Kasei Co., Ltd. 50 parts by weight As a cresol novolac resin (c) having a softening point of 150 ° C. or higher, resin X-H, M n = 2400, softening point manufactured by Yuka Denshi Co., Ltd. 165 ° C. (c 1 ) 50 parts by weight As cross-linked nitrile rubber (d), XER-91 (d 1 ) manufactured by Nippon Synthetic Rubber Co., Ltd. 5 parts by weight As a curing accelerator (e) 2E4MZ (e 1 ) ... 0.1 parts by weight These resin compositions (1) to (4) were dissolved in a solvent such as MEK, methyl cellosolve and DMF to form a varnish, which was impregnated in a glass cloth and then pre-dried to obtain a prepreg sheet. Further, a plurality of this prepreg sheet and a copper foil were laid on the prepreg sheet, and heat and pressure molding was performed to measure and evaluate a copper clad laminate having a thickness of 1.6 mm. Table 1 shows the measurement results.
【００１１】[0011]
【比較例１】実施例１のジシクロペンタジエン・フェノ
ール類変性エポキシ樹脂（ａ）を１０重量部とし、他の
エポキシ樹脂（ｂ）として、東都化成（株）製クレゾー
ルノボラックエポキシ樹脂ＹＤＣＮ−７０４（ｂ２）を
４０重量部とした以外は、実施例１と同様に行った。測
定結果を表１に示す。Comparative Example 1 The dicyclopentadiene / phenol modified epoxy resin (a) of Example 1 was used as 10 parts by weight, and another epoxy resin (b) was used as a cresol novolac epoxy resin YDCN-704 (manufactured by Toto Kasei Co., Ltd.). Example 1 was repeated except that b 2 ) was changed to 40 parts by weight. Table 1 shows the measurement results.
【００１２】[0012]
【比較例２】実施例１の軟化点１５０℃以上のクレゾー
ルノボラック樹脂（ｃ）を、油化電子（株）製Ｔ−８，
Ｍｎ＝７５０，軟化点１１８℃（ｃ２）に変更した以外
は、実施例１と同様に行った。測定結果を表１に示す。Comparative Example 2 The cresol novolac resin (c) having a softening point of 150 ° C. or higher obtained in Example 1 was used as T-8, manufactured by Yuka Denshi Co., Ltd.
M n = 750, except for changing the softening point 118 ℃ (c 2), was performed in the same manner as in Example 1. Table 1 shows the measurement results.
【００１３】[0013]
【比較例３】実施例１の架橋ニトリルゴム（ｄ）の配合
量を、０重量部とした以外は、実施例１と同様に行っ
た。測定結果を表１に示す。Comparative Example 3 The procedure of Example 1 was repeated, except that the amount of the crosslinked nitrile rubber (d) used in Example 1 was 0 parts by weight. Table 1 shows the measurement results.
【００１４】[0014]
【比較例４】実施例１の架橋ニトリルゴム（ｄ）を、Ｂ
Ｆグッドリッチ社製 ＨｙｃａｒＣＴＢＮ１３００×１
３（ｄ２）に変更した以外は、実施例１と同様に行っ
た。測定結果を表１に示す。Comparative Example 4 The crosslinked nitrile rubber (d) of Example 1 was replaced with B
F Goodrich Hycar CTBN1300 × 1
3 except that the (d 2) was performed in the same manner as in Example 1. Table 1 shows the measurement results.
【００１５】[0015]
【表１】 [Table 1]
【００１６】[0016]
（１） ガラス転移温度：動的粘弾性測定装置により１
℃／分の昇温速度の条件で測定した。 （２） 曲げ強度保持率：銅箔をエッチング除去したも
のを試料とし、常態の曲げ強度を測定した後、２３０℃
×７２時間の加熱処理を行った後の曲げ強度を測定し、
状態に対する処理後の保持率を求めた。処理条件はＪＩ
Ｓ Ｋ−６９１１に準拠した。 （３） 煮沸後半田耐熱性：銅箔を除去した５０ｍｍ×
５０ｍｍの試料を８時間、沸騰水中で処理した後、２６
０℃の半田に浸漬し、ふくれの発生するまでの時間を測
定した。 （４） ピール強度：ＪＩＳ Ｃ−６４８１に準拠し
た。(1) Glass transition temperature: 1 by dynamic viscoelasticity measuring device
The measurement was performed under the condition of a temperature rising rate of ° C / min. (2) Bending strength retention rate: 230 ° C. after measuring the normal bending strength using a sample obtained by etching away the copper foil as a sample
Bending strength after heat treatment for 72 hours is measured,
The retention rate after treatment with respect to the state was obtained. Processing conditions are JI
It was based on SK-6911. (3) Solder heat resistance after boiling: 50 mm x with copper foil removed
After treating a 50 mm sample for 8 hours in boiling water,
It was dipped in solder at 0 ° C., and the time until blistering occurred was measured. (4) Peel strength: Based on JIS C-6481.
【００１７】[0017]
【発明の効果】本発明のプリプレグシート及びこのプリ
プレグシートで成形した積層板は耐熱性、耐湿性、接着
性に優れるため積層板およびプリント配線板材料として
非常に有用である。EFFECTS OF THE INVENTION The prepreg sheet of the present invention and the laminated plate formed from the prepreg sheet are excellent in heat resistance, moisture resistance and adhesiveness, and therefore are very useful as materials for laminated plates and printed wiring boards.
─────────────────────────────────────────────────────
────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成８年３月４日[Submission date] March 4, 1996
【手続補正１】[Procedure amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００１５[Correction target item name] 0015
【補正方法】変更[Correction method] Change
【補正内容】[Correction contents]
【００１５】[0015]
【表１】 [Table 1]
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０８Ｌ 9:02 ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI technical display area C08L 9:02
Claims (2)
性エポキシ樹脂をエポキシ樹脂の総量に対し２０〜１０
０重量％、軟化点１５０℃以上のクレゾールノボラック
樹脂、架橋ニトリルゴム、及び硬化促進剤を必須成分と
した樹脂組成物を補強基材に含浸し、予備乾燥したこと
を特徴とするプリプレグシート。1. A dicyclopentadiene / phenol-modified epoxy resin in an amount of 20 to 10 relative to the total amount of the epoxy resin.
A prepreg sheet characterized in that a reinforcing base material is impregnated with a resin composition containing 0 wt% of a cresol novolac resin having a softening point of 150 ° C. or higher, a cross-linked nitrile rubber, and a curing accelerator as essential components, and preliminarily dried.
加圧成形したことを特徴とする積層品。2. A laminated product obtained by hot pressing the prepreg sheet according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34465395A JP3561359B2 (en) | 1995-11-24 | 1995-11-24 | Prepreg sheet and laminated products |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34465395A JP3561359B2 (en) | 1995-11-24 | 1995-11-24 | Prepreg sheet and laminated products |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09143287A true JPH09143287A (en) | 1997-06-03 |
| JP3561359B2 JP3561359B2 (en) | 2004-09-02 |
Family
ID=18370941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP34465395A Expired - Lifetime JP3561359B2 (en) | 1995-11-24 | 1995-11-24 | Prepreg sheet and laminated products |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3561359B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005082624A (en) * | 2003-09-04 | 2005-03-31 | Nippon Kayaku Co Ltd | Epoxy resin composition and its cured product |
| JP2006290997A (en) * | 2005-04-08 | 2006-10-26 | Hitachi Chem Co Ltd | Thermosetting resin composition, adhesive sheet using the composition and adhesive sheet with copper foil |
| WO2006121090A1 (en) * | 2005-05-12 | 2006-11-16 | Risho Kogyo Co., Ltd. | White prepreg, white laminated plate, and metal foil clad white laminated plate |
| JP2008024806A (en) * | 2006-07-20 | 2008-02-07 | Fujikura Ltd | Epoxy adhesive, cover lay, prepreg, metal-clad laminated plate and printed wiring board |
| JP2009073990A (en) * | 2007-09-21 | 2009-04-09 | Panasonic Electric Works Co Ltd | Epoxy resin composition, continuous manufacturing method for metal-clad lamination plate, and metal-clad lamination plate |
-
1995
- 1995-11-24 JP JP34465395A patent/JP3561359B2/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005082624A (en) * | 2003-09-04 | 2005-03-31 | Nippon Kayaku Co Ltd | Epoxy resin composition and its cured product |
| JP4702764B2 (en) * | 2003-09-04 | 2011-06-15 | 日本化薬株式会社 | Epoxy resin composition and cured product thereof |
| JP2006290997A (en) * | 2005-04-08 | 2006-10-26 | Hitachi Chem Co Ltd | Thermosetting resin composition, adhesive sheet using the composition and adhesive sheet with copper foil |
| WO2006121090A1 (en) * | 2005-05-12 | 2006-11-16 | Risho Kogyo Co., Ltd. | White prepreg, white laminated plate, and metal foil clad white laminated plate |
| TWI403545B (en) * | 2005-05-12 | 2013-08-01 | Risho Kogyo Kk | White prepreg, white laminates, and metal foil-cladded white laminates |
| JP2008024806A (en) * | 2006-07-20 | 2008-02-07 | Fujikura Ltd | Epoxy adhesive, cover lay, prepreg, metal-clad laminated plate and printed wiring board |
| JP2009073990A (en) * | 2007-09-21 | 2009-04-09 | Panasonic Electric Works Co Ltd | Epoxy resin composition, continuous manufacturing method for metal-clad lamination plate, and metal-clad lamination plate |
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| Publication number | Publication date |
|---|---|
| JP3561359B2 (en) | 2004-09-02 |
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