JPH0250129B2 - - Google Patents
Info
- Publication number
- JPH0250129B2 JPH0250129B2 JP17269985A JP17269985A JPH0250129B2 JP H0250129 B2 JPH0250129 B2 JP H0250129B2 JP 17269985 A JP17269985 A JP 17269985A JP 17269985 A JP17269985 A JP 17269985A JP H0250129 B2 JPH0250129 B2 JP H0250129B2
- Authority
- JP
- Japan
- Prior art keywords
- migration
- 2p4m5bz
- resin
- polyepoxy resin
- polyepoxy
- 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
- 229920005989 resin Polymers 0.000 claims description 16
- 239000011347 resin Substances 0.000 claims description 16
- NKVXEXBFJUACKT-UHFFFAOYSA-N 4-benzyl-5-methyl-2-phenyl-1h-imidazole Chemical compound CC=1NC(C=2C=CC=CC=2)=NC=1CC1=CC=CC=C1 NKVXEXBFJUACKT-UHFFFAOYSA-N 0.000 claims 1
- 238000001723 curing Methods 0.000 claims 1
- 238000013508 migration Methods 0.000 description 10
- 230000005012 migration Effects 0.000 description 8
- 238000009472 formulation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 239000011810 insulating material Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 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 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000004034 viscosity adjusting agent Substances 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- -1 cycloaliphatic Chemical group 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
Description
(産業上の利用分野)
本発明はポリエポキシ樹脂の硬化方法に関する
ものである。
本発明の方法によつて硬化させたポリエポキシ
樹脂は、配線回路を構成する金、銀、銅等のマイ
グレーシヨン防止作用が顕著であるため、本発明
は電子部品用封止材、銅張積層板および有機質、
無機質基板用塗布材等の製造分野において特に有
用と考えられる。
(従来の技術)
エポキシ樹脂は耐熱性、電気絶縁性および接着
性に優れているので、特に電子部品およびプリン
ト基板関係の分野では封止材料、絶縁材料および
基板用マトリツクス材料として、従来から広く使
用されて来た。
しかしながら、エポキシ樹脂はマイグレーシヨ
ン、すなわち絶縁材上の配線あるいは電極を構成
する金属が高湿度の環境下、電位差の作用によつ
て絶縁材上を移行する現象を防止する作用が低い
ため、絶縁不良あるいは短絡等のトラブルを伴な
うものである。
(発明が解決しようとする問題点)
部品の小型化と高密度化及び配線回路の微細化
が進むに連れて、特にマイグレーシヨンで防止は
業界内できびしく要求されて来た。
マイグレーシヨン防止を目的とした各種の市販
樹脂は、硬化条件が苛酷なこと、硬化収縮が大き
いこと、または密着性が低いことなどの欠陥を有
し、必ずしも満足しうる状態にあるとは云えな
い。
また、セラミツク基板に使用されているガラス
フリツトは、優れたマイグレーシヨン防止作用を
有するものであるが、このものは高価であり、且
つ焼付温度が高いなどの欠点を有している。
(問題点を解決するための手段)
本発明者等は、このような事情に鑑み鋭意研究
を重ねた結果、ポリエポキシ樹脂に必須成分とし
て下式で示される2−フエニル−4−メチル−5
−ベンジルイミダゾール(以下2P4M5BZと略称
する)
(Industrial Application Field) The present invention relates to a method for curing polyepoxy resin. The polyepoxy resin cured by the method of the present invention has a remarkable effect of preventing migration of gold, silver, copper, etc. constituting wiring circuits. board and organic,
It is considered to be particularly useful in the field of manufacturing coating materials for inorganic substrates. (Prior art) Epoxy resin has excellent heat resistance, electrical insulation, and adhesive properties, so it has traditionally been widely used as a sealing material, insulating material, and substrate matrix material, especially in the fields of electronic components and printed circuit boards. I've been However, epoxy resin has a low ability to prevent migration, a phenomenon in which the metal constituting the wiring or electrode on the insulating material migrates on the insulating material due to the action of potential difference in a high humidity environment, resulting in poor insulation. Alternatively, problems such as short circuits may occur. (Problems to be Solved by the Invention) As the miniaturization and density of components and the miniaturization of wiring circuits progress, prevention of migration, in particular, has been increasingly required within the industry. Various commercially available resins aimed at preventing migration have flaws such as harsh curing conditions, large curing shrinkage, and low adhesion, and are not necessarily in a satisfactory state. . Furthermore, although the glass frit used in ceramic substrates has an excellent anti-migration effect, it is expensive and has drawbacks such as a high baking temperature. (Means for Solving the Problems) In view of the above circumstances, the present inventors have conducted intensive research and found that 2-phenyl-4-methyl-5, which is represented by the following formula, is an essential component of polyepoxy resin.
-Benzylimidazole (hereinafter abbreviated as 2P4M5BZ)
【式】
を加えることによつて、耐熱性、絶縁性、密着性
に富み、且つマイグレーシヨン防止作用に優れた
硬化物を生じることを見い出し、本発明を完成し
たものである。
2P4M5BZは、1倍モル2−フエニル−4−メ
チルミダゾールと等モル以上の塩化ベンジルを
300ないし320℃で数時間加熱することにより合成
される。その場合、反応促進をはかる意味で少量
の沃化カリを反応系に加えてもよい。
ポリエポキシ樹脂の硬化剤として2P4M5BZを
用いた場合、その硬化物は煮沸吸収率及び電気特
性に優れ、且つマイグレーシヨン防止効果を備え
ている。本発明におけるポリエポキシ樹脂は1分
子当り平均1個以上のエポキシ基を含有するもの
であつて、この基は分子末端位置にある
The present invention was completed based on the discovery that by adding the following formula, a cured product having high heat resistance, insulation properties, and adhesion properties and excellent anti-migration properties can be produced. 2P4M5BZ contains 1 mole of 2-phenyl-4-methylmidazole and more than the same mole of benzyl chloride.
It is synthesized by heating at 300 to 320°C for several hours. In that case, a small amount of potassium iodide may be added to the reaction system in order to promote the reaction. When 2P4M5BZ is used as a curing agent for polyepoxy resin, the cured product has excellent boiling absorption rate and electrical properties, and has migration prevention effects. The polyepoxy resin in the present invention contains an average of one or more epoxy groups per molecule, and this group is located at the terminal position of the molecule.
【式】でもよく、あるいは分子の途中に介 在して[Formula] may be used, or there may be an intervention in the middle of the molecule. exist
【式】の形を構成してもよい。
このポリエポキシ化合物は脂肪族、環式脂肪
族、芳香族、または複素環式のものでもよく、そ
して水酸基、アルキル基、アルコキシ基、エステ
ル基、アセタール基、エーテル基のような非妨害
性の置換基で置換されても良い。
本発明の実施に適する代表的なポリエポキシ樹
脂は、多価フエノールのポリグリシジルエーテ
ル、例えばビスフエノールAのジグリシジルエー
テル、ビスフエノールFのジグリシジルエーテ
ル、その他エポキシ化フエノール・ノボラツク樹
脂、脂環式エポキシ樹脂およびそれらの臭素化エ
ポキシ樹脂等である。
ポリエポキシ樹脂に対して添加される
2P4M5BZの量は、ポリエポキシ樹脂100重量部
に対して3ないし5重量部の割合が望ましい。ポ
リエポキシ樹脂の硬化条件は、樹脂及び硬化剤の
添加量の相違によつて多少変化させる必要はある
が、通常100ないし150℃の温度で最大8時間加熱
が良い。
以下、本発明を実施例及び比較例によつて具体
的に説明する。
実施例 1ないし2
100重量部のポリエポキシ樹脂(商品名:エピ
コート#
828、油化シエルエポキシ製)に7およ
び10重量部の2P4M5BZおよび3重量部の粘度調
整剤(商品名:エロジル#
300、日本アエロジル
製)の3者を加えて3本ロールミルで混合して、
脱泡後、厚みが3mmになるように調製した2枚の
ガラス板間に流し込み、100℃で4時間、150℃で
4時間硬化させ、その硬化物についてガラス転移
温度、煮沸吸収率および電気特性を測定したとこ
ろ、煮沸吸収率および電気特性は非常に優れたも
のであつた。
その試験結果を表1に示す。It may also be constructed in the form [Formula]. The polyepoxy compound may be aliphatic, cycloaliphatic, aromatic, or heterocyclic and may contain non-interfering substitutions such as hydroxyl, alkyl, alkoxy, ester, acetal, or ether groups. It may be substituted with a group. Typical polyepoxy resins suitable for the practice of the present invention include polyglycidyl ethers of polyhydric phenols, such as diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F, other epoxidized phenolic novolac resins, alicyclic These include epoxy resins and their brominated epoxy resins. Added to polyepoxy resin
The amount of 2P4M5BZ is preferably 3 to 5 parts by weight per 100 parts by weight of the polyepoxy resin. The curing conditions for the polyepoxy resin may need to be changed somewhat depending on the amount of resin and curing agent added, but it is usually best to heat the resin at a temperature of 100 to 150° C. for a maximum of 8 hours. Hereinafter, the present invention will be specifically explained using Examples and Comparative Examples. Examples 1 and 2 7 and 10 parts by weight of 2P4M5BZ and 3 parts by weight of a viscosity modifier (product name: Erosil # 300, (manufactured by Nippon Aerosil) and mixed in a three-roll mill.
After defoaming, it was poured between two glass plates prepared to have a thickness of 3 mm, and cured at 100℃ for 4 hours and 150℃ for 4 hours, and the glass transition temperature, boiling absorption rate, and electrical properties of the cured product were determined. When measured, the boiling absorption rate and electrical properties were found to be very excellent. The test results are shown in Table 1.
【表】【table】
【表】
実施例 3ないし4
100重量部のポリエポキシ樹脂(商品名:エピ
コート#
828、油化シエルエポキシ製)に必須成
分として10ないし15重量部の2P4M5BZおよび5
重量部の粘度調整剤(商品名:エロジル#
300、
日本アエロジル製)の3者を加えて3本ロールミ
ルで混合して、各種のポリエポキシ樹脂配合物を
調整し、各配合物の150℃の温度におけるゲルタ
イム及び150℃の温度で15分間加熱して硬化させ
た塗膜の耐マイグレーシヨン性試験を行つた。
これらの試験結果は表2に示したとおりであ
り、2P4M5BZを含む配合物は1500時間以上の耐
マイグレーシヨン性を示したが、これを含まない
ものは48時間以下の耐マイグレーシヨン性しか示
さなかつた。[Table] Examples 3 to 4 100 to 15 parts by weight of 2P4M5BZ and 5 as essential components to 100 parts by weight of polyepoxy resin (trade name: Epicoat #828, manufactured by Yuka Ciel Epoxy)
Parts by weight of viscosity modifier (trade name: Erosil #300,
(manufactured by Nippon Aerosil) and mixed in a three-roll mill to prepare various polyepoxy resin formulations, and the gel time of each formulation at a temperature of 150℃ and heating at a temperature of 150℃ for 15 minutes. A migration resistance test of the cured coating film was conducted. The results of these tests are shown in Table 2, and the formulation containing 2P4M5BZ showed migration resistance for more than 1500 hours, while the formulation that did not contain 2P4M5BZ showed migration resistance for only 48 hours or less. Ta.
Claims (1)
2−フエニル−4−メチル−5−ベンジルイミダ
ゾール 式:【式】 を加えて加熱することを特徴とするポリエポキシ
樹脂の硬化方法。[Claims] 1. A polyepoxy resin characterized in that 2-phenyl-4-methyl-5-benzylimidazole represented by the following formula is added to a polyepoxy resin and heated. Curing method.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP17269985A JPS6232113A (en) | 1985-08-05 | 1985-08-05 | Curing of polyepoxy resin |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP17269985A JPS6232113A (en) | 1985-08-05 | 1985-08-05 | Curing of polyepoxy resin |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6232113A JPS6232113A (en) | 1987-02-12 |
JPH0250129B2 true JPH0250129B2 (en) | 1990-11-01 |
Family
ID=15946707
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP17269985A Granted JPS6232113A (en) | 1985-08-05 | 1985-08-05 | Curing of polyepoxy resin |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6232113A (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW270944B (en) * | 1993-05-10 | 1996-02-21 | Shikoku Kakoki Co Ltd | |
MX9605901A (en) * | 1994-05-27 | 1997-12-31 | Herberts & Co Gmbh | Process for coating phosphatized metal substrates. |
DE602004028223D1 (en) | 2003-03-19 | 2010-09-02 | Shikoku Chem | SOLDERING PROCEDURE USING AN IMIDAZOL CONNECTION |
-
1985
- 1985-08-05 JP JP17269985A patent/JPS6232113A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS6232113A (en) | 1987-02-12 |
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