JPH0340051B2 - - Google Patents
Info
- Publication number
- JPH0340051B2 JPH0340051B2 JP61249138A JP24913886A JPH0340051B2 JP H0340051 B2 JPH0340051 B2 JP H0340051B2 JP 61249138 A JP61249138 A JP 61249138A JP 24913886 A JP24913886 A JP 24913886A JP H0340051 B2 JPH0340051 B2 JP H0340051B2
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- dicyclopentadiene
- curing agent
- resin
- present
- 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 22
- 229920000647 polyepoxide Polymers 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 150000002989 phenols Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000005011 phenolic resin Substances 0.000 claims 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 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 238000003860 storage Methods 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
- 239000000203 mixture Substances 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
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 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 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- 238000013329 compounding Methods 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 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
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 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
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- -1 curing accelerators Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000126 substance Substances 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
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000011282 treatment Methods 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
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、耐熱性、耐湿性に優れたエポキシ樹
脂硬化剤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芳香族ポリ
アミン、ジシアンジアミド、酸無水物、BF3錯体
等が使われており、それらを配合した組生物が多
層プリント板の製造に用いられている。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
シ樹脂組成物には、それぞれ次のような問題があ
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、かつ毒性による労働安全衛生上
の問題があり、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という問題を有して
いる。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
定性に欠けるという問題がある。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
するという問題点がある。このように従来の硬化
剤を用いると、耐熱性、耐湿性に富む硬化物を生
成でき、かつ貯蔵安定性の極めて優れている組成
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〕
そこで、この発明者らは、耐熱性、耐湿性に富
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研究した結果、硬
化剤として、ジシクロペンタジエン変性フエノー
ル樹脂を使用すると目的が達成できることを見い
だし、この発明を完成した。
すなわち本発明は、下記一般式〔〕
〔式中Ｒは炭素数２〜９のアルキル基、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
樹脂を必須成分とするエポキシ樹脂硬化剤を提供
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
ンとフエノール類（パライソプロピルフエノー
ル、ノニルフエノール等）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エポキシ
樹脂のグリシジル基との立体障害が少ないため硬
化特性（耐湿性、耐熱性）が向上する。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。この場合、エポキシ樹脂中のグリシ
ジル基との立体障害等によつてエポキシ樹脂の硬
化性を低下する要因に働きこの結果、耐湿性を低
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フエノール成分であるアルキ
ルフエノール類を含有させることにより耐湿性を
更に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、流動特性が必要で
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。
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、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、１
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。硬
化に際し、所望により硬化促進剤、希釈剤、充填
剤、顔料などの種々の添加剤を加えて使用するこ
とも可能である。
本発明の硬化剤は、エポキシ樹脂との相溶性が
よく、この硬化剤を使用して硬化させたエポキシ
樹脂硬化物は透明性および光沢がよく、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。以下
単に部とあるはいずれも重量部を示す。
実施例 １〜２
第１表に示すエポキシ樹脂に一般式〔〕にお
いてＲがノニル基であるジシクロペンタジエエン
変性ノニルフエノール樹脂およびＲがイソプロピ
ル基であるジシクロペンタジエン変性イソプロピ
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）1.0部を配合
し、130℃で２時間、次いで160℃で５時間加熱し
硬化させた。硬化体の物性を第１表に示した。
比較例 １〜２
実施例１〜２で用いたジシクロペンタジエン変
性ノニルフエノール樹脂、ジシクロペンタジエン
い変性イソプロピ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。
これにより本発明の硬化剤を用いたエポキシ樹
脂硬化体は優れた物性を示すことが認められる。
【表】DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to an epoxy resin curing agent with excellent heat resistance and moisture resistance. [Problems to be solved by conventional techniques and inventions] Currently, aromatic polyamines, dicyandiamide, acid anhydrides, BF 3 complexes, etc. are used as curing agents for epoxy resins, and compositions containing these compounds are used for multilayer printing. Used in the manufacture of boards. However, epoxy resin compositions containing such curing agents have the following problems. That is, products using aromatic polyamines lack storage stability and pose problems in terms of occupational safety and health due to toxicity, and their cured products have poor moisture resistance. Further, although those using dicyandiamide exhibit excellent storage stability, they have the problem that the cured product lacks heat resistance and has a slow curing speed. Those using acid anhydrides produce cured products with relatively excellent heat resistance, but they have problems in that they tend to absorb moisture and lack storage stability. Products using the BF 3 complex have excellent storage stability and quick curing, but there is a problem in that when the resulting cured product absorbs moisture, its electrical properties deteriorate. As described above, when conventional curing agents are used, it has been difficult to obtain a composition that can produce a cured product with excellent heat resistance and moisture resistance and has extremely excellent storage stability. [Means for Solving the Problems] Therefore, the inventors conducted research to obtain an epoxy resin composition that can produce a cured product with high heat resistance and moisture resistance, and has excellent storage stability. It was discovered that the objective could be achieved by using a dicyclopentadiene-modified phenolic resin as a curing agent, and the present invention was completed. That is, the present invention provides the following general formula [] [In the formula, R is an alkyl group having 2 to 9 carbon atoms, and n is 0 to
An integer of 15] An epoxy resin curing agent containing a dicyclopentadiene-modified phenolic resin as an essential component is provided. [Function] The dicyclopentadiene-modified phenolic resin represented by the above general formula [] can be obtained by polymerizing dicyclopentadiene and phenols (paraisopropylphenol, nonylphenol, etc.) 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. Containing a tricyclodecane ring causes less steric hindrance with the glycidyl group of the epoxy resin, and thus improves curing properties (moisture resistance, heat resistance). Conventional novolac type resins are bonded to phenols through methylene groups. In this case, steric hindrance with the glycidyl group in the epoxy resin acts as a factor that reduces the curability of the epoxy resin, resulting in a reduction in moisture resistance. In the curing agent of the present invention, moisture resistance can be further improved by incorporating alkylphenols, which are phenol components in the dicyclopentadiene-modified phenolic resin. It is also possible to impart flexibility to the obtained cured epoxy resin. When applied to molding materials, fluidity is required, and the curing agent of the present invention exhibits fluidity at lower temperatures than when novolak type resins are used. The resin used in the present invention is soluble in organic solvents such as acetone, methyl ethyl ketone, tetrahydrofuran, chloroform, methanol, and ethanol, and is compatible with various epoxy resins, plasticizers, and the like. As the epoxy resin to which the present invention is applied, publicly known epoxy resins are used. These epoxy resins are 1
Examples include glycidyl-type epoxy resins and non-glycidyl-type epoxy resins which have at least two epoxy groups per molecule and are glycidyl compounds such as polyhydric alcohols, polyhydric phenols, polyhydric carboxylic acids, or polyhydric amines. The compounding ratio of the curing agent and epoxy resin of the present invention is:
It is usually determined by the ratio of the active hydrogen equivalent of the curing agent of the present invention to the epoxy equivalent of the epoxy resin, but even if the equivalent ratio deviates slightly, the desired performance can be fully exhibited, so the compounding ratio is particularly limited. do not have to. During curing, various additives such as curing accelerators, diluents, fillers, and pigments may be added if desired. The curing agent of the present invention has good compatibility with epoxy resins, and the cured epoxy resin products cured using this curing agent have good transparency and gloss, are highly flexible, have strong adhesive properties, and are removable. It exhibits various excellent properties such as high strength, impact resistance, 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. Hereinafter, all parts are by weight. Examples 1 to 2 A dicyclopentadiene-modified nonylphenol resin in which R is a nonyl group and a dicyclopentadiene-modified isopropyl resin in which R is an isopropyl group in the general formula [] were added to the epoxy resin shown in Table 1 in a stoichiometric manner. 2 as a hardening accelerator.
-1.0 part of methylimidazole (2-MI) was blended and heated at 130°C for 2 hours and then at 160°C for 5 hours to cure. Table 1 shows the physical properties of the cured product. Comparative Examples 1 and 2 The same treatments were carried out as in Examples 1 and 2, except that a phenol novolac resin was used in place of the dicyclopentadiene-modified nonylphenol resin and dicyclopentadiene-modified isopropyl resin. The physical properties of the obtained cured product are also listed in Table 1. This confirms that the cured epoxy resin using the curing agent of the present invention exhibits excellent physical properties. 【table】
Claims (1)
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
樹脂を必須成分とする多層プリント板用エポキシ
樹脂硬化剤。[Claims] 1 General formula () [In the formula, R is an alkyl group having 2 to 9 carbon atoms, and n is 0 to
An epoxy resin curing agent for multilayer printed boards, which contains a dicyclopentadiene-modified phenol resin represented by the following as an essential component.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24913886A JPS62104830A (en) | 1985-10-31 | 1986-10-20 | Curing agent for epoxy resin |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60244769 | 1985-10-31 | ||
| JP24913886A JPS62104830A (en) | 1985-10-31 | 1986-10-20 | Curing agent for epoxy resin |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60244769 Division | 1985-10-31 | 1985-10-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62104830A JPS62104830A (en) | 1987-05-15 |
| JPH0340051B2 true JPH0340051B2 (en) | 1991-06-17 |
Family
ID=26536903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24913886A Granted JPS62104830A (en) | 1985-10-31 | 1986-10-20 | Curing agent for epoxy resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62104830A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2816774B2 (en) * | 1991-03-29 | 1998-10-27 | 日本石油株式会社 | Phenolic resin, method for producing the resin, and epoxy resin composition for sealing material |
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
- 1986-10-20 JP JP24913886A patent/JPS62104830A/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 |
|---|---|
| JPS62104830A (en) | 1987-05-15 |
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