JP2789002B2 - Epoxy resin composition - Google Patents
Epoxy resin compositionInfo
- Publication number
- JP2789002B2 JP2789002B2 JP83090A JP83090A JP2789002B2 JP 2789002 B2 JP2789002 B2 JP 2789002B2 JP 83090 A JP83090 A JP 83090A JP 83090 A JP83090 A JP 83090A JP 2789002 B2 JP2789002 B2 JP 2789002B2
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- resin composition
- isocyanurate
- tris
- acid
- 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 - Fee Related
Links
- 239000003822 epoxy resin Substances 0.000 title claims description 23
- 229920000647 polyepoxide Polymers 0.000 title claims description 23
- 239000000203 mixture Substances 0.000 title claims description 18
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 20
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 claims description 11
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 239000011347 resin Substances 0.000 claims description 10
- 239000007983 Tris buffer Substances 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 7
- -1 imidazole compound Chemical class 0.000 description 6
- 239000000945 filler Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910000679 solder Inorganic materials 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000565 sealant Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- LIOJOGAWBPJICS-UHFFFAOYSA-N 1-benzyl-2-phenylimidazole;hydrochloride Chemical compound Cl.C1=CN=C(C=2C=CC=CC=2)N1CC1=CC=CC=C1 LIOJOGAWBPJICS-UHFFFAOYSA-N 0.000 description 1
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical group O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 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 1
- 238000010438 heat treatment Methods 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明はエポキシ樹脂組成物に関するものである。本
発明の硬化樹脂は電気絶縁性、耐熱性、密着性に優れて
るので、プリント配線基板のソルダーレジストインキ、
電子部品用封止剤、各種充填剤、接着剤として有用であ
る。Description: TECHNICAL FIELD The present invention relates to an epoxy resin composition. Since the cured resin of the present invention is excellent in electrical insulation, heat resistance, and adhesion, a solder resist ink for printed wiring boards,
It is useful as a sealant for electronic components, various fillers, and adhesives.
従来、プリント配線基板のソルダーレジストインキ、
電子部品用封止剤、各種充填剤及び接着剤には、硬化剤
としてイミダゾール化合物を用いたエポキシ樹脂組成物
（例えば特公昭56−39314号公報）、硬化剤としてヒド
ラジン化合物を用いたエポキシ樹脂組成物（例えば特開
昭58−131953号公報）、ジシアンジアミド及びアミン
類、酸無水物、フェノール類等とポリエポキシ樹脂との
付加物を用いたエポキシ樹脂組成物（例えば特開昭60−
4525号公報）等が知られている。Conventionally, solder resist ink for printed wiring boards,
An epoxy resin composition using an imidazole compound as a curing agent (for example, Japanese Patent Publication No. 56-39314) and an epoxy resin composition using a hydrazine compound as a curing agent for electronic component sealants, various fillers and adhesives Resin composition (for example, JP-A-58-131953), an epoxy resin composition using an adduct of dicyandiamide and amines, acid anhydrides, phenols and the like with a polyepoxy resin
No. 4525) is known.
イソシアヌル酸をイミダゾール化合物の存在下にエポ
キシ樹脂に配合して加熱すると耐熱性及び電気的特性に
優れた硬化物を得られることは既に知られている（鎌形
一夫，水井隆；日化，1985 2081）。このことは、イソ
シアヌル酸がイミダゾール化合物の存在下エポキシ樹脂
と反応して硬化物中にイソシアヌル酸環及びオキサゾリ
ドン環を形成し、耐熱性が向上するためと推測される。It is already known that when isocyanuric acid is mixed with an epoxy resin in the presence of an imidazole compound and heated, a cured product having excellent heat resistance and electrical properties can be obtained (Kazuo Kamagata, Takashi Mizui; Nikka, 1985 2081) ). This is presumably because isocyanuric acid reacts with the epoxy resin in the presence of the imidazole compound to form an isocyanuric acid ring and an oxazolidone ring in the cured product, thereby improving heat resistance.
発明が解決しようとする課題 イミダゾール化合物を硬化剤とするエポキシ樹脂組成
物は耐熱性及び電気的特性に優れた硬化物を与えるが、
組成物の粘度が高いので電子部品の注型材料としては不
向きであった。The epoxy resin composition using an imidazole compound as a curing agent gives a cured product having excellent heat resistance and electrical properties.
Since the viscosity of the composition was high, it was not suitable as a casting material for electronic components.
また酸無水物を硬化剤とするエポキシ樹脂組成物は粘
度が低く、注型剤としては好適であるが、耐熱性が劣る
欠点があった。An epoxy resin composition using an acid anhydride as a curing agent has a low viscosity and is suitable as a casting agent, but has a drawback of poor heat resistance.
分子中にイソシアヌル酸環を持つ三価のアルコールで
あるトリス（ヒドロキシエチル）イソシアヌレートはポ
リエステルの耐熱性を向上させるアルコール成分として
広く使用されているが、エポキシ樹脂との反応性は低
く、エポキシ樹脂組成物に単独で使用することは不可能
であった。Tris (hydroxyethyl) isocyanurate, a trihydric alcohol having an isocyanuric acid ring in the molecule, is widely used as an alcohol component to improve the heat resistance of polyester, but its reactivity with epoxy resin is low. It was not possible to use it alone in the composition.
課題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種々の研究を重
ねた結果、ポリエポキシ樹脂にトリス（ヒドロキシアル
キル）イソシアヌレート及び二価カルボン酸無水物を配
合することにより、硬化前には容易に注型が出来る程度
に粘度が低く、硬化後は耐熱性及び電気特性に優れた硬
化物が得られるエポキシ樹脂組成物を見い出し、本発明
を完遂した。Means for Solving the Problems The present inventors have conducted various studies in view of such circumstances, and as a result, by blending tris (hydroxyalkyl) isocyanurate and a divalent carboxylic anhydride with a polyepoxy resin. An epoxy resin composition having a viscosity low enough to be easily cast before curing, and having a cured product excellent in heat resistance and electrical properties after curing was found, and completed the present invention.
本発明のエポキシ樹脂組成物は、ポリエポキシ樹脂
に、下記の一般式で示されるトリス（ヒドロキシアルキ
ル）イソシアヌレート 一般式 （但し、ｎは２以上の整数を表す） 、二価カルボン酸無水物及びイミダゾール化合物、三級
アミンなどの酸無水物の硬化促進剤並びに充填剤などを
添加して成るものである。The epoxy resin composition of the present invention is obtained by adding tris (hydroxyalkyl) isocyanurate represented by the following general formula to a polyepoxy resin. (Where n represents an integer of 2 or more), a curing accelerator for a dihydric carboxylic acid anhydride, an acid anhydride such as an imidazole compound, and a tertiary amine, and a filler.
本発明の実施において用いられるトリス（ヒドロキシ
アルキル）イソシアヌレートはイソシアヌル酸にエチレ
ンオキシド、プロピレンオキシドなどを反応させて合成
され、特にイソシアヌル酸のジメチルホルムアミド溶液
にエチレンオキシドを吹き込むことによって合成される
トリス（２−ヒドロキシエチル）イソシアヌレート（以
下THEICという）が好適である。Tris (hydroxyalkyl) isocyanurate used in the practice of the present invention is synthesized by reacting isocyanuric acid with ethylene oxide, propylene oxide and the like, and in particular, tris (2- (2-alkyl) isocyanurate) synthesized by blowing ethylene oxide into a dimethylformamide solution of isocyanuric acid. (Hydroxyethyl) isocyanurate (hereinafter referred to as THEIC) is preferred.
THEICは融点が133〜135℃の白色結晶であり、耐熱性
電気絶縁ポリエステルワニスのアルコール成分として多
量に使用されている。THEIC is a white crystal having a melting point of 133 to 135 ° C., and is used in a large amount as an alcohol component of a heat-resistant electrically insulating polyester varnish.
THEICとエポキシ樹脂とを等量混合し、THEICの融点以
上に加熱すると透明な液体が得られ、このことから両者
は相溶性があると推測される。（但し、その透明な溶融
液を室温に冷却すると白濁する） THEICと二価カルボン酸無水物を当モル量混合し、THE
ICの融点以上に加熱すると透明な液体となり、これを室
温迄冷却しても透明性を失わない。このことはTHEICと
二価カルボン酸無水物が反応してエステルを与えること
を意味している。When an equal amount of THEIC and an epoxy resin are mixed and heated above the melting point of THEIC, a transparent liquid is obtained, which suggests that both are compatible. (However, the transparent melt becomes cloudy when cooled to room temperature.) THEIC and divalent carboxylic anhydride are mixed in equimolar amounts,
When heated above the melting point of the IC, it becomes a transparent liquid, which does not lose its transparency when cooled to room temperature. This means that THEIC reacts with the divalent carboxylic anhydride to give the ester.
本発明のエポキシ樹脂組成物はポリエポキシ樹脂にTH
EIC及び二価カルボン酸無水物を混合して製造される
が、ポリエポキシ樹脂及び酸無水物が液体の場合には、
三本ロールミルなどで混合し必要に応じて充填剤を添加
し、電子部品の封止剤、プリント配線基板のソルダーレ
ジストなどの用途に使用できる。The epoxy resin composition of the present invention is obtained by adding TH to polyepoxy resin.
It is manufactured by mixing EIC and divalent carboxylic anhydride, but when the polyepoxy resin and the acid anhydride are liquid,
It can be mixed with a three-roll mill or the like and added with a filler if necessary, and used for applications such as a sealant for electronic parts and a solder resist for printed wiring boards.
ポリエポキシ樹脂、二価カルボン酸無水物が固体の場
合には二本ロール、押し出し機などで混合することがで
きる。When the polyepoxy resin and the divalent carboxylic anhydride are solid, they can be mixed with a two-roll, extruder or the like.
本発明のエポキシ樹脂組成物を加熱すると酸無水物と
THEICとが反応し、エステルを生成する。When the epoxy resin composition of the present invention is heated, acid anhydride and
Reacts with THEIC to produce esters.
エステル生成時には水を副生するが、この水は酸無水
物を開環させるのに働き系外に出ないため、硬化物に気
泡孔などを生じない。At the time of ester formation, water is by-produced, but this water works to open the ring of the acid anhydride and does not come out of the system, so that the cured product does not form pores or the like.
本発明の実施において用いられる二価カルボン酸無水
物としては、エポキシ樹脂の硬化剤として市販されてい
る全ての酸無水物を使用することが出来る。As the divalent carboxylic acid anhydride used in the practice of the present invention, all commercially available acid anhydrides as curing agents for epoxy resins can be used.
作用 ポリエポキシ樹脂にトリス（ヒドロキシアルキル）イ
ソシアヌレートと二価カルボン酸無水物を共存させて加
熱すると、エポキシ樹脂と酸無水物との反応、トリス
（ヒドロキシアルキル）イソシアヌレートと酸無水物と
の反応及びその反応生成物とエポキシ樹脂との反応がほ
ぼ同時に進行し、硬化物中にイソシアヌル酸環が入り、
硬化物の耐熱性及び電気性質が向上すると推測される。Action When tris (hydroxyalkyl) isocyanurate and divalent carboxylic anhydride coexist in polyepoxy resin and heated, the reaction between epoxy resin and acid anhydride, the reaction between tris (hydroxyalkyl) isocyanurate and acid anhydride And the reaction between the reaction product and the epoxy resin proceed almost simultaneously, and an isocyanuric acid ring enters the cured product,
It is estimated that the heat resistance and electrical properties of the cured product are improved.
次に本発明を実施例及び比較例によって具体的に説明
する。Next, the present invention will be specifically described with reference to Examples and Comparative Examples.
実施例１〜２及び比較例 液状のポリエポキシ樹脂〔商品名「エピコート＃82
8」（油化シェルエポキシ（株）製）〕100重量部に対し
て、THEICを10及び50重量部、酸無水物系の硬化剤〔商
品名「リカシッドMH−700」（新日本理化（株）製）〕8
8重量部、硬化促進剤として１−ベンジル−２−フェニ
ルイミダゾールの塩酸塩（以下1B2PZ・HClという）１重
量部を三本ロールミルで混合し、100℃で２時間さらに1
20℃で２時間加熱して透明な硬化物を得た。比較例とし
て、前記実施例からTHEICを除いたエポキシ樹脂組成物
を調製し、同様の硬化処理をして、これらのガラス転移
温度、線膨張係数、体積固有抵抗及び煮沸吸水率を測定
した。Examples 1 and 2 and Comparative Example Liquid polyepoxy resin [trade name “Epicoat # 82”
8 "(manufactured by Yuka Shell Epoxy Co., Ltd.)] and 100 and 100 parts by weight of THEIC, 10 and 50 parts by weight, and an acid anhydride-based curing agent [trade name" RIKACID MH-700 "(Shin Nippon Rika Co., Ltd. ))) 8
8 parts by weight, 1 part by weight of 1-benzyl-2-phenylimidazole hydrochloride (hereinafter referred to as 1B2PZ.HCl) as a curing accelerator were mixed by a three-roll mill, and further mixed at 100 ° C. for 2 hours.
Heating at 20 ° C. for 2 hours gave a transparent cured product. As a comparative example, an epoxy resin composition prepared by removing the THEIC from the above example was prepared and subjected to the same curing treatment, and the glass transition temperature, linear expansion coefficient, volume specific resistance and boiling water absorption were measured.
これらの試験結果は結果は表１に示したとおりであっ
た。The test results were as shown in Table 1.
発明の効果 本発明エポキシ樹脂組成物は、プリント配線基板のソ
ルダーレジストインキや電子部品の注型材料に使用が可
能で、しかも硬化に際して気泡を発生させるような低分
子物質を放出せずに、熱的及び電気的性質に優れた硬化
物を得ることが出来る。 Effect of the Invention The epoxy resin composition of the present invention can be used as a solder resist ink for a printed wiring board or a casting material for an electronic component. A cured product having excellent electrical and electrical properties can be obtained.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.6，ＤＢ名) C03G 59/40 - 59/66──────────────────────────────────────────────────続 き Continued on front page (58) Field surveyed (Int.Cl. 6 , DB name) C03G 59/40-59/66
Claims (3)
式 （但し、ｎは２以上の整数を表す） で示されるトリス（ヒドロキシアルキル）イソシアヌレ
ートと二価カルボン酸無水物を配合したことを特徴とす
るエポキシ樹脂組成物。1. A polyepoxy resin having a general formula as an essential component (Where n represents an integer of 2 or more) An epoxy resin composition comprising tris (hydroxyalkyl) isocyanurate represented by the following formula: and a divalent carboxylic anhydride.
レートとして、トリス（２−ヒドロキシエチル）イソシ
アヌレートを用いる請求項（１）に記載のエポキシ樹脂
組成物。2. The epoxy resin composition according to claim 1, wherein tris (2-hydroxyethyl) isocyanurate is used as tris (hydroxyalkyl) isocyanurate.
イソフタル酸、テレフタル酸、アジピン酸及びテトラヒ
ドロフタル酸無水物から選ばれた化合物を用いる請求項
（１）に記載のエポキシ樹脂組成物。(3) phthalic acid as a divalent carboxylic anhydride;
The epoxy resin composition according to claim 1, wherein a compound selected from isophthalic acid, terephthalic acid, adipic acid and tetrahydrophthalic anhydride is used.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP83090A JP2789002B2 (en) | 1990-01-06 | 1990-01-06 | Epoxy resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP83090A JP2789002B2 (en) | 1990-01-06 | 1990-01-06 | Epoxy resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03205421A JPH03205421A (en) | 1991-09-06 |
| JP2789002B2 true JP2789002B2 (en) | 1998-08-20 |
Family
ID=11484550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP83090A Expired - Fee Related JP2789002B2 (en) | 1990-01-06 | 1990-01-06 | Epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2789002B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2135706C (en) * | 1993-11-15 | 1999-06-15 | Walter E. Cover | Retractable-needle cannula insertion set with refinements to better control leakage, retraction speed, and reuse |
| JP4762659B2 (en) * | 2005-10-04 | 2011-08-31 | 新日鐵化学株式会社 | Epoxy resin and epoxy resin composition |
| JP6362558B2 (en) * | 2014-05-13 | 2018-07-25 | 日本化薬株式会社 | Polyfunctional acid anhydride and thermosetting resin composition |
| CN110437402A (en) * | 2019-08-09 | 2019-11-12 | 中国科学院兰州化学物理研究所 | A kind of preparation method of the interpenetrating net polymer with shape-memory properties |
-
1990
- 1990-01-06 JP JP83090A patent/JP2789002B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03205421A (en) | 1991-09-06 |
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