JPH02300229A - One-component epoxy resin composition - Google Patents
One-component epoxy resin compositionInfo
- Publication number
- JPH02300229A JPH02300229A JP12045689A JP12045689A JPH02300229A JP H02300229 A JPH02300229 A JP H02300229A JP 12045689 A JP12045689 A JP 12045689A JP 12045689 A JP12045689 A JP 12045689A JP H02300229 A JPH02300229 A JP H02300229A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- microencapsulated
- resin composition
- curing accelerator
- curing
- 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.)
- Pending
Links
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 25
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 25
- 239000000203 mixture Substances 0.000 title claims abstract description 22
- 239000002245 particle Substances 0.000 claims abstract description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000839 emulsion Substances 0.000 abstract description 4
- 238000010438 heat treatment Methods 0.000 abstract description 4
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 abstract description 3
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 abstract description 3
- 239000004115 Sodium Silicate Substances 0.000 abstract description 3
- 235000012538 ammonium bicarbonate Nutrition 0.000 abstract description 3
- 239000001099 ammonium carbonate Substances 0.000 abstract description 3
- 239000000377 silicon dioxide Substances 0.000 abstract description 3
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052911 sodium silicate Inorganic materials 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 239000002736 nonionic surfactant Substances 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 238000001035 drying Methods 0.000 abstract 1
- 230000001804 emulsifying effect Effects 0.000 abstract 1
- 229910010272 inorganic material Inorganic materials 0.000 abstract 1
- 239000011147 inorganic material Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000001723 curing Methods 0.000 description 28
- 239000003094 microcapsule Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- -1 alkyl urea compounds Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 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 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
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 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
- 238000013007 heat curing Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009257 reactivity Effects 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)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、保存安定性の優れたー液型エポキシ樹脂組成
物に関し、特に硬化促進剤をマイクロカプセル化するこ
とにより保存安定性を向上させたものである。Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a liquid-type epoxy resin composition with excellent storage stability, and in particular, the storage stability is improved by microencapsulating a curing accelerator. It is something that
（従来の技術）
液状のエポキシ樹脂組成物において、その使用時エポキ
シ樹脂と硬化剤・硬化促進剤との混合工程を省略するた
めに一液型の要求が高まっている。(Prior Art) In liquid epoxy resin compositions, there is an increasing demand for one-component type compositions in order to omit the step of mixing the epoxy resin and a curing agent/curing accelerator during use.
−散型にするために、潜伏性硬化剤といわれるジシアン
ジアミド、ヒドラジッド化合物、三弗化硼素化合物、ア
ルキル尿素化合物等が使用され、イミダゾール化合物、
トリアジン化合物等の硬化促進剤と併用されている場合
が多い。- In order to form a powder, latent curing agents such as dicyandiamide, hydrazide compounds, boron trifluoride compounds, and alkyl urea compounds are used, and imidazole compounds,
It is often used in combination with a curing accelerator such as a triazine compound.
このような−波型エポキシ樹脂組成物は、通常の２液型
のものに比べて当然保存性は優れているが、長期の保存
には粘度上昇により十分耐えうるものではなく、また、
保存性を向上させると、硬化時に高温加熱を必要とする
など実用上問題が残っている。Although such a wave-type epoxy resin composition naturally has better storage stability than a normal two-component type, it cannot sufficiently withstand long-term storage due to an increase in viscosity.
Although improving storage stability, practical problems remain, such as the need for high-temperature heating during curing.
一方、マイクロカプセル化の技術を応用して、−散型に
する検討は最近盛んになっているが、常温付近のカプセ
ルの安定性、加熱時カプセルの破壊による反応性等にお
いて未だ満足すべきものがなく、実用化が遅れている。On the other hand, studies have recently become active in applying microencapsulation technology to create powdered forms, but there are still unsatisfactory aspects such as stability of capsules at room temperature and reactivity due to capsule destruction when heated. However, practical implementation has been delayed.
（発明が解決しようとする課題）
このように、従来硬化促進剤を添加することにより、−
散型エポキシ樹脂組成物のポットライフが短くなる欠点
があったが、本発明はこの硬化促進剤を無機質壁のマイ
クロカプセルとして保護することにより、エポキシ樹脂
組成物の保存性を向上させることを目的とする。(Problem to be solved by the invention) As described above, by adding a conventional curing accelerator, -
Dispersible epoxy resin compositions have had the disadvantage of short pot lives, but the purpose of the present invention is to improve the storage stability of epoxy resin compositions by protecting this curing accelerator as microcapsules with inorganic walls. shall be.
Ｃ！ＪＭを解決するための手段）
本発明は、無ｌ！質壁でマイクロカプセル化され、かつ
その粒子径が５０μｍ以下である硬化促進剤を含有する
ことを特徴とする一散型エボキシ樹脂組成物である。C! Means for solving JM) The present invention is free! This is a monodisperse type epoxy resin composition characterized by containing a curing accelerator that is microencapsulated with a solid wall and has a particle size of 50 μm or less.
本発明のエポキシ樹脂組成物は直接反応に関与する成分
としてエポキシ樹脂、硬化剤及び硬化促進剤を含む。The epoxy resin composition of the present invention contains an epoxy resin, a curing agent, and a curing accelerator as components directly involved in the reaction.
本発明において、エポキシ樹脂は室温で液状のものであ
り、代表的なエポキシ樹脂としては、ビスフェノールＡ
型エポキシ樹脂で、分子Ｎ３６０〜１０００（エポキシ
当１１８０〜５００）のものが好ましい。In the present invention, the epoxy resin is liquid at room temperature, and a typical epoxy resin is bisphenol A.
A type epoxy resin having a molecular N of 360 to 1000 (1180 to 500 per epoxy) is preferred.
その他、ビスフェノールＦ型エポキシ樹脂、ビスフェノ
ールＡＤ型エポキシ樹脂、脂環式エポキシ樹脂等も使用
しうる。また、粘度調整を目的として、反応性希釈剤（
分子中にエポキン基を１〜２固有する低粘度の低分子化
合物）をエポキシ樹脂に対して５〜１０％程度加えるこ
ともできる。In addition, bisphenol F type epoxy resin, bisphenol AD type epoxy resin, alicyclic epoxy resin, etc. can also be used. In addition, reactive diluents (
A low-viscosity, low-molecular compound having 1 to 2 epochine groups in its molecule) can also be added in an amount of about 5 to 10% based on the epoxy resin.
本発明の組成物に用いられる硬化剤ないし硬化促進剤と
しては、一般的なジシアンジアミド（エポキシ樹脂に対
し３〜８％配合）、ヒドラジッド化合物（同２０〜４０
％配合）が用いられ、他にイミダゾールのエポキシ樹脂
付加物（同５〜１５％配合）、あるいはアルキル尿素化
合物（同５〜１５％配合）などの室温で固型のものを粉
末状にして併用することもできる。粉末の粒径は２００
〜４００メツシュ程度のものを用いるのが一般的である
。As curing agents or curing accelerators used in the composition of the present invention, common dicyandiamide (3 to 8% blended with the epoxy resin) and hydrazide compounds (20 to 40% of the epoxy resin) are used.
% blend) is used, and other substances that are solid at room temperature, such as imidazole epoxy resin adducts (5-15% blend) or alkylurea compounds (5-15% blend), are used in combination. You can also. The particle size of the powder is 200
It is common to use a material with a mesh size of about 400 to 400 mesh.
この他、必要に応じて、無機質充填材、カップリング剤
、消泡剤を配合する。In addition, an inorganic filler, a coupling agent, and an antifoaming agent may be added as necessary.
本発明においては、これらの成分のうち、硬化促進剤を
無機質壁のマイクロカプセルとして配合することを特徴
とする。マイクロカプセルの粒子径は５０μｍ以下とす
る。５０μｍより大きい径のものが５％以下含まれてい
ても差しつかえないが、これ以上含まれていると硬化時
にお、いてマイクロカプセル中の硬化促進剤の分散が不
十分となる恐れがある。マイクロカプセルの粒子径は１
０μｍ以下が好ましい。The present invention is characterized in that among these components, the curing accelerator is blended as microcapsules with inorganic walls. The particle size of the microcapsules is 50 μm or less. There is no problem if the microcapsules contain 5% or less of particles with a diameter larger than 50 μm, but if the microcapsules contain more than 5%, there is a risk that the microcapsules will be damaged during curing and the curing accelerator may become insufficiently dispersed in the microcapsules. The particle size of microcapsules is 1
It is preferably 0 μm or less.
硬化促進剤をマイクロカプセル化する方法の一例を以下
に示す。An example of a method for microencapsulating a curing accelerator is shown below.
まず、無機質中空多孔質粒子は一般にいわれている界面
重合法にてｉ製することができる。First, the inorganic hollow porous particles can be manufactured by a commonly known interfacial polymerization method.
その代表例として中空シリカの調製法２例を具体的に示
す。As representative examples, two examples of methods for preparing hollow silica will be specifically shown.
（１）３号ケイ酸ナトリウム６．５ｓｏｌ／ ｌ水溶液
６６７ｄと、非イオン性界面活性剤（ポリオキシエチレ
ンソルビタントリオレート、商品８丁−５ｅｎ−８５）
３０ｇ／ １ヘキサン溶液３３３ ｄとをホモミキサ
ー・（７０００ｒｐ鏝）を用いて４分間乳化し、Ｗ１０
型エマルジゴンを調製する。このエマルシヨンを１．５
ｍｏｌ／ｌ炭酸水素アンモニウム水溶液２０００−と混
合し１．３０分間反応させる０反応終了後７２時間静置
したのち、遠心分離、濾別、水洗、メタノール洗浄し、
１１０’Ｃ，１７〜２４時間乾燥する。さらに無釉薬ｍ
製ルツボに上記で調製した粉末を入れ、電気炉中、昇温
速度１００”Ｃ／ｈｒ、 ５００’Ｃ，１０時間熱処理
を行−２た。平均粒径２．７μｍ。(1) No. 3 sodium silicate 6.5 sol/l aqueous solution 667d and nonionic surfactant (polyoxyethylene sorbitan triolate, product 8-5en-85)
30g/1 hexane solution 333d was emulsified for 4 minutes using a homo mixer (7000 rpm trowel), and W10
Prepare a type emuldigon. This emulsion is 1.5
Mix with 2000 mol/l ammonium hydrogen carbonate aqueous solution and react for 1.30 minutes.After the reaction is finished, leave it for 72 hours, centrifuge, filter, wash with water, wash with methanol,
Dry at 110'C for 17-24 hours. Furthermore, unglazed m
The powder prepared above was placed in a crucible, and heat treated at 500'C for 10 hours in an electric furnace at a heating rate of 100'C/hr.The average particle size was 2.7 μm.
（２）１号ケイ酸ナトリウム３ｓｏｌ／／！水溶液８３
ｄとＴｈｅｅｎ−８５３０ｇ／ ｌ−ヘキサン溶液１６
７ｄとを、４０００ｒｐｍ、１分間乳化してＷ１０型エ
マルジッンを調製する。このエマルシヨンを１．５ｍｏ
ｌ／ｌ炭酸水素アンモニウム水溶液５００Ｉｔ１．：反
応させて沈澱を作り、以下、上記（１）と同じ操作を行
った。平均粒径４．８μｍ。(2) No. 1 sodium silicate 3sol//! Aqueous solution 83
d and Theen-8530g/l-hexane solution 16
7d for 1 minute at 4000 rpm to prepare W10 type emulsion. 1.5mo of this emulsion
l/l ammonium bicarbonate aqueous solution 500It1. : A reaction was made to form a precipitate, and the same operation as in (1) above was performed. Average particle size 4.8 μm.
芯材として用いる物質はＤＢＵ（ｒｌ、８−ジアザ−ビ
シクロ−（５，４，０）−ウンデセン−７の酸塩」の略
称）等のエポキシ樹脂用硬化促進剤であり、マイクロカ
プセル中空部へ注入する方法として含浸法が適当である
。第１図は含浸前後の中空粒子の概念図であって、（ａ
）は多孔質の壁（２）を有する中空粒子（１）であり、
（ｂ）はこの中空粒子の中空部（３）に硬化促進剤（４
）を含浸したものである。The substance used as the core material is a curing accelerator for epoxy resins such as DBU (rl, abbreviation for 8-diaza-bicyclo-(5,4,0)-undecene-7 acid salt), and is used as a hardening accelerator for epoxy resins. An impregnation method is suitable as the injection method. FIG. 1 is a conceptual diagram of hollow particles before and after impregnation, and (a
) are hollow particles (1) with porous walls (2);
(b) is a curing accelerator (4) in the hollow part (3) of this hollow particle.
).
第２図は中空粒子（１）に対（７硬化促進剤（４）を真
空下で滴下し含浸している状態を示している。含浸の条
件は中空粒子１００ｇに対して硬化仇”進剤！ｌＯ〜１
００ｇを１０１↑ｏｒｒ程度の真空下で滴下含浸し、２
〜５時間処理する。Figure 2 shows the condition in which the hardening accelerator (4) is dropped onto the hollow particles (1) under vacuum and impregnated.The conditions for impregnation are as follows. !lO~1
Drop and impregnate 00g under a vacuum of about 101↑orr,
Process for ~5 hours.
以上のようにして得られた硬化促進剤のマイクロカプセ
ルは通常の方法でエポキシ樹脂、硬化剤等を混合される
。The curing accelerator microcapsules obtained as described above are mixed with an epoxy resin, a curing agent, etc. in a conventional manner.
この際マイクロカプセルは無りａ質壁であるので、混合
中に破壊され難い。At this time, since the microcapsules have solid aluminum walls, they are difficult to be destroyed during mixing.
本発明の一散型エボキシ樹脂組成物は、加熱硬化時温度
上昇に伴い、マイクロカプセル内の液体の拡散速度が高
まり、カプセル壁から放散し、樹脂と速やかに反応する
ので、通常の場合、即ちマイクロカプセル化されない場
合と同様に硬化する。In the dispersed epoxy resin composition of the present invention, as the temperature rises during heating and curing, the diffusion rate of the liquid in the microcapsules increases, radiates from the capsule wall, and quickly reacts with the resin. Cures as if it were not microencapsulated.
本発明の組成物の加熱硬化条件は通常１００〜１５０°
Ｃ３０分〜２時間である。The heat curing conditions for the composition of the present invention are usually 100 to 150°
C: 30 minutes to 2 hours.
（実施例） 以下実施例により本発明を説明する。(Example) The present invention will be explained below with reference to Examples.
−叫１−則の１４！タカブセノは
前記（１）の方法に従い、平均粒径２．７μｍの中空シ
リカを得、前記方法にてＤＢＵのマイクロカプセルを調
製した。ＤＢＵ含有率は３０重量％であった。-Scream 1-Rule 14! Takabuseno obtained hollow silica having an average particle size of 2.7 μm according to the method (1) above, and prepared DBU microcapsules using the above method. The DBU content was 30% by weight.
ｆ１月部１１復１合
第１表に示す配合にて１液型工ポキシ樹脂組成物を得た
。この組成物についてゲル化時間及び粘度を測定した。A one-component poxy resin composition was obtained using the formulation shown in Table 1. The gelation time and viscosity of this composition were measured.
硬化物の特性は、前記組成物を１００℃、６０分の条件
で硬化したものを使用した。Regarding the characteristics of the cured product, the above composition was cured at 100° C. for 60 minutes.
称１冊足拮来
組成物及び硬化物の特性測定結果を第１表の下欄に示す
。The results of measuring the properties of the composition and cured product are shown in the lower column of Table 1.
（発明の効果）
本発明の一散型エボキジ樹脂組成物は、硬化促進剤が無
機質壁のマイクロカプセル化されたものであるので、マ
イクロカプセルの強度が比較的大きく、従って、常温（
３０℃以下）での保存性が優れている。また、加熱硬化
時には硬化促進剤がカプセル壁から速やかに拡散するの
で、硬化促進剤がマイクロカプセル化されない場合とほ
ぼ同様に硬化する。(Effects of the Invention) In the monodisperse type Evokiji resin composition of the present invention, since the curing accelerator is microencapsulated with an inorganic wall, the strength of the microcapsules is relatively high.
Excellent storage stability at temperatures below 30°C. Furthermore, during heat curing, the curing accelerator quickly diffuses from the capsule wall, so that curing is almost the same as when the curing accelerator is not microencapsulated.
第１図は、硬化促進剤含浸前後の中空粒子の概念図であ
って、（司は含浸前、０））は含浸後の中空粒子である
。
第２図は１、中空粒子に硬化促進剤を含浸する状態の概
略図である。FIG. 1 is a conceptual diagram of hollow particles before and after being impregnated with a curing accelerator, and (0) is the hollow particle before being impregnated. FIG. 2 is a schematic diagram of 1, a state in which hollow particles are impregnated with a curing accelerator.
Claims (1)
子径が５０μｍ以下である硬化促進剤を含有することを
特徴とする一液型エポキシ樹脂組成物。(1) A one-component epoxy resin composition containing a curing accelerator that is microencapsulated with an inorganic wall and has a particle size of 50 μm or less.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12045689A JPH02300229A (en) | 1989-05-16 | 1989-05-16 | One-component epoxy resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12045689A JPH02300229A (en) | 1989-05-16 | 1989-05-16 | One-component epoxy resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02300229A true JPH02300229A (en) | 1990-12-12 |
Family
ID=14786630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12045689A Pending JPH02300229A (en) | 1989-05-16 | 1989-05-16 | One-component epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02300229A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0590975A1 (en) * | 1992-10-02 | 1994-04-06 | W.R. Grace & Co.-Conn. | Low viscosity and solvent-free one-component type epoxy resin adhesive composition |
| WO2006112396A1 (en) * | 2005-04-15 | 2006-10-26 | Hitachi Chemical Co., Ltd. | Curing accelerating compound-silica composite material, method for producing curing accelerating compound-silica composite material, curing accelerator, curable resin composition, and electronic component |
| JP2011225666A (en) * | 2010-04-16 | 2011-11-10 | Sekisui Chem Co Ltd | Epoxy resin composition |
| JP2013071988A (en) * | 2011-09-27 | 2013-04-22 | Sekisui Chem Co Ltd | Curing agent- and/or curing accelerator-encapsulated capsule, and thermosetting resin composition |
-
1989
- 1989-05-16 JP JP12045689A patent/JPH02300229A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0590975A1 (en) * | 1992-10-02 | 1994-04-06 | W.R. Grace & Co.-Conn. | Low viscosity and solvent-free one-component type epoxy resin adhesive composition |
| WO2006112396A1 (en) * | 2005-04-15 | 2006-10-26 | Hitachi Chemical Co., Ltd. | Curing accelerating compound-silica composite material, method for producing curing accelerating compound-silica composite material, curing accelerator, curable resin composition, and electronic component |
| US8129467B2 (en) | 2005-04-15 | 2012-03-06 | Hitachi Chemical Co., Ltd. | Curing accelerating compound-silica composite material, method for producing curing accelerating compound-silica composite material, curing accelerator, curable resin composition, and electronic component device |
| JP5157444B2 (en) * | 2005-04-15 | 2013-03-06 | 日立化成株式会社 | Curing accelerating compound-silica complex, method for producing curing accelerating compound-silica complex, curing accelerator, curable resin composition, and electronic component device |
| JP2011225666A (en) * | 2010-04-16 | 2011-11-10 | Sekisui Chem Co Ltd | Epoxy resin composition |
| JP2013071988A (en) * | 2011-09-27 | 2013-04-22 | Sekisui Chem Co Ltd | Curing agent- and/or curing accelerator-encapsulated capsule, and thermosetting resin composition |
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