JPH0224305A - Thermosetting resin composition - Google Patents

Thermosetting resin composition

Info

Publication number
JPH0224305A
JPH0224305A JP17266788A JP17266788A JPH0224305A JP H0224305 A JPH0224305 A JP H0224305A JP 17266788 A JP17266788 A JP 17266788A JP 17266788 A JP17266788 A JP 17266788A JP H0224305 A JPH0224305 A JP H0224305A
Authority
JP
Japan
Prior art keywords
resin
molecular weight
phenol
organic
maleimide
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
Application number
JP17266788A
Other languages
Japanese (ja)
Inventor
Kenichi Suzuki
憲一 鈴木
Hisafumi Enoki
尚史 榎
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Bakelite Co Ltd
Original Assignee
Sumitomo Bakelite Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sumitomo Bakelite Co Ltd filed Critical Sumitomo Bakelite Co Ltd
Priority to JP17266788A priority Critical patent/JPH0224305A/en
Publication of JPH0224305A publication Critical patent/JPH0224305A/en
Pending legal-status Critical Current

Links

Landscapes

  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

PURPOSE:To obtain the title composition for molding materials which gives a cured resin having a high glass transition temperature and excellent heat resistance and toughness for a long period of time by mixing a maleimide resin, a specific high-molecular phenol resin and a curing catalyst together. CONSTITUTION:The title composition comprises a maleimide resin produced from an aromatic polyamine such as 4,4'-diaminodiphenylmethane, 3,3'- diaminodiphenyl sulfone or an aniline resin, a high-molecular phenol resin having a melting point of 120-250 deg.C and a number-average molecular weight of 1,500-10,000 obtained by reacting a phenol such as phenol, cresol or xylenol with HCHO, and a curing catalyst which is preferably an organic phosphine (e.g., triphenylphosphine) and/or an organic peroxide (e.g., dicumyl peroxide).

Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明は耐熱性で、しかも硬化性、靭性に優れた成形材
料用熱硬化性樹脂組成物に関するものである。
DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a thermosetting resin composition for molding materials that is heat resistant and has excellent curability and toughness.

〔従来の技術〕[Conventional technology]

近年、軽量化、製造工程の合理化、コストダウン等のた
め金属のプラスチック材料への代替が活発に進められて
いる。
In recent years, metals have been actively replaced by plastic materials in order to reduce weight, rationalize manufacturing processes, and reduce costs.

従来、一般に7ボランク型フエノール樹脂が多く用いら
れているが、成形品を高温で長時間処理すると、強度、
寸法変化などが大巾に悪化し、信頼性に欠けている。
Conventionally, 7-borane phenolic resins have been commonly used, but when molded products are treated at high temperatures for long periods of time, their strength and
Dimensional changes, etc. have significantly worsened, and reliability is lacking.

一方、耐熱性の良好なポリアミノビスマレイミド樹脂を
含む マレイミド樹脂は、一般に硬化物が硬すぎて靭性
に乏しい。
On the other hand, maleimide resins including polyamino bismaleimide resins having good heat resistance generally produce cured products that are too hard and have poor toughness.

本発明者らは、マレイミド樹脂、融点が50℃以上12
0℃以下のレゾール型フェノール樹脂とホスフィン類、
有機過酸化物およびアルカリ土類金属酸化物又は水酸化
物から成る熱硬化性樹脂組成物について検討を進めて来
ている。
The present inventors have developed a maleimide resin with a melting point of 50°C or higher and 12°C.
resol type phenolic resin and phosphines below 0℃,
Studies have been underway on thermosetting resin compositions comprising organic peroxides and alkaline earth metal oxides or hydroxides.

しかしながら、これらの系においては耐熱性、硬化性お
よび靭性に優れておるが、最近では、これらの特性に加
えて、更に−そうの長期にわたる耐熱性と、より高度の
靭性をもつものが要求されて来ている。
However, these systems have excellent heat resistance, hardenability, and toughness, but recently, in addition to these properties, materials with even longer heat resistance and higher toughness are required. It's coming.

〔発明が解決しようとする課題] 本発明は、成形品の高温における長時間処理による強度
、寸法変化の大巾な低下を克服せんとして研究した結果
、ガラス転移温度が高く、低熱膨張のマレイミド樹脂を
用いることにより、成形品の耐熱劣化性が改善されると
の知見を得、更にこの知見を基に種々研究を進めて、本
発明を完成するに至ったものである。その目的とすると
ころは、長時間の耐熱性が良好で、しかも、硬化性、靭
性に優れた成形材料用熱硬化性樹脂組成物を提供するに
ある。
[Problems to be Solved by the Invention] The present invention was developed as a result of research aimed at overcoming the drastic decline in strength and dimensional changes caused by long-term processing at high temperatures of molded products. The inventors have found that the heat deterioration resistance of molded products can be improved by using this method, and based on this knowledge, they have carried out various studies and have completed the present invention. The objective is to provide a thermosetting resin composition for molding materials that has good long-term heat resistance and excellent curability and toughness.

〔課題を解決するための手段〕[Means to solve the problem]

本発明は、マレイミド樹脂、融点が120℃以上250
℃以下であり、かつ数平均分子量が1,500以上10
.000以下の高分子量のフェノール樹脂および硬化用
触媒から成ることを特徴とする熱硬化性樹脂組成物であ
る。
The present invention uses a maleimide resin having a melting point of 120°C or higher and 250°C or higher.
℃ or less, and the number average molecular weight is 1,500 or more 10
.. The present invention is a thermosetting resin composition characterized by comprising a phenolic resin having a high molecular weight of 000 or less and a curing catalyst.

本発明において用いられるマレイミド樹脂は一般式(+
) (ただし020m1(iは0〜nの整数)、mR*1、
m7.2、ff1l、  ffi、、、、l□2は1ま
たは2 Xは−CIl□− −SO□ 一 5−S− またはベンゼン核どうしが直接結合していることを示す
The maleimide resin used in the present invention has the general formula (+
) (However, 020m1 (i is an integer from 0 to n), mR*1,
m7.2, ff1l, ffi, ..., l□2 is 1 or 2.

Yは−CI+□= 〇− −SO□− S S−S またはベンゼン核どうしが直接結合していることを示す
ものであり、Yは上記各結合基の1種又はそれ以上の結
合基の混合でベンゼン核どうしが結合していることを示
す。
Y indicates -CI+□= 〇- -SO□- S S-S or benzene nuclei are directly bonded to each other, and Y indicates a mixture of one or more of the above bonding groups. shows that the benzene nuclei are bonded to each other.

Rは11、C1h、またはC山を示す、)で示される化
合物で、例えば4.4”−ジアミノジフェニルメタン、
4.4’−Iアミノジフェニルエーテル、3,3゛−ジ
アミノジフェニルスルホン、2.2−シ(ρ−アミノフ
ェニル)プロパン、3,4,3”、4゜−テトラアミノ
−ジフェニルメタンとか、アニリンとホルムアルデヒド
から得られるアニリン樹脂などの芳香族ポリアミンをマ
レイミド化したものをあげることもできる。
R is 11, C1h, or C mountain), for example, 4.4''-diaminodiphenylmethane,
4.4'-I aminodiphenyl ether, 3,3'-diaminodiphenyl sulfone, 2,2-(ρ-aminophenyl)propane, 3,4,3'',4'-tetraamino-diphenylmethane, aniline and formaldehyde Maleimidated aromatic polyamines such as aniline resins obtained from

高分子量フェノール樹脂は、フェノール、クレゾール、
キシレノールなどのフェノール類とホルムアルデヒドか
ら得られる融点が120℃以上、250℃以下、好まし
くは150℃以上、220℃以下でかつ数平均分子量が
1,500以上10,000以下で好ましくは2.00
0以上、9,000以下のものでフリーフェノールはな
るべく少ないものが良い。融点が120℃以下で、かつ
数平均分子量が1.5000以下では、より高度な靭性
は得られず、融点が250’C以上で、かつ数平均分子
量が10,000以上ではゲル化物が含まれ、マレイミ
ド樹脂との相溶性が悪く、溶融粘度が高くて作業性が悪
く、好ましくない。
High molecular weight phenolic resins include phenol, cresol,
The melting point obtained from phenols such as xylenol and formaldehyde is 120°C or more and 250°C or less, preferably 150°C or more and 220°C or less, and the number average molecular weight is 1,500 or more and 10,000 or less, preferably 2.00.
It is preferable that the free phenol content is 0 or more and 9,000 or less and has as little free phenol as possible. If the melting point is 120°C or lower and the number average molecular weight is 1.5000 or less, a higher degree of toughness cannot be obtained, and if the melting point is 250'C or higher and the number average molecular weight is 10,000 or higher, gelled products will be contained. It is not preferred because it has poor compatibility with maleimide resins, has a high melt viscosity, and has poor workability.

高分子量フェノール樹脂はマレイミド樹脂100重量部
に対し5〜200重量部が好ましい。少な過ぎると靭性
に乏しく脆い。多過ぎると硬化性と耐熱性が低下する。
The amount of the high molecular weight phenol resin is preferably 5 to 200 parts by weight per 100 parts by weight of the maleimide resin. If it is too small, it will lack toughness and become brittle. If the amount is too large, curability and heat resistance will decrease.

硬化用触媒としては、有機ホスフィン類、有機過酸化物
または両者の併用が好ましく、特に有機ホスフィン類と
有機過酸化物の併用は有効である。
The curing catalyst is preferably an organic phosphine, an organic peroxide, or a combination of both, and a combination of an organic phosphine and an organic peroxide is particularly effective.

有機ホスフィン類としては、例えばトリフェニルホスフ
ィン、トリー4−メチルフェニルホスフィン、トリー4
−メトキシフェニルホスフィン、トリブチルホスフィン
、トリオクチルホスフィン、トリー2−シアノエチルホ
スフィンなどをあげることができる。
Examples of organic phosphines include triphenylphosphine, tri-4-methylphenylphosphine, tri-4
-methoxyphenylphosphine, tributylphosphine, trioctylphosphine, tri-2-cyanoethylphosphine, and the like.

ホスフィン類の使用量はマレイミド樹脂と高分子量フェ
ノール樹脂の総量100重量部に対し、0.1〜10重
景部重量ましい、少な過ぎると靭性に乏しく機械強度が
低下する。多過ぎるとロール混練時反応が進み過ぎてゲ
ル化したり、保存性が悪化する。
The amount of phosphines to be used is preferably 0.1 to 10 parts by weight per 100 parts by weight of the total amount of maleimide resin and high molecular weight phenol resin; if it is too small, the toughness will be poor and the mechanical strength will be reduced. If the amount is too high, the reaction during roll kneading will proceed too much, resulting in gelation or poor storage stability.

有機過酸化物としては、ジーt−ブチルパーオキサイド
、L−1′チルクミルパーオキサイド、ジクミルパーオ
キサイド、1.3−ビス−(t−ブチルパーオキシ−イ
ソプロビル)ベンゼン、1.1ジーt−ブチルパーオキ
シ−33,5−)リメチルシクロヘキサン、1,1−ジ
ーL−フ゛チルパーオキシシクロヘキサンなどのジアル
キルパーオキサイド、L−フ゛チルパーベンゾエートな
どのアルキルパーエステルをあげることができる。有機
過酸化物の添加量は、マレイミド樹脂100重量部に対
し、0.05〜5重量部が好ましい。
Examples of organic peroxides include di-t-butyl peroxide, L-1'-ticumyl peroxide, dicumyl peroxide, 1.3-bis-(t-butylperoxy-isopropyl)benzene, and 1.1-di-t-butyl peroxide. Examples include dialkyl peroxides such as t-butylperoxy-33,5-)limethylcyclohexane and 1,1-di-L-butylperoxycyclohexane, and alkyl peresters such as L-butylperbenzoate. The amount of organic peroxide added is preferably 0.05 to 5 parts by weight per 100 parts by weight of the maleimide resin.

有機過酸化物が少な過ぎると、ガラス転移温度の向上が
十分でなく、多過ぎると、脆くなり、機械強度が低下す
る。
If the amount of organic peroxide is too small, the glass transition temperature will not be improved sufficiently, and if it is too large, the material will become brittle and the mechanical strength will decrease.

有機ホスフィン類と有機過酸化物を併用した時の配合比
率は、有機ホスフィン類1に対し有機過酸化物0.2〜
5.Oが好ましい、有機ホスフィン類に対する有機過酸
化物の配合比率は少な過ぎるとガラス転移温度や機械強
度が多少低下する傾向がみられる。
When organic phosphines and organic peroxides are used together, the blending ratio is 1 part organic phosphine to 0.2 to 0.2 organic peroxides.
5. If the blending ratio of the organic peroxide to the organic phosphine, preferably O, is too small, the glass transition temperature and mechanical strength tend to decrease to some extent.

有機ホスフィン類と有機過酸化物を併用した時の使用量
は、マレイミド樹脂と高分子量フェノール樹脂の総量1
00重景重量対し、0.05〜10重量部が好ましい、
少な過ぎると硬化性が十分でなく、成形時間に長時間を
要する。多過ぎると、ロール混練時反応が進み過ぎてゲ
ル化したり、保存性が悪化する。
When using organic phosphines and organic peroxides together, the amount used is the total amount of maleimide resin and high molecular weight phenolic resin 1
Preferably 0.05 to 10 parts by weight based on 0.00 weight.
If the amount is too small, the curing properties will be insufficient and the molding time will take a long time. If the amount is too high, the reaction during roll kneading will proceed too much, resulting in gelation or poor storage stability.

本発明の組成物は必要に応じて、充填剤、表面処理剤、
離型剤、着色剤などを配合し、混合または混練して成形
材料にすることが出来る。
The composition of the present invention may contain fillers, surface treatment agents,
A molding material can be obtained by adding a mold release agent, a coloring agent, etc., and mixing or kneading it.

〔発明の効果〕〔Effect of the invention〕

本発明に従うと、硬化性が良好で、ガラス転移温度が高
く、長期にわたる耐熱性と、高度な靭性に優れた硬化樹
脂が得られるので、成形材料用熱硬化性樹脂組成物とし
て好適である。
According to the present invention, a cured resin with good curability, a high glass transition temperature, long-term heat resistance, and high toughness can be obtained, so it is suitable as a thermosetting resin composition for molding materials.

〈高分子量フェノール樹脂の合成例〉 合成例1 22のセパラブルフラスコに水250gと35重量%の
塩酸450gと37重量%のホルマリン800gの混合
水溶液を入れ、さらにフェノール50gと37重量%ホ
ルマリン15gの混合水溶液を添加した。添加後30分
間撹拌し、90分間静置した0次いで時々攪拌しなから
90”Cまで昇温し、15分間保持して高分子量フェノ
ール樹脂(PP−A)を得た。
<Synthesis example of high molecular weight phenolic resin> Synthesis example 1 A mixed aqueous solution of 250 g of water, 450 g of 35 wt% hydrochloric acid, and 800 g of 37 wt% formalin was placed in a 22 separable flask, and then 50 g of phenol and 15 g of 37 wt% formalin were added. A mixed aqueous solution was added. After the addition, the mixture was stirred for 30 minutes and allowed to stand for 90 minutes.Then, while stirring occasionally, the temperature was raised to 90''C and held for 15 minutes to obtain a high molecular weight phenol resin (PP-A).

かくして得た高分子量フェノール樹脂(PP−A)を4
0″〜50℃の温水で3回洗浄後、30℃で1時間乾燥
した。
The thus obtained high molecular weight phenolic resin (PP-A) was
After washing three times with warm water of 0'' to 50°C, it was dried at 30°C for 1 hour.

この高分子量フェノール樹脂(PP−A)の融点は、1
73“Cで数平均分子量は3.500であった。
The melting point of this high molecular weight phenolic resin (PP-A) is 1
73"C and the number average molecular weight was 3.500.

合成例2 水700gにホルムアルデヒ)280g、塩酸35gを
溶かし、これにメタクレゾール530 g。
Synthesis Example 2 280 g of formaldehyde and 35 g of hydrochloric acid were dissolved in 700 g of water, and 530 g of metacresol was dissolved therein.

ノニルフェノール200gの混合液を加えて静置したま
ま、20℃で5時間反応させた。
A mixed solution of 200 g of nonylphenol was added, and the mixture was left standing to react at 20° C. for 5 hours.

沈澱した樹脂を攪拌下に十分水洗いした後冷却し、高分
子量フェノール樹脂(PP−8)を得た。高分子量フェ
ノール樹脂(PP−8)の融点は205℃1数平均分子
量は5,200であった。
The precipitated resin was thoroughly washed with water while stirring and then cooled to obtain a high molecular weight phenol resin (PP-8). The melting point of the high molecular weight phenolic resin (PP-8) was 205°C and the number average molecular weight was 5,200.

実施例1〜4 第1表に示す配合でマレイミド樹脂に合成例12で得ら
れた高分子量フェノール樹脂、ホスフィン類、有機過酸
化物、ガラス繊維、アミノシラン及び離型剤を配合し、
ロール混練して成形材料を得た。これをトランスファー
成形により180℃3分で成形した。成形品は200℃
4時間ポストキュアーした。その特性は第1表に示す。
Examples 1 to 4 The high molecular weight phenolic resin obtained in Synthesis Example 12, phosphines, organic peroxide, glass fiber, aminosilane and mold release agent were blended with maleimide resin in the formulation shown in Table 1,
A molding material was obtained by roll kneading. This was molded by transfer molding at 180°C for 3 minutes. Molded products at 200℃
Post cured for 4 hours. Its properties are shown in Table 1.

比較例1 実施例1のホスフィン類と有機過酸化物を2メチルイミ
ダゾール(以下、2MZという)に替えておこなった。
Comparative Example 1 Comparative Example 1 was conducted by replacing the phosphines and organic peroxide in Example 1 with 2-methylimidazole (hereinafter referred to as 2MZ).

ただし成形時間は10分であった。However, the molding time was 10 minutes.

比較例2 実施例1の高分子量フェノール樹脂を4,4゛−ジアミ
ノジフェニルメタン(以下、DDMという)に、ホスフ
ィン類と有機過酸化物を2MZに替えておこなった。成
形時間は10分であった。
Comparative Example 2 A test was carried out by replacing the high molecular weight phenolic resin of Example 1 with 4,4'-diaminodiphenylmethane (hereinafter referred to as DDM), and replacing the phosphines and organic peroxide with 2MZ. The molding time was 10 minutes.

比較例3 実施例1の高分子量フェノール樹脂を融点95℃2数平
均分子1750のレゾール型フェノール樹脂に替え、さ
らに硬化用触媒として酸化マグ不シウムを加えておこな
った。硬化性はマレイミド樹脂、高分子量フェノール樹
脂および硬化用触媒からなる配合物の熱板(170℃)
ゲルタイムで示した。
Comparative Example 3 The high molecular weight phenolic resin of Example 1 was replaced with a resol type phenolic resin having a melting point of 95° C. and a 2-number average molecular weight of 1750, and magnonium oxide was added as a curing catalyst. Curing properties were determined using a hot plate (170°C) of a compound consisting of maleimide resin, high molecular weight phenolic resin, and curing catalyst.
Shown as gel time.

ホスフィン類および有機過酸化物の硬化用触媒が入った
実施例1〜4は硬化性に優れている。
Examples 1 to 4 containing curing catalysts of phosphines and organic peroxides have excellent curability.

これらは、ガラス転移温度が高く、耐熱劣化性に優れ、
破壊エネルギーも大巾に向上している。
These have a high glass transition temperature and excellent heat deterioration resistance.
Destructive energy has also been greatly improved.

(注)※IBMI   :三井東圧化学株式会社製ビス
マレイミド。
(Note) *IBM: Bismaleimide manufactured by Mitsui Toatsu Chemical Co., Ltd.

※2BMI−M:三井東圧化学株式会社製ポリマレイミ
ド。
*2 BMI-M: Polymaleimide manufactured by Mitsui Toatsu Chemical Co., Ltd.

※3 BMI−DA:三井東圧化学株式会社製ビスマレ
イミド。
*3 BMI-DA: Bismaleimide manufactured by Mitsui Toatsu Chemical Co., Ltd.

※4 DDM   :4.4’−ジアミノジフェニルメ
タン。
*4 DDM: 4.4'-diaminodiphenylmethane.

※5PR:融点95℃1数平均分子 量750の固形レゾール 型フェノール樹脂。*5PR: Melting point 95℃ 1 number average molecule 750 solid resol Type phenolic resin.

※6TPP   :)リフェニルホスフィン。*6TPP:) Riphenylphosphine.

※72MZ   :2−メチルイミダゾール。*72MZ: 2-methylimidazole.

※8DCニジクミルパーオキサイド。*8DC rainbow cum mill peroxide.

※9BB    :L−ブチルパーベンゾエート。*9BB: L-butyl perbenzoate.

※lOマレイミド樹脂、高分子量フェノール樹脂および
硬化用触媒からなる配 合物のV′、!反ゲルタイム。
* V′ of a formulation consisting of lO maleimide resin, high molecular weight phenolic resin, and curing catalyst,! Anti-gel time.

なお、BMIとDDMから常法によ ※11 ※12 り得られるポリアミノビスマレイミ ド(2M21%添加)のゲルタイム は2’42’であった。In addition, from BMI and DDM using the usual method. *11 *12 polyamino bismaleium obtained by Gel time of de (2M21% addition) was 2'42'.

250℃で1ケ月熱処理し室温で測定。Heat treated at 250℃ for 1 month and measured at room temperature.

曲げ試験での、応カー歪み曲線から 破壊に要するエネルギーを算出。From the stress strain curve in the bending test Calculate the energy required for destruction.

Claims (1)

【特許請求の範囲】[Claims] (1)マレイミド樹脂、融点が120℃以上、250℃
以下であり、かつ数平均分子量が1,500以上、10
,000以下の高分子量フェノール樹脂および硬化用触
媒から成ることを特徴とする熱硬化性樹脂組成物。
(1) Maleimide resin, melting point of 120℃ or higher, 250℃
or less, and the number average molecular weight is 1,500 or more, 10
,000 or less and a curing catalyst.
JP17266788A 1988-07-13 1988-07-13 Thermosetting resin composition Pending JPH0224305A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP17266788A JPH0224305A (en) 1988-07-13 1988-07-13 Thermosetting resin composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP17266788A JPH0224305A (en) 1988-07-13 1988-07-13 Thermosetting resin composition

Publications (1)

Publication Number Publication Date
JPH0224305A true JPH0224305A (en) 1990-01-26

Family

ID=15946139

Family Applications (1)

Application Number Title Priority Date Filing Date
JP17266788A Pending JPH0224305A (en) 1988-07-13 1988-07-13 Thermosetting resin composition

Country Status (1)

Country Link
JP (1) JPH0224305A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2664605A1 (en) * 1990-07-16 1992-01-17 Rhone Poulenc Chimie IMIDA GROUPED POLYMERS AND PROCESS FOR PREPARATION.
JP2005314656A (en) * 2004-03-08 2005-11-10 Dainippon Ink & Chem Inc Thermosetting composition and cured product thereof
JP2011056496A (en) * 2009-08-11 2011-03-24 Kurita Water Ind Ltd Water treatment method and water treatment flocculant
JP2013255923A (en) * 2009-08-11 2013-12-26 Kurita Water Ind Ltd Water treatment method and water treatment flocculant

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2664605A1 (en) * 1990-07-16 1992-01-17 Rhone Poulenc Chimie IMIDA GROUPED POLYMERS AND PROCESS FOR PREPARATION.
JP2005314656A (en) * 2004-03-08 2005-11-10 Dainippon Ink & Chem Inc Thermosetting composition and cured product thereof
JP4534802B2 (en) * 2004-03-08 2010-09-01 Dic株式会社 Thermosetting composition and cured product thereof
JP2011056496A (en) * 2009-08-11 2011-03-24 Kurita Water Ind Ltd Water treatment method and water treatment flocculant
JP2013255923A (en) * 2009-08-11 2013-12-26 Kurita Water Ind Ltd Water treatment method and water treatment flocculant
US9403704B2 (en) 2009-08-11 2016-08-02 Kurita Water Industries, Ltd. Water treatment method and water treatment flocculant

Similar Documents

Publication Publication Date Title
JP3434550B2 (en) Thermosetting compound, cured product thereof and method for producing thermosetting compound
JP3094567B2 (en) Thermosetting resin composition and cured product thereof
JP4005006B2 (en) Heat-resistant resin composition for molding
JPH01158038A (en) Latent curable accelerating agent for cyanate esters
JPH0224305A (en) Thermosetting resin composition
JP4750081B2 (en) Molding
JPH024621B2 (en)
JP3429090B2 (en) Thermosetting resin composition and cured product thereof
US3071559A (en) Heat curable epoxy ether resin employing meta-chlor-aniline-formaldehyde hardener and process of curing the same
JP2018104609A (en) One-pack thermosetting resin composition and cured article thereof
JP3408689B2 (en) Thermosetting resin composition
JPS6328099B2 (en)
JPH0343287B2 (en)
Samanta et al. Effectiveness of Amine Functional Polymers as Curing and Toughening Agents for Epoxy Resin
JP3258126B2 (en) Thermosetting resin composition
JPH09137071A (en) Thermosetting resin composition and its cured material
JPS6392651A (en) Polyester imide
JP2640299B2 (en) Modified epoxy resin and composition thereof
JPH08143670A (en) Heat resistant resin composition
JPS5855215A (en) Heat resistant resin molding including metal insert
JPS6159328B2 (en)
JP2837041B2 (en) Thermosetting resin composition
CA1091846A (en) Process for the production of moulded articles, coatings, films and bonds
JPH0418443A (en) Thermosetting resin composition
JPS63191833A (en) Thermosetting resin composition