JPH04139211A - Curing agent for epoxy resin and curable epoxy resin composition - Google Patents
Curing agent for epoxy resin and curable epoxy resin compositionInfo
- Publication number
- JPH04139211A JPH04139211A JP25970990A JP25970990A JPH04139211A JP H04139211 A JPH04139211 A JP H04139211A JP 25970990 A JP25970990 A JP 25970990A JP 25970990 A JP25970990 A JP 25970990A JP H04139211 A JPH04139211 A JP H04139211A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- curing agent
- resin composition
- formula
- epoxy
- 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 37
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 37
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 16
- 239000000203 mixture Substances 0.000 title claims abstract description 8
- YEACGXMAEGBJSM-UHFFFAOYSA-N 1,3,5-triphenyl-1,3,5-triazinane-2,4,6-trione Chemical class O=C1N(C=2C=CC=CC=2)C(=O)N(C=2C=CC=CC=2)C(=O)N1C1=CC=CC=C1 YEACGXMAEGBJSM-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000004593 Epoxy Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 239000004848 polyfunctional curative Substances 0.000 claims 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 abstract description 4
- 239000007983 Tris buffer Substances 0.000 abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 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 4
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- -1 aromatic isocyanates Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- FEHUHAVQGZZDMW-UHFFFAOYSA-N 5-methyl-4-piperidin-1-yl-2-propan-2-ylphenol Chemical compound C1=C(O)C(C(C)C)=CC(N2CCCCC2)=C1C FEHUHAVQGZZDMW-UHFFFAOYSA-N 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 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- 150000001875 compounds Chemical class 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 108010005491 trypsin carboxypeptidase peptide inhibitor Proteins 0.000 description 2
- ZJRAAAWYHORFHN-UHFFFAOYSA-N 2-[[2,6-dibromo-4-[2-[3,5-dibromo-4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenoxy]methyl]oxirane Chemical compound C=1C(Br)=C(OCC2OC2)C(Br)=CC=1C(C)(C)C(C=C1Br)=CC(Br)=C1OCC1CO1 ZJRAAAWYHORFHN-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004844 aliphatic epoxy resin Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 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
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 230000004580 weight loss Effects 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〕
本発明は新規エポキシ樹脂硬化剤及びそれを含有する硬
化性エポキシ樹脂組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel epoxy resin curing agent and a curable epoxy resin composition containing the same.
〔従来の技術及び発明が解決しようとする課題〕有機芳
香族イソシアネートの三量化により得られる芳香族イソ
シアヌレート構造は、ポリウレタン、塗料などに高い耐
熱性、難燃性、耐薬品性、製膜性などの性能の向上をも
たらすことが知られている。[Prior art and problems to be solved by the invention] The aromatic isocyanurate structure obtained by trimerizing organic aromatic isocyanates has high heat resistance, flame retardancy, chemical resistance, and film forming properties for polyurethane, paints, etc. It is known to bring about improved performance.
しかし高い緒特性が期待されるイソシアヌレート構造を
、任意の割合で合成高分子中に導入することは困難であ
る。従来このような芳香族イソシアヌレート構造の高分
子への導入は、主として芳香族ジイソシアネートと種々
のポリオールの三量化を伴うポリウレタン合成によって
いたが、種々の機能団を持つ芳香族イソシアヌレート誘
導体を、添加剤あるいは架橋剤とすれば、高分子に効率
良く組み込むことができる。However, it is difficult to introduce an isocyanurate structure, which is expected to have high properties, into a synthetic polymer in any proportion. Conventionally, the introduction of such aromatic isocyanurate structures into polymers has mainly been through polyurethane synthesis that involves trimerization of aromatic diisocyanates and various polyols. If used as an agent or crosslinking agent, it can be efficiently incorporated into polymers.
一方、本発明者らは、種々の機能団で置換されたトリフ
ェニルイソシアヌレート誘導体を開発している（特願平
２−６２４２８号）。On the other hand, the present inventors have developed triphenyl isocyanurate derivatives substituted with various functional groups (Japanese Patent Application No. 2-62428).
本発明者らは芳香族イソシアヌレート構造を有するエポ
キシ樹脂硬化剤、及び該構造で架橋されたエポキシ樹脂
を得るべく鋭意研究の結果本発明を完成するに到った。The present inventors completed the present invention as a result of intensive research to obtain an epoxy resin curing agent having an aromatic isocyanurate structure and an epoxy resin crosslinked with the structure.
即ち、本発明は、一般式（Ｉ）
（式中ＸはＯＨ基又はＣ０ＯＨ基を示す。）で示される
トリフェニルイソシアヌレート誘導体からなるエポキシ
樹脂硬化剤を提供するものである。That is, the present invention provides an epoxy resin curing agent comprising a triphenyl isocyanurate derivative represented by the general formula (I) (wherein X represents an OH group or a COOH group).
また本発明は、１分子中に少なくとも２個のエポキシ基
を有するエポキシ樹脂と、一般式（Ｉ）（式中ＸはＯＨ
基又はＣ０ＯＨ基を示す。）で示すれるトリフェニルイ
ソシアヌレート誘導体からなるエポキシ樹脂硬化剤を含
有することを特徴とする硬化性エポキシ樹脂組成物を提
供するものである。The present invention also provides an epoxy resin having at least two epoxy groups in one molecule, and a general formula (I) (wherein X is OH
group or C0OH group. ) The present invention provides a curable epoxy resin composition characterized by containing an epoxy resin curing agent made of a triphenyl isocyanurate derivative represented by the following formula.
上記一般式（Ｉ）で示されるトリフェニルイソシアヌレ
ート誘導体は、Ｘに対応する位置にトリアルキルシリル
オキシ基（ＸがＯＨ基の場合）トリアルキルシリルオキ
シカルボニル基（ＸがＣ００）Ｉ基の場合）を有する置
換トリフェニルイソシアヌレート誘導体を、加水分解す
ることにより容易に得られる。The triphenyl isocyanurate derivative represented by the above general formula (I) has a trialkylsilyloxy group (when X is an OH group) or a trialkylsilyloxycarbonyl group (when X is a C00) I group at the position corresponding to X. ) can be easily obtained by hydrolyzing a substituted triphenyl isocyanurate derivative.
本発明の一般式（Ｉ）で表される、置換されたトリフェ
ニルイソシアヌレート誘導体において、置換基であるＯ
Ｈ基又はＣ０ＯＨ基は、メタ、バラ、オルソ位のいずれ
にあっても良い。In the substituted triphenyl isocyanurate derivative represented by the general formula (I) of the present invention, the substituent O
The H group or C0OH group may be in any of the meta, para, or ortho positions.
上記トリフェニルイソシアヌレート誘導体の好ましい例
を以下に示す。Preferred examples of the above triphenyl isocyanurate derivatives are shown below.
ＯＯＨ
本発明の硬化性エポキシ樹脂組成物において、１分子中
に少なくとも２個のエポキシ基を有するエポキシ樹脂と
しては、公知汎用の脂肪族、芳香族、脂環族系エポキシ
樹脂を全て用いることができる。かかるエポキシ樹脂は
、ハロゲン原子により置換されていてもよい。OOH In the curable epoxy resin composition of the present invention, all known general-purpose aliphatic, aromatic, and alicyclic epoxy resins can be used as the epoxy resin having at least two epoxy groups in one molecule. . Such epoxy resins may be substituted with halogen atoms.
かかる芳香族エポキシ樹脂として好ましいものは、少な
くとも１個の芳香核を有する多価フェノールもしくはそ
のアルキレンオキサイド付加体のポリグリシジルエーテ
ルであって、例工ばビスフェノールＡやビスフェノール
Ｆ又はそのアルキレンオキサイド付加体と、エピクロル
ヒドリンとの反応によって製造されるポリグリシジルエ
ーテル、エポキシノボラック樹脂などが挙げられる。そ
の例としては、ビスフェノールＡジグリシジルエーテル
、ビスフェノールＦジグリシジルエーテル、テトラブロ
ムビスフェノールＡジグリシジルエーテルなどがある。Preferred aromatic epoxy resins are polyglycidyl ethers of polyhydric phenols having at least one aromatic nucleus or their alkylene oxide adducts, such as bisphenol A, bisphenol F, or their alkylene oxide adducts. , polyglycidyl ethers produced by reaction with epichlorohydrin, epoxy novolac resins, and the like. Examples include bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, and tetrabromobisphenol A diglycidyl ether.
また、脂環族エポキシ樹脂として好ましいものは、少な
くとも１個の脂環族環を有する多価アルコールのポリグ
リシジルエーテル、又はシクロヘキセン、シクロペンテ
ン環含有化合物を、過酸化水素、過酸などの適当な酸化
剤でエポキシ化することによって得られるシクロヘキセ
ンオキサイド、シクロペンテンオキサイド含有化合物で
ある。その例としては、水素添加ビスフェノールＡジグ
リシジルエーテルなどがある。Preferably, the alicyclic epoxy resin is a polyglycidyl ether of a polyhydric alcohol having at least one alicyclic ring, or a compound containing a cyclohexene or cyclopentene ring, which is oxidized with a suitable oxidation agent such as hydrogen peroxide or peracid. It is a compound containing cyclohexene oxide and cyclopentene oxide obtained by epoxidation with a chemical agent. Examples include hydrogenated bisphenol A diglycidyl ether.
また、脂肪族エポキシ樹脂として好ましいものは、脂肪
族多価アルコール又はそのアルキレンオキサイド付加体
と、エピクロルヒドリンとの反応によって製造されるポ
リグリシジルエーテル、脂肪族長鎖多塩基酸のポリグリ
シジルエステルなどがあり、その例としては、１，４−
ブタンジオールのジグリシジルエーテル、１，６−ヘキ
サンジオールのジグリシジルエーテルなどがある。Preferred aliphatic epoxy resins include polyglycidyl ethers produced by reacting aliphatic polyhydric alcohols or their alkylene oxide adducts with epichlorohydrin, and polyglycidyl esters of aliphatic long-chain polybasic acids. An example is 1,4-
Examples include diglycidyl ether of butanediol and diglycidyl ether of 1,6-hexanediol.
これらのエポキシ樹脂は、一種又は二種以上を組み合わ
せて使用することが出来る。These epoxy resins can be used alone or in combination of two or more.
本発明の硬化性エポキシ樹脂組成物におけるエポキシ樹
脂と硬化剤の配合は、エポキシ樹脂のエポキシ当量に対
して、一般式（Ｉ）の硬化剤を、１／３モルに相当する
割合で配合すると、良好な硬化物が得られるので好まし
い。The epoxy resin and curing agent in the curable epoxy resin composition of the present invention are blended in such a manner that the curing agent of general formula (I) is blended in a proportion corresponding to 1/3 mole based on the epoxy equivalent of the epoxy resin. This is preferred because a good cured product can be obtained.
本発明の硬化性エポキシ樹脂組成物の硬化反応は、無触
媒又は、三級アミン、有機酸もしくは有機水酸化物のア
ルカリ金属塩などの触媒存在下で行われる。触媒の使用
量は概ね０．００５〜０．０５モル％が好ましい。The curing reaction of the curable epoxy resin composition of the present invention is carried out without a catalyst or in the presence of a catalyst such as a tertiary amine, an organic acid, or an alkali metal salt of an organic hydroxide. The amount of catalyst used is preferably approximately 0.005 to 0.05 mol%.
また上記硬化反応は、無溶媒又は、ジメチルホルムアミ
ド、ジメチルアセトアミドなどのアミド類、エステル、
エーテル、スルホキシド類などの溶媒中で、１５０°Ｃ
〜２６０°Ｃ１１〜１０時間加熱して行われる。In addition, the above curing reaction can be carried out without a solvent or with amides such as dimethylformamide and dimethylacetamide, esters, etc.
In a solvent such as ether or sulfoxide, at 150°C
Heating is performed at ~260°C for 11 to 10 hours.
本発明の硬化反応の好ましい一例を次に掲げる。A preferred example of the curing reaction of the present invention is listed below.
一般式（Ｉ）で示されるトリフェニルイソシアヌレート
誘導体と、エポキシ樹脂を必要最小限のジメチルホルム
アミド、ジメチルアセトアミドに溶解させ、１５０〜１
８０°Ｃ１１〜２時間、更に２００〜２４０°Ｃ１２〜
４時間加熱することにより、エポキシ樹脂硬化物が得ら
れる。The triphenyl isocyanurate derivative represented by the general formula (I) and the epoxy resin are dissolved in the necessary minimum amount of dimethylformamide and dimethylacetamide.
80°C 11~2 hours, then 200~240°C 12~
A cured epoxy resin product is obtained by heating for 4 hours.
本発明によれば、新規トリフェニルイソシアヌレート誘
導体を硬化剤としてエポキシ樹脂を硬化することにより
、芳香族イソシアヌレート構造で架橋されたエポキシ樹
脂硬化物が得られる。本発明のエポキシ樹脂硬化剤はこ
の硬化物に、高い耐熱性、難燃性、耐薬品性、絶縁性、
製膜性などの著しい性能向上を与える。According to the present invention, by curing an epoxy resin using a novel triphenyl isocyanurate derivative as a curing agent, a cured epoxy resin crosslinked with an aromatic isocyanurate structure can be obtained. The epoxy resin curing agent of the present invention provides this cured product with high heat resistance, flame retardancy, chemical resistance, insulation properties,
Provides significant performance improvements such as film formability.
以下、実施例により本発明を更に詳細に説明するが、本
発明はこれらの実施例に限定されるものではない。EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.
実施例１
トリス（４−ヒドロキシフェニル）イソシアヌレート（
以下ＴＨＰＩと略す） ７．０ｇ （Ｉ７ｍｍｏｌ）と
、ビスフェノールＡジグリシジルエーテル（エポキシ当
量１９０、以下ＤＧＢＡと略す） ９．８ｇ （２５ｍ
ｍｏｌ）をジメチルアセトアミド２０−によく溶かし、
ガラス板上にキャストして１６０℃で１時間、更に２２
０″Ｃで１．５時間加熱すると、エポキシ基に基づ＜Ｉ
Ｒ吸収（９０５ｃｍ−’）は完全に消失し、透明な樹脂
膜が得られた。Example 1 Tris(4-hydroxyphenyl)isocyanurate (
7.0 g (I7 mmol) (hereinafter abbreviated as THPI) and 9.8 g (25 m
mol) in dimethylacetamide 20- well,
Cast on a glass plate and heat at 160℃ for 1 hour, then 22 hours.
Heating for 1.5 hours at 0″C results in <I
R absorption (905 cm-') completely disappeared, and a transparent resin film was obtained.
得られた樹脂の熱重量分析（Ｉ０”Ｃ／分）において、
１０％重量重量減変温５４”Ｃと高い熱安定性を示した
。In the thermogravimetric analysis (I0''C/min) of the obtained resin,
It exhibited high thermal stability with a 10% weight loss and temperature change of 54''C.
実施例２
トリス（４−ヒドロキシカルボニルフェニル）イソシア
ヌレート（以下ＴＣＰＩと略す） ７．０ｇ （Ｉ４肩
信０１）と、ＤＧＢＡ （エポキシ当１１８３）７．３
ｇ （２１ｎ＋ｍｏｌ）をジメチルアセトアミド１１ａ
／によく溶かし、実施例１と同様に硬化させるとエポキ
シ樹脂硬化物が得られた。Example 2 Tris (4-hydroxycarbonylphenyl) isocyanurate (hereinafter abbreviated as TCPI) 7.0 g (I4 shoulder 01) and DGBA (epoxy weight 1183) 7.3
g (21n+mol) in dimethylacetamide 11a
/ and cured in the same manner as in Example 1 to obtain a cured epoxy resin.
実施例３
ＴＣＰＩ ７．Ｏｇ （Ｉ４ｎ＋ｍｏｌ）と、次のエポ
キシ樹脂５．４ｇ （２１＋＋＠ｏｌ）をジメチルアセ
トアミド１４−によ（溶かし、実施例１と同様に硬化さ
せるとエポキシ樹脂硬化物が得られた。Example 3 TCPI 7. Og (I4n+mol) and 5.4g (21++@ol) of the following epoxy resin were dissolved in dimethylacetamide 14- and cured in the same manner as in Example 1 to obtain a cured epoxy resin.
比較例１
ＤＧＢＡ （エポキシ当量１８３） ｌｏｇをジシアン
ジアミド１．７２ｇ 、 ２−エチル−４−メチルイミ
ダゾール０．０４ｇを硬化剤としてエポキシ樹脂硬化物
を得た。Comparative Example 1 A cured epoxy resin was obtained using 1.72 g of dicyandiamide and 0.04 g of 2-ethyl-4-methylimidazole as a curing agent.
実施例１〜３及び比較例１の硬化条件、硬化物のガラス
転移温度（Ｔｇ ； ＤＳＣにより測定）を表１に示し
た。本発明の実施例ではいずれも比較例に比べ、高いＴ
ｇが得られた。特にＴＨＰＩによるビスフェノールＡ型
エポキシ樹脂の硬化では、高い耐熱性を示す透明膜状エ
ポキシ樹脂硬化物が得られた。Table 1 shows the curing conditions of Examples 1 to 3 and Comparative Example 1, and the glass transition temperature (Tg; measured by DSC) of the cured products. All of the examples of the present invention have higher T than the comparative examples.
g was obtained. In particular, when bisphenol A type epoxy resin was cured with THPI, a transparent film-like cured epoxy resin product exhibiting high heat resistance was obtained.
表 １Table 1
Claims (1)
トリフェニルイソシアヌレート誘導体からなるエポキシ
樹脂硬化剤。 ２ １分子中に少なくとも２個のエポキシ基を有するエ
ポキシ樹脂と、一般式（ I ） ▲数式、化学式、表等があります▼（ I ） （式中ＸはＯＨ基又はＣＯＯＨ基を示す。）で示される
トリフェニルイソシアヌレート誘導体からなるエポキシ
樹脂硬化剤を含有することを特徴とする硬化性エポキシ
樹脂組成物。[Claims] 1 General formula (I) ▲ Numerical formula, chemical formula, table, etc. ▼ (I) Epoxy consisting of a triphenyl isocyanurate derivative represented by (in the formula, X represents an OH group or a COOH group) Resin hardener. 2 An epoxy resin having at least two epoxy groups in one molecule and the general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, X represents an OH group or a COOH group.) A curable epoxy resin composition comprising an epoxy resin curing agent comprising the triphenyl isocyanurate derivative shown below.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25970990A JPH04139211A (en) | 1990-09-28 | 1990-09-28 | Curing agent for epoxy resin and curable epoxy resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25970990A JPH04139211A (en) | 1990-09-28 | 1990-09-28 | Curing agent for epoxy resin and curable epoxy resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04139211A true JPH04139211A (en) | 1992-05-13 |
Family
ID=17337851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25970990A Pending JPH04139211A (en) | 1990-09-28 | 1990-09-28 | Curing agent for epoxy resin and curable epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04139211A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0553702A2 (en) * | 1992-01-27 | 1993-08-04 | BASF Corporation | Carboxy-functional polyurethane and curable coating composition |
| WO2011155459A1 (en) | 2010-06-11 | 2011-12-15 | 株式会社Adeka | Silicon-containing curable composition, cured product of the silicon-containing curable composition and lead frame substrate formed of the silicon-containing curable composition |
| WO2013021717A1 (en) | 2011-08-10 | 2013-02-14 | 株式会社Adeka | Silicon-containing curable composition and cured product of same |
-
1990
- 1990-09-28 JP JP25970990A patent/JPH04139211A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0553702A2 (en) * | 1992-01-27 | 1993-08-04 | BASF Corporation | Carboxy-functional polyurethane and curable coating composition |
| WO2011155459A1 (en) | 2010-06-11 | 2011-12-15 | 株式会社Adeka | Silicon-containing curable composition, cured product of the silicon-containing curable composition and lead frame substrate formed of the silicon-containing curable composition |
| WO2013021717A1 (en) | 2011-08-10 | 2013-02-14 | 株式会社Adeka | Silicon-containing curable composition and cured product of same |
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