JPH01271414A - Novel epoxy resin composition - Google Patents
Novel epoxy resin compositionInfo
- Publication number
- JPH01271414A JPH01271414A JP10025388A JP10025388A JPH01271414A JP H01271414 A JPH01271414 A JP H01271414A JP 10025388 A JP10025388 A JP 10025388A JP 10025388 A JP10025388 A JP 10025388A JP H01271414 A JPH01271414 A JP H01271414A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- resin composition
- curing
- curing agent
- formula
- 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 description 50
- 229920000647 polyepoxide Polymers 0.000 title claims description 50
- 239000000203 mixture Substances 0.000 title claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims abstract description 13
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract description 8
- 239000003513 alkali Substances 0.000 abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract description 2
- 239000004845 glycidylamine epoxy resin Substances 0.000 abstract 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 abstract 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 10
- 239000000463 material Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- -1 laminates Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-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 3
- 230000000052 comparative effect Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 239000012772 electrical insulation material Substances 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- ASNOFHCTUSIHOM-UHFFFAOYSA-N 4-[10-(4-aminophenyl)anthracen-9-yl]aniline Chemical compound C1=CC(N)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(N)C=C1 ASNOFHCTUSIHOM-UHFFFAOYSA-N 0.000 description 1
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003733 fiber-reinforced composite Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は新規な特に耐熱性、耐水性にすぐれたエポキシ
樹脂組成物に関し、さらに詳細には必須のエポキシ樹脂
成分として９．１０−ビス（４−７ミノフエニル）アン
トラセンとエピクロルヒドリンとからなるエポキシ樹脂
を用い、耐熱性および耐水性が飛躍的に優れた積層品樹
脂材料、電気絶縁材料、繊維強化複合材料、塗装材料、
成型材料、接着材料などに極めて有用なエポキシ樹脂組
成物に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a novel epoxy resin composition particularly excellent in heat resistance and water resistance, and more particularly, it relates to a novel epoxy resin composition containing 9.10-bis(9.10-bis()) as an essential epoxy resin component. Laminated resin materials, electrical insulation materials, fiber-reinforced composite materials, coating materials, which use epoxy resins consisting of 4-7 minophenyl anthracene and epichlorohydrin and have dramatically superior heat resistance and water resistance.
This invention relates to epoxy resin compositions that are extremely useful as molding materials, adhesive materials, etc.
（従来の技術）
エポキシ樹脂は、種々の硬化剤で硬化させることにより
、一般的に機械的性質、耐水性、耐薬品性、耐熱性、電
気的性質などの優れた硬化物となシ、接着剤、塗料、積
層板、成型材料、注型材料等、＠広い分野Ｋ（！２！用
されている。(Prior art) Epoxy resins can be cured with various curing agents to produce cured products with excellent mechanical properties, water resistance, chemical resistance, heat resistance, electrical properties, etc. It is used in a wide range of fields, such as agents, paints, laminates, molding materials, and casting materials.
（発明が解決しようとする課題）
最も代表的なエポキシ樹脂は、ビスフェノールＡにエピ
クロルヒドリンを反応させて得られる液状および固型の
ビスフェノールＡｆｉエポキシ樹脂が挙げられるが、こ
れらは１分子当たシのダリシゾル基が２個よシは多くは
ないために硬化時の架橋密度が低く、耐熱性が劣る傾向
にある。(Problems to be Solved by the Invention) The most typical epoxy resins include liquid and solid bisphenol Afi epoxy resins obtained by reacting bisphenol A with epichlorohydrin, but these resins have a high content of 100 ml per molecule. Since there are not many groups than two, the crosslinking density during curing is low and the heat resistance tends to be poor.
この様な欠点を改良するために、いわゆるノーラック型
エポキシ樹脂やジアミノジフェニルメタン、アミノフェ
ノール等をベースとするグリシジルアミンｍおよびグリ
シジルアミンエーテル型工４キシ樹脂等の多官能エポキ
シ樹脂が使用されているが、これらの場合確かに耐熱性
は向上するものの、その向上の度合は充分でなく、シか
も耐水性は逆に劣るという欠点を有する。In order to improve these drawbacks, polyfunctional epoxy resins such as so-called nolac type epoxy resins and glycidylamine m and glycidylamine ether type engineered 4xy resins based on diaminodiphenylmethane, aminophenol, etc. have been used. In these cases, although the heat resistance is certainly improved, the degree of improvement is not sufficient, and the water resistance is, on the contrary, inferior.
（課題を解決するための手段）
本発明者らは、こうした実情に鑑みて鋭意研究した結果
、９．１０−ビス（４−７ミノフエニル）アントラセン
に工ぎクロルヒドリンを反応させて得られる特定のグリ
シジルアミン型エポキシ樹脂を用いると耐熱性と耐水性
に優れるエポキシ樹脂組成物が得られることを見出して
、本発明を完成するに至った。(Means for Solving the Problems) As a result of intensive research in view of the above circumstances, the present inventors have found that a specific glycidyl compound obtained by reacting 9,10-bis(4-7minophenyl)anthracene with chlorohydrin. The inventors have discovered that an epoxy resin composition with excellent heat resistance and water resistance can be obtained by using an amine type epoxy resin, and have completed the present invention.
すなわち１本発明は、エポキシ樹脂および硬化剤、更に
必要により硬化促進剤から構成されるエポキシ樹脂組成
物において、該エポキシ樹脂成分として。That is, one aspect of the present invention is an epoxy resin composition comprising an epoxy resin, a curing agent, and, if necessary, a curing accelerator, as the epoxy resin component.
構造式（１）
で示される化合物にエピクロルヒドリンを反応させて得
られるグリシジルアミン型エポキシ樹脂を含有すること
を特徴とする新規なエポキシ樹脂組成物、
あるいは該エポキシ樹脂成分として。A novel epoxy resin composition, or as an epoxy resin component, characterized by containing a glycidylamine type epoxy resin obtained by reacting a compound represented by the structural formula (1) with epichlorohydrin.
構造式（ＩＩ）
・・・〔■〕
で示されるグリシゾルアミン型エポキシ樹脂を含有する
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 provides a curable epoxy resin composition characterized by containing a glycizolamine type epoxy resin represented by the structural formula (II) [■].
本発明で用いる構造式（ＩＩ）で示されるグリシジルア
ミン型エポキシ樹脂は、例えば構造式（１）で示される
９、１０−ビス（４−アミノフェニル）アントラセンに
アルカリの存在下、エピクロルヒドリンを反応させるこ
とにより得られる。The glycidylamine type epoxy resin represented by the structural formula (II) used in the present invention can be obtained by reacting, for example, 9,10-bis(4-aminophenyl)anthracene represented by the structural formula (1) with epichlorohydrin in the presence of an alkali. It can be obtained by
この場合の反応条件は従来より行なわれているエポキシ
樹脂の製造条件と同じであシ、特に制限されるものでは
ない、即ち、９，１０−ビス（４−アミノフェニル）ア
ントラセンのアミン性活性水素１個に対しエピクロルヒ
ドリンを１〜１０モル添加し、水酸化ナトリウムのよう
なアルカリの存在下に２０〜１２０℃でエポキシ化反応
を行なうことが出来、アミン性活性水素に対するエピク
ロルヒドリンの過剰率を調節することにより、得られる
工？キシ化合物の分子量、エポキシ当量、軟化点を調整
することができる。エピクロルヒドリンの過剰率を下げ
るとエポキシ樹脂の分子量が高くな夛、靭性の高い硬化
物となり、逆に上げると分子量が低くなり、耐熱性の高
い硬化物を得ることが出来る。ただし一般にはエピクロ
ルヒドリンの過剰率が４倍をこえるとあまシ変化しなく
なるので、過剰率は５倍以下が好ましい。The reaction conditions in this case are the same as those conventionally used for producing epoxy resins, and are not particularly limited. It is possible to add 1 to 10 moles of epichlorohydrin per unit and carry out the epoxidation reaction at 20 to 120°C in the presence of an alkali such as sodium hydroxide, and adjust the excess ratio of epichlorohydrin to aminic active hydrogen. What can be gained by doing this? The molecular weight, epoxy equivalent, and softening point of the oxygen compound can be adjusted. If the excess ratio of epichlorohydrin is lowered, the molecular weight of the epoxy resin will be higher, resulting in a cured product with high toughness, while if it is increased, on the other hand, the molecular weight will be lowered, making it possible to obtain a cured product with high heat resistance. However, in general, if the excess ratio of epichlorohydrin exceeds 4 times, no change will occur, so the excess ratio is preferably 5 times or less.
本発明に使用される硬化剤としては、通常エポキシ樹脂
の硬化剤として常用されている化合物はすべて使用する
ことができ、ジエチレントリアミン、トリエチレンテト
ラミンなどの脂肪族アミン類、メタフェニレンジアミン
、ジアミノジフェニルメタン、シアミノジフェニルスル
ホンなどの芳香族アミン類、Ｉリアミド樹脂およびこれ
らの変往動、無水マレイン酸、無水フタル酸、無水へキ
サヒドロフタル酸、無水ピロメリット酸などの酸無水物
系硬化剤、ジシアンジアミド、イミダゾール、ＢＦ、−
アミン錯体、グアニシン誘導体などの潜在性硬化剤など
があげられる。As the curing agent used in the present invention, all compounds commonly used as curing agents for epoxy resins can be used, including aliphatic amines such as diethylenetriamine and triethylenetetramine, metaphenylenediamine, diaminodiphenylmethane, Aromatic amines such as cyamino diphenyl sulfone, I-lyamide resins and their variations, acid anhydride curing agents such as maleic anhydride, phthalic anhydride, hexahydrophthalic anhydride, and pyromellitic anhydride, dicyandiamide , imidazole, BF, -
Examples include latent curing agents such as amine complexes and guanisine derivatives.
上掲された如き各化合物を硬化剤として用いる際は、多
くの場合、さらに硬化促進剤をも使用することが必要と
なるが、そうした場合にはジメチルペンジルアミンなど
の如き三級アミン類、イきダゾール類または各種金属化
合物などをはじめ。When using each of the compounds listed above as a curing agent, it is often necessary to also use a curing accelerator, but in such cases, tertiary amines such as dimethylpenzylamine, etc. Including kidazoles or various metal compounds.
例えば垣内弘編エポキシ樹脂（昭晃堂）Ｐ３３０〜３３
１に記載されている公知慣用の硬化促進剤すべてを使用
できる。For example, Hiroshi Kakiuchi ed. Epoxy resin (Shokodo) P330-33
All known and customary curing accelerators listed in 1 can be used.
本発明のエポキシ樹脂組成物には、さらに必要に応じて
充填剤、着色剤などの公知慣用の各種添加剤をも添加配
合せしめることができ、またタール、ピッチ、アミノ樹
脂、アルキッド樹脂、フェノール樹脂なども併用するこ
とができる。The epoxy resin composition of the present invention may further contain various known and commonly used additives such as fillers and colorants, as required, and may also contain tar, pitch, amino resin, alkyd resin, phenol resin, etc. etc. can also be used together.
（実施例）
次に本発明を製造例、実施例および比較例により具体的
に説明する。尚、例中において部は特に断りのない限シ
すべて重量部である。(Example) Next, the present invention will be specifically explained using manufacturing examples, examples, and comparative examples. In the examples, all parts are by weight unless otherwise specified.
製造例１
９、ｌＯ−ビス（４−アミノフェニル）アントラセン３
６０部をエピクロルヒドリン７４０部に溶解させた後、
撹拌しながら５０〜６０℃で２０％水酸化ナトリウム水
溶液８００部を５時間かけて滴下し、更に１時間反応さ
せ、次いで水層を棄却した後、過剰のエピクロルヒドリ
ンを蒸留回収して反応組成物を得た。この反応組成物に
トルエン８８０部を加えて均一に溶解させ、水２９０部
を加えて水洗した後、油水分離し、油層からトルエンを
留去させることによりて、エポキシ当量が１５６なるエ
ポキシ樹脂（ａ） ５５５部を得た。Production Example 1 9, 1O-bis(4-aminophenyl)anthracene 3
After dissolving 60 parts in 740 parts of epichlorohydrin,
While stirring, 800 parts of a 20% aqueous sodium hydroxide solution was added dropwise at 50 to 60°C over 5 hours, and the reaction was allowed to proceed for an additional hour. After discarding the aqueous layer, the excess epichlorohydrin was recovered by distillation to obtain the reaction composition. Obtained. To this reaction composition, 880 parts of toluene was added and dissolved uniformly, 290 parts of water was added and washed, oil and water were separated, and toluene was distilled off from the oil layer to obtain an epoxy resin (a) having an epoxy equivalent of 156. ) 555 copies were obtained.
製造例２
エピクロルヒドリンの使用量を５５５部とし九以外は製
造例１と同様にしてエポキシ当量が１７５なるエポキシ
樹脂伽）５４５部を得た。Production Example 2 545 parts of an epoxy resin having an epoxy equivalent of 175 was obtained in the same manner as in Production Example 1 except that the amount of epichlorohydrin used was 555 parts.
実施例１〜２および比較例１〜２
エポキシ樹脂として製造例１〜２で得られたエポキシ樹
脂（、）〜（ｂ）、フェノールノゴラックエデキシ樹脂
エビクロンＮ−７３８（大日本インキ化学工業＠）製、
エポキシ当量１８０〕又はジアミノジフェニルメタン盟
グリシゾルアミンエポキシ樹脂エビクロン４３０（同社
製、エポキシ当量１２０）を、硬化剤としてエピクロン
Ｂ−５７０（同社製。Examples 1 to 2 and Comparative Examples 1 to 2 Epoxy resins (,) to (b) obtained in Production Examples 1 to 2 as epoxy resins, phenol nogolac edexy resin Evicron N-738 (Dainippon Ink Chemical Industry @ ) made,
Epoxy equivalent: 180] or diaminodiphenylmethane glycizolamine epoxy resin Eviclon 430 (manufactured by the same company, epoxy equivalent: 120) was used as a curing agent, Epiclon B-570 (manufactured by the same company).
メチルテトラヒドロフタル酸無水物）を、硬化促進剤と
して２−エチル−４−メチルイＺダゾールをそれぞれ用
い、エポキシ樹脂のエポキシ基１個に対して硬化剤の酸
無水物基が１個になる様に表−１に示す組成で配合して
、本発明および比較対照用のエポキシ樹脂組成物を得た
。methyltetrahydrophthalic anhydride) and 2-ethyl-4-methylidazole as a curing accelerator, so that the number of acid anhydride groups in the curing agent is one for each epoxy group in the epoxy resin. Epoxy resin compositions for the present invention and for comparison were obtained by blending the compositions shown in Table 1.
これらのエポキシ樹脂゛組成物を１００℃で２時間、次
いで１６０℃で２時間、更に１８０℃で２時間の条件で
硬化せしめて試験片とし、ＪＩＳＫ−６９１１に準拠し
て熱変形温度、曲げ強度、曲げ弾性率、引張シ強度、引
張り伸び率および煮沸吸水率を測定した。結果を表−１
に示す。These epoxy resin compositions were cured at 100°C for 2 hours, then at 160°C for 2 hours, and then at 180°C for 2 hours to prepare test pieces, and the heat distortion temperature and bending strength were determined according to JISK-6911. , flexural modulus, tensile strength, tensile elongation and boiling water absorption were measured. Table 1 shows the results.
Shown below.
実施例３〜４および比較例３〜４
エポキシ樹脂として前記と同様にエポキシ樹脂（、）〜
伽）％工♂クロンＮ−７３８又ｄエヒクロン４３０を、
硬化剤としてＤＤＭ （ジアミノジフェニルメタン）を
それぞれ用い、エポキシ樹脂のニブキシ基１個に対して
硬化剤の活性水素基が１個になるように表−ＩＫ示す組
成で配合して、本発明および比較対照用のエポキシ樹脂
組成物を得た。Examples 3-4 and Comparative Examples 3-4 Epoxy resin (,) ~
伽）%Ehikron N-738 or d Ehikron 430,
DDM (diaminodiphenylmethane) was used as a curing agent, and the compositions shown in Table IK were blended so that the number of active hydrogen groups in the curing agent was one per niboxy group in the epoxy resin. An epoxy resin composition was obtained.
これらのエポキシ樹脂組成物を８０℃で５時間、更に１
６０℃で４時間の条件で、硬化せしめて試験片とし、Ｊ
ＩＳ Ｋ −６９１１に準拠して前記例と同様の項目を
測定した。結果を表−１に示す。These epoxy resin compositions were heated at 80°C for 5 hours and then for 1 hour.
Cured at 60°C for 4 hours to prepare a test piece, J
The same items as in the above example were measured in accordance with IS K-6911. The results are shown in Table-1.
／
（発明の効果）
本発明の工４キシ樹脂組成物から得られた硬化物は、飛
躍的に優れた耐熱性および耐水性を有するという特徴が
ある。/ (Effects of the Invention) The cured product obtained from the polyurethane resin composition of the present invention is characterized by dramatically superior heat resistance and water resistance.
従って本発明のエポキシ樹脂組成物は成散材料、注型材
料、治工具用、積層材料、電気絶縁材料、塗料、土木・
建築材料、接着剤、複合材料などの用途に極めて有用で
ある。Therefore, the epoxy resin composition of the present invention can be used for dispersion materials, casting materials, jigs and tools, laminated materials, electrical insulation materials, paints, civil engineering, etc.
Extremely useful in applications such as building materials, adhesives, and composite materials.
代理人 弁理士 高 橋 勝 利Agent: Patent Attorney Katsutoshi Takahashi
Claims (1)
進剤から構成されるエポキシ樹脂組成物において、該エ
ポキシ樹脂成分として、 構造式〔 I 〕 ▲数式、化学式、表等があります▼…〔 I 〕 で示される化合物にエピクロルヒドリンを反応させて得
られるグリシジルアミン型エポキシ樹脂を含有すること
を特徴とする硬化性エポキシ樹脂組成物。 ２、エポキシ樹脂および硬化剤、更に必要により硬化促
進剤から構成されるエポキシ樹脂組成物において、該エ
ポキシ樹脂成分として、 構造式〔II〕 ▲数式、化学式、表等があります▼…〔II〕 で示されるグリシジルアミン型エポキシ樹脂を含有する
ことを特徴とする硬化性エポキシ樹脂組成物。[Claims] 1. In an epoxy resin composition composed of an epoxy resin, a curing agent, and, if necessary, a curing accelerator, the epoxy resin components include the following structural formula [I] ▲ mathematical formula, chemical formula, table, etc. ▼... A curable epoxy resin composition characterized by containing a glycidylamine type epoxy resin obtained by reacting the compound represented by [I] with epichlorohydrin. 2. In an epoxy resin composition composed of an epoxy resin, a curing agent, and, if necessary, a curing accelerator, the epoxy resin components include the following structural formula [II] ▲ Numerical formula, chemical formula, table, etc. ▼... [II] A curable epoxy resin composition comprising the following glycidylamine type epoxy resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10025388A JPH01271414A (en) | 1988-04-25 | 1988-04-25 | Novel epoxy resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10025388A JPH01271414A (en) | 1988-04-25 | 1988-04-25 | Novel epoxy resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01271414A true JPH01271414A (en) | 1989-10-30 |
Family
ID=14269058
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10025388A Pending JPH01271414A (en) | 1988-04-25 | 1988-04-25 | Novel epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01271414A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103254407A (en) * | 2013-05-16 | 2013-08-21 | 长春工业大学 | Anthryl alcamine multi-functional group epoxy resin curing agent and preparation method thereof |
-
1988
- 1988-04-25 JP JP10025388A patent/JPH01271414A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103254407A (en) * | 2013-05-16 | 2013-08-21 | 长春工业大学 | Anthryl alcamine multi-functional group epoxy resin curing agent and preparation method thereof |
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