JPS6381119A - One-pack type epoxy resin compositon - Google Patents
One-pack type epoxy resin compositonInfo
- Publication number
- JPS6381119A JPS6381119A JP22647286A JP22647286A JPS6381119A JP S6381119 A JPS6381119 A JP S6381119A JP 22647286 A JP22647286 A JP 22647286A JP 22647286 A JP22647286 A JP 22647286A JP S6381119 A JPS6381119 A JP S6381119A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- epoxy resin
- dibasic acid
- composition
- type 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.)
- Granted
Links
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 21
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract description 6
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 2
- 235000006408 oxalic acid Nutrition 0.000 abstract description 2
- JJOJFIHJIRWASH-UHFFFAOYSA-N icosanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCCCC(O)=O JJOJFIHJIRWASH-UHFFFAOYSA-N 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 1
- RXFZJKXZSLVQJV-UHFFFAOYSA-N icosa-8,12-dienedihydrazide Chemical compound NNC(=O)CCCCCCC=CCCC=CCCCCCCC(=O)NN RXFZJKXZSLVQJV-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 7
- 150000007513 acids Chemical class 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- -1 imidazole compound Chemical class 0.000 description 3
- NFVPEIKDMMISQO-UHFFFAOYSA-N 4-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=C(O)C=C1 NFVPEIKDMMISQO-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000003490 Thiodipropionic acid Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 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、−液性エポキシ樹脂組成物に関し、さらに詳
しくは、常温での安定性に優れ、かつ加熱時には比較的
低温で速やかに硬化し、可どう性の優れた硬化物が得ら
れることを特徴とする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 liquid-based epoxy resin composition, and more specifically, it has excellent stability at room temperature and hardens quickly at a relatively low temperature when heated. , relates to an epoxy resin composition characterized in that a cured product with excellent flexibility can be obtained.
一液性エボキシ樹脂は二液性エポキシ樹脂に比べ、使用
直前の計量、混合、攪はんなどの繁雑な工程が不用であ
り、ポットライフが長いので品質が安定していて、材料
のロスが少ないなどの特徴を有しており、最近盛んに開
発が行われている。Compared to two-component epoxy resins, one-component epoxy resins do not require complicated processes such as measuring, mixing, and stirring immediately before use, and have a long pot life, resulting in stable quality and reduced material loss. Recently, it has been actively developed.
しかし、硬化物の物性という面ではまだ二液性エポキシ
樹脂に及ばない点も多く、特に可どう性等の物性や又、
速硬化性に於いてはまだ二液性エポキシ樹脂に比べ、十
分満足いくものが得られていないのが現状である。However, in terms of the physical properties of the cured product, there are still many points where it is not as good as two-component epoxy resins, especially physical properties such as flexibility,
At present, it is not yet possible to obtain a fast curing property that is fully satisfactory compared to two-component epoxy resins.
アジピン酸ジヒドラジドに代表されるヒドラジド化合物
は保存安定性の優れたー液性エポキシ樹履用の潜在性硬
化剤としてよく使用されている。Hydrazide compounds, typified by adipic acid dihydrazide, are often used as latent curing agents for liquid-based epoxy resins, which have excellent storage stability.
その中で、エイコサンニ酸ジヒドラジド（１）、８．１
２−エイコサジエンニ酸ジヒドラジド（２）はその特有
の長鎖構造により、硬化物が可どう性を有し、剥離強度
、耐熱衝撃性等に優れた性質を示す。Among them, eicosanniic acid dihydrazide (1), 8.1
Due to its unique long chain structure, 2-eicosadienioic acid dihydrazide (2) has flexibility in its cured product and exhibits excellent properties such as peel strength and thermal shock resistance.
ＮＨ２ＮＨＣＯ（ＣＨ２）１８ＣＯＮＨＮＨ２ＮＨ２Ｎ
ＨＣＯ（ＣＨ２）６ＣＨ＝ＣＨ−（ＣＨ２）２ＣＨ＝Ｃ
Ｈ（ＣＨ２）ｅｃ’０ＮＨＮＨｚしかし、これらの長鎖
ヒドラジド化合物は他の多くのヒドラジド化合物同様、
高融点化合物であり、エポキシ樹脂の硬化に高温、長時
間を有するという欠点があり、より低温、短時間で硬化
することが望まれている。NH2NHCO(CH2)18CONHNH2NH2N
HCO(CH2)6CH=CH-(CH2)2CH=C
H(CH2)ec'0NHNHzHowever, these long chain hydrazide compounds, like many other hydrazide compounds,
Since it is a high melting point compound, it has the drawback of requiring high temperature and long time to cure epoxy resin, and it is desired to cure at lower temperature and in a shorter time.
その解決法として硬化性を速めるため、例えばイミダゾ
ール化合物や２，４．６− ）リス（ジメチルアミノメ
チル）フェノールを促進剤として加える方法がある。し
かし、これらの促進剤を用いると一般的に、上記のヒド
ラジド化合物の特徴である硬化物の可どう性が損なわれ
るという欠点がある。As a solution to this problem, there is a method of adding, for example, an imidazole compound or 2,4.6-)lis(dimethylaminomethyl)phenol as an accelerator in order to speed up the curing property. However, the use of these accelerators generally has the disadvantage that the flexibility of the cured product, which is a characteristic of the above-mentioned hydrazide compounds, is impaired.
又、イミダゾール化合物や２，４．６− ）リス（ジメ
チルアミノメチル）フェノールは組成物の保存安定性を
損なうという欠点もある。Furthermore, imidazole compounds and 2,4.6-)lis(dimethylaminomethyl)phenol have the disadvantage of impairing the storage stability of the composition.
本発明者らは、保存安定性および硬化物の可どう性を損
なうことなくエイコサンニ酸ジヒドラジド、８，１２−
エイコサジエンニ酸ジヒドラジドの硬化速度を速めるた
め鋭意検討した結果、上記ヒドラジド化合物と共に、二
塩基酸を共存させることにより硬化温度を大きく低下さ
せ、硬化時間を大巾に短縮することが可能であり、かつ
可どう性の優れた硬化物が得られることを発見し、本発
明を完成するに至った。The present inventors have discovered that eicosanniic acid dihydrazide, 8,12-
As a result of intensive studies to speed up the curing speed of eicosadienioic acid dihydrazide, we found that it is possible and possible to greatly reduce the curing temperature and shorten the curing time by coexisting a dibasic acid with the above hydrazide compound. It was discovered that a cured product with excellent properties could be obtained, and the present invention was completed.
すなわち、本発明は
（ａ）エポキシ樹脂
（ｂ）下式（１）及び／または（２）で表されるヒドラ
ジド化合物
ＮＨ２ＮＨＣＯ（ＣＨ２）１８ＣＯＮＨＮＨ２ＮＨ２Ｎ
ＨＣＯ（ＣＨ２）ａｃＨ＝ｃＨ−（ＣＨ２）２ＣＨ＝Ｃ
Ｈ（ＣＨ２）［１ＣＯＮＨＮＨ２（ｃ）二塩基酸
を必須成分とするエポキシ樹脂組成物から成る。That is, the present invention provides (a) an epoxy resin (b) a hydrazide compound NH2NHCO(CH2)18CONHNH2NH2N represented by the following formulas (1) and/or (2).
HCO(CH2)acH=cH-(CH2)2CH=C
Consists of an epoxy resin composition containing H(CH2)[1CONHNH2(c) dibasic acid as an essential component.
本発明に用いられる（ａ）エポキシ樹脂とは１分子中に
２個以上のエポキシ基を有するものであればいかなるも
のであってもよく、たとえばビスフェノールＡ、ビスフ
ェノールＦなどの多価フェノールやグリセリンのような
多価アルコールとエピクロルヒドリンとの反応で得られ
るポリグリシジルエーテル、ポリカルボン酸から得られ
るポリグリシジルエステル、エポキシ化ノボラック、更
には過酸化法で得られる脂環式エポキシ樹脂等が挙げら
れる。又、可どう性という特徴をより生かす為に、ＣＴ
ＢＮ変性エポキシ樹脂、ウレタン変性エポキシ樹脂等の
変性エポキシ樹脂も用いることができる。The epoxy resin (a) used in the present invention may be any resin as long as it has two or more epoxy groups in one molecule, such as polyhydric phenols such as bisphenol A and bisphenol F, and glycerin. Examples include polyglycidyl ethers obtained by reacting polyhydric alcohols with epichlorohydrin, polyglycidyl esters obtained from polycarboxylic acids, epoxidized novolaks, and alicyclic epoxy resins obtained by a peroxidation method. In addition, in order to make more use of the characteristic of flexibility, CT
Modified epoxy resins such as BN-modified epoxy resin and urethane-modified epoxy resin can also be used.
（ｂ）成分であるエイコサンニ酸ジヒドラジド、８．１
２−エイコサジエンニ酸ジヒドラジドはそれぞれエイコ
サンニ酸、８，１２−エイコサジエンニ酸から通常のヒ
ドラジド化反応により得られる。すなわち、それぞれの
酸をメタノール、エタノールなどのアルコールでエステ
ル化を行い、次にそのエステルを抱水ヒドラジンと共に
反応させることにより該ヒドラジド化合物が得られる。(b) Component eicosanniic acid dihydrazide, 8.1
2-eicosadienioic acid dihydrazide can be obtained from eicosanniic acid and 8,12-eicosadienioic acid by a conventional hydrazidation reaction. That is, the hydrazide compound is obtained by esterifying each acid with an alcohol such as methanol or ethanol, and then reacting the ester with hydrazine hydrate.
（ｂ）成分のヒドラジド化合物の配合量は、（ａ）成分
のエポキシ樹脂と等当量数が適当であるが、他の硬化剤
成分が共存する場合や硬化条件によっては、それより少
ない量で用いても良い。The appropriate amount of the hydrazide compound (b) is equivalent to that of the epoxy resin (a), but if other curing agent components are present or depending on the curing conditions, a smaller amount may be used. It's okay.
通常、（ａ）成分１００重量部に対して５〜１００重量
部が適当である。Usually, 5 to 100 parts by weight is suitable for 100 parts by weight of component (a).
（Ｃ）成分の二塩基酸としては、シュウ酸、マロン酸、
コハク酸、グルタル酸、アジピン酸、ビ酸、ジグリコー
ル酸、チオジプロピオン酸などを挙げることができ゛る
。(C) Component dibasic acids include oxalic acid, malonic acid,
Examples include succinic acid, glutaric acid, adipic acid, biic acid, diglycolic acid, and thiodipropionic acid.
又、偶数個の炭素鎖を持つ二塩基酸と奇数個の炭素鎖を
持つ二塩基酸を比べると、偶数個の炭素鎖な持つ二塩基
酸を（Ｃ）成分として用いた方が組成物の保存安定性が
より優れており、保存安定性の観点からは、特に偶数個
の炭素を持つ二塩基酸が好ましい。Also, when comparing dibasic acids with an even number of carbon chains and dibasic acids with an odd number of carbon chains, it is better to use the dibasic acid with an even number of carbon chains as component (C). From the viewpoint of storage stability, dibasic acids having an even number of carbon atoms are particularly preferred.
（ｃ）成分の二塩基酸の配合量は（ａ）成分１００重量
部に対して０．５〜３０重量部が適当である。The appropriate amount of the dibasic acid as component (c) is 0.5 to 30 parts by weight per 100 parts by weight of component (a).
また、本発明の組成物には所望によって、ジシアンジア
ミドやアジピン酸ジヒドラジドの様な他の潜在性硬化剤
やフィラー、顔料、可塑剤、カップリング剤、粘度調節
剤等の成分を加えても良い。In addition, other latent curing agents such as dicyandiamide and adipic acid dihydrazide, fillers, pigments, plasticizers, coupling agents, viscosity modifiers, and other components may be added to the composition of the present invention, if desired.
以下に実施例を挙げて本発明を説明する。 The present invention will be explained below with reference to Examples.
なお、貯蔵安定性の測定は４０℃の恒温槽に配合物試料
を入れ、流動性のなくなるまでの日数を測定した。In addition, storage stability was measured by placing a compound sample in a constant temperature bath at 40° C. and measuring the number of days until fluidity disappeared.
ゲル化時間は、１５０℃に設定した電熱板上に試料約１
ｇを置き、スパチュラで攪はんしなか、ら、流動性を失
いゲル化するまでの時間を測定した。The gelation time was determined by placing approximately 1 sample on an electric heating plate set at 150°C.
While stirring with a spatula, the time required for the mixture to lose fluidity and turn into a gel was measured.
ガラス転移温度は、１５０℃、１時間で硬化させた試料
を熱機械分析装置（ＴＭＡ、理学電気■製）、を用い、
ＴＭＡペネトレーション法にて測定した。The glass transition temperature was determined by using a thermomechanical analyzer (TMA, manufactured by Rigaku Denki ■) on a sample that had been cured at 150°C for 1 hour.
Measured by TMA penetration method.
又、塗膜として使用した時の可どう性、密着性を評価す
る為、ブリキ板に配合物を塗布し１５０℃、１時間で硬
化させ、その塗膜のエリクセン試験を行った。In addition, in order to evaluate the flexibility and adhesion when used as a coating film, the formulation was applied to a tin plate and cured at 150° C. for 1 hour, and the coating film was subjected to an Erichsen test.
実施例
エピコート８２８（油化シェル■製ビスフェノールＡ系
エポキシ樹脂、エポキシ当量１８５〜１９０）１００重
量部とエイコサンニ酸ジヒドラジド（１）５０重量部及
びアジピン酸５重量部をらいかい機で混合し白色ペース
ト状の組成物を得た。Example 100 parts by weight of Epicoat 828 (bisphenol A epoxy resin manufactured by Yuka Shell ■, epoxy equivalent: 185-190), 50 parts by weight of eicosanniic acid dihydrazide (1) and 5 parts by weight of adipic acid were mixed in a sieve machine to form a white paste. A composition of the form was obtained.
このようにして、表１に示すような配合にて組成物を調
製し、貯蔵安定性、ゲル化時間、ガラス転移温度及びエ
リクセン試験の測定の測定を行い、その結果を表２に示
した。In this way, a composition was prepared with the formulation shown in Table 1, and the storage stability, gelation time, glass transition temperature, and Erichsen test were measured, and the results are shown in Table 2.
二塩基酸を加えない場合（比較例５，６）と比べ、本発
明の組成物は大きく硬化時間が短縮され、しかも促進剤
としてイミダゾール化合物を用いた場合（比較例７）の
ごとく保存安定性及び可どう性を損うことがないことが
表２よりわかり、本発明の効果が理解できる。Compared to the case where no dibasic acid is added (Comparative Examples 5 and 6), the curing time of the composition of the present invention is greatly shortened, and the composition has excellent storage stability as in the case where an imidazole compound is used as an accelerator (Comparative Example 7). It can be seen from Table 2 that there is no loss of stability and flexibility, and the effects of the present invention can be understood.
表 １Table 1
Claims (2)
ジド化合物 ＮＨ＿２ＮＨＣＯ（ＣＨ＿２）＿１＿８ＣＯＮＨＮＨ＿
２（１） ＮＨ＿２ＮＨＣＯ（ＣＨ＿２）＿６ＣＨ＝ＣＨ−（ＣＨ
＿２）＿２ＣＨ＝ＣＨ（ＣＨ＿２）＿６ＣＯＮＨＮＨ＿
２（２） （ｃ）二塩基酸 を必須成分とするエポキシ樹脂組成物(1) (a) Epoxy resin (b) Hydrazide compound NH_2NHCO (CH_2)_1_8CONHNH_ represented by the following formulas (1) and/or (2)
2(1) NH_2NHCO(CH_2)_6CH=CH-(CH
_2)_2CH=CH(CH_2)_6CONHNH_
2(2) (c) Epoxy resin composition containing dibasic acid as an essential component
る特許請求範囲第１項記載のエポキシ樹脂組成物(2) The epoxy resin composition according to claim 1, wherein the dibasic acid (c) is a dibasic acid having an even number of carbon chains.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61226472A JPH0657741B2 (en) | 1986-09-25 | 1986-09-25 | One-part epoxy resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61226472A JPH0657741B2 (en) | 1986-09-25 | 1986-09-25 | One-part epoxy resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6381119A true JPS6381119A (en) | 1988-04-12 |
| JPH0657741B2 JPH0657741B2 (en) | 1994-08-03 |
Family
ID=16845635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61226472A Expired - Lifetime JPH0657741B2 (en) | 1986-09-25 | 1986-09-25 | One-part epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0657741B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002079294A1 (en) * | 2001-03-30 | 2002-10-10 | Sunstar Giken Kabushiki Kaisha | One-component hot-setting epoxy resin composition and semiconductor mounting underfill material |
| WO2005016988A1 (en) * | 2003-08-15 | 2005-02-24 | Ajinomoto Co., Inc. | Curable resin composition |
| KR20240021722A (en) | 2022-08-10 | 2024-02-19 | 아지노모토 가부시키가이샤 | Curing agent for epoxy resin and epoxy resin composition |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55147565A (en) * | 1979-05-04 | 1980-11-17 | Kurimoto Iron Works Ltd | Powdered painting material |
| JPS61171722A (en) * | 1985-01-24 | 1986-08-02 | Ajinomoto Co Inc | One-pack epoxy resin composition |
| JPS61192721A (en) * | 1985-02-22 | 1986-08-27 | Ajinomoto Co Inc | One-pack epoxy resin composition |
| JPS61192722A (en) * | 1985-02-21 | 1986-08-27 | Asahi Chem Ind Co Ltd | Curable composition |
-
1986
- 1986-09-25 JP JP61226472A patent/JPH0657741B2/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55147565A (en) * | 1979-05-04 | 1980-11-17 | Kurimoto Iron Works Ltd | Powdered painting material |
| JPS61171722A (en) * | 1985-01-24 | 1986-08-02 | Ajinomoto Co Inc | One-pack epoxy resin composition |
| JPS61192722A (en) * | 1985-02-21 | 1986-08-27 | Asahi Chem Ind Co Ltd | Curable composition |
| JPS61192721A (en) * | 1985-02-22 | 1986-08-27 | Ajinomoto Co Inc | One-pack epoxy resin composition |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002079294A1 (en) * | 2001-03-30 | 2002-10-10 | Sunstar Giken Kabushiki Kaisha | One-component hot-setting epoxy resin composition and semiconductor mounting underfill material |
| US7449362B2 (en) | 2001-03-30 | 2008-11-11 | Sunstar Giken Kabushiki Kaisha | One-component hot-setting epoxy resin composition and semiconductor mounting underfill material |
| WO2005016988A1 (en) * | 2003-08-15 | 2005-02-24 | Ajinomoto Co., Inc. | Curable resin composition |
| KR20240021722A (en) | 2022-08-10 | 2024-02-19 | 아지노모토 가부시키가이샤 | Curing agent for epoxy resin and epoxy resin composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0657741B2 (en) | 1994-08-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |