JPS61166826A - Epoxy resin composition - Google Patents
Epoxy resin compositionInfo
- Publication number
- JPS61166826A JPS61166826A JP582985A JP582985A JPS61166826A JP S61166826 A JPS61166826 A JP S61166826A JP 582985 A JP582985 A JP 582985A JP 582985 A JP582985 A JP 582985A JP S61166826 A JPS61166826 A JP S61166826A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- amine
- melting point
- aromatic
- 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
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- Epoxy Resins (AREA)
Abstract
Description
【発明の詳細な説明】
〔発明の技術分野〕
本発明は、耐熱性、耐水性、破断伸び等に優れており、
さらに、無溶剤下に比較的低温（１４０℃以下）におい
て短時間で加工可能なエポキシ樹脂組成物に関する。[Detailed Description of the Invention] [Technical Field of the Invention] The present invention has excellent heat resistance, water resistance, elongation at break, etc.
Furthermore, the present invention relates to an epoxy resin composition that can be processed in a short time at a relatively low temperature (140° C. or less) without a solvent.
最近、カーボン繊維に樹脂を含浸させ、硬化させること
により得られる複合材、いわゆるカーボン繊維強化プラ
スチックス（以下、ＣＦＲＰという）が航空機の一次構
造材等として広範囲に亘って使用されるようになった。Recently, composite materials obtained by impregnating carbon fibers with resin and curing them, so-called carbon fiber reinforced plastics (hereinafter referred to as CFRP), have come to be widely used as primary structural materials for aircraft. .
従来、カーボン繊維含浸用樹脂としては、主としてエポ
キシ樹脂組成物が用いられており、特に耐熱性を目的と
する場合にはテトラグリシジルジアミノジフヱニルメタ
ン（ＴＧＤＤＭ）のエポキシ樹脂に硬化剤としてジアミ
ノジフェニルスルホン（ＤＤＳ）を加えてなるエポキン
樹脂組成物が広く用いらり、できた。し、かし、ごのｒ
ｃｎｏＭ／ＤＤＳ系のエポキシ樹脂組成物は、優れた初
回耐熱性およびカーボン繊維との接着性を有するが 吸
湿により耐熱性が著しく低下することおよび極めて硬度
が大きくかつ伸度が小さい等の欠点がある。さらに硬化
剤の融点が高い（約１８０℃）ために、樹脂組成物製造
時にエポキシ樹脂と硬化剤とを１５０℃以上の温度で１
時間以と溶融混合しなければならないので作業条件とし
ても好ましいものではない。−か、特開昭５８−１７１
８号公報に開示さね、ているように溶剤系で製造する方
法もあるが、この方法では加工Ｖる際に溶剤除去工程が
必°要なことおＬび残存／８刑の樹脂組成物の物性−・
の影響等の点で問題が残っている。Conventionally, epoxy resin compositions have been mainly used as carbon fiber impregnating resins, and in particular when heat resistance is desired, diaminodiphenyl is added to an epoxy resin of tetraglycidyl diaminodiphenylmethane (TGDDM) as a curing agent. Epoquine resin compositions containing sulfone (DDS) have been widely used and developed. shi, kashi, gono r
cnoM/DDS-based epoxy resin compositions have excellent initial heat resistance and adhesion to carbon fibers, but they have drawbacks such as a significant decrease in heat resistance due to moisture absorption, extremely high hardness, and low elongation. . Furthermore, since the curing agent has a high melting point (approximately 180°C), the epoxy resin and the curing agent are combined at a temperature of 150°C or higher during the production of the resin composition.
Since melting and mixing must take place for a long time, the working conditions are not favorable. - Or, JP-A-58-171
There is also a method of manufacturing using a solvent system, as disclosed in Publication No. 8, but this method requires a solvent removal step during processing and leaves a residual resin composition. Physical properties of
Problems remain regarding the impact of
このように、従来のエポキシ樹脂組成物は、商い耐軌性
および２％以上の伸度を必要とする等の航空機用−次槽
造材としての用途には満足的なものではない。As described above, conventional epoxy resin compositions are not satisfactory for use as aircraft tank building materials, which require track resistance and elongation of 2% or more.
（発明の目的〕
本発明は、耐熱性、耐水性（特に吸湿後におけるガラス
転移点（Ｔｇ）の低下）、破断時の伸度に優れ、さらに
作業性が良い、高伸度カーボン繊維の含浸用として好適
なエポキシ樹脂組成物を提供することを目的とする。(Object of the invention) The present invention is an impregnated carbon fiber with high elongation, which has excellent heat resistance, water resistance (especially lowering of glass transition point (Tg) after moisture absorption), and elongation at break, and has good workability. The object of the present invention is to provide an epoxy resin composition suitable for use.
〔発明の構成〕
このため、本発明は、芳香族グリシジルアミンエポキシ
を５０重量％以上含んだエポキシ樹脂と、融点が１５０
℃以上の芳香族ジアミン化合物（ａ）と融点が１３０℃
以下の芳香族ジアミン化合物（ｂ）とを
５／９５≦ａ ／ ｂ≦７５／２５
（活性水素アミン当量比）
の範囲内で共溶融して得られる共溶融アミンからなり、
Ｒ＝Ｂ／Ａ
Ａ：配合物中におけるエポキシ樹脂中のエポキン基の政
Ｂ：配合物中における共溶融アミン中の活性水素の数
の場合に０．３ ≦Ｒ≦１．２であることを特徴とする
エポキシ樹脂組成物を要旨とするものである。[Structure of the Invention] Therefore, the present invention provides an epoxy resin containing 50% by weight or more of aromatic glycidylamine epoxy, and an epoxy resin having a melting point of 150% by weight or more.
Aromatic diamine compound (a) with a melting point of 130°C or higher
Consists of a co-melted amine obtained by co-melting the following aromatic diamine compound (b) within the range of 5/95≦a/b≦75/25 (active hydrogen amine equivalent ratio), R=B/A A: Characteristics of epoxy groups in the epoxy resin in the formulation B: Epoxy resin characterized in that the number of active hydrogens in the co-melted amine in the formulation is 0.3≦R≦1.2 The gist is the composition.
以上、本発明の構成について詳しく説明する。The configuration of the present invention will be described in detail above.
本発明においては、テトラグリシジルジアミノレフｌニ
ルメタン（ＴＧＤＤＭ） 、）リグリンジルｐ−アミン
フェノール等で代表される芳香族グリンジルアミンエボ
キシを５０重景％以上、好ましくは７０〜１６重看％の
範囲で含んだエポキシ樹脂を使用する。芳香族グリシジ
ルアミンエボキノ以外のエポキシ、例えば、ビスフェノ
ールＡタイプのエポキシ、ノボラックタイプのエポキシ
等のエポキシがエポキシ樹脂中に５０重７％以上含まれ
ると、芳香族グリシジルアミンエポキシの特徴である耐
熱性が悪くなると共にカーボン繊維との接着性が劣って
しまうからである。In the present invention, aromatic glycidylamine eboxy represented by tetraglycidyl diaminoreflenylmethane (TGDDM), ligrindyl p-amine phenol, etc. is contained in an amount of 50% or more, preferably in the range of 70 to 16%. Use epoxy resin containing When an epoxy other than aromatic glycidylamine epoxy, such as bisphenol A type epoxy or novolak type epoxy, is contained in an epoxy resin at a concentration of 50% or more by 7%, the heat resistance, which is a characteristic of aromatic glycidylamine epoxy, may deteriorate. This is because the adhesion to carbon fibers deteriorates as well.
また、本発明で用いる共溶融アミンとは、硬化剤であっ
て、融点が１５０℃以上の芳香族ジアミン（ａ）と融点
が１３０℃以下の芳香族ジアミン（ｂ）とを予め高融点
側のアミンの融点以上で溶融混合したものである。この
場合、高融点芳香族ジアミン（ａ）と低融点芳香族ジア
ミン（ｂ）との混合割合に適量範囲があり、それを逸脱
した場合には目的とする共溶融アミンは得られない。す
なわち、前記ａ／ｂの比が５／９５未満では硬化後の樹
脂の耐熱特性が不十分となり、逆に７５／２５を越える
場合には共溶融化の処理後の冷却時に高融点側のアミン
が析出し、均一な共溶融アミンが得られないからである
。Furthermore, the co-melting amine used in the present invention is a curing agent, in which an aromatic diamine (a) having a melting point of 150°C or higher and an aromatic diamine (b) having a melting point of 130°C or lower are pre-coated on the high melting point side. The amine is melted and mixed at a temperature higher than the melting point of the amine. In this case, there is a suitable range for the mixing ratio of the high melting point aromatic diamine (a) and the low melting point aromatic diamine (b), and if it deviates from this range, the desired co-molten amine cannot be obtained. That is, if the a/b ratio is less than 5/95, the heat resistance of the cured resin will be insufficient, and if it exceeds 75/25, the amine on the high melting point side will is precipitated, making it impossible to obtain a uniform co-molten amine.
ここで、融点が１５０℃以上の芳香族ジアミン（ａ）と
しては、例えば、３，３゛−ジアミノジフェニルスルホ
ン、４．４′−ジアミノジフェニルスルホン、４，４゛
−ジアミノジフェニルエーテル、３．３°−ジアミノア
ゾキシトルエン、４，４°−ビス（ρ−アミノフェノキ
シ）ジフェニルスルホン等に代表される芳香族ジアミン
化合物が挙げられろ。Here, examples of the aromatic diamine (a) having a melting point of 150° C. or higher include 3,3′-diaminodiphenylsulfone, 4,4′-diaminodiphenylsulfone, 4,4′-diaminodiphenyl ether, 3.3° Examples include aromatic diamine compounds represented by -diaminoazoxytoluene, 4,4°-bis(ρ-aminophenoxy)diphenylsulfone, and the like.
また、融点か日０゛Ｃ以下の芳香咋−アミン（ｂ）とし
ては、す１１えば、４．４’ −７’？ミノン゛−７１
丁−ニルメタン、３．．３’−ジクロル−４，４’ −
７了ミノジフエニルメタン ２，２゛−ジアミノシフ□
ニルジスルフィド トＩＩメチレン−ビス（４−アミノ
ヘンシェード、４．４”−ヒス（ｐ−アミノノエノキン
フェニル）プロパン等に代表される芳香族ジアミン化合
物が挙げられる。Further, as an aromatic amine (b) with a melting point of 0°C or less, for example, 4.4'-7'? Minon-71
D-nylmethane, 3. ．． 3'-dichloro-4,4'-
7. Minodiphenylmethane 2,2゛-diaminosif□
Examples include aromatic diamine compounds typified by nil disulfide, methylene-bis(4-aminohenshade, 4.4"-his(p-aminoenoquinphenyl)propane, etc.).
本発明のエポキシ樹脂組成物は、上記のエボキン樹脂と
Ｌ記の共溶融アミンとかニアなるもので、
Ｒ＝ Ｐ 、／ Ａ
の場合に０．３ ≦Ｒ≦１．２、好ましくは（１，５ｉ
Ｒ５１０のイＩＮを有するものである。The epoxy resin composition of the present invention is composed of the above-mentioned Evoquin resin and the co-melted amine of L, and when R=P, /A, 0.3≦R≦1.2, preferably (1, 5i
It has an IN of R510.
］二記式中、Ａは配合物中における工丁キ―／閘脂中の
エポキノ基の数を７Ｂは配合物中における共溶融アミン
中の活性水素の数をそれぞれ表わす。] In the two notation formulas, A represents the number of epochino groups in the mixture, and 7B represents the number of active hydrogens in the co-melted amine in the mixture.
１記式において、Ｒ＜０．３の場合には共溶融ア）ンの
計が過少となり、１）；、机ろＪげ訃、・（Ｍ指絹成物
の伸度が小さく、耐２に性 耐熱性の・ｊｉにおいて劣
ることになる。士な、Ｒ）１．２０陽合Ｃごは共溶融ア
ミンの贋が過剰となり、耐水性耐熱性の点において劣る
ので本発明の目的を達し得ない。In formula 1, when R<0.3, the total amount of co-melted A) is too small, and 1);, the elongation of the M finger silk composition is small, and The object of the present invention cannot be achieved because the co-melted amine is excessive and the co-melting amine is inferior in terms of water resistance and heat resistance. I don't get it.
なお、このエポキシ樹脂組成物には、必要に応じて２．
硬化促進剤等を添加してもよい。In addition, this epoxy resin composition may contain 2.
A curing accelerator or the like may be added.
〔発明の効果］
以と説明したように本発明のエボキン樹脂（ｌ′Ｎ成物
は、ヒ述したような配合内容のものζあるため、耐熱性
を１員なうことなく耐水性および破断伸びを改良でき
さらに、作刹性を大幅に１友片できるから、高伸（ｆｚ
カーボン繊維の含浸［１１とＬ７て好適であり、このた
め航空殿の−・次購曲材等の用途に極めて有用である。[Effects of the Invention] As explained below, the Evokin resin (l'N composition of the present invention has the formulation content as described in Can improve elongation
Furthermore, since the ease of construction can be greatly improved by one piece, Takashin (fz
Impregnation of carbon fibers [11 and L7] is suitable, and therefore extremely useful for applications such as aviation materials.
以下に実施例および比較例を示して本発明の効果を具体
的に説明する。 １実施例
１〜３、比較例１〜４
下記表−１に示す配合（配合量の数値は甲晒部を表わす
）の樹脂組成物を１８０°Ｃ１２時間硬化させ、得られ
る硬化物のせん断弾性率（Ｇ′。EXAMPLES The effects of the present invention will be specifically explained below with reference to Examples and Comparative Examples. 1 Examples 1 to 3, Comparative Examples 1 to 4 A resin composition of the formulation shown in Table 1 below (the numerical value of the blending amount represents the exposed part of the instep) was cured at 180°C for 12 hours, and the shear elasticity of the resulting cured product was rate (G'.
ａｔ１２１”ｃ）をＤＭＡ （Ｄｙｎａｍｉｃ Ｍｅｃ
ｈａｎｉｃａｌ＾ｎａＩｙｓｉｓ 、レオメトリックス
社製）により測定した。また、Ｔｇ （オリジナル）お
よび８０°Ｃ温水１０日’１９ ？ｌ後のＴｇをＴ Ｍ
Ａ ＜Ｔｈｅｒｍａｌ ＩＩｅｃｈａｎｉｃ、ａｌ
へｎａｌｙｓｉｓ、真空理工１掬製）シこより測定し、
さらに曲げ試験での歪みを測定した。これらの結果を下
記表−２に示す。at121”c) to DMA (Dynamic Mec
hanical^naIysis, manufactured by Rheometrics). Also, Tg (original) and 80°C heated water 10 days '19? Tg after l is T M
A <Thermal IIechanic, al
measurement,
Furthermore, the strain in the bending test was measured. These results are shown in Table 2 below.
なお、表−１における硬化剤Ａ、Ｂ、Ｃ１Ｄは、下記の
ように調製したものである。In addition, curing agents A, B, and C1D in Table 1 were prepared as follows.
■硬化剤Ａ：
４．４゛−ジアミノジフェニルスルホン（以下、ＤＤＳ
という）と３，３°−ジクロル−４，４゛−ジアミノジ
フェニルメタン（以下、ＭＯＣＡという）とを活性水素
アミン当量比でｔ／ｌの割合で、粉末を常温でトライブ
レンドする。■Curing agent A: 4.4゛-diaminodiphenylsulfone (hereinafter referred to as DDS
) and 3,3°-dichloro-4,4′-diaminodiphenylmethane (hereinafter referred to as MOCA) in an active hydrogen amine equivalent ratio of t/l, and the powders are triblended at room temperature.
ついで、得られる混合物を１８０°Ｃまで加温し、均一
な溶液になるまで攪拌混合するつ均一溶液になった後、
徐冷により常温まで冷却し、得られる融点１２０°Ｃの
共溶融アミンを硬化剤へと１−る。Then, the resulting mixture was heated to 180°C and stirred and mixed until it became a homogeneous solution.
The resulting co-molten amine having a melting point of 120° C. is slowly cooled to room temperature and converted into a curing agent.
■硬化剤Ｂ：
ＤＤＳと１，３−プロパンジオールジパうアミノへンゾ
エート（以下、ＣｕＡ４という）とを゛活性水素アミン
当量比でｌ／１９の割合で、（支）末を常温でトライブ
レンドする。■Curing agent B: Tri-blend DDS and 1,3-propanediol dipaminohenzoate (hereinafter referred to as CuA4) at room temperature at an active hydrogen amine equivalent ratio of 1/19. .
ついで、得られる混合物を１８０℃まで加温し、均一な
溶液になるまで撹拌混合する。吻−Ｉ容液になった後、
徐冷により常温まで冷却し、得られる融点１２５°Ｃの
共溶融アミンを硬化剤１３とする。The resulting mixture is then heated to 180° C. and stirred and mixed until a homogeneous solution is obtained. After becoming proboscis-I fluid,
The resulting co-molten amine having a melting point of 125° C. is used as the curing agent 13.
■硬化剤Ｃ：
４．４”−ジアミノジフェニルニーテルト４，４“−ジ
アミノジフェニルメタンとを゛活性水素アミン当量比で
３／１の割合で、粉末を常温でトライブレンドする。(2) Curing agent C: The powders are triblended with 4.4''-diaminodiphenylnitrate and 4,4''-diaminodiphenylmethane in an active hydrogen amine equivalent ratio of 3/1 at room temperature.
ついで、得られる混合物を１９５℃まで加温し、均一な
溶液になるまで撹拌混合する。均−曾容液になった後、
徐冷により常温まで冷却し、得られる融点１４２°Ｃの
共溶融アミンを硬化剤Ｃとする。The resulting mixture is then heated to 195° C. and stirred and mixed until a homogeneous solution is obtained. After becoming a homogeneous liquid,
The resulting co-molten amine having a melting point of 142° C. is used as a curing agent C.
■硬化剤Ｄ：
ＤＤＳとＣｕΔ−４とを活性水素アミン当量比で１／１
の割合で、粉末を常温でトライブレンドする。■Curing agent D: Active hydrogen amine equivalent ratio of DDS and CuΔ-4 is 1/1.
Tri-blend the powders at room temperature in the following proportions.
ついで、得られる混合物を１８０℃まで加温し、均一な
溶液になるまで撹拌混合する。均一溶液になった後、徐
冷により常温まで冷却し、得られる融点１３１ ’Ｃの
共溶融アミンを硬化剤りとする。The resulting mixture is then heated to 180° C. and stirred and mixed until a homogeneous solution is obtained. After it becomes a homogeneous solution, it is slowly cooled to room temperature, and the resulting co-molten amine with a melting point of 131'C is used as a curing agent.
（本頁以下余白）
上記表−２から明らかなように、本発明のエポキシ樹脂
組成物は、従来のものに比し、樹脂特性において優れて
いることが判る。すなわち、芳香族グリシジルアミンエ
ポキシを５０重量％以上含有するエーボキシ樹脂を用い
ているので、耐熱性、耐湿熱性、カーボン繊維との接着
性および破断伸びに優れ、かつ、硬化剤として共溶融ア
ミンを用いているので、比較的低温短時間で混合ができ
、大幅に作業性が向上する。(Blank below this page) As is clear from Table 2 above, the epoxy resin composition of the present invention is found to be superior in resin properties compared to conventional ones. That is, since an epoxy resin containing 50% by weight or more of aromatic glycidylamine epoxy is used, it has excellent heat resistance, moist heat resistance, adhesion to carbon fibers, and elongation at break, and also uses co-melted amine as a curing agent. This allows mixing at relatively low temperatures and in a short time, greatly improving work efficiency.
代理人 弁理士 小 川 信 − 野口賢照 斎下和彦Agent: Patent Attorney Nobuo Kogawa - Kenteru Noguchi Kazuhiko Saishita
Claims (1)
だエポキシ樹脂と、融点が１５０℃以上の芳香族ジアミ
ン化合物（ａ）と融点が１３０℃以下の芳香族ジアミン
化合物（ｂ）とを ５／９５≦ａ／ｂ≦７５／２５ （活性水素アミン当量比） の範囲内で共溶融して得られる共溶融アミンからなり、 Ｒ＝Ｂ／Ａ Ａ：配合物中におけるエポキシ樹脂中のエポキシ基の数 Ｂ：配合物中における共溶融アミン中の活性水素の数 の場合に０．３≦Ｒ≦１．２であることを特徴とするエ
ポキシ樹脂組成物。[Scope of Claims] An epoxy resin containing 50% by weight or more of aromatic glycidylamine epoxy, an aromatic diamine compound (a) having a melting point of 150°C or higher, and an aromatic diamine compound (b) having a melting point of 130°C or lower. 5/95≦a/b≦75/25 (active hydrogen amine equivalent ratio). Number of epoxy groups B: An epoxy resin composition characterized in that 0.3≦R≦1.2 in the case of the number of active hydrogens in the co-melted amine in the formulation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP582985A JPS61166826A (en) | 1985-01-18 | 1985-01-18 | Epoxy resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP582985A JPS61166826A (en) | 1985-01-18 | 1985-01-18 | Epoxy resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61166826A true JPS61166826A (en) | 1986-07-28 |
Family
ID=11621935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP582985A Pending JPS61166826A (en) | 1985-01-18 | 1985-01-18 | Epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61166826A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992007133A1 (en) * | 1990-10-23 | 1992-04-30 | Sumitomo Chemical Company, Limited | Process for producing aromatic polyamide fiber for rubber reinforcement |
| US5371153A (en) * | 1990-10-23 | 1994-12-06 | Sumitomo Chemical Company Limited | Polyamide fibers |
| WO2001042330A1 (en) | 1999-12-13 | 2001-06-14 | Mitsubishi Rayon Co., Ltd. | Epoxy resin composition and fiber-reinforced composite material formed with the epoxy resin composition |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59207920A (en) * | 1983-05-12 | 1984-11-26 | Toho Rayon Co Ltd | Heat-resistant epoxy resin composition |
| JPS606722A (en) * | 1984-04-11 | 1985-01-14 | Toray Ind Inc | Epoxy resin composition for carbon fiber prepreg |
-
1985
- 1985-01-18 JP JP582985A patent/JPS61166826A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59207920A (en) * | 1983-05-12 | 1984-11-26 | Toho Rayon Co Ltd | Heat-resistant epoxy resin composition |
| JPS606722A (en) * | 1984-04-11 | 1985-01-14 | Toray Ind Inc | Epoxy resin composition for carbon fiber prepreg |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992007133A1 (en) * | 1990-10-23 | 1992-04-30 | Sumitomo Chemical Company, Limited | Process for producing aromatic polyamide fiber for rubber reinforcement |
| US5371153A (en) * | 1990-10-23 | 1994-12-06 | Sumitomo Chemical Company Limited | Polyamide fibers |
| WO2001042330A1 (en) | 1999-12-13 | 2001-06-14 | Mitsubishi Rayon Co., Ltd. | Epoxy resin composition and fiber-reinforced composite material formed with the epoxy resin composition |
| EP1302495A4 (en) * | 1999-12-13 | 2004-08-25 | Mitsubishi Rayon Co | Epoxy resin composition and fiber-reinforced composite material formed with the epoxy resin composition |
| US6875825B2 (en) | 1999-12-13 | 2005-04-05 | Mitsubishi Rayon Co., Ltd. | Composition of bisphenol or novolak epoxy resin, epoxy resin from monoaromatic backbone and aromatic amine |
| US7230052B2 (en) | 1999-12-13 | 2007-06-12 | Mitsubishi Rayon Co., Ltd. | Epoxy resin composition and fiber reinforced composite material using epoxy resin composition |
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