JPH03227316A - Heat-resistant epoxy resin composition - Google Patents
Heat-resistant epoxy resin compositionInfo
- Publication number
- JPH03227316A JPH03227316A JP2043390A JP2043390A JPH03227316A JP H03227316 A JPH03227316 A JP H03227316A JP 2043390 A JP2043390 A JP 2043390A JP 2043390 A JP2043390 A JP 2043390A JP H03227316 A JPH03227316 A JP H03227316A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- pts
- weight
- parts
- resin composition
- 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 30
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 30
- 239000000203 mixture Substances 0.000 title claims abstract description 16
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims abstract description 8
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims description 4
- 239000004918 carbon fiber reinforced polymer Substances 0.000 abstract description 8
- 239000011159 matrix material Substances 0.000 abstract description 5
- 229920005989 resin Polymers 0.000 abstract description 5
- 239000011347 resin Substances 0.000 abstract description 5
- 239000004593 Epoxy Substances 0.000 abstract description 3
- 229920000049 Carbon (fiber) Polymers 0.000 description 7
- 239000004917 carbon fiber Substances 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011151 fibre-reinforced plastic Substances 0.000 description 3
- 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 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 239000012783 reinforcing fiber Substances 0.000 description 3
- 238000005452 bending Methods 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
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Landscapes
- Reinforced Plastic Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Abstract
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は耐熱性エポキシ樹脂組成物に関する。[Detailed description of the invention] [Industrial application field] The present invention relates to a heat-resistant epoxy resin composition.
さらに詳細には炭素繊維強化プラスチック（ＣＦＲＰ）
等の繊維強化プラスチックのマトリックス樹脂として用
いられる耐熱性エポキシ樹脂組成物に関する。More details: Carbon fiber reinforced plastic (CFRP)
The present invention relates to a heat-resistant epoxy resin composition used as a matrix resin for fiber-reinforced plastics such as.
［従来の技術］
ＣＦＲＰはその軽量性、高剛性等の特徴を生かし、ゴル
フシャフトやテニスラケットなどのスポーツ・レジャー
用品、航空機の構造材、スピーカーコーン等の用途にお
いて、産業上広く用いられている。[Conventional technology] Taking advantage of its light weight and high rigidity, CFRP is widely used industrially for sports and leisure goods such as golf shafts and tennis rackets, aircraft structural materials, and speaker cones. .
ＣＦＲＰのマトリックス樹脂としては炭素繊維との接着
性に優れるビスフェノールＡ型エポキシ樹脂等のエポキ
シ樹脂が用いられているが、従来より用いられているエ
ポキシ樹脂は耐熱性に劣るためＣＦＲＰの使用温度範囲
が低いという課題があった。Epoxy resins such as bisphenol A epoxy resins, which have excellent adhesion to carbon fibers, are used as matrix resins for CFRP.However, the epoxy resins that have been used in the past have poor heat resistance, so the operating temperature range of CFRP is limited. The problem was that it was low.
［発明が解決しようとする課題］
本発明らは易成形性に優れ、かつ耐熱性に優れたエポキ
シ樹脂組成物を提供することを目的とし、このことにつ
いて研究した結果、本発明を完成した。[Problems to be Solved by the Invention] The present inventors aimed to provide an epoxy resin composition with excellent moldability and heat resistance, and as a result of research on this subject, they completed the present invention.
［課題を解決するための手段］
すなわち、
本発明は、
（Ｂ）ビスフェノールＦ型エポキシ樹脂を７５〜２０重
量部、および
（ｅ）ジアミノジフェニルスルホンを前記（Ａ）および
（Ｂ）の総量１００重量部に対して２５〜５０重量部、
を必須成分として含有するエポキシ樹脂組成物に関する
。[Means for Solving the Problems] That is, the present invention comprises (B) 75 to 20 parts by weight of a bisphenol F type epoxy resin, and (e) diaminodiphenylsulfone in a total amount of 100 parts by weight of the above (A) and (B). 25 to 50 parts by weight,
The present invention relates to an epoxy resin composition containing as an essential component.
本発明においてエポキシ樹脂成分として用いられる成分
（Ａ）および成分（Ｂ）の配合割合は、成分（Ａ）：成
分（Ｂ）が２５〜８０重量部ニア５〜２０重量部である
ことがが好ましく、より好ましくは３０〜７０重量部ニ
ア０〜３０重量部である。The blending ratio of component (A) and component (B) used as the epoxy resin component in the present invention is preferably 25 to 80 parts by weight, 5 to 20 parts by weight of component (A):component (B). , more preferably 30 to 70 parts by weight, preferably 0 to 30 parts by weight.
成分（Ａ）が２５重量部より少ないとＣＦＲＰとしての
耐熱性が不充分であり、一方８０重量部より多くなると
、エポキシ樹脂成分の粘度が高くなりすぎて炭素繊維等
の繊維束への含浸が困難となる。If component (A) is less than 25 parts by weight, the heat resistance as CFRP is insufficient, while if it is more than 80 parts by weight, the viscosity of the epoxy resin component becomes too high, making it difficult to impregnate fiber bundles such as carbon fibers. It becomes difficult.
本発明において硬化剤として用いられる成分（Ｃ）の配
合割合は成分（Ａ）および（Ｂ）の総量１００重量部に
対して、通常２５〜５０重量部、好ましくは３０〜４５
重量部である。The blending ratio of component (C) used as a curing agent in the present invention is usually 25 to 50 parts by weight, preferably 30 to 45 parts by weight, based on 100 parts by weight of the total amount of components (A) and (B).
Parts by weight.
本発明における成分（Ａ）の例としては、Ｔａｃｔｉｘ
７４２（ダウケミカル日本−製）が挙げられる。Examples of component (A) in the present invention include Tactix
742 (manufactured by Dow Chemical Japan).
また成分（Ｂ）の例としてはＹＤＰ １７０ （東部
化成観製）、エピコート８０７（油化シェルエポキシ■
製）、エピクロン８３０（大日本インキ■製）、エボミ
ック １１４（三井石油化学■製）、アデカレジ：／４
９００（旭電化■製） 、ＸＤ−７８１８（ダウケミカ
ル日本■製）が挙げられる。Examples of component (B) include YDP 170 (manufactured by Tobu Kaseikan Co., Ltd.), Epicoat 807 (Yuka Shell Epoxy ■
), Epicron 830 (manufactured by Dainippon Ink ■), Evomic 114 (manufactured by Mitsui Petrochemical ■), Adecare: /4
900 (manufactured by Asahi Denka ■) and XD-7818 (manufactured by Dow Chemical Japan ■).
成分（Ｃ）のジアミノジフェニルスルホンとしては、４
．４°−ジアミノジフェニルスルホンおよび３゜３°−
ジアミノジフェニルスルホンのいずれも使用できる。The diaminodiphenylsulfone of component (C) is 4
．． 4°-diaminodiphenylsulfone and 3°3°-
Any of the diaminodiphenylsulfones can be used.
本発明のエポキシ樹脂組成物においては、その性能を損
わない範囲で他のエポキシ樹脂を配合することかできる
。例えばビスフェノールＡ型エポキシ樹脂、フェノール
ノボラック型エポキシ樹脂、クレゾールノボラック型エ
ポキシ樹脂、グリシジルアミン型エポキシ樹脂、脂環式
エポキシ樹脂、臭素化エポキシ樹脂を挙げることができ
る。In the epoxy resin composition of the present invention, other epoxy resins can be blended within a range that does not impair its performance. Examples include bisphenol A type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, glycidylamine type epoxy resin, alicyclic epoxy resin, and brominated epoxy resin.
また成分（Ｃ）の硬化剤の他、必要に応じ他の硬化剤、
硬化促進剤を配合することもできる。これらの例として
、ジシアンジアミド、ＢＦ３ Φアミン錯体、３− （
３，４−ジクロロフェニル−１，１’ジメチルウレア等
の尿素誘導体を挙げることができる。In addition to the curing agent of component (C), other curing agents may be used as necessary.
A curing accelerator can also be blended. Examples of these include dicyandiamide, BF3 Φ amine complex, 3-(
Urea derivatives such as 3,4-dichlorophenyl-1,1' dimethylurea can be mentioned.
本発明のエポキシ樹脂組成物は炭素繊維等を強化繊維と
する繊維強化プラスチックのマトリックス樹脂として用
いられる。The epoxy resin composition of the present invention is used as a matrix resin for fiber-reinforced plastics whose reinforcing fibers are carbon fibers or the like.
強化繊維としては炭素繊維が好ましく用いられるが、ア
ラミド繊維、ガラス繊維、アルミナ繊維、シリコーンカ
ーバイド繊維、チタン酸カリウム繊維、ボロン繊維、ポ
リエチレン繊維等の各種繊維も用いられる。Carbon fibers are preferably used as reinforcing fibers, but various fibers such as aramid fibers, glass fibers, alumina fibers, silicone carbide fibers, potassium titanate fibers, boron fibers, and polyethylene fibers can also be used.
本発明のエポキシ樹脂組成物は強化繊維束への含浸性に
優れており、かつ高耐熱性の繊維強化プラスチックを製
造することができる。The epoxy resin composition of the present invention has excellent impregnation properties into reinforcing fiber bundles, and can produce highly heat-resistant fiber-reinforced plastics.
なお、本発明のエポキシ樹脂組成物には必要に応じてポ
リエーテルスルホン、ポリエーテルイミド、ポリスルホ
ン、ポリフェニレンサルファイド等のエンジニャリング
プラスチックを添加して、マトリックス樹脂として用い
ることも可能である。It is also possible to add engineering plastics such as polyether sulfone, polyetherimide, polysulfone, polyphenylene sulfide, etc. to the epoxy resin composition of the present invention, if necessary, and use it as a matrix resin.
［実施例コ
以下に実施例等を挙げ本発明を具体的に説明するが本発
明はこれらに制限されるものではない。[Example] The present invention will be specifically described below with reference to Examples, but the present invention is not limited thereto.
実施例１
エポキシ樹脂成分（Ａ）としてＴａｃｔｌｘ ７４２
（ダウケミカル日本■製）８０重量部、成分（Ｂ）とし
てＹＤＰ１７０（東部化成■製）４０重量部および成分
（Ｃ）として４．４′−ジアミノジフェニルスルホン８
４重量部を１３０℃で１時間混合し、エポキシ樹脂組成
物を得た。Example 1 Tactlx 742 as epoxy resin component (A)
(manufactured by Dow Chemical Japan ■), 40 parts by weight of YDP170 (manufactured by Tobu Kasei ■) as component (B), and 8 parts by weight of 4,4'-diaminodiphenylsulfone as component (C).
4 parts by weight were mixed at 130°C for 1 hour to obtain an epoxy resin composition.
このエポキシ樹脂組成物を１８０℃で２時間、次いで２
５０℃で２時間硬化してガラス転移点を測定したところ
２９０℃であった。なお、ガラス転移点はセイコー電子
■製のＤ Ｓ Ｃ２００で測定した。This epoxy resin composition was heated at 180°C for 2 hours, then 2 hours.
After curing at 50°C for 2 hours, the glass transition point was measured and found to be 290°C. The glass transition point was measured using DSC200 manufactured by Seiko Electronics.
上記エポキシ樹脂組成物を、引張強さ３５０に’Ｊ／１
１１１１Ｊ２、引張弾性率２３ｔ／ｓｇ＋２の炭素繊維
に含浸し一方向ブリブレグを作製した（Ｖｆは６０ｖｏ
１％）。The above epoxy resin composition was heated to a tensile strength of 350'J/1.
1111J2 and a tensile modulus of 23t/sg+2 were impregnated into carbon fiber to produce a unidirectional blob leg (Vf was 60vo
1%).
このプリプレグを積層して１８０℃で２時間、次いで２
５０℃で２時間硬化させた後のＣＦＲＰ板の引張強さは
２０ＯＮｇ／ｍ２、引張弾性率は１３．５ｔ／ｍ２ 曲
げ強さは２０５Ｎｇ／ｍ２ 曲げ弾性率は１３．４ｔ
／ｍ２、圧縮強度は１３０Ｋｙ／ｍ２、圧縮弾性率は１
３．２ｔ／履２１ＬＳＳは１２Ｎｇ／ｓ＋２であった。This prepreg was laminated and heated at 180°C for 2 hours, then 2 hours.
After curing at 50°C for 2 hours, the tensile strength of the CFRP board is 20ONg/m2, the tensile modulus is 13.5t/m2, the bending strength is 205Ng/m2, and the bending modulus is 13.4t.
/m2, compressive strength is 130Ky/m2, compressive modulus is 1
3.2t/21LSS was 12Ng/s+2.
実施例２〜３および比較例１〜２
実施例１において成分（Ａ）および（Ｂ）の配合割合を
変え、実施例１と同様の方法でガラス転移点を測定した
。この結果を第１表に示す。Examples 2 to 3 and Comparative Examples 1 to 2 The glass transition point was measured in the same manner as in Example 1, except that the proportions of components (A) and (B) were changed. The results are shown in Table 1.
第
表
第１表から明らかなように、成分（＾）および（Ｂ）が
本発明で規定する範囲から外れる比較例１ではガラス転
移温度が低く、また比較例２ではガラス転移温度は高い
もののエポキシ樹脂組成物としての粘度が著しく高いた
め炭素繊維束への含浸が不可能であった。As is clear from Table 1, Comparative Example 1 in which components (^) and (B) are outside the range specified by the present invention has a low glass transition temperature, and Comparative Example 2 has a high glass transition temperature, but the epoxy Since the viscosity of the resin composition was extremely high, it was impossible to impregnate carbon fiber bundles.
比較例３
実施例１においてビスフェノールＦ型エポキシ樹脂に代
え、ビスフェノールＡ型エポキシ樹脂を用いてエポキシ
樹脂組成物を作製したが、常温で固体であり、炭素繊維
束への含浸は著しく困難であるばかりか、プリプレグに
必要なタックは全くなかった。Comparative Example 3 In Example 1, an epoxy resin composition was prepared using a bisphenol A epoxy resin instead of the bisphenol F epoxy resin, but it was solid at room temperature and it was extremely difficult to impregnate carbon fiber bundles. Or there was no tack required for prepreg at all.
Claims (1)
数式、化学式、表等があります▼（Ｂ）ビスフェノール
Ｆ型エポキシ樹脂を７５〜２０重量部、および （Ｃ）ジアミノジフェニルスルホンを前記（Ａ）および
（Ｂ）の総量１００重量部に対して２５〜５０重量部、
を必須成分として含有するエポキシ樹脂組成物。[Claims] (A) 25 to 80 parts by weight of a compound represented by the following formula, ▲
There are mathematical formulas, chemical formulas, tables, etc. ▼ (B) 75 to 20 parts by weight of bisphenol F type epoxy resin, and (C) 25 to 20 parts by weight of diaminodiphenylsulfone per 100 parts by weight of the total amount of (A) and (B). 50 parts by weight,
An epoxy resin composition containing as an essential component.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2043390A JPH03227316A (en) | 1990-02-01 | 1990-02-01 | Heat-resistant epoxy resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2043390A JPH03227316A (en) | 1990-02-01 | 1990-02-01 | Heat-resistant epoxy resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03227316A true JPH03227316A (en) | 1991-10-08 |
Family
ID=12026912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2043390A Pending JPH03227316A (en) | 1990-02-01 | 1990-02-01 | Heat-resistant epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03227316A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6620510B1 (en) | 1998-12-25 | 2003-09-16 | Mitsubishi Rayon Co., Ltd. | Epoxy resin composition, prepreg, and roll made of resin reinforced with reinforcing fibers |
| JP2011132332A (en) * | 2009-12-24 | 2011-07-07 | Mitsubishi Rayon Co Ltd | Epoxy resin composition |
| JP2016523313A (en) * | 2013-06-28 | 2016-08-08 | スリーエム イノベイティブ プロパティズ カンパニー | High modulus epoxy adhesive for shim processing applications |
-
1990
- 1990-02-01 JP JP2043390A patent/JPH03227316A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6620510B1 (en) | 1998-12-25 | 2003-09-16 | Mitsubishi Rayon Co., Ltd. | Epoxy resin composition, prepreg, and roll made of resin reinforced with reinforcing fibers |
| JP2011132332A (en) * | 2009-12-24 | 2011-07-07 | Mitsubishi Rayon Co Ltd | Epoxy resin composition |
| JP2016523313A (en) * | 2013-06-28 | 2016-08-08 | スリーエム イノベイティブ プロパティズ カンパニー | High modulus epoxy adhesive for shim processing applications |
| JP2018123336A (en) * | 2013-06-28 | 2018-08-09 | スリーエム イノベイティブ プロパティズ カンパニー | High elasticity epoxy adhesive for shim treatment application |
| US10059862B2 (en) | 2013-06-28 | 2018-08-28 | 3M Innovative Properties Company | High modulus epoxy adhesives for shimming applications |
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