JP2019048929A - 繊維強化複合材料用組成物、プリプレグ、及び繊維強化複合材料 - Google Patents
繊維強化複合材料用組成物、プリプレグ、及び繊維強化複合材料 Download PDFInfo
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- JP2019048929A JP2019048929A JP2017173053A JP2017173053A JP2019048929A JP 2019048929 A JP2019048929 A JP 2019048929A JP 2017173053 A JP2017173053 A JP 2017173053A JP 2017173053 A JP2017173053 A JP 2017173053A JP 2019048929 A JP2019048929 A JP 2019048929A
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
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- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- DLSMLZRPNPCXGY-UHFFFAOYSA-N tert-butylperoxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOOC(C)(C)C DLSMLZRPNPCXGY-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
また、本発明の他の目的は、上記の繊維強化複合材料用組成物を強化繊維に含浸させて形成され、高い耐熱性及び耐熱老化性を有する繊維強化複合材料を形成できるプリプレグを提供することにある。
さらに、本発明の他の目的は、高い耐熱性及び耐熱老化性を有する繊維強化複合材料を提供することにある。
耐熱老化性=a/b×100
[式中、aは240℃で100時間保管した後の曲げ強度(MPa)を示し、bは前記加熱保管前(初期)の曲げ強度(MPa)を示す。]
本発明の繊維強化複合材料用組成物(単に「本発明の組成物」と称する場合がある)は、一分子中にラジカル重合性基を2個以上有するラジカル重合性化合物(A)、一分子中にエポキシ基を2個以上有するエポキシ化合物(B)、アミン系硬化剤(C)、及びラジカル重合開始剤(D)を含む。
本発明の組成物における前記ラジカル重合性化合物(A)は、一分子中に2個以上のラジカル重合性基を有する化合物である。
[ラジカル重合性基の官能基当量]=[ラジカル重合性化合物(A)の分子量]/[ラジカル重合性化合物(A)が有するラジカル重合性基の数]
本発明の組成物における前記エポキシ化合物(B)は、一分子中にエポキシ基を2個以上有する化合物である。エポキシ化合物(B)は2個以上のエポキシ基を有するが、これらのエポキシ基はそれぞれ同一であってもよいし、異なっていてもよい。
[エポキシ基の官能基当量]=[エポキシ化合物(B)の分子量]/[エポキシ化合物(B)が有するエポキシ基の数]
本発明の組成物におけるアミン系硬化剤(C)は、エポキシ化合物(B)等のエポキシ基と反応することによって硬化性組成物を硬化させる働きを有する化合物である。本発明の組成物においてアミン系硬化剤(C)を使用することにより、高い耐熱性及び耐熱老化性を有する繊維強化複合材料を形成することができる。
本発明の組成物におけるラジカル重合開始剤(D)は、組成物における硬化性化合物(重合性基を有する化合物、特にラジカル重合性基及びカチオン重合性基のいずれか一方又は両方を有する化合物)の中でも、ラジカル重合性基を有する化合物(ラジカル重合性化合物(A)など)の重合反応(ラジカル重合反応)を開始させる化合物である。ラジカル重合開始剤(D)としては、公知乃至慣用のラジカル重合開始剤を使用することができ、特に限定されないが、例えば、熱ラジカル重合開始剤、光ラジカル重合開始剤などが挙げられる。
本発明の組成物は、硬化促進剤をさらに含んでいてもよい。硬化促進剤は、エポキシ化合物の反応(特に、エポキシ化合物(B)とアミン系硬化剤(C)との反応)を促進する機能を有する化合物である。
本発明の組成物は、ラジカル重合性化合物(A)、エポキシ化合物(B)以外の重合性化合物として、さらに、マレイミド化合物を含んでいてもよい。本発明の組成物がマレイミド化合物を含むことにより、硬化物や繊維強化複合材料の耐熱性、耐熱老化性がさらに向上する傾向があるため、好ましい。
本発明の組成物は、保存安定性(ポットライフ)を向上させることを目的として、重合安定剤を含有することが好ましい。重合安定剤は、ラジカル及び/又はカチオンをトラップすることにより、ラジカル重合及び/又はカチオン重合の進行を抑制して保存安定性(ポットライフ)を向上させ、加熱等することで重合安定剤が失活して硬化を進行させる化合物である。
耐熱老化性=a/b×100
[式中、aは240℃で100時間保管した後の曲げ強度(MPa)を示し、bは前記加熱保管前(初期)の曲げ強度(MPa)を示す。]
本発明の組成物を強化繊維(E)に含浸させることにより、プリプレグ(「本発明のプリプレグ」と称する場合がある)が形成される。即ち、本発明のプリプレグは、本発明の組成物と強化繊維(E)とを必須成分として含む。
[繊維強化複合材料用組成物の製造]
酸素7%、窒素93%の混気条件下、室温で、5Lのガラス製反応器に、トリシクロデカンジメタノールジアクリレート[ダイセル・オルネクス社製、商品名「IRR214−K」]を8000g、クレゾールノボラック型エポキシ樹脂[DIC社製、商品名「N−670−EXP−S」]を2500g、ジシクロペンタジエン型エポキシ樹脂[DIC社製、商品名「HP−7200」]を2500g、グリシジルアミン型エポキシ樹脂[Huntsman社製、商品名「Araldite(登録商標)MY0510」]を2000g、及びフィノチアジン[和光純薬工業社製]を7.5g入れ、95℃まで昇温させた。エポキシ樹脂が溶解したら、4,4’−ジアミノジフェニルスルホンを2040g、及び3,3’−ジアミノジフェニルスルホンを680g入れ110℃まで昇温した。固形分が溶解したら温度を下げて、樹脂配合物を取り出した。
得られた樹脂配合物177gに対して、ラジカル開始剤として1,1−ジ(t−ブチルパーオキシ)シクロヘキサン[日油社製、商品名「パーヘキサ(登録商標)C」]を0.28g入れて、自転公転型ミキサーで攪拌・混合することにより、繊維強化複合材料用組成物を得た。
[繊維強化複合材料用組成物の製造]
酸素7%、窒素93%の混気条件下、室温で10Lのガラス製反応器にトリシクロデカンジメタノールジアクリレート[ダイセル・オルネクス社製、商品名「IRR214−K」]を3000g、グリシジルアミン型エポキシ樹脂[Huntsman社製、商品名「Araldite(登録商標)MY0510」]を200g、及びフィノチアジン[和光純薬工業社製]を2.6g入れて、60℃に昇温させフィノチアジンを溶解させる。フィノチアジンが溶解したら、クレゾールノボラック型エポキシ樹脂[DIC社製、商品名「N−670−EXP−S」]を1600g入れ95℃まで昇温させた。N−670−EXP−Sが溶解したら、4,4’−ジフェニルメタンビスマレイミド[ケイ・アイ化成社製、商品名「BMI」]を200g、ビス(3−エチル−5−メチル−4−マレイミドフェニル)メタン[ケイ・アイ化成社製、商品名「BMI−70」]を200g、4,4’−ジアミノジフェニルスルホンを468g、及び3,3’−ジアミノジフェニルスルホンを156g入れ、110℃まで昇温した。固形分が溶解したら温度を下げて、樹脂配合物を取り出した。
得られた樹脂配合物292gに対して、ラジカル開始剤として1,1−ジ(t−ブチルパーオキシ)シクロヘキサン[日油社製、商品名「パーヘキサ(登録商標)C」]を0.48g入れて、自転公転型ミキサーで攪拌・混合することにより、繊維強化複合材料用組成物を得た。
[繊維強化複合材料用組成物の製造]
酸素7%、窒素93%の混気条件下、室温で10Lのガラス製反応器にトリシクロデカンジメタノールジアクリレート[ダイセル・オルネクス社製、商品名「IRR214−K」]を3000g、ビスフェノールA型エポキシ樹脂[新日鉄住金社製、商品名「YD8125」]を200g、及びフィノチアジン[和光純薬工業社製]を2.6g入れて、60℃に昇温させフィノチアジンを溶解させる。フィノチアジンが溶解したら、クレゾールノボラック型エポキシ樹脂[DIC社製、商品名「N−670−EXP−S」]を1600g入れ95℃まで昇温させた。N−670−EXP−Sが溶解したら、4,4’−ジフェニルメタンビスマレイミド[ケイ・アイ化成社製、商品名「BMI」]を200g、ビス(3−エチル−5−メチル−4−マレイミドフェニル)メタン[ケイ・アイ化成社製、商品名「BMI−70」]を200g、4,4’−ジアミノジフェニルスルホンを468g、及び3,3’−ジアミノジフェニルスルホンを156g入れ110℃まで昇温した。固形分が溶解したら温度を下げて、樹脂配合物を取り出した。
得られた樹脂配合物292gに対して、ラジカル開始剤として1,1−ジ(t−ブチルパーオキシ)シクロヘキサン[日油社製、商品名「パーヘキサ(登録商標)C」]を0.48g入れて、自転公転型ミキサーで攪拌・混合することにより、繊維強化複合材料用組成物を得た。
[繊維強化複合材料用組成物の製造]
酸素5%、窒素95%の混気条件下、室温で3Lのガラス製反応器にトリシクロデカンジメタノールジアクリレート[ダイセル・オルネクス社製、商品名「IRR214−K」]を500g、とフィノチアジン[和光純薬工業社製]を0.5g入れて、65℃に昇温した。フィノチアジンが溶解したら、ジシクロペンタジエン型エポキシ樹脂[DIC社製、商品名「HP−7200」]を250g入れ溶解させた。溶解後、クレゾールノボラック型エポキシ樹脂[DIC社製、商品名「N−670−EXP−S」]を250g入れ75℃まで昇温させた。エポキシ樹脂が溶解したら温度を下げて、樹脂配合物を取り出した。
得られた樹脂配合物100gに対して、ラジカル開始剤として1,1−ジ(t−ブチルパーオキシ)シクロヘキサン[日油社製、商品名「パーヘキサ(登録商標)C」]を0.28gと酸発生剤[三新化学工業社製、商品名「サンエイドSI−100L」]を1.0g入れて、自転公転型ミキサーで攪拌・混合することにより、繊維強化複合材料用組成物を得た。
実施例及び比較例で得られた繊維強化複合材料用組成物及び硬化物について、以下の評価を行った。
実施例及び比較例で得られた繊維強化複合材料用組成物の40℃における粘度(mPa・s)を、該組成物を調製した直後(調製後1時間以内)に測定した(初期粘度)。また、上記繊維強化複合材料用組成物を調製後、40℃の環境下で3日間(72時間)保管した後、40℃における粘度(mPa・s)を測定した(40℃72時間後粘度)。「組成物の40℃72時間保管後の粘度上昇率(%)」を下記式から算出した。
(組成物の40℃72時間保管後の粘度上昇率)=(40℃72時間後粘度)/(初期粘度)×100
結果を表1の「40℃72時間保管後の粘度上昇率」の欄に示す。なお、粘度の測定装置、測定条件は下記の通りである。
<測定装置及び測定条件>
測定装置:粘度測定装置(商品名「TV−22H」、東機産業社製)
測定温度:40℃
ローター:1°34’×R24
回転数:1.0rpm
実施例及び比較例で得られた硬化物(厚み:0.5mm)を幅4mm、長さ3cmに切り出し、これをサンプルとして使用した。
上記で得たサンプルの動的粘弾性測定(DMA)を、下記の条件で実施した。
<測定装置及び測定条件>
測定装置:固体粘弾性測定装置(DMS6100(株式会社日立ハイテクサイエンス[旧エスアイアイ・ナノテクノロジー株式会社]))
雰囲気:窒素
温度範囲:25〜350℃
昇温温度:5℃/分
変形モード:引っ張りモード
上記動的粘弾性測定で測定されたE’(貯蔵弾性率)の変曲点の温度を硬化物のガラス転移温度(E’−Tg)として求めた。結果を表1の「E’−Tg」の欄に示した。
実施例及び比較例で得られた硬化物(厚さ4mm×幅10mm×長さ80mm)を240℃のオーブンに保管して、初期(0hr)、48時間後(48hr)、100時間後(100hr)のサンプルについて、テンシロン万能試験機((株)オリエンテック製)を使用して、エッジスパン:67mm、曲げ速度2mm/分の条件で、3点曲げ試験を行うことにより、硬化物の曲げ強度(MPa)、曲げ弾性率(MPa)、及び曲げ伸度(%GL)を測定した。結果を表2−1(実施例1)、表2−2(実施例2)、表2−3(実施例3)、表2−4(比較例1)に示した。表2−1〜2−4中のカッコは、初期(0hr)対する比率(%)で示したものである。
また、表1及び表2−1〜2−4に示すように、本発明の繊維強化複合材料用組成物を硬化させて得られた硬化物は、高いガラス転移温度、耐熱老化性を有していた。
[ラジカル重合性化合物(A)]
IRR214−K:ジメチロールジシクロペンタンジアクリレート(ダイセル・サイテック社製、分子量:304、一分子中のアクリロイル基の数:2個、官能基当量:152)
[エポキシ化合物(B)]
HP−7200:ジシクロペンタジエン型エポキシ樹脂(DIC社製、官能基当量:250−280)
N−670−EXP−S:オルソクレゾールノボラック型エポキシ樹脂(DIC社製、官能基当量:200−210)
MY0510:グリシジルアミン型エポキシ樹脂(Huntsman社製、官能基当量:95−106)
YD8125:ビスフェノールA型エポキシ樹脂(新日鉄住金化学社製、官能基当量:168−178)
[アミン系硬化剤(C)]
p−DDS:4,4’−ジアミノジフェニルスルホン
m−DDS:3,3’−ジアミノジフェニルスルホン
[ラジカル重合開始剤(D)]
パーヘキサC:1,1−ジ(t−ブチルパーオキシ)シクロヘキサン(日油社製;10時間半減期分解温度:90.7℃)
[マレイミド化合物]
BMI:4,4’−ジフェニルメタンビスマレイミド(ケイ・アイ化成社製)
BMI−70:ビス(3−エチル−5−メチル−4−マレイミドフェニル)メタン(ケイ・アイ化成社製)
[酸発生剤]
SI−100L:サンエイドSI−100L(芳香族スルホニウム塩;三新化学工業社製;示差走査型熱量測定装置(DSC)を用いて昇温速度10℃/分で測定した際の発熱開始温度:124.1℃)
[重合安定剤]
PTZ:フィノチアジン(和光純薬工業社製)
Claims (17)
- 一分子中にラジカル重合性基を2個以上有するラジカル重合性化合物(A)、一分子中にエポキシ基を2個以上有するエポキシ化合物(B)、アミン系硬化剤(C)、及びラジカル重合開始剤(D)を含むことを特徴とする繊維強化複合材料用組成物。
- 前記アミン系硬化剤(C)の含有量が、エポキシ化合物(B)100重量部に対して、20〜200重量部である請求項1に記載の繊維強化複合材料用組成物。
- 前記ラジカル重合性化合物(A)とエポキシ化合物(B)の割合(重量比)[(A)/(B)]が0/100より大きく且つ80/20以下である請求項1又は2に記載の繊維強化複合材料用組成物。
- 前記ラジカル重合開始剤(D)の含有量が、ラジカル重合性化合物(A)とエポキシ化合物(B)の総量100重量部に対して、0.01〜10重量部である請求項1〜3のいずれか一項に記載の繊維強化複合材料用組成物。
- 前記ラジカル重合性化合物(A)が環状構造を有する化合物である請求項1〜4のいずれか一項に記載の繊維強化複合材料用組成物。
- 前記ラジカル重合性化合物(A)がトリシクロデカン骨格を有する化合物である請求項1〜5のいずれか一項に記載の繊維強化複合材料用組成物。
- 前記エポキシ化合物(B)が環状構造を有する化合物である請求項1〜6のいずれか一項に記載の繊維強化複合材料用組成物。
- 前記エポキシ化合物(B)がトリシクロデカン骨格を有する化合物である請求項1〜7のいずれか一項に記載の繊維強化複合材料用組成物。
- さらに、マレイミド化合物を含有する請求項1〜8のいずれか一項に記載の繊維強化複合材料用組成物。
- さらに、重合安定剤を含有する請求項1〜9のいずれか一項に記載の繊維強化複合材料用組成物。
- 調製後1時間以内で測定される40℃の粘度(初期粘度)に対する、40℃で72時間保管した場合の40℃の粘度の上昇率が200%以下である請求項1〜10のいずれか一項に記載の繊維強化複合材料用組成物。
- 硬化して得られる硬化物のガラス転移温度(E’−Tg)が195℃以上である請求項1〜11のいずれか一項に記載の繊維強化複合材料用組成物。
- 硬化して得られる硬化物の下記式により算出される耐熱老化性が68%以上である請求項1〜12のいずれか一項に記載の繊維強化複合材料用組成物。
耐熱老化性=a/b×100
[式中、aは240℃で100時間保管した後の曲げ強度(MPa)を示し、bは前記加熱保管前(初期)の曲げ強度(MPa)を示す。] - 請求項1〜13のいずれか一項に記載の繊維強化複合材料用組成物を強化繊維(E)に含浸させたプリプレグ。
- 強化繊維(E)の含有率(Wf)が50〜90重量%である請求項14に記載のプリプレグ。
- 強化繊維(F)が、炭素繊維、ガラス繊維、及びアラミド繊維からなる群より選択される少なくとも一種である請求項14又は15に記載のプリプレグ。
- 請求項14〜16のいずれか一項に記載のプリプレグを硬化させた繊維強化複合材料。
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JP7437306B2 (ja) | 2018-08-31 | 2024-02-22 | 株式会社Adeka | 組成物、これを含有する接着剤、その硬化物およびその製造方法 |
CN114605770A (zh) * | 2022-03-28 | 2022-06-10 | 吉林重通成飞新材料股份公司 | 一种新型聚环戊二烯纤维复合材料及其制备方法 |
CN114605597A (zh) * | 2022-03-28 | 2022-06-10 | 吉林重通成飞新材料股份公司 | 具有后固化与高表面活性的聚环戊二烯复合材料及其制备方法 |
CN114605770B (zh) * | 2022-03-28 | 2023-05-09 | 吉林重通成飞新材料股份公司 | 一种聚环戊二烯纤维复合材料及其制备方法 |
CN114605597B (zh) * | 2022-03-28 | 2023-06-02 | 吉林重通成飞新材料股份公司 | 具有后固化与高表面活性的聚环戊二烯复合材料及其制备方法 |
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