JP7268355B2 - エポキシ樹脂組成物、プリプレグおよび繊維強化複合材料 - Google Patents
エポキシ樹脂組成物、プリプレグおよび繊維強化複合材料 Download PDFInfo
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- JP7268355B2 JP7268355B2 JP2018555289A JP2018555289A JP7268355B2 JP 7268355 B2 JP7268355 B2 JP 7268355B2 JP 2018555289 A JP2018555289 A JP 2018555289A JP 2018555289 A JP2018555289 A JP 2018555289A JP 7268355 B2 JP7268355 B2 JP 7268355B2
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- LSSWPDUBLAOHKT-UHFFFAOYSA-N 4-(4-nitrophenoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(N(CC2OC2)CC2OC2)C=C1 LSSWPDUBLAOHKT-UHFFFAOYSA-N 0.000 description 1
- YXFXYFVEDLLAOJ-UHFFFAOYSA-N 4-(4-tert-butylphenoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1=CC=C(N(CC2OC2)CC2OC2)C=C1 YXFXYFVEDLLAOJ-UHFFFAOYSA-N 0.000 description 1
- AHIPJALLQVEEQF-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1COC(C=C1)=CC=C1N(CC1OC1)CC1CO1 AHIPJALLQVEEQF-UHFFFAOYSA-N 0.000 description 1
- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 description 1
- GTYAMROJMXVPHD-UHFFFAOYSA-N 4-methyl-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1=CC(C)=CC=C1N(CC1OC1)CC1OC1 GTYAMROJMXVPHD-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
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- HDCSPSHJBICITE-UHFFFAOYSA-N NC1=C(C=CC=C1)C(C1=C(C=CC=C1)N)[PH2]=O Chemical compound NC1=C(C=CC=C1)C(C1=C(C=CC=C1)N)[PH2]=O HDCSPSHJBICITE-UHFFFAOYSA-N 0.000 description 1
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- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- IWZNWGDJJJKIOC-UHFFFAOYSA-N bis(3-aminophenyl)methyl-oxidophosphanium Chemical compound NC=1C=C(C=CC1)C(C1=CC(=CC=C1)N)[PH2]=O IWZNWGDJJJKIOC-UHFFFAOYSA-N 0.000 description 1
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- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
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- AZHPCFQBBJISDG-UHFFFAOYSA-N ethyl(oxido)phosphanium Chemical compound CC[PH2]=O AZHPCFQBBJISDG-UHFFFAOYSA-N 0.000 description 1
- 238000009730 filament winding Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
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- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
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- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VQUBWUABRWJYCR-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)-4-(3-phenoxyphenoxy)aniline Chemical compound C1OC1CN(C=1C=CC(OC=2C=C(OC=3C=CC=CC=3)C=CC=2)=CC=1)CC1CO1 VQUBWUABRWJYCR-UHFFFAOYSA-N 0.000 description 1
- SQQCTLWZEJJCNB-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)-4-(4-phenoxyphenoxy)aniline Chemical compound C1OC1CN(C=1C=CC(OC=2C=CC(OC=3C=CC=CC=3)=CC=2)=CC=1)CC1CO1 SQQCTLWZEJJCNB-UHFFFAOYSA-N 0.000 description 1
- GJIHJADPBSMNFZ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)-4-(4-phenylphenoxy)aniline Chemical compound C1OC1CN(C=1C=CC(OC=2C=CC(=CC=2)C=2C=CC=CC=2)=CC=1)CC1CO1 GJIHJADPBSMNFZ-UHFFFAOYSA-N 0.000 description 1
- VJOHYQMELJCMGX-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)-4-(4-propylphenoxy)aniline Chemical compound C1=CC(CCC)=CC=C1OC1=CC=C(N(CC2OC2)CC2OC2)C=C1 VJOHYQMELJCMGX-UHFFFAOYSA-N 0.000 description 1
- ZPEMUYUJMFRLFL-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)-4-[2-(trifluoromethyl)phenoxy]aniline Chemical compound FC(F)(F)C1=CC=CC=C1OC1=CC=C(N(CC2OC2)CC2OC2)C=C1 ZPEMUYUJMFRLFL-UHFFFAOYSA-N 0.000 description 1
- HPQDXWHEPFWTFQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)-4-[3-(trifluoromethyl)phenoxy]aniline Chemical compound FC(F)(F)C1=CC=CC(OC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=C1 HPQDXWHEPFWTFQ-UHFFFAOYSA-N 0.000 description 1
- NJPMKWAHFMFMTF-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)-4-[4-(trifluoromethyl)phenoxy]aniline Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1=CC=C(N(CC2OC2)CC2OC2)C=C1 NJPMKWAHFMFMTF-UHFFFAOYSA-N 0.000 description 1
- SJPFBRJHYRBAGV-UHFFFAOYSA-N n-[[3-[[bis(oxiran-2-ylmethyl)amino]methyl]phenyl]methyl]-1-(oxiran-2-yl)-n-(oxiran-2-ylmethyl)methanamine Chemical compound C1OC1CN(CC=1C=C(CN(CC2OC2)CC2OC2)C=CC=1)CC1CO1 SJPFBRJHYRBAGV-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
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- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000013001 point bending Methods 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Epoxy Resins (AREA)
- Reinforced Plastic Materials (AREA)
Description
(構成1)下記成分[A]~[C]を全て含むエポキシ樹脂組成物。
[A]:下記一般式(1)で表される構造を有し、25℃における粘度が2Pa・s以下である反応性希釈剤
[B]:3官能以上のエポキシ樹脂
[C]:下記一般式(2)で表される構造を有するアミン系硬化剤および下記一般式(3)で表される構造を有するアミン系硬化剤からなる群から選ばれる少なくとも1つのアミン系硬化剤
(構成2)下記成分[A’]、成分[B]、成分[C’]を全て含み、エポキシ樹脂総量100質量部に対して、成分[A’]の含有量が10~50質量部、成分[B]の含有量が50~90質量部である、エポキシ樹脂組成物。
[A’]:4員環以上の環構造を1つ以上有する2官能以下のグリシジルアミン型エポキシ樹脂
[B]:3官能以上のエポキシ樹脂
[C’]:下記一般式(5)で表される構造を有するアミン系硬化剤および下記一般式(6)で表される構造を有するアミン系硬化剤からなる群から選ばれる少なくとも1つのアミン系硬化剤
また、本発明のプリプレグは、上記のエポキシ樹脂組成物を強化繊維に含浸させてなるプリプレグである。
[A]:下記一般式(1)で表される構造を有し、25℃における粘度が2Pa・s以下である反応性希釈剤
[B]:3官能以上のエポキシ樹脂
[C]:下記一般式(2)で表される構造を有するアミン系硬化剤および下記一般式(3)で表される構造を有するアミン系硬化剤からなる群から選ばれる、少なくとも1つのアミン系硬化剤
[A’]:4員環以上の環構造を1つ以上有する2官能以下のグリシジルアミン型エポキシ樹脂
[B]:3官能以上のエポキシ樹脂
[C’]:下記一般式(5)で表される構造を有するアミン系硬化剤および下記一般式(6)で表される構造を有するアミン系硬化剤からなる群から選ばれる、少なくとも1つのアミン系硬化剤。
本発明の(構成1)の実施例および比較例において用いられた材料を次に示す。
・N,N-ジグリシジル-p-フェノキシアニリン(PxGAN、東レファインケミカル(株)製)
・N,N-ジグリシジル-o-トルイジン(GOT、日本化薬(株)製)
・1,4-シクロヘキサンジメタノールジグリシジルエーテル(“デナコール(登録商標)”EX-216L、ナガセケムテックス(株)製)。
・1,4-ブタンジオールジグリシジルエーテル(“デナコール(登録商標)”EX-214L、ナガセケムテックス(株)製)。
・テトラグリシジルジアミノジフェニルメタン(“アラルダイト(登録商標)”MY721、ハンツマン・アドバンスト・マテリアルズ社製)
<成分[C]:前記一般式(2)または(3)で表される構造を有するアミン系硬化剤>
・トリス(3-アミノフェニル)ホスフィンオキサイド(片山化学工業(株)製)
・ビス(3-アミノフェニル)n-ブチルホスフィンオキサイド(片山化学工業(株)製)。
・3,3’-ジアミノジフェニルスルホン(小西化学(株)製)。
・ポリエーテルスルホン(“VIRANTAGE(登録商標)”VW-10700RFP、Solvay Advanced Polymers社製)。
本発明の(構成2)の実施例および比較例において用いられた材料を次に示す。
・N,N-ジグリシジルアニリン(GAN、日本化薬(株)製)
・N,N-ジグリシジル-p-フェノキシアニリン(PxGAN、東レファインケミカル(株)製)。
・ビスフェノールF型エポキシ樹脂(“EPICLON(登録商標)”830、DIC(株)製)。
・テトラグリシジルジアミノジフェニルメタン(“アラルダイト(登録商標)”MY721、ハンツマン・アドバンスト・マテリアルズ社製)
・テトラグリシジルジアミノジフェニルメタン(“スミエポキシ(登録商標)”ELM434、住友化学(株)製)
・トリグリシジル(p-アミノフェノール)(“アラルダイト(登録商標)”MY510、ハンツマン・アドバンスト・マテリアルズ社製)。
・トリス(3-アミノフェニル)ホスフィンオキサイド(片山化学工業(株)製)
・ビス(3-アミノフェニル)n-ブチルホスフィンオキサイド(片山化学工業(株)製)。
・4,4’-ジアミノジフェニルスルホン(セイカキュアS、和歌山精化工業(株)製)
・3,3’-ジアミノジフェニルスルホン(小西化学(株)製)。
・ポリエーテルスルホン(“スミカエクセル(登録商標)”PES5003P、住友化学(株)製)
・ポリエーテルスルホン(“VIRANTAGE(登録商標)”VW-10700RFP、Solvay Advanced Polymers社製)。
混練装置中に、表1~4に記載の成分[A](あるいは[A’])に該当するエポキシ樹脂、成分[A](あるいは[A’])以外のエポキシ樹脂、および成分[B]に該当するエポキシ樹脂、成分[D]に該当する熱可塑性樹脂を投入後、加熱混練を行い、熱可塑性樹脂を溶解させた。次いで、80℃以下の温度まで降温させ、表1~4に記載の成分[C](あるいは[C’])および成分[C](あるいは[C’])以外の硬化剤を加えて撹拌し、エポキシ樹脂組成物を得た。
樹脂組成物の粘度安定性評価は以下の様にして行った。
熱重量測定TGAによる難燃性の評価は以下の様にして行った。
(1)で調製したエポキシ樹脂組成物を真空中で脱泡した後、2mm厚の“テフロン(登録商標)”製スペーサーにより厚み2mmになるように設定したモールド中で、所定の硬化条件で硬化させて、厚さ2mmのエポキシ樹脂硬化物を得た。難燃性の評価は熱重量測定装置TG-DTA(ブルカーAXS社WS003システム)を用いて行った。エポキシ樹脂硬化物から約10mgの試験片を切り出し、昇温速度10℃/minで単純昇温し、650℃におけるチャー生成率(%)を難燃性の指標とした。ここでいうチャー生成率とは、(650℃における熱分解残渣の質量(g))/(測定前のエポキシ樹脂硬化物の質量(g))×100で表される値である。
樹脂硬化物の力学特性の評価は以下の様にして行った。
(3)で作製したエポキシ樹脂硬化物を10mm×60mmのサイズにカットした試験片の3点曲げ試験をJIS K7171(2006)に基づいて行い、力学特性を評価した。インストロン5565万能試験機(インストロン社製)を用いて、クロスヘッドスピード2.5mm/min、スパン長40mm、圧子径10mm、支点径4mmの条件で曲げ試験を行い、曲げ弾性率を測定した。
各成分を表1~4に示すとおりの比率(質量部)で用いて、上記(1)エポキシ樹脂組成物の調製方法により、エポキシ樹脂組成物の調製を行った。得られた樹脂組成物の粘度安定性評価を行った。また、180℃の温度で2時間硬化させて得られた樹脂硬化物の難燃性評価、力学特性評価を行った。評価結果は表1~4のとおりであった。
Claims (14)
- 下記成分[A]~[C]を全て含むエポキシ樹脂組成物。
[A]:下記一般式(4)、(7)、および(8)からなる群から選択される一般式で表される構造を有し、25℃における粘度が2Pa・s以下である反応性希釈剤
[B]:3官能以上のエポキシ樹脂
[C]:下記一般式(2)で表される構造を有するアミン系硬化剤および下記一般式(3)で表される構造を有するアミン系硬化剤からなる群から選ばれる少なくとも1つのアミン系硬化剤
- エポキシ樹脂総量100質量部に対して、成分[A]の含有量が10~50質量部、成分[B]の含有量が50~90質量部である、請求項1に記載のエポキシ樹脂組成物。
- さらに成分[D]熱可塑性樹脂を含む、請求項1~3のいずれかに記載のエポキシ樹脂組成物。
- 樹脂硬化物の空気下650℃におけるチャー生成率が1%以上30%以下であり、かつ、80℃2時間後の増粘率が7%以上51%以下である、請求項1~4のいずれかに記載のエポキシ樹脂組成物。
- 成分[A]が一般式(4)で表される構造を有し、成分[C]が一般式(3)で表される構造を有し、全エポキシ樹脂組成物中のリン濃度が0.3質量%~4.0質量%である、請求項1~5のいずれかに記載のエポキシ樹脂組成物。
- 成分[C]がトリス(3-アミノフェニル)ホスフィンオキシドである、請求項6に記載のエポキシ樹脂組成物。
- 樹脂硬化物の空気下650℃におけるチャー生成率が3%以上25%以下であり、かつ、80℃2時間後の増粘率が7%以上29%以下である、請求項7に記載のエポキシ樹脂組成物。
- 成分[D]がポリエーテルスルホンである、請求項4~8のいずれかに記載のエポキシ樹脂組成物。
- ポリエーテルスルホンが末端水酸基を有し、重量平均分子量が21000g/molである、請求項9に記載のエポキシ樹脂組成物。
- ポリエーテルスルホンが、“VIRANTAGE(登録商標)”VW-10700RFPである、請求項9に記載のエポキシ樹脂組成物。
- 請求項1~11のいずれかに記載のエポキシ樹脂組成物を強化繊維に含浸させてなるプリプレグ。
- 請求項12に記載のプリプレグを硬化させてなる繊維強化複合材料。
- 請求項1~11のいずれかに記載のエポキシ樹脂組成物を硬化させてなる樹脂硬化物と、強化繊維とを含む繊維強化複合材料。
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