JP5681328B2 - エポキシ−アミン付加物、樹脂組成物、サイジング剤、サイジング剤塗布炭素繊維、及び繊維強化複合材料 - Google Patents
エポキシ−アミン付加物、樹脂組成物、サイジング剤、サイジング剤塗布炭素繊維、及び繊維強化複合材料 Download PDFInfo
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- JP5681328B2 JP5681328B2 JP2014515568A JP2014515568A JP5681328B2 JP 5681328 B2 JP5681328 B2 JP 5681328B2 JP 2014515568 A JP2014515568 A JP 2014515568A JP 2014515568 A JP2014515568 A JP 2014515568A JP 5681328 B2 JP5681328 B2 JP 5681328B2
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- RANDTSYDUPETTO-UHFFFAOYSA-M tetrabutylphosphanium;tetradecanoate Chemical compound CCCCCCCCCCCCCC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC RANDTSYDUPETTO-UHFFFAOYSA-M 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- VNXUJPCYZSNXDG-UHFFFAOYSA-N thiopyran-4-one Chemical group O=C1C=CSC=C1 VNXUJPCYZSNXDG-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- UONOETXJSWQNOL-UHFFFAOYSA-N tungsten carbide Chemical compound [W+]#[C-] UONOETXJSWQNOL-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical group CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
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Description
また、本発明の他の目的は、反応性が高く、樹脂と強化繊維の密着性に優れた繊維強化複合材料を形成できる樹脂組成物を提供することにある。
さらに、本発明の他の目的は、樹脂と強化繊維の密着性に優れ、高い機械物性(例えば、強靭性)を有する繊維強化複合材料を提供することにある。
さらに、本発明の他の目的は、炭素繊維の高次加工性を向上させることができ、また、炭素繊維とマトリックス樹脂の接着性を向上させることができるサイジング剤を提供することにある。
さらに、本発明の他の目的は、高次加工性に優れ、かつ炭素繊維とマトリックス樹脂の接着性に優れたサイジング剤塗布炭素繊維及び該サイジング剤塗布炭素繊維を含む繊維強化複合材料を提供することにある。
本発明のエポキシ−アミン付加物は、分子内に2個以上のアミノ基を有するエポキシ−アミン付加物であって、分子内に2個以上の脂環式エポキシ基を有するエポキシ化合物(A)(単に「エポキシ化合物(A)」と称する場合がある)と、分子内に2個以上のアミノ基を有するアミン化合物(B)(単に「アミン化合物(B)」と称する場合がある)との反応により得られるエポキシ−アミン付加物である。より詳しくは、本発明のエポキシ−アミン付加物は、エポキシ化合物(A)が有する脂環式エポキシ基と、アミン化合物(B)が有するアミノ基とを反応させて得られる、分子内に2個以上のアミノ基を有するエポキシ−アミン付加物である。なお、本明細書においては、単に「アミノ基」という場合には−NH2(無置換アミノ基)を意味するものとし、「−NH−基」には当該無置換アミノ基(−NH2)は含まれないものとする。
本発明のエポキシ−アミン付加物の原料(前駆体)であるエポキシ化合物(A)は、分子内に2個以上の脂環式エポキシ基を有するポリエポキシ化合物(脂環式エポキシ化合物)である。なお、本明細書における「脂環式エポキシ基」とは、脂環(脂肪族環)を構成する隣接する2つの炭素原子と、酸素原子とで構成されるエポキシ基を意味する。
本発明のエポキシ−アミン付加物の原料(前駆体)であるアミン化合物(B)は、分子内に2個以上のアミノ基(−NH2;無置換アミノ基)を有するポリアミン化合物である。アミン化合物(B)が分子内に有するアミノ基の数は2個以上であればよく、特に限定されないが、2〜6個が好ましく、より好ましくは2〜5個、さらに好ましくは2個又は3個である。アミノ基の数が6個を超えると、エポキシ化合物(A)との反応で生成するエポキシ−アミン付加物の他の成分に対する配合が困難となる場合がある。
本発明のエポキシ−アミン付加物は、エポキシ化合物(A)とアミン化合物(B)とを反応させることにより製造できる。より具体的には、エポキシ化合物(A)が有する脂環式エポキシ基と、アミン化合物(B)が有するアミノ基とを反応させることにより、本発明のエポキシ−アミン付加物が生成する。
本発明のエポキシ−アミン付加物と、公知乃至慣用の樹脂とを配合(混合)することにより、樹脂組成物(「本発明の樹脂組成物」と称する場合がある)が得られる。上記樹脂としては、特に限定されないが、例えば、ポリオレフィン(例えば、ポリエチレン、ポリプロピレン、ポリブタジエンなど)、ビニル系重合体(例えば、アクリル樹脂、ポリスチレンなど)、ポリアミド(例えば、ナイロン6、ナイロン66、ナイロン11、ナイロン12、ナイロン610、ナイロン612、ナイロン61、ナイロン6T、ナイロン9Tなど)、ポリエステル(例えば、ポリエチレンテレフタレート、ポリブチレンテレフタレート)、ポリ塩化ビニル、ポリ塩化ビニリデン、ポリカーボネート、ポリアセタール、ポリフェニレンオキサイド、ポリフェニレンサルファイド、ポリエーテルスルホン、ポリエーテルエーテルケトンなどの熱可塑性樹脂;エポキシ樹脂、不飽和ポリエステル、ビニルエステル樹脂、アリル樹脂(例えば、ジアリルフタレート樹脂など)、フェノール樹脂、ポリイミド、シアネート樹脂、マレイミド樹脂、ユリア樹脂、メラミン樹脂、シリコーン樹脂などの硬化性樹脂(硬化性化合物)(例えば、熱硬化性樹脂(熱硬化性化合物)、光硬化性樹脂(光硬化性化合物)など)などが挙げられる。但し、上記「樹脂」には本発明のエポキシ−アミン付加物は含まれない。なお、本発明の樹脂組成物において上記樹脂は1種を単独で使用することもできるし、2種以上を組み合わせて使用することもできる。
本発明のエポキシ−アミン付加物は、上述のように、強化繊維の表面に存在する水酸基、カルボキシル基、エポキシ基などの官能基に対する反応性が高く、繊維強化複合材料における樹脂と強化繊維の密着性を効果的に向上させることができるため、サイジング剤(特に、炭素繊維用サイジング剤)としても好ましく使用することができる。なお、サイジング剤とは、強化繊維の製造工程や、高次加工工程(織物工程、プリプレグ工程、その他の成形工程)での取り扱い性を向上させるために強化繊維に塗布(塗工)される処理剤であり、収束剤と称される場合もある。本明細書においては、本発明のエポキシ−アミン付加物を含むサイジング剤を「本発明のサイジング剤」と称する場合がある。
本発明のサイジング剤を炭素繊維に塗布(塗工)することによって、サイジング剤塗布炭素繊維(「本発明のサイジング剤塗布炭素繊維」と称する場合がある)が得られる。
エポキシ化合物(A)として、3,4−エポキシシクロヘキシルメチル(3,4−エポキシ)シクロヘキサンカルボキシレート[(株)ダイセル製、商品名「セロキサイド2021P」]を使用し、アミン化合物(B)として、アミン末端ポリプロピレングリコール[HUNTSMAN社製、商品名「JEFFAMINE D−230」]を使用した。
表1に示すように、上述のエポキシ化合物(A)30.0重量部と、アミン化合物(B)35.9重量部とを混合し、その後、160℃で2時間攪拌しながら反応させることにより、エポキシ−アミン付加物(アミンアダクト)を得た。
得られたエポキシ−アミン付加物の性状(評価結果)を表1に示す。また、図3には、得られたエポキシ−アミン付加物の1H−NMRスペクトルのチャートを示す。また、上記で得られたエポキシ−アミン付加物を、ラボプラストミルによりポリカーボネートと溶融混合することにより、プレス成形可能な樹脂組成物が得られることを確認した。
エポキシ化合物(A)として、3,4−エポキシシクロヘキシルメチル(3,4−エポキシ)シクロヘキサンカルボキシレート[(株)ダイセル製、商品名「セロキサイド2021P」]を使用し、アミン化合物(B)として、アミン末端ポリプロピレングリコール[HUNTSMAN社製、商品名「JEFFAMINE D−230」]を使用した。
表1に示すように、上述のエポキシ化合物(A)20.0重量部と、アミン化合物(B)34.6重量部とを混合し、その後、160℃で2時間攪拌しながら反応させることにより、エポキシ−アミン付加物を得た。なお、得られたエポキシ−アミン付加物は水溶性を有していた。
得られたエポキシ−アミン付加物の性状(評価結果)を表1に示す。また、図4には、得られたエポキシ−アミン付加物の1H−NMRスペクトルのチャートを示す。また、上記で得られたエポキシ−アミン付加物を、ラボプラストミルによりポリカーボネートと溶融混合することにより、プレス成形可能な樹脂組成物が得られることを確認した。
ビスフェノールA型エポキシ樹脂[新日鐵化学(株)製、商品名「エポトートYD128」]30.0重量部、及びアミン末端ポリプロピレングリコール[HUNTSMAN社製、商品名「JEFFAMINE D−230」]41.3重量部を混合し、その後、160℃で2時間攪拌させることによって両成分を反応させた。その結果、熱可塑性を有しない樹脂が得られた。
実施例で得られたエポキシ−アミン付加物について、下記の評価を実施した。
実施例で得られたエポキシ−アミン付加物のガラス転移温度(Tg)を、示差走査熱量計(DSC)[セイコーインスツルメント(株)製]で測定した。なお、測定条件は、昇温速度:10℃/分、測定温度:−50〜250℃、スキャン回数:2回とした。なお、ガラス転移温度は、2回目のスキャンで得られたDSC曲線より求めた。結果を表1に示す。
実施例で得られたエポキシ−アミン付加物の70℃における粘度を、E型粘度計[「TV−22」、東機産業(株)製]にて測定した(測定温度:70℃)。結果を表1に示す。
また、実施例2で得られたエポキシ−アミン付加物については、25℃における粘度、45℃における粘度も同様に測定した。結果を表1に示す。
実施例1で得られたエポキシ−アミン付加物を溶離液(30mM臭化リチウムを添加したジメチルホルムアミド(DMF))に溶解させた後、0.45μmメンブレンフィルターでろ過したもの(ろ液)を分子量の測定サンプルとして用いた。上記測定サンプルを用い、エポキシ−アミン付加物の重量平均分子量(Mw)、数平均分子量(Mn)、ピークトップ分子量(Mp)、分子量分布(Mw/Mn)を測定した。結果を表1に示す。なお、上記分子量(Mw、Mn、Mp)は、標準ポリスチレン換算の値として求めた。
これに対して、比較例で得られた樹脂は熱可塑性を有しないため、他の成分との混合が困難なものであった。
実施例1で得られたエポキシ−アミン付加物をエタノールと水の混合液(エタノール6%)に均一に溶解させ、該エポキシ−アミン付加物の含有量が約2重量%の溶液(サイジング剤)を得た(即ち、実施例1で得られたエポキシ−アミン付加物は上記混合液に対する溶解性を有していた)。このサイジング剤を浸漬法により、表面処理された炭素繊維に塗布した後、210℃の温度で90秒間熱処理をした。その後、続いて、ビスフェノールA型エポキシ樹脂[新日鐵化学(株)製、商品名「エポトートYD128」]に浸漬し、100℃で30分間処理したところ、タックの無い炭素繊維束(サイジング剤塗布炭素繊維束)が得られた。
[エポキシ化合物]
セロキサイド2021P:3,4−エポキシシクロヘキシルメチル(3,4−エポキシ)シクロヘキサンカルボキシレート、(株)ダイセル製
エポトートYD−128:ビスフェノールA型エポキシ樹脂、新日鐵化学(株)製
[アミン化合物]
JEFFAMINE D−230:アミン末端ポリプロピレングリコール、HUNTSMAN社製
Claims (8)
- 請求項1に記載のエポキシ−アミン付加物と、熱可塑性樹脂とを含む樹脂組成物。
- 繊維強化複合材料用樹脂組成物である請求項2に記載の樹脂組成物。
- 請求項3に記載の樹脂組成物を強化繊維に含浸又は塗工して得られるプリプレグ。
- 請求項4に記載のプリプレグより形成される繊維強化複合材料。
- 請求項1に記載のエポキシ−アミン付加物を含むサイジング剤。
- 請求項6に記載のサイジング剤を炭素繊維に塗布して得られるサイジング剤塗布炭素繊維。
- 請求項7に記載のサイジング剤塗布炭素繊維と、熱可塑性樹脂又は硬化性化合物を硬化させて得られる硬化物とを含む繊維強化複合材料。
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WO2015151348A1 (ja) * | 2014-04-04 | 2015-10-08 | 株式会社ダイセル | エポキシ-アミン付加物、熱可塑性樹脂組成物、サイジング剤、サイジング剤塗布炭素繊維、及び繊維強化複合材料 |
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WO2016209796A1 (en) * | 2015-06-23 | 2016-12-29 | Arkema Inc. | Water soluble polymers and polymeric adducts along with aqueous solutions thereof |
US10733911B2 (en) | 2015-10-14 | 2020-08-04 | Humanetics Innovative Solutions, Inc. | Three-dimensional ribs and method of three-dimensional printing of ribs for crash test dummy |
JP7083641B2 (ja) * | 2017-12-28 | 2022-06-13 | 株式会社ダイセル | 有機繊維用サイジング剤、有機繊維、織物、及び積層物 |
CN110258118B (zh) * | 2019-07-12 | 2021-07-13 | 开封大学 | 水溶性耐温型碳纤维上胶剂及其制备方法 |
CN111058187B (zh) * | 2019-12-27 | 2021-03-19 | 中南大学 | 一种附着界面层的SiC纤维预浸带的制备方法及设备 |
KR102648969B1 (ko) * | 2023-08-30 | 2024-03-19 | 주식회사 하이퍼콘 | 바닥난방을 위한 발열 탄소시멘트 복합체 조성물 및 이의 제조방법 |
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US9777135B2 (en) | 2017-10-03 |
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US20150111994A1 (en) | 2015-04-23 |
TWI585121B (zh) | 2017-06-01 |
US20160369087A1 (en) | 2016-12-22 |
EP3287478A1 (en) | 2018-02-28 |
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