JP2021508748A - 硬化性エポキシ系 - Google Patents
硬化性エポキシ系 Download PDFInfo
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- JP2021508748A JP2021508748A JP2020534592A JP2020534592A JP2021508748A JP 2021508748 A JP2021508748 A JP 2021508748A JP 2020534592 A JP2020534592 A JP 2020534592A JP 2020534592 A JP2020534592 A JP 2020534592A JP 2021508748 A JP2021508748 A JP 2021508748A
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- Prior art keywords
- epoxy system
- curable epoxy
- curing
- fiber
- curable
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
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- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
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Abstract
Description
適用なし
本開示は一般に、航空宇宙産業を含む様々な産業で使用されることができる複合材の生産に有用な硬化性エポキシ系(curable epoxy system)に関する。特に本開示は、(i)ビスフェノールCジグリシジル エーテル、ビスフェノールCジグリシジル エーテルの1もしくは複数の誘導体、およびそれらの組み合わせから選択されるエポキシ成分;および(ii)9,9−ビス(4−アミノ−3−クロロフェニル)フルオレンを含んでなる硬化性エポキシ系に関する。また本開示は、硬化性繊維強化型エポキシ系、およびそれらから生成される複合材に関する。
硬化性エポキシ化合物は、種々の成分と混合されて硬化性エポキシ系を形成することができ、これは硬化した時にグリーンエネルギー、スポーツ用品、電子部品、建設、自動車、および航空宇宙のような無数の産業で使用できる複合材を形成する。そのような硬化性エポキシ系は、多くの応用に有用なコーティングまたは強化型発泡体を形成するためにも使用することができる。
本開示の少なくとも1つの態様を詳細に説明する前に、本開示はその応用を以下の記載で説明する構成要素または工程または方法論の構成および配置の詳細に限定されないと理解されるべきである。本開示は他の態様、または様々な方法で実施または実行することが可能である。また本明細書で採用する表現法および用語法は、説明を目的とするものであり、限定と見なすべきではないと理解される。
。
えば示差走査熱量測定法(DSC)を使用して測定され、そしてグラム当たりジュールの単位(J/g)で表される。当該技術分野では、硬化エンタルピーは硬化性組成物が硬化中に経験する、特に硬化サイクルが短縮化されるような温度発熱の可能性に直接的に相関し得ることが知られている。硬化性エポキシ系の最大硬化温度を越える温度発熱は、硬化性エポキシ系、生じる複合材、および恐らくは硬化した時に存在する基材および型を損傷する恐れがある。
R9−R20は存在せず、そしてR1−R4の1もしくは複数が水素ではなく、そして式中、R1−R20はそれぞれ水素、ハロゲン、ヒドロキシル、アルコキシ、直鎖脂肪族、分岐脂肪族、環式脂肪族、置換脂肪族、非置換脂肪族、飽和脂肪族,不飽和脂肪族、芳香族、多芳香族、置換脂肪族、ヘテロ芳香族、アミン、一級アミン、二級アミン、三級アミン、脂肪族アミン、カルボニル、カルボキシル、アミド、エステル、アミノ酸、ペプチド、ポリペプチド、およびそれらの組み合わせから独立して選択される。
満、または200J/g未満の硬化エンタルピーを有する。別の態様では、硬化性エポキシ系は、150J/gから300 J/g、または175J/gから300J/g、または200J/gから300J/gまたは200J/gから250J/gの範囲の硬化エンタルピーを有する。
0℃から200℃、または約170℃から約190℃、または約175℃から約185℃の設定硬化温度で、約1時間から4時間、または約1.5時間から約2.5時間、または約1.75時間から約2.25時間の範囲の時間、または約2時間加熱することを含んでなる。
きる。トウは一般に、3から7mmの幅を有し、そして櫛を使用してトウを保持し、そしてトウを平行かつ一方向に維持する装置での含浸に供給される。
比較(“Comp.”)実施例1−1Eは、以下の表2に示す成分を使用して配合した。各比較実施例1−1Eについて、エポキシをAradur(登録商標)9664−1硬化剤と1:1の化学量論的重量比で、23℃で5分間、均一な混合物が得られるまで混合した。各化合物の量(グラムで)を表2に与える。
比較実施例2−2Bおよび実施例2Cは、以下の表4に示す成分を使用して配合した。各比較実施例2−2Bについて、ビスフェノールCグリシジル エーテル(“BCDGE”)を、Aradur(登録商標)9664−1硬化剤、Aradur(登録商標)9719−1硬化剤、またはAradur(登録商標)5200US硬化剤のいずれかと、1:1の化学量論的重量比で23℃にて5分間、均一な混合物が得られるまで混合した。実施例2Cは硬化剤として9,9−ビス(4−アミノ−3−クロロフェニル)フルオレン(CAF)を使用した点を除き、同じ手順に従った。各成分の量を表4に提供する(グラムで)。
表6は、プリプレグを形成するために使用した比較実施例3および実施例3Aに関する配合を説明する。表6の成分はグラムで提供される。
プリプレグ実施例のILSSは、ASTM D2344を使用していた。
プリプレグ実施例に関する引張強さ、モジュラスおよび歪は、ASTM D3039を使用して測定した。
プリプレグ実施例に関する圧縮強さおよびモジュラスは、ASTM D695を使用して測定した。
プリプレグ実施例に関するCAI強さおよびモジュラス測定値は、ASTM D7136およびASTM D7137を使用して得た。
実施例3Aおよび比較実施例3の予測可能な硬化挙動を評価するために、実施例3Aおよび比較実施例3を注入した炭素繊維系部品のシミュレーションを、以下の式を使用して行った:
比較実施例3および実施例3Aを含み、そして15mmの厚さおよび60%の繊維体積画分を含有する炭素繊維系部品を評価した。各サンプルは180℃で2時間の硬化プロファイル、および表9に特定する異なる硬化ランプ速度を使用して評価した。
一性で硬化できると予想されることを示す。
比較実施例3よび実施例3Aを含み、厚さ15mmおよび60%、55%および50%の間で変動する繊維画分体積を有する炭素繊維系部品を評価した。各サンプルは180℃で2時間の硬化プロファイルおよび3℃/分の硬化ランプ速度を使用して評価した。各サンプルについて測定した5つのパラメーターを以下の表10で説明する。
比較実施例3よび実施例3Aを含み、そして5から55mmの間で変動する厚さ、および60%の繊維画分体積を含有する炭素繊維系部品を評価した。180℃で2時間の硬化スケジュールおよび1℃/分の硬化ランプ速度を、5および15mmの厚さを有する部品に使用した(すなわちサンプル8および9)。2回の一時停止(dwell)を含む硬化プロファイルを、30および50の厚さの部品に使用した(すなわちサンプル10および11):150℃で3時間、続いて180℃で2時間、および1℃/分の硬化ランプ速度。各サンプルについて測定した5つのパラメーターを、以下の表11に説明する。
施例3では6.8から59.3℃へのオーバーシュートが予想され、一方、実施例3Aでのオーバーシュートはわずか2.7から16.7℃である。
Claims (18)
- ビスフェノールCジグリシジル エーテル、ビスフェノールCジグリシジル エーテルの1もしくは複数の誘導体、およびそれらの組み合わせから選択されるエポキシ成分;および9,9−ビス(4−アミノ−3−クロロフェニル)フルオレンを含んでなる硬化性エポキシ系。
- さらに少なくとも1つの樹脂成分、およびアミン、無水物、ポリオールおよびそれらの組み合わせから選択される硬化剤を含んでなる請求項1に記載の硬化性エポキシ系。
- 硬化剤が、1,3−ジアミノベンゼン、1,4−ジアミノベンゼン、4,4’ジアミノジフェニルメタン、4,4’−ジアミノジフェニル スルホン、4−アミノフェニル スルホン、3,3’−ジアミノジフェニル スルホン、4,4’−メチレンビス(3−クロロ−2,6−ジエチルアニリン)、4,4’−メチレンビス(2,6−ジエチルアニリン)およびそれらの組み合わせから選択される芳香族アミンである請求項2に記載の硬化性エポキシ系。
- さらに熱可塑性粒子、軟化剤、強化剤、促進剤、コアシェルゴム、湿潤剤、難燃剤、顔料または染料、可塑剤、UV吸収剤、粘性調整剤、およびそれらの組み合わせから選択される少なくとも1つの添加剤を含んでなる請求項1に記載の硬化性エポキシ系。
- エポキシ成分と9,9−ビス(4−アミノ−3−クロロフェニル)フルオレンの合わせた量が、硬化性エポキシ系の重量に基づき40重量%より多い請求項1に記載の硬化性エポキシ系。
- 硬化性エポキシ系が、300J/g未満の硬化エンタルピー、および190℃より高いガラス転移温度を有する請求項1ないし5のいずれか1項に記載の硬化性エポキシ系。
- 請求項1ないし5のいずれか1項に記載の硬化性エポキシ系を、100℃から220℃の範囲の設定硬化温度で、少なくとも部分的に硬化した複合材を生成するために十分な時間加熱することを含んでなる複合材の生成法。
- 設定硬化温度が、硬化性エポキシ系を環境温度から0.5℃/分から25℃/分の範囲の硬化ランプ速度で加熱することにより達成される請求項7に記載の方法。
- 設定硬化温度と硬化性エポキシ系の中心で到達する最大温度との間の差が、20℃未満である請求項7に記載の方法。
- 請求項7ないし9のいずれか1項に記載の方法により得られる複合材。
- 請求項1に記載の硬化性エポキシ系と接触した繊維材料を含んでなるプリプレグ。
- 繊維強化型複合材構造の生成法であって、繊維材料を請求項1ないし5のいずれか1項に記載の硬化性エポキシ系と接触させて硬化性繊維強化型エポキシ系を形成し;そして繊維強化型エポキシ系を硬化して繊維強化型複合材構造を形成することを含んでなる前記方法。
- 繊維強化型エポキシ系を硬化する工程が、繊維強化型エポキシ系を100℃から220℃の範囲の設定硬化温度で、少なくとも部分的に硬化した繊維強化型複合材構造を生成するために十分な時間加熱することを含んでなる請求項12に記載の方法。
- 設定硬化温度が、硬化性エポキシ系を環境温度から0.5℃/分から25℃/分の範囲の硬化ランプ速度で加熱することにより達成される請求項13に記載の方法。
- 設定硬化温度と硬化性繊維強化型エポキシ系の中心で到達する最大温度との間の差が、20℃未満である請求項13に記載の方法。
- 繊維強化型エポキシ系が、最大60mmの厚さを有する請求項12に記載の方法。
- 請求項12の方法により得られる繊維強化型複合材構造。
- 請求項17の繊維強化型複合材構造を含んでなる航空宇宙用構成要素。
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BR112022010075A2 (pt) * | 2019-12-10 | 2022-08-30 | Huntsman Advanced Mat Americas Llc | Composições de resina curável e de resina reforçada por fibra, métodos para preparar uma composição de resina curável, para produzir um artigo compósito reforçado por fibra, e, artigo compósito reforçado por fibra |
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US11548978B2 (en) | 2023-01-10 |
EP3728390B1 (en) | 2023-03-01 |
MX2020006392A (es) | 2020-09-07 |
CN111819215B (zh) | 2024-03-19 |
US20200385515A1 (en) | 2020-12-10 |
AU2018388985A1 (en) | 2020-06-11 |
KR20200103059A (ko) | 2020-09-01 |
EP3728390A4 (en) | 2021-09-15 |
BR112020012027A2 (pt) | 2020-11-24 |
AR114008A1 (es) | 2020-07-08 |
ES2944118T3 (es) | 2023-06-19 |
TW201934602A (zh) | 2019-09-01 |
CA3083519A1 (en) | 2019-06-27 |
AU2018388985B2 (en) | 2024-03-14 |
CN111819215A (zh) | 2020-10-23 |
BR112020012027B1 (pt) | 2023-12-12 |
RU2020123958A (ru) | 2022-01-21 |
TWI791718B (zh) | 2023-02-11 |
JP7241078B2 (ja) | 2023-03-16 |
EP3728390A1 (en) | 2020-10-28 |
WO2019126073A1 (en) | 2019-06-27 |
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