JP2021095542A - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
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- JP2021095542A JP2021095542A JP2019229220A JP2019229220A JP2021095542A JP 2021095542 A JP2021095542 A JP 2021095542A JP 2019229220 A JP2019229220 A JP 2019229220A JP 2019229220 A JP2019229220 A JP 2019229220A JP 2021095542 A JP2021095542 A JP 2021095542A
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 24
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- 125000003118 aryl group Chemical group 0.000 description 13
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- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 4
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Images
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Abstract
Description
本発明の他の目的は、加工性に優れ、低い温度での加熱でも硬化して、超耐熱性を有する硬化物を形成することができる硬化性組成物を提供することにある。
本発明の他の目的は、超耐熱性と可とう性を有する硬化物を形成することができる硬化性組成物を提供することにある。
本発明の他の目的は、超耐熱性を有する硬化物又はその半硬化物を提供することにある。
本発明の他の目的は超耐熱性を有する硬化物又はその半硬化物を含む構造物を提供することにある。
本発明の他の目的は、超耐熱性を有する硬化物又はその半硬化物と基板とが積層された構成を有する積層体を提供することにある。
本発明の他の目的は、超耐熱性を有する硬化物又はその半硬化物と基板とが積層された構成を有する積層体の製造方法を提供することにある。
本発明の他の目的は、超耐熱性を有する硬化物又はその半硬化物と繊維とを含む複合材を提供することにある。
本発明の他の目的は、加工性に優れ、超耐熱性が求められる環境下で使用可能な接着剤、封止剤、又は塗料を提供することにある。
また、本発明の硬化性組成物の硬化物若しくは硬化物は、超耐熱性及び良好な誘電特性が求められる分野(例えば、電子情報機器、家電、自動車、精密機械、航空機、宇宙産業用機器等)において好適に使用することができる。
本発明の硬化性組成物は、硬化性化合物と硬化剤を少なくとも含有する。
上記式(1)で表される化合物は、例えば、Polymer 1989 p978 に記載されている合成法を利用して製造することができる。下記に、上記式(1)で表される化合物の製造方法の一例を示すが、本発明はこの製造方法によって製造されるものに限定されない。
工程[1]:反応基質である下記式(2)で表される化合物と下記式(3)で表される化合物とを、塩基の存在下で反応させることにより、下記式(4)で表される化合物を得る。
工程[2]:下記式(4)で表される化合物に、アミノアルコール(下記式(5)で表される化合物)を反応させることにより、下記式(6)で表されるジアミンを得る。
工程[3]:下記式(6)で表されるジアミンに環状酸無水物(下記式(7)で表される化合物)を反応させることにより下記式(1a)で表される化合物を得る。
上記式(2)で表される化合物としては、例えば、ベンゾフェノン、2−ナフチルフェニルケトン、及びビス(2−ナフチル)ケトン等のハロゲン化物、及びこれらの誘導体等が挙げられる。
上記式(5)で表される化合物としては、例えば、4−アミノフェノール、2−アミノ−6−ヒドロキシナフタレン、及びこれらの位置異性体や誘導体等が挙げられる。
前記環状酸無水物(上記式(7)で表される化合物)としては、例えば、無水マレイン酸、2−フェニル無水マレイン酸、4−フェニルエチニル−無水フタル酸、4−(1−ナフチルエチニル)−無水フタル酸、ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボン酸無水物、及びこれらの誘導体等が挙げられる。
本発明における硬化剤は、上記硬化性化合物と3次元架橋構造を形成して、硬化物を形成する化合物である。また、本発明の硬化性組成物において、前記硬化剤は硬化開始温度を低温化する効果を発揮する。そして、前記硬化剤を含有する硬化性組成物は、低温でも硬化反応を完了させることができ、可とう性に優れた硬化物を形成することができる。
Ar4、Ar5は、同一又は異なって、アリーレン基、又は2個以上のアリーレン基が単結合若しくは連結基を介して結合した基を示す。Xは−CO−、−S−、又は−SO2−を示し、Yは、同一又は異なって、−S−、−SO2−、−O−、−CO−、−COO−、又は−CONH−を示す。nは0以上の整数を示す
本発明の硬化性組成物は、式(1)で表される化合物と硬化剤以外にも、必要に応じて他の成分を含有していても良い。他の成分としては、例えば、触媒、フィラー、有機樹脂(シリコーン樹脂、エポキシ樹脂、フッ素樹脂など)、溶剤、安定化剤(酸化防止剤、紫外線吸収剤、耐光安定剤、熱安定化剤など)、難燃剤(リン系難燃剤、ハロゲン系難燃剤、無機系難燃剤など)、難燃助剤、補強材、核剤、カップリング剤、滑剤、ワックス、可塑剤、離型剤、耐衝撃性改良剤、色相改良剤、流動性改良剤、着色剤(染料、顔料など)、分散剤、消泡剤、脱泡剤、抗菌剤、防腐剤、粘度調整剤、増粘剤等が挙げられる。これらは、1種を単独で、又は2種以上を組み合わせて使用することができる。
本発明の硬化物(或いは、半硬化物)は、上記硬化性組成物の硬化物(或いは、半硬化物)である。
硬化度(%)=[1−(半硬化物の発熱量/硬化性組成物の発熱量)]×100
(1)燃焼持続時間は30秒以下
(2)5個の試料の燃焼持続時間の合計が250秒以下
(3)2回目の接炎後の赤熱持続時間が60秒以下
(4)固定用クランプ部まで燃えない
(5)燃焼する粒子を落下させて、下に敷いた綿を燃やすことがない
本発明の構造物は、上記硬化物又は半硬化物を含む構造物である。前記構造物の形状は特に制限が無いが、例えば、粒子状又は平面状である。本発明の構造物は、上記硬化性組成物を射出成形、トランスファー成形、コンプレッション成形、押出成形等の成形法に付すことにより製造することができる。
本発明の積層体は、上記硬化性組成物の硬化物又は半硬化物と基板とが積層された構成を有する。本発明の積層体には、硬化性組成物の硬化物又は半硬化物/基板、及び基板/硬化性組成物の硬化物又は半硬化物/基板の構成が含まれる。
本発明の積層体は、また、上記硬化性組成物を支持体上に塗布し、加熱処理を施して半硬化させて得られた半硬化物を支持体から剥離し、それを基板上に載置して、更に加熱処理を施す方法でも製造することができる。
本発明の複合材は、上記硬化性組成物の硬化物又は半硬化物と繊維とを含む。複合材の形状としては、繊維状やシート状など特に制限がない。
<NMR測定>
測定装置:BRUKER 400MHz/54mm又はBRUKER AVANCE600MHz
測定溶剤:重DMSO、重クロロホルム、又は重クロロホルム/ペンタフルオロフェノール(PFP)=2/1(wt/wt)の混合液
化学シフト:TMSを規準とした
<GPC測定>
装置:ポンプ「LC−20AD」((株)島津製作所製)
検出器:RID−10A((株)島津製作所製)又はTDA−301およびUV2501(Viscotek製)
溶剤:THF又はクロロホルム
カラム:shodex GPC K-806L×1本+shodex GPC K-803×1本+shodex GPC K-801×2本
流速:1.0mL/min
温度:40℃
試料濃度:0.1%(wt/vol)
標準ポリスチレン換算
<DSC測定>
装置:TA Q20
昇温速度:10℃/min
雰囲気:窒素雰囲気
<TG/DTA測定>
装置:NETZSCH TG209F3
昇温速度:10℃/min
雰囲気:窒素雰囲気
<IR測定>
装置:Perkin Elmer Spectrum RX1(ATR法)
ジアミン(1)の調製
撹拌装置、窒素導入管、およびディーンスターク装置を備えた500mL(三ツ口)フラスコに、4,4’−ジフルオロベンゾフェノン27.50g、ビスフェノールA23.98g、無水炭酸カリウム(K2CO3)21.77g、N−メチル−2−ピロリドン220mL、およびトルエン110mLを入れ、窒素雰囲気下で撹拌しながら加熱し、130〜140℃で4時間トルエンを還流させた。その後、さらに加熱して170〜180℃でトルエンを留去した。さらに、170〜180℃で10時間撹拌を継続した後、室温に戻した。
撹拌装置、窒素導入管および乾燥管を備えた1000mL(三ツ口)フラスコに、無水マレイン酸を5.88g、N−メチル−2−ピロリドンを50mL、トルエンを200mL入れ、窒素置換した。そこへ、得られたジアミン(1)48.57gを330mLのNMPに溶解させた溶液を添加し、窒素雰囲気下、室温で24時間撹拌した。その後、パラトルエンスルホン酸一水和物0.761gを添加し、140℃に加熱して、8時間攪拌を継続し、トルエンを還流して水分を除去した。反応液を室温に戻した後、反応液を3000mLのメタノールに添加、ろ過することで粉末状固体を得た。この粉末状固体をメタノールおよび水で繰返し洗浄した後、100℃で8時間減圧乾燥して、粉末状固体(硬化性化合物A、下記式(A)で表される化合物、芳香環由来の構造の割合:71重量%、収率:90%)を得た。硬化性化合物Aの1H−NMRスペクトルを図3に、FTIRスペクトルを図4に示す。
1H-NMR(CDCl3)δ:1.71(s), 6.87(s), 7.02(m), 7.09(m), 7.17(d,J=8.8Hz),7.26(m), 7.37(d,J=8.8Hz), 7.80(m)
硬化性化合物Aを、下記表に示す溶剤(100g)と混合し、25℃で24時間撹拌し、溶剤への溶解性を下記基準で評価した。また、参考例としてPEEK(市販PEEKパウダー、ポリエーテルエーテルケトン、VICTREX151G、融点343℃、Tg147℃)の溶解性を同様の方法で評価した。
評価基準
○(良好):完全に溶解した
×(不良):少なくとも一部が溶解せずに残存した
下記表に記載の通り、調製例で得られた硬化性化合物A50重量部とトルエン50重量部とを混合し、超音波を25℃で5分間あて、完全に硬化性化合物Aを溶解させた。そこへ、硬化剤としてのトリフェニルホスフィン0.5重量部を配合し、更にマイカを27重量部(すなわち、硬化性化合物Aに対して20体積%)となる割合で配合して、撹拌し、硬化性組成物1を得た。
硬化剤の種類及び含有量を下記表に記載の通りに変更した以外は実施例1と同様にして、硬化性組成物を得た。尚、実施例2では、調製例1で得られたジアミン(1)を硬化剤として使用した。
硬化剤を添加しなかった以外は実施例1と同様にして、硬化性組成物を得た。
硬化性化合物としてPEEKを使用した以外は実施例1と同様にした。その結果、PEEKは140℃で5分加熱撹拌しても溶剤に溶けず、硬化性組成物が形成できなかった。
得られた硬化性組成物をガラス板上に厚さ0.5mm程度で均一になるように乗せ、マッフル炉で加熱(25℃から371℃まで10℃/minで昇温し、その後、371℃で2時間保持)して、前記硬化性組成物を硬化させ、硬化物を得た。
上記[硬化物の熱重量減少分析]と同様の方法で得られた硬化物をCHN元素分析に付して、窒素原子含有量を求めた。尚、標準試料にはアンチピリンを使用した。
得られた硬化性組成物を、銅箔(厚み:18μm)上に均一に広げ、これを一次乾燥(60℃の乾燥機中で2時間乾燥)に付して塗膜(厚み:50μm)を得た。得られた塗膜を熱硬化(200℃、若しくは240℃の乾燥機中、真空で1時間)させて、硬化物/銅箔の積層体を得た。
可とう性の評価基準
○:直径3mm、直径5mmともに積層体に割れが発生しなかった。
△:直径5mmでは積層体に割れが発生しなかったが、直径3mmでは積層体に割れが発生した。
×:直径5mmでも積層体に割れが生じた
特に硬化剤としてリン系硬化剤又はアミン系硬化剤を使用した場合は、硬化温度の低温化効果に優れ、200℃で加熱することにより、可とう性に優れた硬化物を形成することができた。
一方、硬化剤を使用しなかった比較例1の硬化性組成物は硬化性の点で劣り、200℃又は240℃で加熱して得られた硬化物は可とう性を有しなかった。
Claims (21)
- 硬化剤が環状骨格を備えた硬化剤である、請求項1に記載の硬化性組成物。
- 硬化剤がリン系硬化剤である、請求項1又は2に記載の硬化性組成物。
- 式(1)中のR1、R2が、同一又は異なって、環状イミド構造を有する硬化性官能基である、請求項1〜3の何れか1項に記載の硬化性組成物。
- 式(I)、及び式(II)中のAr1〜Ar3が、同一又は異なって、炭素数6〜14のアリーレン基、又は炭素数6〜14のアリーレン基の2個以上が、単結合、炭素数1〜5の直鎖状又は分岐鎖状アルキレン基、又は炭素数1〜5の直鎖状又は分岐鎖状アルキレン基の水素原子の1個以上がハロゲン原子で置換された基を介して結合した基である、請求項1〜6の何れか1項に記載の硬化性組成物。
- 式(I)で表される構造が、ベンゾフェノン由来の構造である、請求項1〜7の何れか1項に記載の硬化性組成物。
- 式(1)で表される化合物全量における、ベンゾフェノン由来の構造単位の占める割合が5重量%以上である、請求項8に記載の硬化性組成物。
- 式(II)で表される構造が、ハイドロキノン、レゾルシノール、2,6−ナフタレンジオール、2,7−ナフタレンジオール、4,4'−ジヒドロキシビフェニル、4,4'−ジヒドロキシジフェニルエーテル、4,4'−ジヒドロキシベンゾフェノン、4,4'−ジヒドロキシジフェニルスルフィド、4,4'−ジヒドロキシジフェニルスルフォン、及びビスフェノールAから選択される少なくとも1種の化合物由来の構造である、請求項1〜9の何れか1項に記載の硬化性組成物。
- 式(1)で表される化合物全量における、ハイドロキノン、レゾルシノール、2,6−ナフタレンジオール、2,7−ナフタレンジオール、4,4’−ジヒドロキシビフェニル、4,4’−ジヒドロキシジフェニルエーテル、4,4’−ジヒドロキシベンゾフェノン、4,4’−ジヒドロキシジフェニルスルフィド、4,4’−ジヒドロキシジフェニルスルフォン、及びビスフェノールA由来の構造単位の占める割合が5重量%以上である、請求項10に記載の硬化性組成物。
- 請求項1〜11の何れか1項に記載の硬化性組成物の硬化物。
- 請求項1〜11の何れか1項に記載の硬化性組成物の半硬化物。
- 請求項1〜11の何れか1項に記載の硬化性組成物の硬化物又は半硬化物を含む構造物。
- 請求項1〜11の何れか1項に記載の硬化性組成物の硬化物又は半硬化物と基板とが積層された構成を有する積層体。
- 請求項1〜11の何れか1項に記載の硬化性組成物を基板上に載置し、加熱処理を施すことで、前記硬化性組成物の硬化物又は半硬化物と基板とが積層された構成を有する積層体を得る、積層体の製造方法。
- プラスチック製の支持体上に、前記硬化性組成物の溶融物を塗布し、固化して、前記硬化性化合物を含む薄膜を得、得られた薄膜を、前記支持体から剥離して基板上に積層し、加熱処理を施す、請求項16に記載の積層体の製造方法。
- 請求項1〜11の何れか1項に記載の硬化性組成物の硬化物又は半硬化物と繊維とを含む複合材。
- 請求項1〜11の何れか1項に記載の硬化性組成物を含む接着剤。
- 請求項1〜11の何れか1項に記載の硬化性組成物を含む塗料。
- 請求項1〜11の何れか1項に記載の硬化性組成物を含む封止剤。
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