JP2019052098A - テトラカルボン酸二無水物、ポリアミド酸、ポリイミド及びポリイミド溶液 - Google Patents
テトラカルボン酸二無水物、ポリアミド酸、ポリイミド及びポリイミド溶液 Download PDFInfo
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- JP2019052098A JP2019052098A JP2017175294A JP2017175294A JP2019052098A JP 2019052098 A JP2019052098 A JP 2019052098A JP 2017175294 A JP2017175294 A JP 2017175294A JP 2017175294 A JP2017175294 A JP 2017175294A JP 2019052098 A JP2019052098 A JP 2019052098A
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- Prior art keywords
- polyimide
- reaction
- solution
- acid
- solvent
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 127
- 239000004642 Polyimide Substances 0.000 title claims abstract description 107
- -1 Tetracarboxylic acid dianhydride Chemical class 0.000 title abstract description 29
- 239000002253 acid Substances 0.000 title description 23
- 239000004952 Polyamide Substances 0.000 title description 3
- 229920002647 polyamide Polymers 0.000 title description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000004185 ester group Chemical group 0.000 claims abstract description 12
- 125000001033 ether group Chemical group 0.000 claims abstract description 10
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 63
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 52
- 229920005575 poly(amic acid) Polymers 0.000 claims description 34
- 230000009477 glass transition Effects 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 239000000178 monomer Substances 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 description 80
- 239000000243 solution Substances 0.000 description 65
- 238000006243 chemical reaction Methods 0.000 description 54
- 238000000034 method Methods 0.000 description 48
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Images
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- Plural Heterocyclic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
本発明のポリイミドのモノマーである、本発明のテトラカルボン酸二無水物は上記一般式(1)で表される。上記一般式(1)中、X1はエステル基またはエーテル基を表し、テトラカルボン酸二無水物の製造容易性の観点からエステル基が好ましい。
で表されるN―置換ニトロフタルイミドとを縮合反応させて芳香族ビスイミド化合物を得、該芳香族ビスイミド化合物をアルカリ加水分解してテトラカルボン酸の塩とし、得られたテトラカルボン酸の塩を酸性化することでテトラカルボン酸とし、さらに脱水することにより得ることができる。
本発明のポリアミド酸は上記一般式(2)で表され、本発明のポリイミドは上記一般式(3)で表される。上記一般式(2)及び(3)中、X1はエステル基又はエーテル基を表し、上記一般式(1)で表されるテトラカルボン酸二無水物の製造容易性の観点からエステル基が好ましい。
本発明のポリイミド溶液は、上述したポリイミドと有機溶媒とを含有する。ポリイミド溶液中のポリイミド濃度は、ポリイミドフィルムの製造容易性の観点から、固形分濃度で5重量%以上であることが好ましく、ポリイミド溶液を用いて塗工されたフィルムの平滑性を確保する観点から5〜40重量%、特に5〜20重量%であることが好ましい。
本発明のポリアミド酸を製造する方法は特に限定されず、公知の方法を適用することができる。より具体的には、上述した本発明のポリアミド酸及びポリイミドを構成するジアミンを後述する重合溶媒に溶解し、これに上記一般式(1)で表されるテトラカルボン酸二無水物、及び必要に応じ併用するテトラカルボン酸二無水物を徐々に添加し、0〜100℃、好ましくは20〜60℃で、0.5〜100時間、好ましくは1〜72時間攪拌する。
本発明のポリイミドは、上記の方法で得られたポリアミド酸を脱水閉環反応(イミド化反応)することで製造することができる。イミド化反応の方法としては、熱イミド化反応と化学イミド化反応が例示される。
・装置:(株)島津製作所製 LC−2010C
・カラム:一般財団法人 化学物質評価研究機構製 L−column ODS(5μm、4.6mmφ×250mm)
・移動相:A液=50%メタノール水、B液=メタノール。なお、B液濃度に付、下記の通り濃度を変化させ分析を行った。
・B液濃度:0%(0分)→100%(30分)→100%(40分)。
・流量:1.0ml/分
・カラム温度:40℃
・検出波長:UV 254nm
なお、以下実施例にて記載した各成分の含量及び純度は上記条件で測定したHPLCの面積百分率である。
1H−NMR及び13C−NMRは、内部標準としてテトラメチルシランを用い、溶媒としてDMSO−d6を用いて、JEOL−ESC400分光計によって記録した。
・装置:Waters社製 Xevo G2 Q−Tof
・カラム:化学物質評価研究機構製 L−Column2 ODS(2μm、2.1mmφ×100mm)
・カラム温度:40℃
・検出波長:UV 220−500nm
・移動相:A液=10mM酢酸アンモニウム水、B液=メタノール。なお、B液濃度に付、下記の通り濃度を変化させ分析を行った。
B液濃度:60%(0min)→65%(25min)→100%(35min)
・移動相流量:0.3ml/min
・検出法:Q−Tof
・イオン化法:ESI(+、−)法
・Ion Source:電圧(+)2.0kV、(−)1.5kV、温度120℃
・Sampling Cone :電圧 30V、ガスフロー50L/h
・Desolvation Gas:温度500℃、ガスフロー1000L/h
フーリエ変換赤外分光光度計(日本分光社製FT−IR4100)を用い、KBrプレート法にて本発明のテトラカルボン酸二無水物の赤外線吸収スペクトルを測定した。
1H−NMR及び13C−NMRは、内部標準としてテトラメチルシランを用い、溶媒としてDMSO−d6を用いて、JEOL−ECP400分光計によって記録した。
ネッチジャパン社製示差走査熱量分析装置(DSC3100)を用いて、窒素雰囲気中、昇温速度5℃/分で測定した。
本発明のジアミンが十分高い純度を有していることを確認するため、ジェイ・サイエンス・ラボ(株)社製 有機微量元素分析装置(JM10)を用いて、元素分析を行った。
フーリエ変換赤外分光光度計(日本分光社製FT−IR4100)を用い、透過法にて本発明のポリイミド薄膜の赤外線吸収スペクトルを測定した。
ポリイミドの粉末をN,N−ジメチルアセトアミド(DMAc)に溶解し、またはポリアミド酸ワニスを希釈して0.5重量%のDMAc溶液とし、オストワルド粘度計を用いて30℃で還元粘度を測定した。この値は実質的に固有粘度と見なすことができ、この値が高い程分子量が高いことを表す。
ネッチジャパン社製熱機械分析装置(TMA4000)を用いて動的粘弾性測定により、周波数0.1Hz、昇温速度5℃/分における損失エネルギー曲線のピーク温度からポリイミドフィルム(膜厚約20μm)のガラス転移温度(Tg)を求めた。Tgが高いほど、物理的耐熱性が高いことを表す。
ネッチジャパン社製熱機械分析装置(TMA4000)を用いて、熱機械分析により、荷重0.5g/膜厚1μm、昇温速度5℃/分における試験片の伸びより、100〜200℃の範囲での平均値としてポリイミドフィルム(膜厚約20μm)のCTEを求めた。この値が低い程、熱寸法安定性に優れていることを表す。
ネッチジャパン社製熱重量分析装置(TG−DTA2000)を用いて、窒素中(Td 5 N2)または空気中(Td 5 air)、昇温速度10℃/分での昇温過程において、ポリイミドフィルム(膜厚約20μm)の初期重量が5%減少した時の温度を測定した。Td 5の値が高いほど、熱安定性が高いことを表す。
得られたポリイミド粉末10mgに対し、有機溶媒1mL(固形分濃度約1重量%)をサンプル管に入れ、試験管ミキサーを用いて5分間撹拌して溶解状態を目視で確認した。評価基準は以下の通り。
++:室温で溶解
+:加熱して溶解
―:不溶
製造例1に記載の方法と同様の製法により製造した、上記式(4)で表されるビスフェノール1.833g(5.0mmol)を脱水アセトン27mLに溶かし、更に脱酸剤としてピリジン2.43mL(30.0mmol)を添加し、セプタムキャップで密栓してA液とした。次に別の三口フラスコ中、トリメリット酸無水物クロリド3.161g(15.0mmol)を脱水アセトン9.4mLに溶解し、セプタムキャップで密栓してB液とした。B液を氷浴で冷却し、マグネチックスターラーで攪拌しながら、B液にA液をシリンジでゆっくりと滴下した。滴下終了後、冷却下で数時間攪拌し、更に室温で12時間撹拌した。反応終了後、アセトンをエバポレーターにて留去した。析出物をトルエンで洗浄したのち、塩化物イオンが検出されなくなるまで水で洗浄した。これを200℃で12時間真空乾燥することで、淡黄色の粗生成物2.41g(収率:72%)を得た。
・FT−IRスペクトル(KBr、cm−1):3066(芳香族C−H伸縮振動)、1863/1780(酸無水物C=O伸縮振動)、1736(エステルC=O伸縮振動)、1488(置換フェニル基)、1223(エステル+キサンテン基C−O−C伸縮振動)。
1H−NMRスペクトル(400MHz,DMSO−d6,δ,ppm):8.63−8.59(m、2H、無水フタル酸3,6−プロトン)、8.48−8.45(m、2H、無水フタル酸3’,6’−プロトン)、8.28(d、1H、、J=7.9Hz、無水フタル酸5−プロトン)、8.16(d、1H、、J=7.8Hz、無水フタル酸5’−プロトン)、8.02(d、2H、J=7.6Hz、フルオレン基4,8−プロトン)、7.50−7.45(m、4H、フルオレン基3,7−プロトン+キサンテン基の4,7−プロトン)、7.37−7.31(m、3H、フルオレン基2,6−プロトン+キサンテン基8−プロトン)、6.92(dd、1H、J=8.6、2.3Hz、キサンテン基2−プロトン)、6.37−6.35(m、2H、キサンテン基1,5−プロトン)。
・元素分析(分子量712.63):推定値(%)C;72.47、H;2.83、分析値C;72.44、H;3.16。
よく乾燥した密閉反応容器に、2,2’−ビス(トリフルオロメチル)ベンジジン(TFMB)1mmolを入れ、モレキュラーシーブス4Aで十分に脱水したN,N−ジメチルアセトアミド(以下、DMAcと称することがある)を入れて溶解した。この溶液に、実施例1と同様の方法により製造した、上記式(5)で表されるテトラカルボン酸二無水物1mmolを加え、初期の全溶質濃度30重量%より重合反応を開始した。反応開始後、室温で72時間攪拌することで均一で粘稠なポリアミド酸溶液が得られた。なお、反応中、溶液粘度が高くなりすぎたため、DMAcを適宜追加し、最終溶質濃度は21%であった。
・ガラス転移温度(Tg):268℃
・CTE:25.4ppm/K
・5%重量減少温度;窒素中:499℃、空気中:475℃。
ジアミンとしてTFMBの代わりに、4,4’−オキシジアニリン(ODA)を用いた以外は、実施例2に記載した方法に従ってポリアミド酸を重合し、化学イミド化、ワニス化、製膜、および膜物性評価を行った。得られたポリイミドの溶媒溶解性を表1に、各物性値を表2に記載する。
テトラカルボン酸二無水物として、上記式(5)で表されるテトラカルボン酸二無水物を単独で使用する代わりに、上記式(5)で表されるテトラカルボン酸二無水物と他のテトラカルボン酸二無水物として2,2’−ビス(3,4−ジカルボキシフェニル)ヘキサフルオロプロパン酸二無水物(6FDA)をモル比で1:1の比率で併用し共重合した以外は、実施例2に記載した方法に従って、ポリアミド酸の重合、化学イミド化、ワニス化、製膜および特性評価を行った。得られたポリイミドの溶媒溶解性を表1に、各物性値を表2に記載する。
テトラカルボン酸二無水物成分としてピロメリット酸無水物(PMDA)を用いる以外は実施例3に準じてを行った後、熱イミド化工程を経てポリイミドフィルムを作製し、膜物性評価を行った。得られたポリイミドは如何なる溶媒にも不溶であり、溶液加工性を有していなかった。
テトラカルボン酸二無水物成分として以下式(8):
テトラカルボン酸二無水物成分として上記式(8)で表されるテトラカルボン酸二無水物を用いる以外は実施例3に準じて重合、化学イミド化及び製膜し、膜物性評価を行った。得られたポリイミドの溶媒溶解性を表1に、各物性値を表2に記載する。
DMF:N,N−ジメチルホルムアミド
DMAc:N,N−ジメチルアセトアミド
NMP:N−メチルピロリドン
GBL:γ―ブチロラクトン
THF:テトラヒドロフラン
CPN:シクロペンタノン
Claims (6)
- 請求項3に記載のポリイミドを固形分濃度で5重量%以上含むポリイミド溶液。
- 請求項3に記載のポリイミドを含むポリイミドフィルム。
- ガラス転移温度が250℃以上である、請求項3に記載のポリイミド、又は請求項5に記載のポリイミドフィルム。
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