JP3976036B2 - 高分子フィルムの製造方法 - Google Patents
高分子フィルムの製造方法 Download PDFInfo
- Publication number
- JP3976036B2 JP3976036B2 JP2004210547A JP2004210547A JP3976036B2 JP 3976036 B2 JP3976036 B2 JP 3976036B2 JP 2004210547 A JP2004210547 A JP 2004210547A JP 2004210547 A JP2004210547 A JP 2004210547A JP 3976036 B2 JP3976036 B2 JP 3976036B2
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- JP
- Japan
- Prior art keywords
- film
- bis
- support
- aminophenoxy
- drying
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
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- HHLMWQDRYZAENA-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)C=C1 HHLMWQDRYZAENA-UHFFFAOYSA-N 0.000 description 1
- UXBSLADVESNJEO-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]butan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(CC)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 UXBSLADVESNJEO-UHFFFAOYSA-N 0.000 description 1
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 1
- AUOBMHBCOTUSTJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propyl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)CC(C=C1)=CC=C1OC1=CC=C(N)C=C1 AUOBMHBCOTUSTJ-UHFFFAOYSA-N 0.000 description 1
- HBVLEOCILWODGB-UHFFFAOYSA-N 4-[4-[3-[4-(4-aminophenoxy)phenyl]butan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)C(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 HBVLEOCILWODGB-UHFFFAOYSA-N 0.000 description 1
- GIQDBONDPVCPBF-UHFFFAOYSA-N 4-[4-[3-[4-(4-aminophenoxy)phenyl]butyl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)CCC(C=C1)=CC=C1OC1=CC=C(N)C=C1 GIQDBONDPVCPBF-UHFFFAOYSA-N 0.000 description 1
- IEPTWJUEKGSTAQ-UHFFFAOYSA-N 4-[4-[3-[4-(4-aminophenoxy)phenyl]propyl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1CCCC(C=C1)=CC=C1OC1=CC=C(N)C=C1 IEPTWJUEKGSTAQ-UHFFFAOYSA-N 0.000 description 1
- LDFYRFKAYFZVNH-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenoxy]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 LDFYRFKAYFZVNH-UHFFFAOYSA-N 0.000 description 1
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- VSZMHWHJMHITJR-UHFFFAOYSA-N [3-(3-amino-4-phenoxybenzoyl)phenyl]-(3-amino-4-phenoxyphenyl)methanone Chemical compound NC1=CC(C(=O)C=2C=C(C=CC=2)C(=O)C=2C=C(N)C(OC=3C=CC=CC=3)=CC=2)=CC=C1OC1=CC=CC=C1 VSZMHWHJMHITJR-UHFFFAOYSA-N 0.000 description 1
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- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 150000001408 amides Chemical class 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
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- LRSFHOCOLGECMQ-UHFFFAOYSA-N bis(4-amino-3-phenoxyphenyl)methanone Chemical compound NC1=CC=C(C(=O)C=2C=C(OC=3C=CC=CC=3)C(N)=CC=2)C=C1OC1=CC=CC=C1 LRSFHOCOLGECMQ-UHFFFAOYSA-N 0.000 description 1
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- 230000007797 corrosion Effects 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
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- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
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- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- BUZHLYBJNNZTPL-UHFFFAOYSA-N pentane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)CC(C(O)=O)CC(O)=O BUZHLYBJNNZTPL-UHFFFAOYSA-N 0.000 description 1
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- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Moulding By Coating Moulds (AREA)
Description
(1)主鎖にイミド結合またはアミド結合を有する高分子化合物を含む溶液を支持体上に塗布することで支持体上に前記高分子化合物を含む塗膜を形成する工程と、前記支持体上の塗膜の上側の雰囲気温度よりも前記塗膜の下側の雰囲気温度が10〜50℃高い条件下で上記塗膜を乾燥する工程とを有する、高分子フィルムの製造方法。
(2)上記高分子化合物がポリイミド前駆体である、上記(1)記載の高分子フィルムの製造方法。
(3)上記溶液に含まれる高分子化合物が主鎖にベンザゾール環を有する、上記(1)または(2)記載の高分子フィルムの製造方法。
(4)上記支持体が長手方向および幅方向のいずれの方向についても3GPa以上の引張弾性率を有する有機高分子フィルムからなる、上記(1)〜(3)のいずれかに記載の高分子フィルムの製造方法。
本発明で用いるベンゾオキサゾール構造を有する芳香族ジアミン類としては、具体的には以下のものが挙げられる。
本発明で用いられるテトラカルボン酸無水物は芳香族テトラカルボン酸無水物類である。芳香族テトラカルボン酸無水物類としては、具体的には、以下のものが挙げられる。
「塗膜の下側の雰囲気温度」とは、塗膜の直下(支持体部分)から塗膜の下方30mmに至る領域(支持体および支持体の下方の部分を含むことが多い)の温度であり、塗膜から下方向に5〜30mm離れた位置の温度を熱電対などで計測することで、塗膜の下側の雰囲気温度を求めることができる。
ポリマー濃度が0.2g/dlとなるようにN−メチル−2−ピロリドンに溶解した溶液をウベローデ型の粘度管により30℃で測定した。
マイクロメーター(ファインリューフ社製、ミリトロン1245D)を用いて測定した。
測定対象のフィルムを、長手方向(MD方向)および幅方向(TD方向)にそれぞれ100mm×10mmの短冊状に切り出したものを試験片とした。引張試験機(島津製作所製、オートグラフ(R) 機種名AG−5000A)を用い、引張速度50mm/分、チャック間距離40mmの条件で、MD方向、TD方向それぞれについて、引張弾性率、引張強度及び引張破断伸度を測定した。
測定対象のフィルムについて、下記条件で示差走査熱量測定(DSC)を行い、融点(融解ピーク温度Tpm)とガラス転移点(Tmg)をJIS K 7121に準拠して求めた。
装置名 ; MACサイエンス社製DSC3100S
パン ; アルミパン(非気密型)
試料重量 ; 4mg
昇温開始温度 ; 30℃
昇温終了温度 ; 600℃
昇温速度 ; 20℃/min
雰囲気 ; アルゴン
支持体の上下両面からそれぞれ5mm離れた位置に下記熱電対の検出部を設置した。尚、熱電対は幅方向の中央付近に設けた。乾燥ゾーン内で実際の塗布−乾燥工程と同様の乾燥速度(乾燥時間)で支持体を搬送し、その際の各ゾーンでの検出温度を記録した。
熱電対:K熱電対(φ;1.0mm, 長さ12m)
データ取り込み装置:キーエンス(株)製 NR−250
目視によりフィルム表面付近の気泡の有無を確認した。
マイクロマップ社製三次元非接触表面形状計測システムを用い、133.1μm×133.1μmの範囲においてRaの測定を行った。
測定対象のフィルムについて、下記条件にてMD方向TD方向の伸縮率を測定し、30℃〜40℃、40℃〜50℃、…と10℃の間隔での伸縮率/温度を測定し、この測定を100℃まで行い、全測定値の平均値をCTEとして算出した。
装置名 ; MACサイエンス社製TMA4000S
試料長さ ; 20mm
試料幅 ; 2mm
昇温開始温度 ; 30℃
昇温終了温度 ; 100℃
昇温速度 ; 5℃/min
雰囲気 ; アルゴン
(ポリアミド酸溶液の調製)
窒素導入管、温度計、攪拌棒を備えた反応容器内を窒素置換した後、500重量部の5−アミノ−2−(p−アミノフェニル)ベンゾオキサゾールを入れた。次いで、5000重量部のN−メチル−2−ピロリドンを加えて完全に溶解させてから、485重量部のピロメリット酸二無水物を加えて、25℃にて48時間攪拌すると、褐色の粘調なポリアミド酸溶液が得られた。この還元粘度(ηsp/C)は4.5であった。
得られたポリアミド酸溶液を、鏡面仕上げ(表面粗さ Ra:0.5nm)したエンドレスのステンレスベルト上にスキージを用いてコーティングした(スキージ/ベルト間のギャップは、650μm)。3つのゾーンを有する連続式の乾燥炉を用いて、表1記載の条件で乾燥した。表1中、「ゾーン上」は塗膜の上側の雰囲気温度を意味し、「ゾーン下」は塗膜の下側の雰囲気温度を意味する。乾燥により得られた自己支持性のポリアミド酸フィルムを支持体から剥離した。このようにして、幅650mm、長さ60m、厚さ40μmのポリアミド酸フィルムを得た。
得られたポリアミド酸フィルムを連続式の熱処理炉に通し、表1に記載の条件にて2段階の加熱処理を施すことによってイミド化反応を進行させた。その後、5分間で室温にまで冷却して、褐色を呈するポリイミドフィルムを得た。得られたフィルムの物性を表3に記載する。表1における「熱処理条件」の欄で、例えば、「200 ℃×5 min → 450 ℃×5 min」であるのは、支持体より剥離したフィルムを200℃で5分間処理した後に、450℃で5分間処理することを意味する。
ポリアミド酸フィルムを得るための乾燥条件を表1記載の条件に変えたことのほかは実施例1と同様にしてポリイミドフィルムを得た。
480重量部のピロメリット酸無水物と、480重量部の4,4’−ジシアノジフェニルエーテルとを5000重量部のジメチルアセトアミドに溶解して、温度を20℃以下に保ちながら48時間攪拌することでポリアミド酸溶液を得た。得られた溶液の還元粘度(ηsp/C)は4.5であった。このポリアミド酸溶液を用いたことの他は実施例1と同様の操作により、ポリイミドフィルムを得た。
上述のポリアミド酸溶液の代わりに、1モルのトリメリット酸無水物に対して、0.25モルの2,4−トリレンジイソシアネート、0.75モルのo−トリジンジイソシアネートが反応してなるポリアミドイミド樹脂を20wt%含有するn−メチル−2−ピロリドン溶液を用いた。その他は実施例1の操作に準じて表1記載の条件によりポリアミドイミドフィルムを得た。
乾燥工程において、ステンレスベルトに代えて、ポリエステルフィルム コスモシャインA−4100(東洋紡績(株)製)を支持体として用いた。前記ポリエステルフィルムの長手方向の線膨張係数は20ppm/℃であり、幅方向の線膨張係数は18ppm/℃であり、Raは0.5nmであり、長手方向の引張弾性率は4.1GPaであり、幅方向の引張弾性率は4.2GPaである。前記ポリエステルフィルムの無滑剤面にポリアミド酸溶液を塗布した。エンドレスのステンレスベルトの場合とは異なり、上記ポリエステルフィルムを巻き出す装置と巻き取り装置とを乾燥機に設置した。以上の条件以外は実施例1と同様の操作によりポリイミドフィルムを製造した。
ポリアミド酸フィルムを得るための乾燥条件を表2記載の条件に変えたことのほかは実施例1と同様の操作によりポリイミドフィルムを得た。
実施例5と同様のポリエステルフィルムを支持体に用いて、表2記載の条件によりポリイミドフィルムを得た。比較例1〜4にて得られたポリイミドフィルムの物性を表4にまとめる。
Claims (4)
- 主鎖にイミド結合またはアミド結合を有する高分子化合物を含む溶液を支持体上に塗布することで支持体上に前記高分子化合物を含む塗膜を形成する工程と、前記支持体上の塗膜の上側の雰囲気温度よりも前記塗膜の下側の雰囲気温度が10〜50℃高い条件下で上記塗膜を乾燥する工程とを有する、高分子フィルムの製造方法。
- 上記高分子化合物がポリイミド前駆体である、請求項1記載の高分子フィルムの製造方法。
- 上記溶液に含まれる高分子化合物が主鎖にベンザゾール環を有する、請求項1または2記載の高分子フィルムの製造方法。
- 上記支持体が長手方向および幅方向のいずれの方向についても3GPa以上の引張弾性率を有する有機高分子フィルムからなる、請求項1〜3のいずれか一項に記載の高分子フィルムの製造方法。
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