JP6035632B2 - ポリアミド酸繊維からポリイミド繊維への高速熱転化 - Google Patents
ポリアミド酸繊維からポリイミド繊維への高速熱転化 Download PDFInfo
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- JP6035632B2 JP6035632B2 JP2013532899A JP2013532899A JP6035632B2 JP 6035632 B2 JP6035632 B2 JP 6035632B2 JP 2013532899 A JP2013532899 A JP 2013532899A JP 2013532899 A JP2013532899 A JP 2013532899A JP 6035632 B2 JP6035632 B2 JP 6035632B2
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- 229920005575 poly(amic acid) Polymers 0.000 title claims description 93
- 239000000835 fiber Substances 0.000 title claims description 86
- 229920001721 polyimide Polymers 0.000 title claims description 55
- 239000004642 Polyimide Substances 0.000 title claims description 54
- 238000006243 chemical reaction Methods 0.000 title description 22
- 238000000034 method Methods 0.000 claims description 44
- 238000010438 heat treatment Methods 0.000 claims description 24
- 238000000354 decomposition reaction Methods 0.000 claims description 7
- 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 description 20
- 239000002904 solvent Substances 0.000 description 17
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 16
- 239000002121 nanofiber Substances 0.000 description 16
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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- 238000000926 separation method Methods 0.000 description 1
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- 238000001228 spectrum Methods 0.000 description 1
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- 239000010935 stainless steel Substances 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
- B01D69/06—Flat membranes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/58—Other polymers having nitrogen in the main chain, with or without oxygen or carbon only
- B01D71/62—Polycondensates having nitrogen-containing heterocyclic rings in the main chain
- B01D71/64—Polyimides; Polyamide-imides; Polyester-imides; Polyamide acids or similar polyimide precursors
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D10/00—Physical treatment of artificial filaments or the like during manufacture, i.e. during a continuous production process before the filaments have been collected
- D01D10/02—Heat treatment
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/74—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polycondensates of cyclic compounds, e.g. polyimides, polybenzimidazoles
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01H—SPINNING OR TWISTING
- D01H1/00—Spinning or twisting machines in which the product is wound-up continuously
- D01H1/14—Details
- D01H1/42—Guards or protectors for yarns or threads, e.g. separator plates, anti-ballooning devices
-
- D—TEXTILES; PAPER
- D02—YARNS; MECHANICAL FINISHING OF YARNS OR ROPES; WARPING OR BEAMING
- D02J—FINISHING OR DRESSING OF FILAMENTS, YARNS, THREADS, CORDS, ROPES OR THE LIKE
- D02J13/00—Heating or cooling the yarn, thread, cord, rope, or the like, not specific to any one of the processes provided for in this subclass
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/42—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties characterised by the use of certain kinds of fibres insofar as this use has no preponderant influence on the consolidation of the fleece
- D04H1/4326—Condensation or reaction polymers
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/42—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties characterised by the use of certain kinds of fibres insofar as this use has no preponderant influence on the consolidation of the fleece
- D04H1/4326—Condensation or reaction polymers
- D04H1/4334—Polyamides
- D04H1/4342—Aromatic polyamides
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/70—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres
- D04H1/72—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres the fibres being randomly arranged
- D04H1/728—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres the fibres being randomly arranged by electro-spinning
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/0007—Electro-spinning
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- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- Mechanical Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Artificial Filaments (AREA)
- Spinning Methods And Devices For Manufacturing Artificial Fibers (AREA)
Description
本出願の主題は、2009年12月15日に出願された同時係属出願である米国仮特許出願第61/286618号明細書、米国仮特許出願第61/286628号明細書および米国仮特許出願第61/286623号明細書に関連する。
イミド化度(DOI)の測定
所与の試験片の赤外スペクトルを測定し、1375cm-1のイミドのC−N吸収対1500cm-1のp−置換C−Hの吸収の比を求めた。この比をイミド化度(DOI)とした。最大限にイミド化させるのに必要と思われる時間を十分に超える時間イミド化条件に付したPMDA/ODAポリアミド酸ナノウェブのDOIは0.57であることが分かった。これと比較すると、PMDA/ODAフィルム試験片のDOIは0.65であった。この差は、フィルムには存在しないナノウェブ中のナノ繊維の配向等の、試験片の影響に起因する可能性がある。
本明細書において用いる「結晶度」というパラメータは、広角X線回折(WAXD)により求められる相対的な結晶化度のパラメータを指す。X線用放物面鏡(Parabolic X−ray Mirror)および平行平板コリメータを取り付けたPANalytical X’Pert MPDでCu放射線を用いてX線回折データを収集した。薄肉のフィルムを全体の厚みが約0.7mmになるように重ねることによって透過法用の試験片を作製した。2θが3〜45°の範囲でステップ幅を0.1°としてデータを収集した。データポイント毎の計数時間を最低10秒間とし、透過軸(transmission axis)に対し0.1回転/秒の回転数で試験片を回転させた。
RV/HA/HB−5または−6スピンドルを取り付けたプログラム機能を有する粘度計であるBrookfield Engineering HADV−II+をNISTトレーサブルなシリコーンオイルを用いて較正し、これを用いて溶液粘度を測定した。スピンドルを室温でポリマー溶液中に、液面がスピンドルの凹みに達するまで、浸漬した。モーターを公称トルクの10〜20%となるRPMに設定して駆動させた。40〜70ポイズの溶液の場合はRV/HA/HB−5スピンドルを用いると10〜20rpmが適切であることが分かり、RV/HA/HB−6スピンドルでは20rpmが適切であることが分かった。
以下の方法を用いて繊維径を測定した。
1.ナノウェブ表面のSEM(走査型電子顕微鏡)画像を、測定可能な繊維が20〜60本含まれる倍率で1または2枚以上撮影した。
2.目視で観察して各画像毎にナノウェブの平均的な外観を示しているように見える3つの位置を選択した。
3.画像解析ソフトウェアを使用して60〜180本の繊維の繊維径を測定し、選択した範囲の平均値を求めた。
ポリ(アミド酸)溶液1(PAA−1)
100ガロン容のステンレス鋼製撹拌型反応器内で、PMDA(DuPont Mitsubishi Gas Ltd.)34.10kgを、4,4ODA(和歌山精化工業)32.19kgおよび無水フタル酸(Aldrich Chemical)1.30kgとDMF(DuPont)234.33kg中で合一した。まず最初にODAをDMFに添加し、次いでPMDAを添加し、最後に無水フタル酸を添加することによりこれらを混合して、室温で30時間撹拌しながら反応させることによりポリアミド酸を形成した。結果として得られたポリアミド酸の室温における溶液粘度は68ポイズであった。
装置
電界紡糸による細径繊維の生産性の問題を解決するためにエレクトロブローイングを導入した。エレクトロブローイングでは、紡糸される繊維に乱気流を当て、それによって、ターゲット面上に吹き落とされる高分子繊維の「雲」を形成すると同時に静電気によって付着させる。送風および静電気力を組み合わせることにより、系の生産性が大幅に増大する。エレクトロブローイングは米国特許出願公開第20050067732号明細書に詳述されている。
ナノウェブ#3(NW−1)
図1に示す装置にPAA−1を60ccを手作業で装入した。ノズル104から金属板コレクタ110までの距離を35.6cmとし、ノズルおよびベルトの間に110kVの電位差を印加した。溶液の吐出圧を57psigとし、温度23℃におけるプロセスガスの流量を15cfmとした。補助空気供給装置115を55℃に加熱し、繊維紡糸室107に10立方フィート毎分の流量で吹き込んだ。ナノウェブ構造体を回転式ドラムコレクタで捕集した。
PAA−2〜PAA−6を使用し、NW−1の作製に用いた設備および手順を用いてナノウェブを作製した。NW−1〜NW−6の作製に用いた具体的な条件を表4にまとめた。
次いで、カレンダー処理したポリアミド酸ナノウェブ(NW−1〜NW−5)を、同一のパネルがナノウェブの上方および下方に位置するように配置された加熱パネルを有し、放射器間の距離が9インチであるGlenro Radplane(登録商標)赤外線オーブンを通過させることによって加熱した。図2に、赤外オーブンの一部200の略図を示す。オーブンの筐体222は4つの加熱パネル223を収容しており、それぞれが3つの温度領域に分割されているものとした。パネル223の互いに対面している領域は、ナノウェブ221の上方および下方の温度が等しくなるように制御し、それによってオーブン200に合計6つの温度領域が生じるようにした。オーブン200内の加熱される長さの全長を48インチとした。オーブン200は、図2に示すように、ナノウェブ221用の任意選択的な支持媒体225を備えるものとした。ナノウェブNW−1およびNW−2はオーブン内でガラス繊維織布225により支持し、これをスクリムまたは支持材としてナノウェブと一緒に搬送した。ナノウェブNW−3、NM−4およびNW−5は支持体を用いなかった。赤外線オーブン200は、溶媒の蒸気が実験室に侵入するのを防止するための排気システムも備えるものとした。室温の空気をオーブン200の入口および出口の開口部から引き込み、プレナム224を介して排気した。放射器の各温度領域の温度およびナノウェブのオーブン200内の総滞留時間を表5にまとめる。ナノウェブの温度は測定しなかった。
PMDAを0.98モル、ODAを1モルおよび無水フタル酸を0.04モルを用いてPMDA、ODAおよび無水フタル酸のDMF中ポリアミド酸溶液を形成した。図1の装置を用いて、以下の表7に示す条件に従い、固形分22重量%のポリアミド酸溶液を紡糸してナノウェブにした。
次に、本発明の態様を示す。
1. ポリイミド繊維を形成するためにポリアミド酸繊維を第1温度〜第2温度の範囲の温度で5秒間〜5分間の範囲の時間加熱する工程を含む方法であって、
前記第1温度が前記ポリアミド酸のイミド化温度であり、前記第2温度が前記ポリイミドの分解温度である、方法。
2. 前記ポリアミド酸繊維を第1温度〜第2温度の範囲の温度で加熱する前記工程の前に、前記ポリアミド酸繊維を室温〜前記第1温度の範囲の温度で予備加熱する工程をさらに含む、態様1に記載の方法。
3. 前記ポリアミド酸繊維をある温度に加熱する前記工程が、前記ポリアミド酸繊維を60℃/分〜250℃/秒の範囲の速度で加熱することを含む、態様1に記載の方法。
4. 前記ポリアミド酸繊維を加熱する前記工程が、ポリアミド酸繊維を赤外線オーブンで加熱することを含む、態様1に記載の方法。
5. 前記ポリアミド酸繊維が全芳香族ポリアミド酸繊維を含む、態様1に記載の方法。
6. 前記全芳香族ポリアミド酸繊維がPMDA/ODAを含む、態様5に記載の方法。
7. 前記ポリイミド繊維がPMDA/ODAを含む、態様1に記載の方法。
8. 前記ポリアミド酸繊維が複数のポリアミド酸ナノ繊維を含む、態様1に記載の方法。
9. 前記複数のポリアミド酸ナノ繊維がポリアミド酸ナノウェブの形態にある、態様8に記載の方法。
10. 前記ポリアミド酸繊維をある温度で加熱する前記工程の前に、前記ポリアミド酸ナノウェブをカレンダー処理する工程をさらに含む、態様9に記載の方法。
11. 前記ポリアミド酸繊維の数平均繊維径が10ミクロン以下である、態様1に記載の方法。
12. 前記ポリアミド酸繊維の数平均繊維径が1500nm以下である、態様1に記載の方法。
13. 前記ポリアミド酸繊維の数平均繊維径が100nm〜1000nmの範囲にある、態様1に記載の方法。
Claims (1)
- ポリイミド繊維を形成するためにポリアミド酸繊維を第1温度〜第2温度の範囲の温度で5秒間〜5分間の範囲の時間加熱する工程を含む方法であって、
前記第1温度が前記ポリアミド酸のイミド化温度であり、前記第2温度が前記ポリイミドの分解温度であり、
前記ポリアミド酸繊維の数平均繊維径が1500nm以下である、
方法。
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Application Number | Priority Date | Filing Date | Title |
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US12/899,770 US20110144297A1 (en) | 2009-12-15 | 2010-10-07 | Rapid thermal conversion of a polyamic acid fiber to a polyimide fiber |
US12/899,770 | 2010-10-07 | ||
PCT/US2011/054863 WO2012047960A2 (en) | 2010-10-07 | 2011-10-05 | Rapid thermal conversion of a polyamic acid fiber to a polyimide fiber |
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JP2013539824A JP2013539824A (ja) | 2013-10-28 |
JP2013539824A5 JP2013539824A5 (ja) | 2014-11-20 |
JP6035632B2 true JP6035632B2 (ja) | 2016-11-30 |
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EP (1) | EP2625322B1 (ja) |
JP (1) | JP6035632B2 (ja) |
KR (1) | KR20130115278A (ja) |
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Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102168317B (zh) * | 2011-03-11 | 2012-07-25 | 北京化工大学 | 一种聚酰亚胺纤维的制备方法 |
US8679200B2 (en) | 2011-11-18 | 2014-03-25 | E I Du Pont De Nemours And Company | Method for reducing self discharge in an electrochemical cell |
WO2013181333A1 (en) * | 2012-06-01 | 2013-12-05 | E. I. Du Pont De Nemours And Company | An electrochemical cell comprising a nanoweb comprising nanofibers of a cross-linked polyimide |
US9090996B2 (en) * | 2012-08-15 | 2015-07-28 | E I Du Pont De Nemours And Company | Multizone electroblowing process |
CN103337595B (zh) * | 2013-07-04 | 2016-04-06 | 上海和辉光电有限公司 | 柔性封装衬底及其制造方法和使用该衬底的oled封装方法 |
JP5946565B1 (ja) * | 2015-06-23 | 2016-07-06 | 紘邦 張本 | 紡糸口金及び極細繊維製造装置 |
CN105040276B (zh) * | 2015-06-23 | 2017-08-01 | 北京化工大学常州先进材料研究院 | 一种具有交联形貌的聚酰亚胺纤维膜及其制备方法 |
WO2017007302A2 (en) * | 2015-07-06 | 2017-01-12 | Universiti Putra Malaysia | Post conditioning machine |
CN105040512A (zh) * | 2015-09-09 | 2015-11-11 | 长春高琦聚酰亚胺材料有限公司 | 一种聚酰亚胺纸模塑制品及其制备方法 |
US11077325B2 (en) | 2016-04-01 | 2021-08-03 | Dupont Safety & Construction, Inc. | Flame and particulate resistant knit article |
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EP3491178B1 (en) * | 2017-01-06 | 2019-11-20 | SABIC Global Technologies B.V. | Apparatus for continuous needleless electrospinning a nanoscale or submicron scale polymer fiber web onto a substrate |
CN106958047B (zh) * | 2017-04-06 | 2019-10-25 | 中国科学院长春应用化学研究所 | 一种热酰亚胺化制备聚酰亚胺纤维的方法 |
US20190330766A1 (en) * | 2018-04-28 | 2019-10-31 | Dennis Joseph Steibel, JR. | Apparatus for removing moisture from a section of polymer filament |
CN110681266B (zh) * | 2018-07-06 | 2021-11-30 | 中国石油化工股份有限公司 | 分离非质子极性溶剂中小分子溶剂的方法 |
CN109509678A (zh) * | 2018-11-22 | 2019-03-22 | 漳州雅宝电子有限公司 | 一种熔点为236±2℃的耐高温热敏材料 |
WO2022064917A1 (ja) | 2020-09-25 | 2022-03-31 | 富士フイルム株式会社 | 硬化物の製造方法、積層体の製造方法、及び、半導体デバイスの製造方法 |
Family Cites Families (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB903272A (en) * | 1959-04-01 | 1962-08-15 | Du Pont | Method of preparing polyimides |
US3814719A (en) * | 1972-05-01 | 1974-06-04 | Ciba Geigy Corp | Zeta-triazine-imide copolymers |
US4167620A (en) * | 1978-02-01 | 1979-09-11 | Standard Oil Company (Indiana) | Method for heat treating shaped articles of amide-imide or amic acid polymers |
US4874368A (en) * | 1988-07-25 | 1989-10-17 | Micromedics, Inc. | Fibrin glue delivery system |
JPH02234911A (ja) * | 1988-11-07 | 1990-09-18 | Mitsui Toatsu Chem Inc | ポリイミド繊維の製造方法 |
CA2002147A1 (en) * | 1988-11-07 | 1990-05-07 | Shuichi Morikawa | Production process for polyimide fibers |
JPH0314617A (ja) * | 1989-06-12 | 1991-01-23 | Asahi Chem Ind Co Ltd | 高強度、高弾性率ポリイミド成形物の製造方法 |
US5374708A (en) * | 1989-12-22 | 1994-12-20 | Mitsui Toatsu Chemicals, Incorporated | Formed polyimide article |
US5089360A (en) * | 1990-02-08 | 1992-02-18 | Tonen Chemical Corporation | High-strength non-woven fabric, method of producing same and battery separator constituted thereby |
JP2626827B2 (ja) * | 1990-03-15 | 1997-07-02 | 宇部興産株式会社 | ポリイミド延伸成形体及びその製造法 |
US5367046A (en) * | 1992-04-10 | 1994-11-22 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Low dielectric polyimide fibers |
US5518779A (en) * | 1992-12-16 | 1996-05-21 | Industrial Technology Research Institute | Forming copper clad laminates |
KR0161313B1 (ko) * | 1994-10-31 | 1999-01-15 | 강박광 | 폴리이미드 아미 에스테르 화합물 및 그 제조방법 |
EP0751168B1 (en) * | 1995-06-28 | 1999-02-10 | Mitsui Chemicals, Inc. | Linear polyamic acid, linear polyimide and thermoset polyimide |
JPH11269268A (ja) * | 1998-03-20 | 1999-10-05 | Mitsui Chem Inc | 線状ポリアミド酸、線状ポリイミド及び熱硬化性ポリイミド |
JP2000071268A (ja) * | 1998-08-31 | 2000-03-07 | Du Pont Toray Co Ltd | ポリイミドフィルムおよびその製造方法 |
ATA49899A (de) * | 1999-03-19 | 2002-06-15 | Immuno Ag | Verfahren und vorrichtung zum mischen von komponenten |
CN1216092C (zh) * | 1999-09-24 | 2005-08-24 | 液态空气-乔治克罗德方法研究监督及咨询股份有限公司 | 新的聚酰亚胺酰胺酸盐以及由此形成的聚酰亚胺膜 |
DE60105754T2 (de) * | 2000-04-28 | 2005-06-23 | Mitsui Chemicals, Inc. | Polyimid und polyamidsäure |
JP4390028B2 (ja) * | 2000-10-04 | 2009-12-24 | 日産化学工業株式会社 | ポジ型感光性ポリイミド樹脂組成物 |
EP1229066A1 (en) * | 2001-02-05 | 2002-08-07 | Rolic AG | Photoactive polymer |
US20040166311A1 (en) * | 2003-02-25 | 2004-08-26 | Clemson University | Electrostatic spinning of aromatic polyamic acid |
JP2004308031A (ja) * | 2003-04-03 | 2004-11-04 | Teijin Ltd | ポリアミド酸不織布、それから得られるポリイミド不織布およびそれらの製造方法 |
DE602005027862D1 (de) * | 2004-10-07 | 2011-06-16 | Du Pont | Polymer auf basis von polysaccharide für gewebekleber zur medizinischen verwendung |
JP2008002011A (ja) * | 2006-06-22 | 2008-01-10 | Toyobo Co Ltd | ポリイミド不織布およびその製造方法 |
JP2009203314A (ja) * | 2008-02-27 | 2009-09-10 | Toyobo Co Ltd | ポリイミド繊維補強熱可塑性樹脂板状体およびその製造方法 |
CA2640517A1 (en) * | 2008-05-19 | 2009-11-19 | Industry-University Cooperation Foundation, Hanyang University | Polyamic acids dope composition, preparation method of hollow fiber using the same and hollow fiber prepared therefrom |
JP2010077565A (ja) * | 2008-09-26 | 2010-04-08 | Kaneka Corp | ポリイミド繊維及びその利用、並びに当該ポリイミド繊維の製造方法。 |
JP5429101B2 (ja) * | 2009-11-25 | 2014-02-26 | 宇部興産株式会社 | 高耐熱性ポリイミド微細繊維の製造方法、高耐熱性ポリイミド微細繊維及び該ポリイミド微細繊維からなる不織布 |
US20110139331A1 (en) * | 2009-12-15 | 2011-06-16 | E. I. Du Pont De Nemours And Company | Method for increasing the strength and solvent resistance of polyimide nanowebs |
JP6003261B2 (ja) * | 2012-06-12 | 2016-10-05 | 宇部興産株式会社 | ポリイミド繊維の製造方法 |
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- 2011-10-05 CN CN201180047942.XA patent/CN103154335B/zh active Active
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- 2011-10-05 WO PCT/US2011/054863 patent/WO2012047960A2/en active Application Filing
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EP2625322A2 (en) | 2013-08-14 |
CN103154335A (zh) | 2013-06-12 |
WO2012047960A3 (en) | 2012-08-02 |
WO2012047960A2 (en) | 2012-04-12 |
EP2625322A4 (en) | 2017-04-19 |
JP2013539824A (ja) | 2013-10-28 |
CN103154335B (zh) | 2016-08-24 |
US20110144297A1 (en) | 2011-06-16 |
KR20130115278A (ko) | 2013-10-21 |
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