JP6196731B2 - 新規酸二無水物、この製造方法、及びこれから製造されたポリイミド - Google Patents
新規酸二無水物、この製造方法、及びこれから製造されたポリイミド Download PDFInfo
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- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1075—Partially aromatic polyimides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/33—Amino carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3719—Polyamides or polyimides
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- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
<化学式1>
<化学式1>
<化学式1>
<化学式1>
<化学式1>
[反応式1]
<化学式1>
<実施例1>
1−1:化学式3で表される化合物の合成
化学式2で表される化合物(L−アスパラギン酸)50.73g(0.38mol)に水酸化カリウム30ml(50%水溶液)、水酸化カリウム13.94g(0.19mol)および蒸留水70mlを混合して1リットルの三つ口フラスコに投入し、前記フラスコに凝縮器、50mlの等圧滴下ロート、還流凝縮器および磁石攪拌器を取り付けた。1,2−ジブロモエタン28ml(50%水溶液)を注意深く前記フラスコの三つ目の口に添加した後、60℃で加熱して還流させ、ここに水酸化カリウム(24ml、50%水溶液)を、6時間ドロップワイズ(dropwise)を行いながら継続還流させた。前記還流が完了したら、水をフラスコに加えた後、溶液をさらに1時間還流させた。前記還流物を1時間冷却させながら撹拌した後、前記得られた還流物を濃い塩酸でpH3まで酸性化して白色沈殿物を形成させた。前記白色沈殿物を濾過させ、ここに蒸留水(225ml)を添加した後、水酸化ナトリウム(50%水溶液)でpH11に調整した。前記pH11に調整された混合物を塩酸でpH3.5に再調整して沈殿物を形成させ、水で塩酸を洗浄した後、65℃で真空乾燥させた(17.9g、収率30%)。前記化学式2で表される化合物の製造方法はNeal JA.,などによって報告されたことがある(Neal J.A.,Rose N.J.,Inorg Chem,1968,7,2408)。
1H NMR (400 MHz, D2O/KOH) δ 2.38-2.50 (m, 2H, CH2CO2), 2.62-2.67 (m, 2H, CH2CO2), 2.91-3.01 (m, 4H, CH2CH2), 3.55-3.58 (m, 2H, CH), (NH and CO2H not observed at this pH); Anal. Calcd. for C10H16N2O8; C: 41.10, H: 5.52, N: 9.59%. Found: C: 40.97, H: 5.60, N: 9.64%; IR (KBr, cm-1): 3530 (νO-H), 3422 (νN-H), 3044, 2807, 1723 (νC=O)
1−2:化学式1で表される酸二無水物の合成
実施例1−1で得られた化学式3で表される化合物4.96g(17mmol)、ピリジン3.18g(35.7mmol)および無水酢酸3.6g(35.7mmol)を、凝縮器と磁石攪拌器が取り付けられた50mlのフラスコに投入し、60℃で24時間反応を行った。反応完了の後、反応物を冷却し、濾過した。前記濾過された濾過物を無水酢酸200mlと精製されたジエチルエーテル200mlで洗浄し、真空状態のオーブンにて40℃で乾燥させた後、無水酢酸100mlで再結晶を行い、化学式1で表される化合物2.48gを得た(収率50%)。
1H NMR (400 MHz, d6-DMSO) δ 2.01 (s, 3H, -NCOCH3), 2.12 (s, 3H, -NCOCH3), 2.83-2.91 (m, 2H, CH2CO2), 3.30 (dd, 2H, overlapped signals, CH2CO2), 3.65 (bd, 4H, CH2CH2), 4.66-4.60 (m, 2H, CH); 13C NMR (100 MHz, d6-DMSO): δ 173.8 (-NCOCH3), 173.4 (COOCO), 172.9 (COOCO), 59.7 (α-CH), 51.2 (N-CH2CH2), 51.0 (N-CH2CH2), 37.1 (β-CH2), 23.3 (-NCOCH3); Anal. Calcd. for C14H16N2O8; C: 49.41, H: 4.74, N: 8.23%. Found: C: 49.32, H: 4.80, N: 8.26%; IR (KBr, cm-1): 2955, 1869, 1790 (νC=O), 1222, 1196, 1075 (C-O-C)
本発明の単純な変形または変更はいずれも、当該分野における通常の知識を有する者によって容易に実施でき、それらの変形または変更もすべて本発明の領域に含まれるものと理解すべきである。
Claims (8)
- 下記化学式1で表される酸二無水物。
<化学式1>
- (a)塩基触媒の存在下で、下記化学式2で表される化合物をN−アルキル化反応させ、下記化学式3で表される化合物を得る段階と、
(b)前記得られた化学式3で表される化合物を無水酢酸の存在下で脱水閉環反応させ、下記化学式1で表される酸二無水物を製造する段階とを含んでなる、酸二無水物の製造方法。
<化学式1>
<化学式2>
<化学式3>
- 前記(a)段階の塩基触媒は、水酸化カリウム、水酸化ナトリウム、水酸化バリウム、水酸化カルシウム、水酸化アルミニウムおよび水酸化マグネシウムよりなる群から選ばれる1種以上であることを特徴とする、請求項2に記載の酸二無水物の製造方法。
- 前記(b)段階の脱水閉環反応は40〜100℃で4〜28時間行うことを特徴とする、請求項2に記載の酸二無水物の製造方法。
- 前記(b)段階の無水酢酸は、化学式3で表される化合物1モルに対して、2〜10モルで投入することを特徴とする、請求項2に記載の酸二無水物の製造方法。
- 前記(b)段階の脱水閉環反応は、ピリジン、イソキノリン、および第3級アミンよりなる群から選ばれる1種以上の存在下で行われることを特徴とする、請求項2に記載の酸二無水物の製造方法。
- 下記化学式1で表される酸二無水物とジアミンとを反応して得られるポリアミック酸。
<化学式1>
- 請求項7のポリアミック酸を脱水閉環させて得られることを特徴とするポリイミド。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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KR10-2013-0055392 | 2013-05-16 | ||
KR1020130055392A KR101595614B1 (ko) | 2013-05-16 | 2013-05-16 | 신규 산 이무수물, 이의 제조방법 및 이로부터 제조된 폴리이미드 |
PCT/KR2014/004394 WO2014185739A1 (ko) | 2013-05-16 | 2014-05-16 | 신규 산 이무수물, 이의 제조방법 및 이로부터 제조된 폴리이미드 |
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JP2016520078A JP2016520078A (ja) | 2016-07-11 |
JP6196731B2 true JP6196731B2 (ja) | 2017-09-13 |
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US (1) | US9676739B2 (ja) |
EP (1) | EP2998302B1 (ja) |
JP (1) | JP6196731B2 (ja) |
KR (1) | KR101595614B1 (ja) |
CN (1) | CN105246886A (ja) |
HU (1) | HUE037322T2 (ja) |
WO (1) | WO2014185739A1 (ja) |
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JP2017514972A (ja) * | 2014-05-15 | 2017-06-08 | コーロン インダストリーズ インク | ポリイミド及びこれを用いたフィルム |
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US3158635A (en) * | 1959-03-18 | 1964-11-24 | Stauffer Chemical Co | Bis-adduction products and methods of preparing same |
DE2910131A1 (de) * | 1979-03-15 | 1980-09-25 | Basf Ag | Verfahren zur herstellung von 2,5-dimethyl-4-hydroxy-2,3-dihydrofuran- 3-on |
JPS58208322A (ja) | 1982-05-31 | 1983-12-05 | Japan Synthetic Rubber Co Ltd | ポリイミド化合物の製造方法 |
US4454310A (en) | 1981-12-21 | 1984-06-12 | Japan Synthetic Rubber Co., Ltd. | Polyamide acid, process for producing same and polyimide obtained therefrom |
JPS60188427A (ja) | 1984-03-09 | 1985-09-25 | Nissan Chem Ind Ltd | 新規なポリイミド樹脂及びその製造方法 |
US4931540A (en) * | 1987-11-24 | 1990-06-05 | Hoechst Celanese Corporation | Polymers prepared from 4,4'-bis[2-(3,4-(dicarboxyphenyl)hexafluoroisopropyl] diphenyl ether dianhydride |
JP2722008B2 (ja) * | 1990-04-27 | 1998-03-04 | 東邦レーヨン株式会社 | ポリイミド樹脂組成物及びその製造方法 |
US5438105A (en) * | 1990-04-27 | 1995-08-01 | Toho Rayon Co., Ltd. | Polyamic acid composite, polyimide composite and processes for producing the same |
GB9322648D0 (en) | 1993-11-03 | 1993-12-22 | Ass Octel | Process for the production of s.s.e.d.d.s |
US5466867A (en) * | 1994-07-11 | 1995-11-14 | Albemarle Corporation | Method for producing [S,S]-ethylenediamine-N,N'-disuccinic acid from its calcium salt |
US7005165B2 (en) | 1998-12-23 | 2006-02-28 | Elsicon, Inc. | Photosensitive polyimides for optical alignment of liquid crystals |
US6103322A (en) * | 1998-12-23 | 2000-08-15 | Elsicon Inc. | Materials for inducing alignment of liquid crystals and liquid crystal optical elements |
JP2006232960A (ja) | 2005-02-24 | 2006-09-07 | Fuji Photo Film Co Ltd | 光学フィルムおよび画像表示装置 |
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- 2013-05-16 KR KR1020130055392A patent/KR101595614B1/ko active IP Right Grant
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- 2014-05-16 EP EP14797631.0A patent/EP2998302B1/en active Active
- 2014-05-16 JP JP2016513878A patent/JP6196731B2/ja active Active
- 2014-05-16 CN CN201480028547.0A patent/CN105246886A/zh active Pending
- 2014-05-16 WO PCT/KR2014/004394 patent/WO2014185739A1/ko active Application Filing
- 2014-05-16 US US14/890,658 patent/US9676739B2/en active Active
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Cited By (1)
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JP2017514972A (ja) * | 2014-05-15 | 2017-06-08 | コーロン インダストリーズ インク | ポリイミド及びこれを用いたフィルム |
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KR20140135341A (ko) | 2014-11-26 |
US9676739B2 (en) | 2017-06-13 |
EP2998302B1 (en) | 2018-04-04 |
EP2998302A4 (en) | 2017-01-11 |
HUE037322T2 (hu) | 2018-08-28 |
EP2998302A1 (en) | 2016-03-23 |
JP2016520078A (ja) | 2016-07-11 |
CN105246886A (zh) | 2016-01-13 |
US20160108014A1 (en) | 2016-04-21 |
WO2014185739A1 (ko) | 2014-11-20 |
KR101595614B1 (ko) | 2016-02-18 |
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