JPS58208322A - ポリイミド化合物の製造方法 - Google Patents
ポリイミド化合物の製造方法Info
- Publication number
- JPS58208322A JPS58208322A JP9129582A JP9129582A JPS58208322A JP S58208322 A JPS58208322 A JP S58208322A JP 9129582 A JP9129582 A JP 9129582A JP 9129582 A JP9129582 A JP 9129582A JP S58208322 A JPS58208322 A JP S58208322A
- Authority
- JP
- Japan
- Prior art keywords
- polyamic acid
- polyimide compound
- present
- polyimide
- reaction
- 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.)
- Granted
Links
- 239000004642 Polyimide Substances 0.000 title claims description 37
- 229920001721 polyimide Polymers 0.000 title claims description 37
- 150000001875 compounds Chemical class 0.000 title description 34
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000000034 method Methods 0.000 title description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 229940125782 compound 2 Drugs 0.000 claims 1
- 229920005575 poly(amic acid) Polymers 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000000843 powder Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- -1 aromatic tetracarboxylic acid Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241001474791 Proboscis Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 150000002847 norbornane derivatives Chemical class 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 241001330002 Bambuseae Species 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 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 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-OUBTZVSYSA-N oxygen-17 atom Chemical compound [17O] QVGXLLKOCUKJST-OUBTZVSYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 101150036507 tcaf gene Proteins 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9129582A JPS58208322A (ja) | 1982-05-31 | 1982-05-31 | ポリイミド化合物の製造方法 |
US06/450,041 US4454310A (en) | 1981-12-21 | 1982-12-15 | Polyamide acid, process for producing same and polyimide obtained therefrom |
DE8282306847T DE3265912D1 (en) | 1981-12-21 | 1982-12-21 | A polyamide acid, a process for its production and a polyimide produced therefrom |
EP82306847A EP0082724B1 (en) | 1981-12-21 | 1982-12-21 | A polyamide acid, a process for its production and a polyimide produced therefrom |
JP63316722A JPH01198630A (ja) | 1982-05-31 | 1988-12-15 | ポリイミド化合物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9129582A JPS58208322A (ja) | 1982-05-31 | 1982-05-31 | ポリイミド化合物の製造方法 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP63316722A Division JPH01198630A (ja) | 1982-05-31 | 1988-12-15 | ポリイミド化合物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS58208322A true JPS58208322A (ja) | 1983-12-05 |
JPH025774B2 JPH025774B2 (enrdf_load_stackoverflow) | 1990-02-05 |
Family
ID=14022474
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP9129582A Granted JPS58208322A (ja) | 1981-12-21 | 1982-05-31 | ポリイミド化合物の製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS58208322A (enrdf_load_stackoverflow) |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61275352A (ja) * | 1985-05-31 | 1986-12-05 | Japan Synthetic Rubber Co Ltd | 可溶性ポリイミド溶液 |
JP2006347931A (ja) * | 2005-06-15 | 2006-12-28 | Nissan Chem Ind Ltd | ジアルキルシクロブタン酸二無水物及びその製造法 |
JP2010030972A (ja) * | 2008-07-31 | 2010-02-12 | Nissan Chem Ind Ltd | 脂環式テトラカルボン酸二無水物、その製造法およびポリイミド |
US7872148B2 (en) | 2004-10-20 | 2011-01-18 | Nissan Chemical Industries, Ltd. | Cage-shaped cyclobutanoic dianhydrides and process for production thereof |
US7906611B2 (en) | 2006-04-04 | 2011-03-15 | Nissan Chemical Industries, Ltd. | Polyamic acid and polyimide |
US8067527B2 (en) | 2006-07-10 | 2011-11-29 | Nissan Chemical Industries, Ltd. | Polyamic acid and polyimide |
KR20110129907A (ko) | 2009-02-23 | 2011-12-02 | 닛산 가가쿠 고교 가부시키 가이샤 | 지환식 테트라카르복실산의 제조 방법 |
KR20120024591A (ko) | 2009-04-10 | 2012-03-14 | 닛산 가가쿠 고교 가부시키 가이샤 | 케이지상 시클로펜탄산 2무수물 화합물, 그 제조법 및 폴리이미드 |
WO2014185739A1 (ko) | 2013-05-16 | 2014-11-20 | 코오롱인더스트리 주식회사 | 신규 산 이무수물, 이의 제조방법 및 이로부터 제조된 폴리이미드 |
WO2014185740A1 (ko) | 2013-05-16 | 2014-11-20 | 코오롱인더스트리 주식회사 | 신규 산 이무수물, 이의 제조방법 및 이로부터 제조된 폴리이미드 |
WO2015111982A1 (ko) | 2014-01-27 | 2015-07-30 | 코오롱인더스트리 주식회사 | 폴리이미드 및 이를 이용한 필름 |
KR20160108336A (ko) | 2014-01-17 | 2016-09-19 | 닛산 가가쿠 고교 가부시키 가이샤 | 시클로부탄테트라카르복실산 유도체의 제조 방법 |
KR20160108331A (ko) | 2014-01-17 | 2016-09-19 | 닛산 가가쿠 고교 가부시키 가이샤 | 고순도의 1,3-디알킬시클로부탄-1,2,3,4-테트라카르복실산-1,2:3,4-2무수물의 제조 방법 |
KR20160108335A (ko) | 2014-01-17 | 2016-09-19 | 닛산 가가쿠 고교 가부시키 가이샤 | 시클로부탄테트라카르복실산 유도체의 제조 방법 |
KR20160138980A (ko) | 2014-03-31 | 2016-12-06 | 닛산 가가쿠 고교 가부시키 가이샤 | 수지 박막의 제조방법 및 수지 박막형성용 조성물 |
KR20170131514A (ko) | 2015-03-25 | 2017-11-29 | 닛산 가가쿠 고교 가부시키 가이샤 | 디아민 및 그의 이용 |
KR20180063137A (ko) | 2015-09-30 | 2018-06-11 | 닛산 가가쿠 고교 가부시키 가이샤 | 수지박막형성용 조성물 |
KR20180069252A (ko) | 2016-12-15 | 2018-06-25 | 연세대학교 산학협력단 | 유연한 구조의 다이아민 단량체, 이를 포함하는 투명 폴리이미드, 및 이의 제조방법 |
-
1982
- 1982-05-31 JP JP9129582A patent/JPS58208322A/ja active Granted
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61275352A (ja) * | 1985-05-31 | 1986-12-05 | Japan Synthetic Rubber Co Ltd | 可溶性ポリイミド溶液 |
US7872148B2 (en) | 2004-10-20 | 2011-01-18 | Nissan Chemical Industries, Ltd. | Cage-shaped cyclobutanoic dianhydrides and process for production thereof |
JP2006347931A (ja) * | 2005-06-15 | 2006-12-28 | Nissan Chem Ind Ltd | ジアルキルシクロブタン酸二無水物及びその製造法 |
US7906611B2 (en) | 2006-04-04 | 2011-03-15 | Nissan Chemical Industries, Ltd. | Polyamic acid and polyimide |
US8067527B2 (en) | 2006-07-10 | 2011-11-29 | Nissan Chemical Industries, Ltd. | Polyamic acid and polyimide |
JP2010030972A (ja) * | 2008-07-31 | 2010-02-12 | Nissan Chem Ind Ltd | 脂環式テトラカルボン酸二無水物、その製造法およびポリイミド |
KR20110129907A (ko) | 2009-02-23 | 2011-12-02 | 닛산 가가쿠 고교 가부시키 가이샤 | 지환식 테트라카르복실산의 제조 방법 |
US8975365B2 (en) | 2009-04-10 | 2015-03-10 | Nissan Chemical Industries, Ltd. | Cage-shaped cyclopentanoic dianhydride, method for production thereof, and polyimide |
KR20120024591A (ko) | 2009-04-10 | 2012-03-14 | 닛산 가가쿠 고교 가부시키 가이샤 | 케이지상 시클로펜탄산 2무수물 화합물, 그 제조법 및 폴리이미드 |
US8658743B2 (en) | 2009-04-10 | 2014-02-25 | Nissan Chemical Industries, Ltd. | Cage-shaped cyclopentanoic dianhydride, method for production thereof, and polyimide |
KR20160044593A (ko) | 2009-04-10 | 2016-04-25 | 닛산 가가쿠 고교 가부시키 가이샤 | 케이지상 시클로펜탄산 2무수물 화합물, 그 제조법 및 폴리이미드 |
WO2014185740A1 (ko) | 2013-05-16 | 2014-11-20 | 코오롱인더스트리 주식회사 | 신규 산 이무수물, 이의 제조방법 및 이로부터 제조된 폴리이미드 |
WO2014185739A1 (ko) | 2013-05-16 | 2014-11-20 | 코오롱인더스트리 주식회사 | 신규 산 이무수물, 이의 제조방법 및 이로부터 제조된 폴리이미드 |
KR20210100756A (ko) | 2014-01-17 | 2021-08-17 | 닛산 가가쿠 가부시키가이샤 | 시클로부탄테트라카르복실산 유도체의 제조 방법 |
KR20160108336A (ko) | 2014-01-17 | 2016-09-19 | 닛산 가가쿠 고교 가부시키 가이샤 | 시클로부탄테트라카르복실산 유도체의 제조 방법 |
KR20160108331A (ko) | 2014-01-17 | 2016-09-19 | 닛산 가가쿠 고교 가부시키 가이샤 | 고순도의 1,3-디알킬시클로부탄-1,2,3,4-테트라카르복실산-1,2:3,4-2무수물의 제조 방법 |
KR20160108335A (ko) | 2014-01-17 | 2016-09-19 | 닛산 가가쿠 고교 가부시키 가이샤 | 시클로부탄테트라카르복실산 유도체의 제조 방법 |
KR20220162884A (ko) | 2014-01-17 | 2022-12-08 | 닛산 가가쿠 가부시키가이샤 | 시클로부탄테트라카르복실산 유도체의 제조 방법 |
KR20220063315A (ko) | 2014-01-17 | 2022-05-17 | 닛산 가가쿠 가부시키가이샤 | 시클로부탄테트라카르복실산 유도체의 제조 방법 |
KR20210134078A (ko) | 2014-01-17 | 2021-11-08 | 닛산 가가쿠 가부시키가이샤 | 시클로부탄테트라카르복실산 유도체의 제조 방법 |
WO2015111982A1 (ko) | 2014-01-27 | 2015-07-30 | 코오롱인더스트리 주식회사 | 폴리이미드 및 이를 이용한 필름 |
KR20160138980A (ko) | 2014-03-31 | 2016-12-06 | 닛산 가가쿠 고교 가부시키 가이샤 | 수지 박막의 제조방법 및 수지 박막형성용 조성물 |
KR20170131514A (ko) | 2015-03-25 | 2017-11-29 | 닛산 가가쿠 고교 가부시키 가이샤 | 디아민 및 그의 이용 |
KR20180063137A (ko) | 2015-09-30 | 2018-06-11 | 닛산 가가쿠 고교 가부시키 가이샤 | 수지박막형성용 조성물 |
KR20180069252A (ko) | 2016-12-15 | 2018-06-25 | 연세대학교 산학협력단 | 유연한 구조의 다이아민 단량체, 이를 포함하는 투명 폴리이미드, 및 이의 제조방법 |
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