JPH023820B2 - - Google Patents
Info
- Publication number
- JPH023820B2 JPH023820B2 JP56014945A JP1494581A JPH023820B2 JP H023820 B2 JPH023820 B2 JP H023820B2 JP 56014945 A JP56014945 A JP 56014945A JP 1494581 A JP1494581 A JP 1494581A JP H023820 B2 JPH023820 B2 JP H023820B2
- Authority
- JP
- Japan
- Prior art keywords
- composition
- polyamic acid
- solution
- reaction
- bpda
- 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
Links
- 239000000203 mixture Substances 0.000 description 94
- 229920005575 poly(amic acid) Polymers 0.000 description 76
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 47
- 238000000034 method Methods 0.000 description 40
- 229920001721 polyimide Polymers 0.000 description 22
- 125000003118 aryl group Chemical group 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 19
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- 238000003860 storage Methods 0.000 description 18
- 239000004642 Polyimide Substances 0.000 description 16
- -1 aromatic diamine compound Chemical class 0.000 description 14
- 239000002798 polar solvent Substances 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 150000004984 aromatic diamines Chemical class 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000007810 chemical reaction solvent Substances 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- FYYYKXFEKMGYLZ-UHFFFAOYSA-N 4-(1,3-dioxo-2-benzofuran-5-yl)-2-benzofuran-1,3-dione Chemical compound C=1C=C2C(=O)OC(=O)C2=CC=1C1=CC=CC2=C1C(=O)OC2=O FYYYKXFEKMGYLZ-UHFFFAOYSA-N 0.000 description 4
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 3
- 238000003109 Karl Fischer titration Methods 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-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
- 230000007423 decrease Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000005057 refrigeration Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 230000009974 thixotropic effect Effects 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- CQMIJLIXKMKFQW-UHFFFAOYSA-N 4-phenylbenzene-1,2,3,5-tetracarboxylic acid Chemical group OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C1C1=CC=CC=C1 CQMIJLIXKMKFQW-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920001646 UPILEX Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Landscapes
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Paints Or Removers (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1494581A JPS57131248A (en) | 1981-02-05 | 1981-02-05 | Polyamic acid solution composition and preparation thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1494581A JPS57131248A (en) | 1981-02-05 | 1981-02-05 | Polyamic acid solution composition and preparation thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS57131248A JPS57131248A (en) | 1982-08-14 |
JPH023820B2 true JPH023820B2 (fr) | 1990-01-25 |
Family
ID=11875099
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1494581A Granted JPS57131248A (en) | 1981-02-05 | 1981-02-05 | Polyamic acid solution composition and preparation thereof |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS57131248A (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008035647A1 (fr) | 2006-09-19 | 2008-03-27 | Gunze Limited | Composition de solution d'acide polyamique au noir de carbone dispersé, et procédé de fabrication d'une courroie de résine de polyimide semi-conductrice |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58155162A (ja) * | 1982-03-12 | 1983-09-14 | Hitachi Ltd | 研摩機 |
JPS59164328A (ja) * | 1983-03-08 | 1984-09-17 | Ube Ind Ltd | 芳香族ポリアミツク酸溶液組成物 |
JPS59204619A (ja) * | 1983-05-09 | 1984-11-20 | Ube Ind Ltd | 芳香族ポリアミツク酸溶液組成物 |
JPS6175602A (ja) * | 1984-09-21 | 1986-04-18 | Ube Ind Ltd | 誘電体共振器装置 |
JPS61141732A (ja) * | 1984-12-14 | 1986-06-28 | Ube Ind Ltd | 透明な芳香族ポリイミドおよび組成物 |
JPS627733A (ja) * | 1985-03-10 | 1987-01-14 | Nitto Electric Ind Co Ltd | 無色透明なポリイミド成形体およびその製法 |
JPS61258836A (ja) * | 1985-05-10 | 1986-11-17 | Hitachi Chem Co Ltd | ポリアミド酸溶液の製造方法 |
JPH0672184B2 (ja) * | 1986-05-06 | 1994-09-14 | 三菱化成株式会社 | ポリイミドの製法 |
JPS63248868A (ja) * | 1988-01-20 | 1988-10-17 | Toshiba Corp | 耐熱性絶縁被覆材 |
JPH08225645A (ja) * | 1995-12-18 | 1996-09-03 | Nitto Denko Corp | 無色透明なポリイミド成形体およびその製法 |
EP2090609A4 (fr) * | 2006-11-13 | 2012-08-01 | Ube Industries | Procédé de fabrication d'une solution d'acide polyamide et solution d'acide polyamique |
JP2009084536A (ja) * | 2007-10-03 | 2009-04-23 | Nitto Denko Corp | ポリアミド酸溶液の製造方法及びポリイミドベルトの製造方法 |
WO2009069797A1 (fr) | 2007-11-29 | 2009-06-04 | Ube Industries, Ltd. | Procédé de fabrication d'une solution d'acide polyamique et solution d'acide polyamique |
JP5233344B2 (ja) * | 2008-03-18 | 2013-07-10 | 宇部興産株式会社 | ポリアミック酸溶液の製造方法 |
JP5831460B2 (ja) | 2010-12-15 | 2015-12-09 | 宇部興産株式会社 | ポリイミドシームレスベルト、その製造方法、ポリイミド前駆体溶液組成物 |
JP6179795B2 (ja) * | 2013-03-21 | 2017-08-16 | 東洋紡株式会社 | 保存安定性に優れたポリアミドイミド樹脂溶液 |
EP2876129B1 (fr) * | 2013-11-25 | 2021-05-12 | Samsung Electronics Co., Ltd. | Composition pour la préparation d'un polyimide, un polyimide et article comprenant ladite composition |
JP7375318B2 (ja) * | 2018-05-16 | 2023-11-08 | 東レ株式会社 | ポリイミド前駆体樹脂組成物、ポリイミド樹脂組成物およびその膜状物、それを含む積層体、ならびにフレキシブルデバイス |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5527326A (en) * | 1978-08-17 | 1980-02-27 | Ube Ind Ltd | Polyimide resin composition and its preparation |
JPS5528822A (en) * | 1978-08-23 | 1980-02-29 | Ube Ind Ltd | Method for manufacturing polyimide film |
-
1981
- 1981-02-05 JP JP1494581A patent/JPS57131248A/ja active Granted
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5527326A (en) * | 1978-08-17 | 1980-02-27 | Ube Ind Ltd | Polyimide resin composition and its preparation |
JPS5528822A (en) * | 1978-08-23 | 1980-02-29 | Ube Ind Ltd | Method for manufacturing polyimide film |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008035647A1 (fr) | 2006-09-19 | 2008-03-27 | Gunze Limited | Composition de solution d'acide polyamique au noir de carbone dispersé, et procédé de fabrication d'une courroie de résine de polyimide semi-conductrice |
Also Published As
Publication number | Publication date |
---|---|
JPS57131248A (en) | 1982-08-14 |
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