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 (US07345094-20080318-C00003.png) | 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 (US07345094-20080318-C00003.png) |
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 (en) * | 2006-11-13 | 2012-08-01 | Ube Industries | METHOD FOR PRODUCING A POLYAMIDE ACID SOLUTION AND POLYAMIDE ACID SOLUTION |
| 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 (ja) | 2007-11-29 | 2009-06-04 | Ube Industries, Ltd. | ポリアミック酸溶液の製造方法およびポリアミック酸溶液 |
| 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 (en) * | 2013-11-25 | 2021-05-12 | Samsung Electronics Co., Ltd. | Composition for preparing polyimide, polyimide, and article including same |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH023820B2 (US07345094-20080318-C00003.png) | ||
| Bower et al. | Aromatic polyimides | |
| TWI535760B (zh) | 高耐熱聚醯胺酸溶液及聚醯亞胺薄膜 | |
| KR101657113B1 (ko) | 폴리이미드 전구체 용액 조성물 | |
| US4470944A (en) | Process for producing an aromatic polyimide film | |
| EP0532953B1 (en) | Polyimide precursor solution, process for producing the solution, and moldings and coatings obtained therefrom | |
| EP3578590A1 (en) | Polyimide precursor solution and polyimide film produced using same | |
| JPWO2009069797A1 (ja) | ポリアミック酸溶液の製造方法およびポリアミック酸溶液 | |
| EP0082724A1 (en) | A polyamide acid, a process for its production and a polyimide produced therefrom | |
| JPH08231719A (ja) | ポリ（イミド−アミックエステル）及びその製造方法並びにそれを用いたポリイミド、ポリイミドフィルム、ポリイミドファイバー及びそれらの製造方法 | |
| US20220135797A1 (en) | Polyimide film and method for manufacturing same | |
| JPS61195130A (ja) | 芳香族ポリイミドフイルムの製造方法 | |
| JPH047333A (ja) | 新規ポリイミド | |
| JPS6337821B2 (US07345094-20080318-C00003.png) | ||
| JPH036225A (ja) | １２―ｆフッ素含有連結基を有するポリイミドポリマー | |
| WO2004031270A1 (ja) | ポリイミドフィルムおよびその製造法 | |
| US5162454A (en) | Polyamide-polyimide block copolymers | |
| JP2910796B2 (ja) | ポリアミック酸共重合体及びそれからなるポリイミドフィルム並びにそれらの製造方法 | |
| JP2831867B2 (ja) | ポリアミック酸共重合体、それからなるポリイミド共重合体、ポリイミドフィルム、並びにそれらの製造方法 | |
| JPS59204619A (ja) | 芳香族ポリアミツク酸溶液組成物 | |
| JP3375346B2 (ja) | ポリアミド酸とポリイミドフィルム及びそれらの製造方法 | |
| JPH02209923A (ja) | 新規ポリアミド | |
| JPS6317092B2 (US07345094-20080318-C00003.png) | ||
| JPH08120040A (ja) | 耐熱性電気絶縁材料およびそれを用いた耐熱性電気絶縁膜の製造方法 | |
| US3789048A (en) | Oligomer polyimide precursors |
