JPH0122290B2 - - Google Patents
Info
- Publication number
- JPH0122290B2 JPH0122290B2 JP58169292A JP16929283A JPH0122290B2 JP H0122290 B2 JPH0122290 B2 JP H0122290B2 JP 58169292 A JP58169292 A JP 58169292A JP 16929283 A JP16929283 A JP 16929283A JP H0122290 B2 JPH0122290 B2 JP H0122290B2
- Authority
- JP
- Japan
- Prior art keywords
- polyamic acid
- viscosity
- acid solution
- molding
- molar ratio
- 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
Links
- 229920005575 poly(amic acid) Polymers 0.000 claims description 107
- 238000000465 moulding Methods 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 29
- 239000000178 monomer Substances 0.000 claims description 27
- 150000004985 diamines Chemical class 0.000 claims description 26
- 229920001721 polyimide Polymers 0.000 claims description 26
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 claims description 25
- 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 claims description 24
- 239000004642 Polyimide Substances 0.000 claims description 13
- 150000004984 aromatic diamines Chemical class 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000002798 polar solvent Substances 0.000 claims description 5
- 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 claims description 3
- CQMIJLIXKMKFQW-UHFFFAOYSA-N 4-phenylbenzene-1,2,3,5-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C1C1=CC=CC=C1 CQMIJLIXKMKFQW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 101
- 238000000034 method Methods 0.000 description 20
- 238000003756 stirring Methods 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 8
- UEJAKHGKSSMXIS-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid;dihydrate Chemical compound O.O.C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 UEJAKHGKSSMXIS-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- -1 diester compounds Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XKGPQKUHMQMOBK-UHFFFAOYSA-N 4-(4-carboxy-3-methoxycarbonylphenyl)-2-methoxycarbonylbenzoic acid Chemical compound C1=C(C(O)=O)C(C(=O)OC)=CC(C=2C=C(C(C(O)=O)=CC=2)C(=O)OC)=C1 XKGPQKUHMQMOBK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-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
- LALMPTKAUXVISB-UHFFFAOYSA-N 3,4-bis(methoxycarbonyl)-5-phenylphthalic acid Chemical compound C1=C(C(O)=O)C(C(O)=O)=C(C(=O)OC)C(C(=O)OC)=C1C1=CC=CC=C1 LALMPTKAUXVISB-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IWXCYYWDGDDPAC-UHFFFAOYSA-N 4-[(3,4-dicarboxyphenyl)methyl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C(C(O)=O)=C1 IWXCYYWDGDDPAC-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
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 1
- JCRLIUMXGPJBFK-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid;dihydrate Chemical compound O.O.OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JCRLIUMXGPJBFK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010959 steel 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16929283A JPS6063226A (ja) | 1983-09-16 | 1983-09-16 | ポリイミド成形物の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16929283A JPS6063226A (ja) | 1983-09-16 | 1983-09-16 | ポリイミド成形物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6063226A JPS6063226A (ja) | 1985-04-11 |
| JPH0122290B2 true JPH0122290B2 (de) | 1989-04-26 |
Family
ID=15883809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16929283A Granted JPS6063226A (ja) | 1983-09-16 | 1983-09-16 | ポリイミド成形物の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6063226A (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005085324A1 (ja) | 2004-03-03 | 2005-09-15 | Gunze Limited | 無端管状ポリイミドフイルム |
| 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 (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6361030A (ja) * | 1986-09-01 | 1988-03-17 | Kanegafuchi Chem Ind Co Ltd | ポリイミドフイルム及びその製造法 |
| JPS6361029A (ja) * | 1986-09-01 | 1988-03-17 | Kanegafuchi Chem Ind Co Ltd | ポリイミドフイルム及びその製造方法 |
| WO2010050491A1 (ja) * | 2008-10-31 | 2010-05-06 | 宇部興産株式会社 | ポリイミド前駆体溶液組成物 |
| JP5428295B2 (ja) * | 2008-10-31 | 2014-02-26 | 宇部興産株式会社 | ポリイミド前駆体溶液組成物 |
| EP2602848A4 (de) * | 2010-08-02 | 2015-05-20 | Nissan Motor | Negativelektrode für eine lithiumionensekundärbatterie und herstellungsverfahren dafür |
| WO2019004677A1 (ko) * | 2017-06-30 | 2019-01-03 | 에스케이씨코오롱피아이 주식회사 | 폴리이미드 전구체 조성물, 이의 제조방법 및 이로부터 제조된 폴리이미드 기재 |
| JP6573655B2 (ja) * | 2017-12-27 | 2019-09-11 | ユニチカ株式会社 | ガラス基板への塗工用溶液 |
| JP6661206B2 (ja) * | 2019-08-09 | 2020-03-11 | ユニチカ株式会社 | フレキシブルポリイミド基板の製造方法 |
| JP6690802B1 (ja) * | 2020-02-03 | 2020-04-28 | ユニチカ株式会社 | フレキシブルポリイミド基板の製造方法 |
-
1983
- 1983-09-16 JP JP16929283A patent/JPS6063226A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005085324A1 (ja) | 2004-03-03 | 2005-09-15 | Gunze Limited | 無端管状ポリイミドフイルム |
| 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 |
|---|---|
| JPS6063226A (ja) | 1985-04-11 |
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