GB903271A - Polyimides and their production - Google Patents
Polyimides and their productionInfo
- Publication number
- GB903271A GB903271A GB861560A GB861560A GB903271A GB 903271 A GB903271 A GB 903271A GB 861560 A GB861560 A GB 861560A GB 861560 A GB861560 A GB 861560A GB 903271 A GB903271 A GB 903271A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetracarboxylic
- formamide
- specified
- dimethyl
- dicarboxyphenyl
- 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
- 239000004642 Polyimide Substances 0.000 title abstract 3
- 229920001721 polyimide Polymers 0.000 title abstract 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract 3
- 150000004985 diamines Chemical class 0.000 abstract 3
- 239000000376 reactant Substances 0.000 abstract 3
- -1 tetracarboxylic acid dianhydride Chemical class 0.000 abstract 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 abstract 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 239000001294 propane Substances 0.000 abstract 2
- RLFFWWKJSJOYMQ-UHFFFAOYSA-N 1,3-diazepan-2-one Chemical compound O=C1NCCCCN1 RLFFWWKJSJOYMQ-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- YLHUPYSUKYAIBW-UHFFFAOYSA-N 1-acetylpyrrolidin-2-one Chemical compound CC(=O)N1CCCC1=O YLHUPYSUKYAIBW-UHFFFAOYSA-N 0.000 abstract 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 abstract 1
- 229930188620 butyrolactone Natural products 0.000 abstract 1
- 150000001718 carbodiimides Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000006159 dianhydride group Chemical group 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- AIJZIRPGCQPZSL-UHFFFAOYSA-N ethylenetetracarboxylic acid Chemical compound OC(=O)C(C(O)=O)=C(C(O)=O)C(O)=O AIJZIRPGCQPZSL-UHFFFAOYSA-N 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 abstract 1
- NWRSLSNMQXMRHQ-UHFFFAOYSA-N octadecane-7,7-diamine Chemical compound CCCCCCCCCCCC(N)(N)CCCCCC NWRSLSNMQXMRHQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 abstract 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- 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
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
-
- 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
- C08G73/1003—Preparatory processes
-
- 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
- C08G73/1003—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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Polyimides are made by reacting approximately equimolar proportions of at least one diamine having the structural formula H2N-R1-NH2 where R1 is a divalent radical containing at least two carbon atoms, the two amino groups of said diamine each attached to separate carbon atoms of said divalent radical; with at least one tetracarboxylic acid dianhydride having the structural formula <FORM:0903271/IV(a)/1> where R is a tetravalent radical containing at least 2 carbon atoms; no more than 2 carbonyl groups of said dianhydride attached to any one carbon atom of said tetravalent radical; in an organic solvent for at least one reactant whose functional groups do not react with either of the reactants to a greater extent than the reactants do with each other, under substantially anhydrous conditions while maintaining the temperature throughout the reaction below 60 DEG C. to provide a polymer containing at least 50% polyamide-acid having a viscosity measured at 30 DEG C. in a 0,5% by weight solution, of at least 0,1 and reacting the polymer with an aliphatic acid anhydride or carbodiimide to convert the polyamide-acid to a polyimide. Many suitable diamines are specified, examples being 4:41-diaminodiphenyl propane, m-xylylene diamine and 1:12-diaminooctadecane. Specified dianhydrides are pyromellitic, 2:3:6:7-naphthalene tetracarboxylic, 1:2:5:6-naphthalene tetracarboxylic, 2:21:3:31-diphenyl tetracarboxylic, 2:2-bis(3:4-dicarboxyphenyl) propane, bis(3:4-dicarboxyphenyl) sulphone, perylene-3:4:9:10-tetracarboxylic, bis(3:4-dicarboxyphenyl) ether and ethylene tetracarboxylic acid dianhydride. Specified solvents are N:N-dimethyl formamide, N:N-dimethyl acetamide, N:N-diethyl formamide, N:N-diethyl acetamide, N:N-dimethylmethoxy acetamide, N-methyl caprolactam, dimethyl sulphoxide, N-methyl-2-pyrrolidone, tetramethylene urea, pyridine, dimethyl sulphone, formamide, N-methyl formamide or N-acetyl pyrrolidone alone or in admixture with benzene, benzonitrile, dioxane, butyrolactone, xylene, toluene or cyclohexane. Specified aliphatic acid anhydrides are acetic, propionic, butyric and valeric anhydride. Many examples are given. Specification 898,651 is referred to.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80334859A | 1959-04-01 | 1959-04-01 | |
| US80334759A | 1959-04-01 | 1959-04-01 | |
| US80334959A | 1959-04-01 | 1959-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB903271A true GB903271A (en) | 1962-08-15 |
Family
ID=27419997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB861560A Expired GB903271A (en) | 1959-04-01 | 1960-03-11 | Polyimides and their production |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE589179A (en) |
| CH (1) | CH445846A (en) |
| DE (1) | DE1202981C2 (en) |
| DK (1) | DK109110C (en) |
| GB (1) | GB903271A (en) |
| NL (1) | NL6917578A (en) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3356759A (en) * | 1962-12-19 | 1967-12-05 | Du Pont | Composition comprising a polypyromellitimide and a fluorocarbon resin |
| US3356760A (en) * | 1967-03-16 | 1967-12-05 | Du Pont | Resinous material containing an aromatic polyimide, a fluorocarbon polymer and a polyamide |
| US3364166A (en) * | 1964-06-30 | 1968-01-16 | Gen Electric | Polycarboxylic aromatic imide enamels |
| DE1266427B (en) * | 1963-01-08 | 1968-04-18 | Bayer Ag | Process for the production of lacquer coatings based on polyisocyanates |
| DE1283933B (en) * | 1964-12-11 | 1968-11-28 | Haveg Industries Inc | Electrical conductor |
| US3415782A (en) * | 1964-03-30 | 1968-12-10 | Du Pont | Formation of polypyromellitimide filaments |
| DE1494457A1 (en) * | 1965-06-01 | 1969-12-11 | Herberts & Co Gmbh Dr Kurt | Process for the production of insulating coatings on electrical conductors |
| DE2022665A1 (en) * | 1969-05-08 | 1970-11-19 | Gen Electric | Improved process for making polyamide coating material |
| JPS4826723A (en) * | 1971-08-06 | 1973-04-09 | ||
| US4299787A (en) | 1978-10-19 | 1981-11-10 | International Harvester Company | Melt spinning polyimide fibers |
| US4470944A (en) * | 1982-02-23 | 1984-09-11 | Toray Industries, Inc. | Process for producing an aromatic polyimide film |
| GB2157303A (en) * | 1984-03-05 | 1985-10-23 | Rogers Corp | Co-solvent accelerator and method for conversion of polyamide-acid, solution to polylmide |
| US5229039A (en) * | 1988-11-11 | 1993-07-20 | International Business Machines Corporation | Color liquid crystal display and method of manufacture |
| EP0281923B1 (en) * | 1987-03-09 | 1994-06-15 | Kanegafuchi Chemical Industry Co., Ltd. | Polyimide film |
| US20140054062A1 (en) * | 2011-11-16 | 2014-02-27 | Sumitomo Electric Wintec, Inc. | Insulating varnish and insulated electrical wire using same |
| CN111512153A (en) * | 2018-10-05 | 2020-08-07 | 株式会社Lg化学 | Method for analyzing dianhydride |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1019888A (en) * | 1972-12-29 | 1977-10-25 | General Electric Company | Polyetherimides |
| EP0116297B1 (en) * | 1983-01-15 | 1987-12-02 | Akzo GmbH | Polyimide laminate with peel-resistance and method of manufacturing it |
| DE3411660A1 (en) * | 1984-03-29 | 1985-10-03 | Siemens AG, 1000 Berlin und 8000 München | METHOD FOR PRODUCING POLYIMIDE AND POLYISOINDOLOCHINAZOLINDION PRE-STAGES |
| DE3411697A1 (en) * | 1984-03-29 | 1985-10-10 | Siemens AG, 1000 Berlin und 8000 München | METHOD FOR PRODUCING POLYIMIDE AND POLYISOINDOLOCHINAZOLINDION RELIEF STRUCTURES |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1031510B (en) * | 1953-10-19 | 1958-06-04 | Du Pont | Process for the preparation of polypyromellitic acid imides |
| US2781359A (en) * | 1953-12-21 | 1957-02-12 | Du Pont | Cyclohexene-4, 5, 4, 5-tetracarboxylic diimides and preparation of same |
| US2867609A (en) * | 1955-06-13 | 1959-01-06 | Du Pont | Preparation of polypyromellitimides |
| DE1037112B (en) * | 1955-10-28 | 1958-08-21 | Basf Ag | Process for the production of chipboard |
-
1960
- 1960-03-11 DK DK94560A patent/DK109110C/en active
- 1960-03-11 GB GB861560A patent/GB903271A/en not_active Expired
- 1960-03-11 DE DE1960P0024596 patent/DE1202981C2/en not_active Expired
- 1960-03-11 CH CH275860A patent/CH445846A/en unknown
- 1960-03-29 BE BE589179A patent/BE589179A/en unknown
-
1969
- 1969-11-21 NL NL6917578A patent/NL6917578A/xx unknown
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3356759A (en) * | 1962-12-19 | 1967-12-05 | Du Pont | Composition comprising a polypyromellitimide and a fluorocarbon resin |
| DE1266427B (en) * | 1963-01-08 | 1968-04-18 | Bayer Ag | Process for the production of lacquer coatings based on polyisocyanates |
| US3415782A (en) * | 1964-03-30 | 1968-12-10 | Du Pont | Formation of polypyromellitimide filaments |
| US3364166A (en) * | 1964-06-30 | 1968-01-16 | Gen Electric | Polycarboxylic aromatic imide enamels |
| DE1283933B (en) * | 1964-12-11 | 1968-11-28 | Haveg Industries Inc | Electrical conductor |
| DE1494457A1 (en) * | 1965-06-01 | 1969-12-11 | Herberts & Co Gmbh Dr Kurt | Process for the production of insulating coatings on electrical conductors |
| US3356760A (en) * | 1967-03-16 | 1967-12-05 | Du Pont | Resinous material containing an aromatic polyimide, a fluorocarbon polymer and a polyamide |
| DE2022665A1 (en) * | 1969-05-08 | 1970-11-19 | Gen Electric | Improved process for making polyamide coating material |
| JPS4826723A (en) * | 1971-08-06 | 1973-04-09 | ||
| US4299787A (en) | 1978-10-19 | 1981-11-10 | International Harvester Company | Melt spinning polyimide fibers |
| US4470944A (en) * | 1982-02-23 | 1984-09-11 | Toray Industries, Inc. | Process for producing an aromatic polyimide film |
| GB2157303A (en) * | 1984-03-05 | 1985-10-23 | Rogers Corp | Co-solvent accelerator and method for conversion of polyamide-acid, solution to polylmide |
| EP0281923B1 (en) * | 1987-03-09 | 1994-06-15 | Kanegafuchi Chemical Industry Co., Ltd. | Polyimide film |
| US5229039A (en) * | 1988-11-11 | 1993-07-20 | International Business Machines Corporation | Color liquid crystal display and method of manufacture |
| US20140054062A1 (en) * | 2011-11-16 | 2014-02-27 | Sumitomo Electric Wintec, Inc. | Insulating varnish and insulated electrical wire using same |
| US9378863B2 (en) * | 2011-11-16 | 2016-06-28 | Sumitomo Electric Industries, Ltd. | Insulating varnish and insulated electrical wire using same |
| CN111512153A (en) * | 2018-10-05 | 2020-08-07 | 株式会社Lg化学 | Method for analyzing dianhydride |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1202981C2 (en) | 1975-06-12 |
| DE1202981B (en) | 1965-10-14 |
| NL6917578A (en) | 1970-05-25 |
| DK109110C (en) | 1968-03-18 |
| CH445846A (en) | 1967-10-31 |
| BE589179A (en) | 1960-09-29 |
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