CA1076749A - Copolyimide foams, precursors therefor, and processes for converting the precursors to the foam - Google Patents
Copolyimide foams, precursors therefor, and processes for converting the precursors to the foamInfo
- Publication number
- CA1076749A CA1076749A CA239,174A CA239174A CA1076749A CA 1076749 A CA1076749 A CA 1076749A CA 239174 A CA239174 A CA 239174A CA 1076749 A CA1076749 A CA 1076749A
- Authority
- CA
- Canada
- Prior art keywords
- diamines
- diamine
- diamino diphenyl
- diamino
- precursor
- 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
- 239000006260 foam Substances 0.000 title claims abstract description 60
- 239000002243 precursor Substances 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 37
- 230000008569 process Effects 0.000 title claims abstract description 25
- 150000004985 diamines Chemical class 0.000 claims abstract description 63
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims abstract description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 3
- -1 heterocyclic diamine Chemical class 0.000 claims description 25
- 239000003039 volatile agent Substances 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 19
- 239000004642 Polyimide Substances 0.000 claims description 17
- 150000004984 aromatic diamines Chemical class 0.000 claims description 17
- 229920001721 polyimide Polymers 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims description 8
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 7
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 6
- LXJLFVRAWOOQDR-UHFFFAOYSA-N 3-(3-aminophenoxy)aniline Chemical compound NC1=CC=CC(OC=2C=C(N)C=CC=2)=C1 LXJLFVRAWOOQDR-UHFFFAOYSA-N 0.000 claims description 6
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- ABYXFACYSGVHCW-UHFFFAOYSA-N pyridine-3,5-diamine Chemical compound NC1=CN=CC(N)=C1 ABYXFACYSGVHCW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000003949 imides Chemical class 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 5
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims 5
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 description 19
- 238000005187 foaming Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 230000001066 destructive effect Effects 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000779 smoke Substances 0.000 description 4
- 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 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 210000003850 cellular structure Anatomy 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- GFWRVVCDTLRWPK-KPKJPENVSA-N sofalcone Chemical compound C1=CC(OCC=C(C)C)=CC=C1\C=C\C(=O)C1=CC=C(OCC=C(C)C)C=C1OCC(O)=O GFWRVVCDTLRWPK-KPKJPENVSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- ZCKAMNXUHHNZLN-UHFFFAOYSA-N Chlorphentermine Chemical compound CC(C)(N)CC1=CC=C(Cl)C=C1 ZCKAMNXUHHNZLN-UHFFFAOYSA-N 0.000 description 1
- 229920008712 Copo Polymers 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- CQGRLHBOVUGVEA-UHFFFAOYSA-N OOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOO CQGRLHBOVUGVEA-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000003398 denaturant Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000004620 low density foam Substances 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical group C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/02—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by the reacting monomers or modifying agents during the preparation or modification of macromolecules
-
- 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
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
-
- 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
- C08G73/1085—Polyimides with diamino moieties or tetracarboxylic segments containing heterocyclic moieties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/522,765 US3966652A (en) | 1974-11-11 | 1974-11-11 | Method of making foamed copolyimides and product obtained therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1076749A true CA1076749A (en) | 1980-04-29 |
Family
ID=24082250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA239,174A Expired CA1076749A (en) | 1974-11-11 | 1975-11-07 | Copolyimide foams, precursors therefor, and processes for converting the precursors to the foam |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US3966652A (OSRAM) |
| JP (1) | JPS5532729B2 (OSRAM) |
| CA (1) | CA1076749A (OSRAM) |
| DE (2) | DE2560068C2 (OSRAM) |
| FR (1) | FR2290463A1 (OSRAM) |
| GB (2) | GB1533590A (OSRAM) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4319000A (en) * | 1975-05-27 | 1982-03-09 | International Harvester Company | Closed cell polyimides |
| GB1527290A (en) * | 1975-11-17 | 1978-10-04 | Roth Sa Freres | Moulding cellular polycarbodiimide |
| CA1131399A (en) * | 1978-02-13 | 1982-09-07 | John Gagliani | Polyimides |
| US4241193A (en) * | 1978-08-21 | 1980-12-23 | International Harvester Company | Polyimides |
| US4273886A (en) * | 1978-08-21 | 1981-06-16 | International Harvester Company | Polyimides |
| US4299787A (en) * | 1978-10-19 | 1981-11-10 | International Harvester Company | Melt spinning polyimide fibers |
| US4255488A (en) * | 1978-10-19 | 1981-03-10 | International Harvester Company | Polyimide fibers |
| US4241114A (en) * | 1980-02-15 | 1980-12-23 | International Harvester Company | Polyimides |
| US4315080A (en) * | 1981-04-14 | 1982-02-09 | International Harvester Company | Polyimides |
| US4346182A (en) * | 1981-04-14 | 1982-08-24 | International Harvester Company | Polyimides |
| US4315076A (en) * | 1980-09-12 | 1982-02-09 | International Harvester Company | Polyimides |
| US4315077A (en) * | 1981-04-14 | 1982-02-09 | International Harvester Company | Polyimides |
| JPS5776031A (en) * | 1980-09-12 | 1982-05-12 | Int Harvester Co | Polyimide |
| US4506038A (en) * | 1982-12-03 | 1985-03-19 | I M L Corporation | Development of polyimide foams with blowing agents |
| US4546115A (en) * | 1985-02-25 | 1985-10-08 | John Gagliani | Polyimide compositions and foams and methods of making same |
| US4556682A (en) * | 1985-02-25 | 1985-12-03 | John Gagliani | Polyimide compositions and foams and methods of making same |
| US4748255A (en) * | 1985-08-27 | 1988-05-31 | Thermal Science, Inc. | Thermally adaptive polymers and prepolymers and methods of making them |
| US4687785A (en) * | 1985-08-27 | 1987-08-18 | Thermal Science, Inc. | Thermally adaptive polymers and prepolymers and methods of making in which an imide is formed from a polyanhydride oligomer and an isocyanate |
| US4738990A (en) * | 1987-08-31 | 1988-04-19 | The Dow Chemical Company | Fire resistant foam composed of predominantly amide and imide linkages |
| US4892896A (en) * | 1988-04-04 | 1990-01-09 | Ethyl Corporation | Processing polyimide precursor compositions |
| US4839398A (en) * | 1988-04-28 | 1989-06-13 | Ethyl Corporation | Polyimide foams and their preparation |
| US4814357A (en) * | 1988-04-28 | 1989-03-21 | Ethyl Corporation | Polyimide foams and their preparation |
| DE3816858A1 (de) * | 1988-05-18 | 1989-11-30 | Basf Ag | Verbundschaumstoff und verfahren zu seiner herstellung |
| US4826886A (en) * | 1988-05-26 | 1989-05-02 | Ethyl Corporation | Polyimide foams and their production |
| US4952611A (en) * | 1988-05-26 | 1990-08-28 | Ethyl Corporation | Polyimide foams and their production |
| US4855332A (en) * | 1988-05-26 | 1989-08-08 | Ethyl Corporation | Polyimide foams and their production |
| US4866104A (en) * | 1988-05-26 | 1989-09-12 | Ethyl Corporation | Polyimide foams and their production |
| US4897432A (en) * | 1988-06-20 | 1990-01-30 | Ethyl Corporation | Production of foamed polymer structures |
| US4855331A (en) * | 1988-06-20 | 1989-08-08 | Ethyl Corporation | Production of foamed polymer structures |
| US4879182A (en) * | 1988-10-24 | 1989-11-07 | Ethyl Corporation | Method of coating carbon bodies |
| US5175241A (en) * | 1989-12-28 | 1992-12-29 | The Dexter Corporation | Polyimide with reduced anhydride content |
| US5077318A (en) * | 1990-01-16 | 1991-12-31 | Ethyl Corporation | Method for producing polyimide foam of desired density |
| US5096932A (en) * | 1990-01-16 | 1992-03-17 | Ethyl Corporation | Polyimide foam products and methods |
| US5122546A (en) * | 1990-01-16 | 1992-06-16 | Ethyl Corporation | Polyimide foam precursor |
| US5064867A (en) * | 1990-04-05 | 1991-11-12 | Ethyl Corporation | Production of foamed polymer structures |
| KR950013539B1 (ko) * | 1991-11-13 | 1995-11-08 | 재단법인한국화학연구소 | 폴리이미드 공중합체 및 그 제조방법 |
| US5296559A (en) * | 1991-12-19 | 1994-03-22 | Dexter-Hysol Aerospace, Inc. | Polyimide composition |
| WO2004072032A2 (en) * | 2003-02-11 | 2004-08-26 | United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Polyimide foams |
| US8268960B2 (en) * | 2006-12-12 | 2012-09-18 | E I Du Pont De Nemours And Company | Process for the synthesis of 3-hydroxyglutaronitrile |
| CN101636387A (zh) * | 2006-12-21 | 2010-01-27 | 纳幕尔杜邦公司 | 由哌啶-2,6-二亚胺合成二氨基吡啶的方法 |
| US8022167B2 (en) * | 2006-12-21 | 2011-09-20 | Aaron Minter | Process for the synthesis of diaminopyridines from glutaronitriles |
| KR20100050524A (ko) | 2007-08-01 | 2010-05-13 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 다이아미노피리딘 및 관련 화합물의 합성 방법 |
| CN101848888A (zh) * | 2007-08-17 | 2010-09-29 | 纳幕尔杜邦公司 | 合成3-羟基戊二腈的方法 |
| US7999057B2 (en) * | 2008-07-08 | 2011-08-16 | E. I. Du Pont De Nemours And Company | Gas-phase process for the synthesis of diaminopyridines from glutaronitriles |
| JP2012512889A (ja) | 2008-12-18 | 2012-06-07 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | グルタロニトリルからジアミノピリジンを合成するための連続液相法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3424718A (en) * | 1964-09-23 | 1969-01-28 | Du Pont | Copolymers of aromatic tetracarboxylic acids with at least two organic diamines |
| US3483144A (en) * | 1966-07-27 | 1969-12-09 | Monsanto Co | Process for the preparation of a polyimide foam |
| US3489696A (en) * | 1966-10-06 | 1970-01-13 | Mobay Chemical Corp | Process of preparing polyimides from isocyanates and polycarboxylic acids |
| US3554935A (en) * | 1968-03-12 | 1971-01-12 | Monsanto Co | Polyimide foams |
| CA982740A (en) * | 1969-06-20 | 1976-01-27 | Luis Acle (Jr.) | Thermoplastic copolyimides |
| US3705118A (en) * | 1971-01-11 | 1972-12-05 | Ibm | Process for forming a microporous cellular polyimide |
| US3726834A (en) * | 1972-07-03 | 1973-04-10 | Int Harvester Co | Thermoplastic copolyimides |
| US3793281A (en) * | 1972-07-14 | 1974-02-19 | Int Harvester Co | Thermoplastic copolyimides |
-
1974
- 1974-11-11 US US05/522,765 patent/US3966652A/en not_active Expired - Lifetime
-
1975
- 1975-05-27 US US05/581,137 patent/US4153783A/en not_active Expired - Lifetime
- 1975-11-07 CA CA239,174A patent/CA1076749A/en not_active Expired
- 1975-11-11 DE DE2560068A patent/DE2560068C2/de not_active Expired
- 1975-11-11 DE DE2550662A patent/DE2550662C2/de not_active Expired
- 1975-11-11 GB GB48099/77A patent/GB1533590A/en not_active Expired
- 1975-11-11 GB GB46546/75A patent/GB1533589A/en not_active Expired
- 1975-11-11 JP JP13561775A patent/JPS5532729B2/ja not_active Expired
- 1975-11-12 FR FR7534459A patent/FR2290463A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5532729B2 (OSRAM) | 1980-08-27 |
| US3966652A (en) | 1976-06-29 |
| GB1533590A (en) | 1978-11-29 |
| GB1533589A (en) | 1978-11-29 |
| FR2290463B1 (OSRAM) | 1980-08-29 |
| FR2290463A1 (fr) | 1976-06-04 |
| DE2550662A1 (de) | 1976-05-13 |
| DE2560068C2 (de) | 1982-08-26 |
| DE2550662C2 (de) | 1983-02-03 |
| JPS5191968A (OSRAM) | 1976-08-12 |
| US4153783A (en) | 1979-05-08 |
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