DE2933819A1 - Polyimidazol- und polyimidazopyrrolon-vorstufen sowie deren herstellung - Google Patents
Polyimidazol- und polyimidazopyrrolon-vorstufen sowie deren herstellungInfo
- Publication number
- DE2933819A1 DE2933819A1 DE19792933819 DE2933819A DE2933819A1 DE 2933819 A1 DE2933819 A1 DE 2933819A1 DE 19792933819 DE19792933819 DE 19792933819 DE 2933819 A DE2933819 A DE 2933819A DE 2933819 A1 DE2933819 A1 DE 2933819A1
- Authority
- DE
- Germany
- Prior art keywords
- polyimidazopyrrolone
- precursors
- polyimidazole
- products
- aromatic
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 239000002243 precursor Substances 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- 125000003277 amino group Chemical group 0.000 claims abstract description 11
- -1 dicarboxylic-acid chlorides Chemical class 0.000 claims abstract description 9
- 150000002148 esters Chemical class 0.000 claims abstract description 8
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 6
- 239000012704 polymeric precursor Substances 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 claims description 18
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- SXEHKFHPFVVDIR-UHFFFAOYSA-N [4-(4-hydrazinylphenyl)phenyl]hydrazine Chemical compound C1=CC(NN)=CC=C1C1=CC=C(NN)C=C1 SXEHKFHPFVVDIR-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 5
- 239000004642 Polyimide Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229920001721 polyimide Polymers 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 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 claims description 2
- 239000013307 optical fiber Substances 0.000 claims description 2
- 239000006223 plastic coating Substances 0.000 claims description 2
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 2
- UJQQHSNSFDJVOT-UHFFFAOYSA-N 2-methylprop-2-enoic acid;oxiran-2-ylmethyl prop-2-enoate Chemical compound CC(=C)C(O)=O.C=CC(=O)OCC1CO1 UJQQHSNSFDJVOT-UHFFFAOYSA-N 0.000 claims 1
- 150000003851 azoles Chemical class 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 239000012713 reactive precursor Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 239000012670 alkaline solution Substances 0.000 description 5
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-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
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- WKIOQNPKWHHOOO-UHFFFAOYSA-N 2,5-dihydrooxazin-6-one Chemical compound O=C1CC=CNO1 WKIOQNPKWHHOOO-UHFFFAOYSA-N 0.000 description 1
- HSTOKWSFWGCZMH-UHFFFAOYSA-N 3,3'-diaminobenzidine Chemical compound C1=C(N)C(N)=CC=C1C1=CC=C(N)C(N)=C1 HSTOKWSFWGCZMH-UHFFFAOYSA-N 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004693 Polybenzimidazole Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- RPDJEKMSFIRVII-UHFFFAOYSA-N oxomethylidenehydrazine Chemical compound NN=C=O RPDJEKMSFIRVII-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920003055 poly(ester-imide) Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 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
- C08G73/18—Polybenzimidazoles
-
- 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
- C08G73/20—Pyrrones
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0387—Polyamides or polyimides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31725—Of polyamide
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Paints Or Removers (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792933819 DE2933819A1 (de) | 1979-08-21 | 1979-08-21 | Polyimidazol- und polyimidazopyrrolon-vorstufen sowie deren herstellung |
| EP80104640A EP0024592B1 (de) | 1979-08-21 | 1980-08-06 | Polyimidazol- und Polyimidazopyrrolon-Vorstufen sowie deren Herstellung |
| AT80104640T ATE3644T1 (de) | 1979-08-21 | 1980-08-06 | Polyimidazol- und polyimidazopyrrolon-vorstufen sowie deren herstellung. |
| DE8080104640T DE3063613D1 (en) | 1979-08-21 | 1980-08-06 | Polyimidazoles and polyimidazopyrrolone precursors and their preparation |
| US06/179,455 US4397999A (en) | 1979-08-21 | 1980-08-19 | Polyimidazole and polyimidazopyrrolone precursor stages and the preparation thereof |
| JP11531780A JPS5636519A (en) | 1979-08-21 | 1980-08-21 | Polyimidazole and polyimidazopyrolo precursor substance and method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792933819 DE2933819A1 (de) | 1979-08-21 | 1979-08-21 | Polyimidazol- und polyimidazopyrrolon-vorstufen sowie deren herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2933819A1 true DE2933819A1 (de) | 1981-03-19 |
Family
ID=6078950
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792933819 Withdrawn DE2933819A1 (de) | 1979-08-21 | 1979-08-21 | Polyimidazol- und polyimidazopyrrolon-vorstufen sowie deren herstellung |
| DE8080104640T Expired DE3063613D1 (en) | 1979-08-21 | 1980-08-06 | Polyimidazoles and polyimidazopyrrolone precursors and their preparation |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8080104640T Expired DE3063613D1 (en) | 1979-08-21 | 1980-08-06 | Polyimidazoles and polyimidazopyrrolone precursors and their preparation |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4397999A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0024592B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5636519A (cg-RX-API-DMAC7.html) |
| AT (1) | ATE3644T1 (cg-RX-API-DMAC7.html) |
| DE (2) | DE2933819A1 (cg-RX-API-DMAC7.html) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0157932A1 (de) * | 1984-03-29 | 1985-10-16 | Siemens Aktiengesellschaft | Verfahren zur Herstellung von Polyimidazol- und Polyimidazopyrrolon-Reliefstrukturen |
| EP0157931A1 (de) * | 1984-03-29 | 1985-10-16 | Siemens Aktiengesellschaft | Verfahren zur Herstellung von Polyimidazol- und Polyimidazopyrrolon-Vorstufen |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3021787A1 (de) * | 1980-06-10 | 1981-12-17 | Siemens AG, 1000 Berlin und 8000 München | Verfahren zur herstellung hochwaermebestaendiger reliefstrukturen und deren verwendung |
| DE3107519A1 (de) * | 1981-02-27 | 1982-09-16 | Siemens AG, 1000 Berlin und 8000 München | "verfahren zur herstellung von orietierungsschichten fuer fluessigkristalldisplays sowie orientierungsschichten aufweisende fluessigkeitskristalle" |
| US4517321A (en) * | 1983-05-20 | 1985-05-14 | Union Carbide Corporation | Preimpregnated reinforcements and high strength composites therefrom |
| JPS606725A (ja) * | 1983-06-27 | 1985-01-14 | Ube Ind Ltd | 有機溶媒可溶性の感光性ポリアミド |
| US4595745A (en) * | 1983-06-27 | 1986-06-17 | Ube Industries, Ltd. | Organic solvent-soluble photosensitive polyamide resin |
| JPS60180197A (ja) * | 1984-02-27 | 1985-09-13 | 宇部興産株式会社 | 多層プリント配線板の製造方法 |
| JP3526117B2 (ja) * | 1994-11-07 | 2004-05-10 | 株式会社小松製作所 | 液体封入サスペンション |
| JPH10221549A (ja) * | 1997-02-07 | 1998-08-21 | Hitachi Ltd | プラスチック製光導波路およびそれを用いた光スイッチ |
| US7617821B2 (en) * | 2005-11-23 | 2009-11-17 | Vibralung, Inc. | Acoustic respiratory therapy apparatus |
| US10934395B2 (en) * | 2018-06-15 | 2021-03-02 | Pbi Performance Products, Inc. | Polybenzimidazole oligomers with reactive end groups |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3483105A (en) * | 1966-05-18 | 1969-12-09 | Ppg Industries Inc | Highly radiation-sensitive telomerized polyamides |
| US3338985A (en) * | 1966-11-14 | 1967-08-29 | Du Pont | Graft copolymers of epoxyethylene groups of polyamide or polyester substrates |
| NL177718C (nl) * | 1973-02-22 | 1985-11-01 | Siemens Ag | Werkwijze ter vervaardiging van reliefstructuren uit warmte-bestendige polymeren. |
| US3988287A (en) * | 1974-02-09 | 1976-10-26 | Teijin Limited | Polyamide compositions |
| DE2462196A1 (de) * | 1974-08-02 | 1976-05-26 | Siemens Ag | Verfahren zur herstellung strahlungsempfindlicher, loeslicher polymerer verbindungen |
| US4026904A (en) * | 1974-10-02 | 1977-05-31 | University Of Notre Dame | Aromatic epoxy-terminated polyimides |
-
1979
- 1979-08-21 DE DE19792933819 patent/DE2933819A1/de not_active Withdrawn
-
1980
- 1980-08-06 EP EP80104640A patent/EP0024592B1/de not_active Expired
- 1980-08-06 AT AT80104640T patent/ATE3644T1/de not_active IP Right Cessation
- 1980-08-06 DE DE8080104640T patent/DE3063613D1/de not_active Expired
- 1980-08-19 US US06/179,455 patent/US4397999A/en not_active Expired - Lifetime
- 1980-08-21 JP JP11531780A patent/JPS5636519A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0157932A1 (de) * | 1984-03-29 | 1985-10-16 | Siemens Aktiengesellschaft | Verfahren zur Herstellung von Polyimidazol- und Polyimidazopyrrolon-Reliefstrukturen |
| EP0157931A1 (de) * | 1984-03-29 | 1985-10-16 | Siemens Aktiengesellschaft | Verfahren zur Herstellung von Polyimidazol- und Polyimidazopyrrolon-Vorstufen |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3063613D1 (en) | 1983-07-07 |
| EP0024592B1 (de) | 1983-06-01 |
| US4397999A (en) | 1983-08-09 |
| JPH0120169B2 (cg-RX-API-DMAC7.html) | 1989-04-14 |
| EP0024592A1 (de) | 1981-03-11 |
| ATE3644T1 (de) | 1983-06-15 |
| JPS5636519A (en) | 1981-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |