JP2002201273A - 回復可能な結晶化度を有する溶融加工可能な熱可塑性ランダムコポリイミドおよびその製造方法 - Google Patents
回復可能な結晶化度を有する溶融加工可能な熱可塑性ランダムコポリイミドおよびその製造方法Info
- Publication number
- JP2002201273A JP2002201273A JP2001390581A JP2001390581A JP2002201273A JP 2002201273 A JP2002201273 A JP 2002201273A JP 2001390581 A JP2001390581 A JP 2001390581A JP 2001390581 A JP2001390581 A JP 2001390581A JP 2002201273 A JP2002201273 A JP 2002201273A
- Authority
- JP
- Japan
- Prior art keywords
- component
- oda
- copolyimide
- bpda
- melt
- 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.)
- Pending
Links
- 229920001169 thermoplastic Polymers 0.000 title claims description 5
- 239000004416 thermosoftening plastic Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 17
- 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 abstract description 96
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims abstract description 83
- 238000002844 melting Methods 0.000 claims abstract description 72
- 230000008018 melting Effects 0.000 claims abstract description 72
- 239000000155 melt Substances 0.000 claims abstract description 57
- 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 abstract description 54
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000004984 aromatic diamines Chemical class 0.000 claims abstract description 28
- 238000000113 differential scanning calorimetry Methods 0.000 claims abstract description 24
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 claims abstract description 18
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 claims abstract description 17
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 7
- 239000004642 Polyimide Substances 0.000 claims description 117
- 229920001721 polyimide Polymers 0.000 claims description 117
- 238000000034 method Methods 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 43
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 42
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 42
- 238000006116 polymerization reaction Methods 0.000 claims description 38
- 238000010438 heat treatment Methods 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 238000001816 cooling Methods 0.000 claims description 23
- 238000002156 mixing Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- 238000010128 melt processing Methods 0.000 claims description 9
- 230000001747 exhibiting effect Effects 0.000 claims description 7
- 239000008188 pellet Substances 0.000 claims description 7
- 239000000835 fiber Substances 0.000 claims description 6
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 3
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 claims 9
- 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 4
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000006835 compression Effects 0.000 claims 1
- 238000007906 compression Methods 0.000 claims 1
- 235000012438 extruded product Nutrition 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 description 42
- 230000008025 crystallization Effects 0.000 description 42
- 229920000642 polymer Polymers 0.000 description 34
- 150000004985 diamines Chemical class 0.000 description 31
- 238000003303 reheating Methods 0.000 description 18
- 229920005575 poly(amic acid) Polymers 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000000178 monomer Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000010791 quenching Methods 0.000 description 6
- 125000006159 dianhydride group Chemical group 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010583 slow cooling Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000004898 kneading Methods 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 230000000171 quenching effect Effects 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000013329 compounding Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000004100 electronic packaging Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- -1 laminates Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 2
- 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 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241001555133 Picrodendron baccatum Species 0.000 description 1
- 235000009984 Pterocarpus indicus Nutrition 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- IZJDCINIYIMFGX-UHFFFAOYSA-N benzo[f][2]benzofuran-1,3-dione Chemical compound C1=CC=C2C=C3C(=O)OC(=O)C3=CC2=C1 IZJDCINIYIMFGX-UHFFFAOYSA-N 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 229910001338 liquidmetal Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229920006126 semicrystalline polymer Polymers 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920006259 thermoplastic polyimide Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 238000004260 weight control 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
- C08G73/10—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
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
- C08G73/1014—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents in the form of (mono)anhydrid
-
- 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
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
-
- 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
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
- C08G73/1017—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents in the form of (mono)amine
-
- 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
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
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)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Treatment Of Fiber Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/741,943 | 2000-12-21 | ||
| US09/741,943 US6469126B1 (en) | 2000-12-21 | 2000-12-21 | Melt-processible, thermoplastic random copolyimides having recoverable crystallinity and associated processes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002201273A true JP2002201273A (ja) | 2002-07-19 |
| JP2002201273A5 JP2002201273A5 (enExample) | 2005-07-14 |
Family
ID=24982874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001390581A Pending JP2002201273A (ja) | 2000-12-21 | 2001-12-21 | 回復可能な結晶化度を有する溶融加工可能な熱可塑性ランダムコポリイミドおよびその製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US6469126B1 (enExample) |
| EP (1) | EP1217027B1 (enExample) |
| JP (1) | JP2002201273A (enExample) |
| DE (1) | DE60110357T2 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6852826B2 (en) * | 2001-12-21 | 2005-02-08 | Kanera Corporation | Manufacturing method of polyamic acid, and polyamic acid solution |
| US6956098B2 (en) * | 2002-09-20 | 2005-10-18 | E. I. Du Pont De Nemours And Company | High modulus polyimide compositions useful as dielectric substrates for electronics applications, and methods relating thereto |
Family Cites Families (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2682802A (en) | 1946-08-23 | 1954-07-06 | Owens Illinois Glass Co | Gauging and detecting apparatus |
| US3489725A (en) | 1965-10-12 | 1970-01-13 | American Cyanamid Co | Process for the preparation of polyimides using a melt polymerization technique |
| US3803085A (en) | 1972-12-29 | 1974-04-09 | Gen Electric | Method for making polyetherimides |
| US3880750A (en) | 1974-06-06 | 1975-04-29 | Owens Illinois Inc | Sealing surface gauge |
| US4046258A (en) | 1976-07-02 | 1977-09-06 | Owens-Illinois, Inc. | Method and apparatus for measuring the eccentricity of containers |
| US4073773A (en) | 1976-12-30 | 1978-02-14 | General Electric Company | Melt polymerization method for making polyetherimides |
| US4281100A (en) | 1979-05-09 | 1981-07-28 | General Electric Company | Injection moldable polyetherimide oligomers and method for making |
| US4378493A (en) | 1980-11-03 | 1983-03-29 | Owens-Illinois, Inc. | Glass container sidewall defect detection system with a diffused and controlled light source |
| US4378495A (en) | 1980-11-07 | 1983-03-29 | Owens-Illinois, Inc. | Method and apparatus for setup of inspection devices for glass bottles |
| US4584469A (en) | 1982-12-30 | 1986-04-22 | Owens-Illinois, Inc. | Optical detection of radial reflective defects |
| US4485140A (en) | 1983-09-21 | 1984-11-27 | E. I. Du Pont De Nemours And Company | Melt-fusible polyimides |
| US4590258A (en) | 1983-12-30 | 1986-05-20 | International Business Machines Corporation | Polyamic acid copolymer system for improved semiconductor manufacturing |
| US4552931A (en) | 1984-09-11 | 1985-11-12 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Process of end-capping a polyimide system |
| US4883718A (en) | 1985-02-12 | 1989-11-28 | Mitsui Toatsu Chemicals, Inc. | Flexible copper-clad circuit substrate |
| GB2174399B (en) | 1985-03-10 | 1988-05-18 | Nitto Electric Ind Co | Colorless transparent polyimide shaped articles and their production |
| US4644151A (en) | 1985-04-05 | 1987-02-17 | Owens-Illinois, Inc. | Identification of a molded container with its mold of origin |
| US4837300A (en) | 1985-06-20 | 1989-06-06 | The United States Of America As Represented By The Administration Of The National Aeronautics And Space Administration | Copolyimide with a combination of flexibilizing groups |
| JP2622678B2 (ja) | 1987-01-12 | 1997-06-18 | チッソ株式会社 | 溶融成形可能な結晶性ポリイミド重合体 |
| US5116939A (en) | 1987-08-11 | 1992-05-26 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Polyimide processing additives |
| JP2574162B2 (ja) | 1988-01-06 | 1997-01-22 | チッソ株式会社 | 低融点ポリイミド共重合体 |
| US5106938A (en) | 1989-06-08 | 1992-04-21 | General Electric Company | Melt crystalline polyetherimides |
| US5077382A (en) | 1989-10-26 | 1991-12-31 | Occidental Chemical Corporation | Copolyimide odpa/bpda/4,4'-oda or p-pda |
| US5171828A (en) | 1989-10-26 | 1992-12-15 | Occidental Chemical Corporation | Copolyimide ODPA/BPDA/4,4'-ODA or P-PDA |
| US5145937A (en) | 1989-11-09 | 1992-09-08 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Polyimides with carbonyl and ether connecting groups between the aromatic rings |
| US5166308A (en) | 1990-04-30 | 1992-11-24 | E. I. Du Pont De Nemours And Company | Copolyimide film with improved properties |
| DE69127137T2 (de) | 1990-06-01 | 1998-02-26 | Mitsui Toatsu Chemicals | Leicht zu verarbeitende Polyimide und deren Herstellung |
| US5268447A (en) | 1990-06-01 | 1993-12-07 | Mitsui Toatsu Chemicals, Inc. | Readily processable polyimide and preparation process of same |
| US5268446A (en) | 1990-08-24 | 1993-12-07 | Mitsui Toatsu Chemicals, Incorporated | Readily processable polyimide and preparation process of same |
| EP0474054B1 (en) | 1990-08-27 | 1995-12-06 | E.I. Du Pont De Nemours And Company | Flexible multi-layer polyimide film laminates and preparation thereof |
| US5202412A (en) | 1990-10-02 | 1993-04-13 | E. I. Du Pont De Nemours And Company | Polyimide copolymer precursors |
| US5484879A (en) | 1990-12-17 | 1996-01-16 | Occidental Chemical Corporation | Polyimides containing fluorine |
| US5219977A (en) | 1990-12-17 | 1993-06-15 | E. I. Du Pont De Nemours And Company | Tetrapolyimide film containing oxydipthalic dianhydride |
| EP0518543B1 (en) | 1991-06-10 | 1997-03-12 | MITSUI TOATSU CHEMICALS, Inc. | Polyimide and process for the preparation thereof |
| US5233186A (en) | 1992-06-19 | 1993-08-03 | Owens-Brockway Glass Container Inc. | Inspection of transparent containers with opposing reflection means |
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| US5302652A (en) | 1992-12-15 | 1994-04-12 | E. I. Du Pont De Nemours And Company | Process for preparing a pigmented polyimide shaped article |
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| US5478913A (en) | 1993-12-22 | 1995-12-26 | E. I. Du Pont De Nemours And Company | Melt-processible polyimides with high Tg |
| US5502157A (en) | 1994-08-31 | 1996-03-26 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Copolyimides prepared from ODPA, BTDA and 3,4'-ODA |
| US5464928A (en) | 1994-09-01 | 1995-11-07 | The United States Of America As Represented By The United States National Aeronautics And Space Administration | Direct process for preparing semi-crystalline polyimides |
| US5478916A (en) | 1994-09-01 | 1995-12-26 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Solvent resistant copolyimide |
| US5637864A (en) | 1994-09-17 | 1997-06-10 | Owens-Brockway Glass Container Inc. | Optical inspection of translucent containers for vertical checks and split seams in the container sidewalls |
| US6048959A (en) * | 1994-12-16 | 2000-04-11 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Tough soluble aromatic thermoplastic copolyimides |
| US5644022A (en) * | 1995-02-14 | 1997-07-01 | The United States Of America As Represented By The Admninistrator Of The National Aeronautics And Space Administration | Copolyimides prepared from 3,4'-oxydianiline and 1,3-bis(3-aminophenoxy) benzene with 3,3'-4,4'-biphenylcarboxylic dianhydride having reactive endgroups |
| US5866676A (en) * | 1995-02-14 | 1999-02-02 | The United States Of America As Represented By The United States National Aeronautics And Space Administration | Copolyimides prepared from 3,4'-oxydianiline and 1,3-bis(3-aminophenoxy) benzene with 3,3', 4, 4'-biphenylcarboxylic dianhydride |
| HU224946B1 (en) | 1995-09-22 | 2006-04-28 | Owens Brockway Glass Container | System for checking containers by a field programmable gate array logic |
| US5896195A (en) | 1997-05-15 | 1999-04-20 | Owens-Brockway Glass Container Inc. | Container sealing surface area inspection |
| US6175107B1 (en) | 1998-05-27 | 2001-01-16 | Owens-Brockway Glass Container Inc. | Inspection of containers employing a single area array sensor and alternately strobed light sources |
-
2000
- 2000-12-21 US US09/741,943 patent/US6469126B1/en not_active Expired - Lifetime
-
2001
- 2001-11-05 DE DE60110357T patent/DE60110357T2/de not_active Expired - Fee Related
- 2001-11-05 EP EP01126196A patent/EP1217027B1/en not_active Expired - Lifetime
- 2001-12-21 JP JP2001390581A patent/JP2002201273A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1217027A2 (en) | 2002-06-26 |
| DE60110357D1 (de) | 2005-06-02 |
| EP1217027B1 (en) | 2005-04-27 |
| US6469126B1 (en) | 2002-10-22 |
| EP1217027A3 (en) | 2003-03-26 |
| DE60110357T2 (de) | 2006-02-02 |
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