DE60110195T2 - Schmelzverarbeitbare, semikristallinische Blockcopolyimiden - Google Patents
Schmelzverarbeitbare, semikristallinische Blockcopolyimiden Download PDFInfo
- Publication number
- DE60110195T2 DE60110195T2 DE60110195T DE60110195T DE60110195T2 DE 60110195 T2 DE60110195 T2 DE 60110195T2 DE 60110195 T DE60110195 T DE 60110195T DE 60110195 T DE60110195 T DE 60110195T DE 60110195 T2 DE60110195 T2 DE 60110195T2
- Authority
- DE
- Germany
- Prior art keywords
- segment
- apb
- bis
- dianhydride
- aminophenoxy
- 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 - Fee Related
Links
- 229920001721 polyimide Polymers 0.000 claims description 128
- 239000004642 Polyimide Substances 0.000 claims description 112
- 150000004985 diamines Chemical class 0.000 claims description 110
- 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 97
- 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 81
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 80
- 150000001408 amides Chemical class 0.000 claims description 75
- 238000002844 melting Methods 0.000 claims description 73
- 230000008018 melting Effects 0.000 claims description 73
- 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 claims description 59
- 229920005575 poly(amic acid) Polymers 0.000 claims description 55
- 239000002253 acid Substances 0.000 claims description 53
- 239000000178 monomer Substances 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 43
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 claims description 37
- 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 description 28
- 238000000034 method Methods 0.000 claims description 22
- 239000002243 precursor Substances 0.000 claims description 20
- 229920001577 copolymer Polymers 0.000 claims description 19
- ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-UHFFFAOYSA-N 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 150000008065 acid anhydrides Chemical class 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 16
- QHHKLPCQTTWFSS-UHFFFAOYSA-N 5-[2-(1,3-dioxo-2-benzofuran-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)(C(F)(F)F)C(F)(F)F)=C1 QHHKLPCQTTWFSS-UHFFFAOYSA-N 0.000 claims description 12
- 239000000376 reactant Substances 0.000 claims description 12
- 238000006358 imidation reaction Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 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 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 6
- 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 claims description 3
- 150000001875 compounds Chemical class 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 88
- 239000011541 reaction mixture Substances 0.000 description 59
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 40
- 239000000203 mixture Substances 0.000 description 37
- 229920000642 polymer Polymers 0.000 description 27
- 238000002425 crystallisation Methods 0.000 description 24
- 230000008025 crystallization Effects 0.000 description 24
- 238000003756 stirring Methods 0.000 description 23
- 239000000155 melt Substances 0.000 description 22
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 21
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 238000005227 gel permeation chromatography Methods 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 17
- 125000006159 dianhydride group Chemical group 0.000 description 17
- 238000001035 drying Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000009477 glass transition Effects 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 230000004927 fusion Effects 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 238000010583 slow cooling Methods 0.000 description 8
- 238000004528 spin coating Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 238000012512 characterization method Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000010791 quenching Methods 0.000 description 7
- 238000010792 warming Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920001400 block copolymer Polymers 0.000 description 6
- 238000013365 molecular weight analysis method Methods 0.000 description 6
- 238000003303 reheating Methods 0.000 description 6
- 230000007704 transition Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 230000014509 gene expression Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 238000010128 melt processing Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 210000003739 neck Anatomy 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 229920006259 thermoplastic polyimide Polymers 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BZXJAHGHOJFYRT-UHFFFAOYSA-N 3-[2-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C(=CC=CC=2)OC=2C=C(N)C=CC=2)=C1 BZXJAHGHOJFYRT-UHFFFAOYSA-N 0.000 description 1
- 241001136792 Alle Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 208000002430 Multiple chemical sensitivity Diseases 0.000 description 1
- ZKGNPQKYVKXMGJ-UHFFFAOYSA-N N,N-dimethylacetamide Chemical compound CN(C)C(C)=O.CN(C)C(C)=O ZKGNPQKYVKXMGJ-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006126 semicrystalline polymer Polymers 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C08G73/14—Polyamide-imides
-
- 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
- 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
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)
- Polyamides (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US741941 | 2000-12-21 | ||
| US09/741,941 US6444783B1 (en) | 2000-12-21 | 2000-12-21 | Melt-processible semicrystalline block copolyimides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60110195D1 DE60110195D1 (de) | 2005-05-25 |
| DE60110195T2 true DE60110195T2 (de) | 2006-03-09 |
Family
ID=24982864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60110195T Expired - Fee Related DE60110195T2 (de) | 2000-12-21 | 2001-10-29 | Schmelzverarbeitbare, semikristallinische Blockcopolyimiden |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US6444783B1 (enExample) |
| EP (1) | EP1219663B1 (enExample) |
| JP (1) | JP4031241B2 (enExample) |
| DE (1) | DE60110195T2 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1561786A4 (en) * | 2002-10-16 | 2007-07-18 | Pi R & D Co Ltd | COMPOSITIONS OF COPOLYIMIDE SEQUENCES COMPRISING PYROMELLIIC DIANHYDRIDE AND PROCESS FOR PRODUCING THE SAME |
| US20040132900A1 (en) * | 2003-01-08 | 2004-07-08 | International Business Machines Corporation | Polyimide compositions and use thereof in ceramic product defect repair |
| US7129318B2 (en) * | 2003-09-02 | 2006-10-31 | I.S.T. (Ma) Corporation | RTM and RI processable polyimide resins |
| EP1910078A4 (en) * | 2005-08-02 | 2012-06-06 | Nexolve Corp | HETEROPOLYMERIC COMPOSITIONS OF POLYIMIDE POLYMER |
| KR101115058B1 (ko) * | 2008-07-09 | 2012-02-13 | 주식회사 엘지화학 | 폴리이미드-폴리아믹산 공중합체, 이의 제조방법, 이를포함하는 감광성 조성물 및 이에 의해 제공된 보호막 |
| FR2980203B1 (fr) * | 2011-09-20 | 2014-12-26 | Rhodia Operations | Copolyimides thermoplastiques |
| WO2013130724A2 (en) | 2012-02-28 | 2013-09-06 | Corning Incorporated | Glass articles with low-friction coatings |
| US11497681B2 (en) | 2012-02-28 | 2022-11-15 | Corning Incorporated | Glass articles with low-friction coatings |
| US10737973B2 (en) | 2012-02-28 | 2020-08-11 | Corning Incorporated | Pharmaceutical glass coating for achieving particle reduction |
| US10273048B2 (en) | 2012-06-07 | 2019-04-30 | Corning Incorporated | Delamination resistant glass containers with heat-tolerant coatings |
| RU2674269C2 (ru) | 2012-06-07 | 2018-12-06 | Корнинг Инкорпорейтед | Стойкие к расслаиванию стеклянные контейнеры |
| US9034442B2 (en) | 2012-11-30 | 2015-05-19 | Corning Incorporated | Strengthened borosilicate glass containers with improved damage tolerance |
| US10117806B2 (en) | 2012-11-30 | 2018-11-06 | Corning Incorporated | Strengthened glass containers resistant to delamination and damage |
| CN107074628B (zh) | 2014-09-05 | 2020-05-19 | 康宁股份有限公司 | 玻璃制品和用于改善玻璃制品的可靠性的方法 |
| US10065884B2 (en) | 2014-11-26 | 2018-09-04 | Corning Incorporated | Methods for producing strengthened and durable glass containers |
| EP3150564B1 (en) | 2015-09-30 | 2018-12-05 | Corning Incorporated | Halogenated polyimide siloxane chemical compositions and glass articles with halogenated polylmide siloxane low-friction coatings |
| MX2018005349A (es) | 2015-10-30 | 2018-05-17 | Corning Inc | Articulos de vidrio con revestimientos de oxido de metal y polimero mezclados. |
| EP3246298A1 (en) | 2016-05-12 | 2017-11-22 | Corning Incorporated | Pharmaceutical glass coating for achieving particle reduction |
| CN109661576A (zh) | 2016-09-02 | 2019-04-19 | 康宁股份有限公司 | 用于检测玻璃包装工艺中的挥发性有机化合物的方法和设备 |
| US20190161399A1 (en) | 2017-11-30 | 2019-05-30 | Corning Incorporated | Glass articles with low-friction coatings and methods for coating glass articles |
| KR102813830B1 (ko) * | 2018-12-28 | 2025-05-28 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 이미드-아미드산 공중합체 및 그의 제조방법, 바니시, 그리고 폴리이미드 필름 |
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| WO2021210640A1 (ja) * | 2020-04-16 | 2021-10-21 | 三菱瓦斯化学株式会社 | イミド－アミド酸共重合体及びその製造方法、ワニス、並びにポリイミドフィルム |
| WO2021210641A1 (ja) * | 2020-04-16 | 2021-10-21 | 三菱瓦斯化学株式会社 | イミド－アミド酸共重合体及びその製造方法、ワニス、並びにポリイミドフィルム |
| MX2023002689A (es) | 2020-09-04 | 2023-05-25 | Corning Inc | Empaques farmaceuticos recubiertos con bloqueo de luz ultravioleta. |
| WO2022211086A1 (ja) * | 2021-04-02 | 2022-10-06 | 旭化成株式会社 | ポリイミド、樹脂組成物、ポリイミドフィルム、及び、その製造方法 |
| JP2023047875A (ja) * | 2021-09-27 | 2023-04-06 | 株式会社カネカ | ポリイミド前駆体とポリイミド、ポリイミドフィルムならびに多層フィルム |
| WO2025239165A1 (ja) * | 2024-05-17 | 2025-11-20 | Jnc株式会社 | ポリイミド前駆体、熱硬化性樹脂組成物、硬化膜、基板、電子部品およびポリイミド前駆体の製造方法 |
| CN119613719A (zh) * | 2024-12-19 | 2025-03-14 | 香港中文大学（深圳） | 一种基于序列调控的含氟聚酰胺酸、聚酰亚胺薄膜及其制备方法 |
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2000
- 2000-12-21 US US09/741,941 patent/US6444783B1/en not_active Expired - Fee Related
-
2001
- 2001-10-29 DE DE60110195T patent/DE60110195T2/de not_active Expired - Fee Related
- 2001-10-29 EP EP01125758A patent/EP1219663B1/en not_active Expired - Lifetime
- 2001-12-21 JP JP2001390598A patent/JP4031241B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002201271A (ja) | 2002-07-19 |
| EP1219663A2 (en) | 2002-07-03 |
| EP1219663A3 (en) | 2003-03-26 |
| EP1219663B1 (en) | 2005-04-20 |
| DE60110195D1 (de) | 2005-05-25 |
| JP4031241B2 (ja) | 2008-01-09 |
| US6444783B1 (en) | 2002-09-03 |
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