JP2014201740A - イミドオリゴマー及びこれを加熱硬化させてなるポリイミド樹脂 - Google Patents
イミドオリゴマー及びこれを加熱硬化させてなるポリイミド樹脂 Download PDFInfo
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- JP2014201740A JP2014201740A JP2013090734A JP2013090734A JP2014201740A JP 2014201740 A JP2014201740 A JP 2014201740A JP 2013090734 A JP2013090734 A JP 2013090734A JP 2013090734 A JP2013090734 A JP 2013090734A JP 2014201740 A JP2014201740 A JP 2014201740A
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- Prior art keywords
- imide oligomer
- imide
- oligomer
- apb
- polyimide resin
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- 150000003949 imides Chemical class 0.000 title claims abstract description 89
- 229920001721 polyimide Polymers 0.000 title claims abstract description 43
- 239000009719 polyimide resin Substances 0.000 title claims abstract description 32
- 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 4
- XROLBZOMVNMIFN-UHFFFAOYSA-N 1-(1-benzofuran-4-yl)propan-2-amine Chemical compound CC(N)CC1=CC=CC2=C1C=CO2 XROLBZOMVNMIFN-UHFFFAOYSA-N 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 17
- FYYYKXFEKMGYLZ-UHFFFAOYSA-N 4-(1,3-dioxo-2-benzofuran-5-yl)-2-benzofuran-1,3-dione Chemical compound C=1C=C2C(=O)OC(=O)C2=CC=1C1=CC=CC2=C1C(=O)OC2=O FYYYKXFEKMGYLZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 238000013007 heat curing Methods 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
- -1 4-aminophenoxy Chemical group 0.000 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- 239000002966 varnish Substances 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229920001823 Aquamid® Polymers 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- AXMANIZPMQZKTG-UHFFFAOYSA-N 4-(2-phenylethynyl)-2-benzofuran-1,3-dione Chemical compound O=C1OC(=O)C2=C1C=CC=C2C#CC1=CC=CC=C1 AXMANIZPMQZKTG-UHFFFAOYSA-N 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
- 239000006227 byproduct Substances 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 238000006358 imidation reaction Methods 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- UPGRRPUXXWPEMV-UHFFFAOYSA-N 5-(2-phenylethynyl)-2-benzofuran-1,3-dione Chemical compound C=1C=C2C(=O)OC(=O)C2=CC=1C#CC1=CC=CC=C1 UPGRRPUXXWPEMV-UHFFFAOYSA-N 0.000 abstract description 20
- 238000000465 moulding Methods 0.000 abstract description 8
- 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 abstract description 3
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 abstract description 3
- NBAUUNCGSMAPFM-UHFFFAOYSA-N 3-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC(C(O)=O)=C1C(O)=O NBAUUNCGSMAPFM-UHFFFAOYSA-N 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 description 12
- 239000004642 Polyimide Substances 0.000 description 10
- 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 10
- 150000001875 compounds Chemical class 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 229920001187 thermosetting polymer Polymers 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 150000004984 aromatic diamines Chemical class 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 125000006159 dianhydride group Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical group C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005979 thermal decomposition reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000049 Carbon (fiber) Polymers 0.000 description 3
- 239000004917 carbon fiber Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000012779 reinforcing material Substances 0.000 description 3
- 229910010271 silicon carbide Inorganic materials 0.000 description 3
- 238000003856 thermoforming Methods 0.000 description 3
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- BEKFRNOZJSYWKZ-UHFFFAOYSA-N 4-[2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(N)C=C1 BEKFRNOZJSYWKZ-UHFFFAOYSA-N 0.000 description 2
- HESXPOICBNWMPI-UHFFFAOYSA-N 4-[2-[4-[2-(4-aminophenyl)propan-2-yl]phenyl]propan-2-yl]aniline Chemical compound C=1C=C(C(C)(C)C=2C=CC(N)=CC=2)C=CC=1C(C)(C)C1=CC=C(N)C=C1 HESXPOICBNWMPI-UHFFFAOYSA-N 0.000 description 2
- HHLMWQDRYZAENA-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)C=C1 HHLMWQDRYZAENA-UHFFFAOYSA-N 0.000 description 2
- 0 C[C@@]12C=*CC1C2 Chemical compound C[C@@]12C=*CC1C2 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- 229910018540 Si C Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000748 compression moulding Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 125000004427 diamine group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- 230000009878 intermolecular interaction Effects 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DDCJHFYXAPQYLA-UHFFFAOYSA-N (3-chlorophenyl)-phenylmethanol Chemical compound C=1C=CC(Cl)=CC=1C(O)C1=CC=CC=C1 DDCJHFYXAPQYLA-UHFFFAOYSA-N 0.000 description 1
- GTACSIONMHMRPD-UHFFFAOYSA-N 2-[4-[2-(benzenesulfonamido)ethylsulfanyl]-2,6-difluorophenoxy]acetamide Chemical compound C1=C(F)C(OCC(=O)N)=C(F)C=C1SCCNS(=O)(=O)C1=CC=CC=C1 GTACSIONMHMRPD-UHFFFAOYSA-N 0.000 description 1
- RYYUUQPLFHRZOY-UHFFFAOYSA-N 4-[2-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1OC1=CC=C(N)C=C1 RYYUUQPLFHRZOY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- DJQPGZPKGHRJOK-UHFFFAOYSA-N 4-[4-[1-[4-(4-aminophenoxy)phenyl]cyclohexyl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C2(CCCCC2)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 DJQPGZPKGHRJOK-UHFFFAOYSA-N 0.000 description 1
- 101710130081 Aspergillopepsin-1 Proteins 0.000 description 1
- 102100031007 Cytosolic non-specific dipeptidase Human genes 0.000 description 1
- 235000015842 Hesperis Nutrition 0.000 description 1
- 235000012633 Iberis amara Nutrition 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 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 description 1
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000013035 low temperature curing Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- CGEXUOTXYSGBLV-UHFFFAOYSA-N phenyl benzenesulfonate Chemical compound C=1C=CC=CC=1S(=O)(=O)OC1=CC=CC=C1 CGEXUOTXYSGBLV-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013090734A JP2014201740A (ja) | 2013-04-05 | 2013-04-05 | イミドオリゴマー及びこれを加熱硬化させてなるポリイミド樹脂 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013090734A JP2014201740A (ja) | 2013-04-05 | 2013-04-05 | イミドオリゴマー及びこれを加熱硬化させてなるポリイミド樹脂 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014201740A true JP2014201740A (ja) | 2014-10-27 |
| JP2014201740A5 JP2014201740A5 (enExample) | 2016-08-18 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013090734A Pending JP2014201740A (ja) | 2013-04-05 | 2013-04-05 | イミドオリゴマー及びこれを加熱硬化させてなるポリイミド樹脂 |
Country Status (1)
| Country | Link |
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| JP (1) | JP2014201740A (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109162101A (zh) * | 2018-07-11 | 2019-01-08 | 中国航发北京航空材料研究院 | 一种低粘度高耐热聚酰亚胺纤维定型剂及其制备方法 |
| JP2021084929A (ja) * | 2019-11-26 | 2021-06-03 | 株式会社カネカ | ポリイミド樹脂、ポリイミド溶液、ポリイミドフィルム |
| CN114276544A (zh) * | 2022-02-18 | 2022-04-05 | 北京航空航天大学 | 一种耐高温的聚酰亚胺复合材料及其制备方法与应用 |
| JP2022104391A (ja) * | 2020-12-28 | 2022-07-08 | 株式会社カネカ | 特定の組成を有するアミド酸オリゴマー、ワニス、硬化物、複合材料 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012197403A (ja) * | 2011-03-19 | 2012-10-18 | Pi R & D Co Ltd | イミドオリゴマー及びこれを加熱硬化させてなるポリイミド樹脂 |
-
2013
- 2013-04-05 JP JP2013090734A patent/JP2014201740A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012197403A (ja) * | 2011-03-19 | 2012-10-18 | Pi R & D Co Ltd | イミドオリゴマー及びこれを加熱硬化させてなるポリイミド樹脂 |
Non-Patent Citations (1)
| Title |
|---|
| SMITH,J.G.,JR.;CONNELL,J.W.;HERGENROTHER,P.M.;YOKOTA,R.;CRISS,J.M.: "High temperature transfer molding resins based on 2,3,3',4'-biphenyltetracarboxylic dianhydride", PLATFORM TO GLOVAL VALUE AND PERFORMANCE,BOOK 2, JPN6017001238, 2002, pages 316-327 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109162101A (zh) * | 2018-07-11 | 2019-01-08 | 中国航发北京航空材料研究院 | 一种低粘度高耐热聚酰亚胺纤维定型剂及其制备方法 |
| CN109162101B (zh) * | 2018-07-11 | 2021-03-26 | 中国航发北京航空材料研究院 | 一种低粘度高耐热聚酰亚胺纤维定型剂及其制备方法 |
| JP2021084929A (ja) * | 2019-11-26 | 2021-06-03 | 株式会社カネカ | ポリイミド樹脂、ポリイミド溶液、ポリイミドフィルム |
| JP7359662B2 (ja) | 2019-11-26 | 2023-10-11 | 株式会社カネカ | ポリイミド樹脂、ポリイミド溶液、ポリイミドフィルム |
| JP2022104391A (ja) * | 2020-12-28 | 2022-07-08 | 株式会社カネカ | 特定の組成を有するアミド酸オリゴマー、ワニス、硬化物、複合材料 |
| JP7679005B2 (ja) | 2020-12-28 | 2025-05-19 | 株式会社カネカ | 特定の組成を有するアミド酸オリゴマー、ワニス、硬化物、複合材料 |
| CN114276544A (zh) * | 2022-02-18 | 2022-04-05 | 北京航空航天大学 | 一种耐高温的聚酰亚胺复合材料及其制备方法与应用 |
| CN114276544B (zh) * | 2022-02-18 | 2022-12-06 | 北京航空航天大学 | 一种耐高温的聚酰亚胺复合材料及其制备方法与应用 |
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