CA2985820C - Process for producing polyimides - Google Patents
Process for producing polyimides Download PDFInfo
- Publication number
- CA2985820C CA2985820C CA2985820A CA2985820A CA2985820C CA 2985820 C CA2985820 C CA 2985820C CA 2985820 A CA2985820 A CA 2985820A CA 2985820 A CA2985820 A CA 2985820A CA 2985820 C CA2985820 C CA 2985820C
- Authority
- CA
- Canada
- Prior art keywords
- monomers
- solvent
- process according
- heating
- mixture
- 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.)
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- 239000004642 Polyimide Substances 0.000 title claims abstract description 57
- 229920001721 polyimide Polymers 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims abstract description 39
- 230000008569 process Effects 0.000 title claims abstract description 26
- 239000000178 monomer Substances 0.000 claims abstract description 71
- 239000002904 solvent Substances 0.000 claims abstract description 53
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- 238000010438 heat treatment Methods 0.000 claims abstract description 32
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 238000002156 mixing Methods 0.000 claims abstract description 10
- 238000009835 boiling Methods 0.000 claims abstract description 6
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims abstract description 6
- 238000004729 solvothermal method Methods 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims description 44
- 229910001868 water Inorganic materials 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 150000004985 diamines Chemical class 0.000 claims description 9
- 230000005855 radiation Effects 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000004984 aromatic diamines Chemical class 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 238000002441 X-ray diffraction Methods 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 15
- 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 description 11
- 238000002411 thermogravimetry Methods 0.000 description 10
- 238000006358 imidation reaction Methods 0.000 description 9
- 150000003949 imides Chemical class 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000013310 covalent-organic framework Substances 0.000 description 5
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 5
- 229910000071 diazene Inorganic materials 0.000 description 5
- 238000001027 hydrothermal synthesis Methods 0.000 description 5
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000010355 oscillation Effects 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 238000001878 scanning electron micrograph Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000001144 powder X-ray diffraction data Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- -1 aromatic tetracarboxylic anhydride Chemical class 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 229940024874 benzophenone Drugs 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000006159 dianhydride group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000004626 scanning electron microscopy Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 2
- QHQSCKLPDVSEBJ-UHFFFAOYSA-N 1,3,5-tri(4-aminophenyl)benzene Chemical compound C1=CC(N)=CC=C1C1=CC(C=2C=CC(N)=CC=2)=CC(C=2C=CC(N)=CC=2)=C1 QHQSCKLPDVSEBJ-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- MQAHXEQUBNDFGI-UHFFFAOYSA-N 5-[4-[2-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)C(C)(C=2C=CC(OC=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)C)=C1 MQAHXEQUBNDFGI-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 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 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229940086255 perform Drugs 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UGQZLDXDWSPAOM-UHFFFAOYSA-N pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone Chemical compound C1=C2C(=O)NC(=O)C2=CC2=C1C(=O)NC2=O UGQZLDXDWSPAOM-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 238000010626 work up procedure 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
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
- C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
-
- 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
-
- 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
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
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)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ATA304/2015 | 2015-05-13 | ||
| ATA304/2015A AT517146A2 (de) | 2015-05-13 | 2015-05-13 | Verfahren zur Herstellung von kristallinen Polyimiden |
| ATA20/2016A AT517148B1 (de) | 2015-05-13 | 2016-01-20 | Verfahren zur Herstellung von kristallinen Polyimiden |
| ATA20/2016 | 2016-01-20 | ||
| PCT/AT2016/050140 WO2016179625A1 (de) | 2015-05-13 | 2016-05-13 | Verfahren zur herstellung von polyimiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2985820A1 CA2985820A1 (en) | 2016-11-17 |
| CA2985820C true CA2985820C (en) | 2023-01-03 |
Family
ID=57227214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2985820A Active CA2985820C (en) | 2015-05-13 | 2016-05-13 | Process for producing polyimides |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10563013B2 (enExample) |
| EP (1) | EP3294794B1 (enExample) |
| JP (1) | JP6994946B2 (enExample) |
| AT (2) | AT517146A2 (enExample) |
| BR (1) | BR112017024199B1 (enExample) |
| CA (1) | CA2985820C (enExample) |
| WO (1) | WO2016179625A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107673417A (zh) * | 2017-08-23 | 2018-02-09 | 天津中油科远石油工程有限责任公司 | 快速除油剂的制备方法 |
| AT520472A2 (de) * | 2017-09-20 | 2019-04-15 | Univ Wien Tech | Verfahren zur Herstellung von Polybenzimidazolen |
| US11718715B2 (en) | 2017-09-20 | 2023-08-08 | Technische Universität Wien | Process for preparing polybenzimidazoles |
| KR102050660B1 (ko) * | 2018-01-22 | 2019-12-02 | 연세대학교 원주산학협력단 | 폴리이미드의 제조방법 |
| KR102198357B1 (ko) * | 2018-12-17 | 2021-01-04 | 연세대학교 원주산학협력단 | 폴리이미드의 제조방법 |
| AT522304B1 (de) | 2019-03-15 | 2023-11-15 | Univ Wien Tech | Verfahren zur Herstellung von Polyimiden |
| CN110218317A (zh) * | 2019-06-06 | 2019-09-10 | 南京邮电大学 | 一种聚酰亚胺型共价有机框架材料及其制备方法与应用 |
| CN112774662B (zh) * | 2019-11-04 | 2023-08-15 | 北京氦舶科技有限责任公司 | 一种单原子催化剂及其制备方法和应用 |
| CA3165736A1 (en) * | 2020-01-09 | 2021-07-15 | ExxonMobil Technology and Engineering Company | Methods for preparing mixed polyamides, polyimides and polyamideimides via hydrothermal polymerization |
| CN111607227B (zh) * | 2020-05-27 | 2023-02-28 | 深圳先进电子材料国际创新研究院 | 三维纳米碳/聚酰亚胺复合气凝胶材料及其制备方法和用途 |
| WO2023080007A1 (ja) | 2021-11-02 | 2023-05-11 | 東レ株式会社 | ポリイミドの製造方法、ポリイミド、ポリイミド樹脂組成物およびその硬化物 |
| KR102714397B1 (ko) * | 2021-12-28 | 2024-10-08 | 연세대학교 원주산학협력단 | 열전도성이 우수한 폴리이미드 복합체 분말 제조방법 |
| CN114231029B (zh) * | 2021-12-29 | 2023-08-22 | 山东华夏神舟新材料有限公司 | 交联型高透明聚酰亚胺薄膜及其制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5288843A (en) * | 1987-05-20 | 1994-02-22 | Mitsui Toatsu Chemicals, Inc. | Polyimides, process for the preparation thereof and polyimide resin compositions |
| JP2624852B2 (ja) | 1988-10-28 | 1997-06-25 | 三井東圧化学株式会社 | ポリイミドの製造方法 |
| US5069848A (en) | 1989-04-05 | 1991-12-03 | Mitsui Toatsu Chemicals, Inc. | Extrusion process of polyimide and polyimide pellet used for the process |
| US5241040A (en) | 1990-07-11 | 1993-08-31 | International Business Machines Corporation | Microwave processing |
| DE4244031A1 (de) | 1992-12-24 | 1994-06-30 | Bayer Ag | Verfahren zur Herstellung und Verwendung von Polyasparaginsäure und ihrer Salze |
| JP2580535B2 (ja) * | 1994-05-09 | 1997-02-12 | 東京工業大学長 | ポリイミド・シリカ複合体の製造方法 |
| US10224258B2 (en) | 2013-03-22 | 2019-03-05 | Applied Materials, Inc. | Method of curing thermoplastics with microwave energy |
| CN104448310A (zh) | 2013-09-16 | 2015-03-25 | 姜丹宁 | 微波辐射合成共缩聚聚酰胺酸和聚酰亚胺方法 |
| JP2015098573A (ja) | 2013-10-18 | 2015-05-28 | 株式会社Kri | 高結晶ポリイミド微粒子およびその製造方法 |
| AT519038B1 (de) * | 2016-08-19 | 2018-11-15 | Univ Wien Tech | Herstellungsverfahren für Polyimide |
-
2015
- 2015-05-13 AT ATA304/2015A patent/AT517146A2/de not_active Application Discontinuation
-
2016
- 2016-01-20 AT ATA20/2016A patent/AT517148B1/de active
- 2016-05-13 US US15/573,273 patent/US10563013B2/en not_active Expired - Fee Related
- 2016-05-13 CA CA2985820A patent/CA2985820C/en active Active
- 2016-05-13 EP EP16732915.0A patent/EP3294794B1/de active Active
- 2016-05-13 BR BR112017024199-4A patent/BR112017024199B1/pt not_active IP Right Cessation
- 2016-05-13 JP JP2017559457A patent/JP6994946B2/ja active Active
- 2016-05-13 WO PCT/AT2016/050140 patent/WO2016179625A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US20180112039A1 (en) | 2018-04-26 |
| JP2018514635A (ja) | 2018-06-07 |
| AT517148A2 (de) | 2016-11-15 |
| US10563013B2 (en) | 2020-02-18 |
| AT517148A3 (de) | 2019-04-15 |
| JP6994946B2 (ja) | 2022-01-14 |
| EP3294794B1 (de) | 2021-11-24 |
| BR112017024199A2 (pt) | 2019-01-22 |
| BR112017024199B1 (pt) | 2022-06-14 |
| AT517148B1 (de) | 2019-07-15 |
| CA2985820A1 (en) | 2016-11-17 |
| EP3294794A1 (de) | 2018-03-21 |
| AT517146A2 (de) | 2016-11-15 |
| WO2016179625A1 (de) | 2016-11-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20210506 |
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| EEER | Examination request |
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