JP2017512244A5 - - Google Patents
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- JP2017512244A5 JP2017512244A5 JP2016557017A JP2016557017A JP2017512244A5 JP 2017512244 A5 JP2017512244 A5 JP 2017512244A5 JP 2016557017 A JP2016557017 A JP 2016557017A JP 2016557017 A JP2016557017 A JP 2016557017A JP 2017512244 A5 JP2017512244 A5 JP 2017512244A5
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- Prior art keywords
- imine
- polymer
- linked polymer
- composite material
- monomer
- Prior art date
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- 229920000642 polymer Polymers 0.000 claims description 136
- 239000000178 monomer Substances 0.000 claims description 53
- 230000007704 transition Effects 0.000 claims description 46
- 239000002131 composite material Substances 0.000 claims description 35
- 150000002466 imines Chemical class 0.000 claims description 26
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 150000004985 diamines Chemical class 0.000 claims description 16
- 239000000945 filler Substances 0.000 claims description 16
- 239000003431 cross linking reagent Substances 0.000 claims description 15
- 125000004989 dicarbonyl group Chemical group 0.000 claims description 15
- 239000000835 fiber Substances 0.000 claims description 13
- 150000003141 primary amines Chemical group 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000005755 formation reaction Methods 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000000879 imine group Chemical group 0.000 claims description 4
- 238000003825 pressing Methods 0.000 claims description 4
- 150000003934 aromatic aldehydes Chemical group 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 229920005596 polymer binder Polymers 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000002209 hydrophobic effect Effects 0.000 claims description 2
- 230000004584 weight gain Effects 0.000 claims description 2
- 235000019786 weight gain Nutrition 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims 1
- 239000004971 Cross linker Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 4
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 4
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical group O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- OJUGVDODNPJEEC-UHFFFAOYSA-N phenylglyoxal Chemical compound O=CC(=O)C1=CC=CC=C1 OJUGVDODNPJEEC-UHFFFAOYSA-N 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 description 2
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 2
- 229940105324 1,2-naphthoquinone Drugs 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- UHKAJLSKXBADFT-UHFFFAOYSA-N 1,3-indandione Chemical compound C1=CC=C2C(=O)CC(=O)C2=C1 UHKAJLSKXBADFT-UHFFFAOYSA-N 0.000 description 2
- OQWMNEVFNLKGMJ-UHFFFAOYSA-N 1,3-oxazole-2,4-diamine Chemical compound NC1=COC(N)=N1 OQWMNEVFNLKGMJ-UHFFFAOYSA-N 0.000 description 2
- 229940005561 1,4-benzoquinone Drugs 0.000 description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 2
- SNICMBLBGTVRFJ-UHFFFAOYSA-N 1h-imidazole-4,5-diamine Chemical compound NC=1N=CNC=1N SNICMBLBGTVRFJ-UHFFFAOYSA-N 0.000 description 2
- PHIMVUDMARQXAQ-UHFFFAOYSA-N 1h-pyrrole-2,3-diamine Chemical compound NC=1C=CNC=1N PHIMVUDMARQXAQ-UHFFFAOYSA-N 0.000 description 2
- BSXFKLAYGCDJLZ-UHFFFAOYSA-N 1h-pyrrole-2,3-dicarbaldehyde Chemical compound O=CC=1C=CNC=1C=O BSXFKLAYGCDJLZ-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- KAPNIDMXEKQLMQ-UHFFFAOYSA-N 2,4,6-trihydroxybenzene-1,3,5-tricarbaldehyde Chemical compound OC1=C(C=O)C(O)=C(C=O)C(O)=C1C=O KAPNIDMXEKQLMQ-UHFFFAOYSA-N 0.000 description 2
- PXJJKVNIMAZHCB-UHFFFAOYSA-N 2,5-diformylfuran Chemical compound O=CC1=CC=C(C=O)O1 PXJJKVNIMAZHCB-UHFFFAOYSA-N 0.000 description 2
- SASIGIIGIJUCTK-UHFFFAOYSA-N C(C)NC(CCN)CCN Chemical compound C(C)NC(CCN)CCN SASIGIIGIJUCTK-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 2
- 229920000271 Kevlar® Polymers 0.000 description 2
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 2
- 239000005700 Putrescine Substances 0.000 description 2
- 239000004699 Ultra-high molecular weight polyethylene Substances 0.000 description 2
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- RUOKPLVTMFHRJE-UHFFFAOYSA-N benzene-1,2,3-triamine Chemical compound NC1=CC=CC(N)=C1N RUOKPLVTMFHRJE-UHFFFAOYSA-N 0.000 description 2
- AEKQNAANFVOBCU-UHFFFAOYSA-N benzene-1,3,5-tricarbaldehyde Chemical compound O=CC1=CC(C=O)=CC(C=O)=C1 AEKQNAANFVOBCU-UHFFFAOYSA-N 0.000 description 2
- IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 239000002041 carbon nanotube Substances 0.000 description 2
- 229910021393 carbon nanotube Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- XRLHAJCIEMOBLT-UHFFFAOYSA-N cyclobutane-1,1-diamine Chemical compound NC1(N)CCC1 XRLHAJCIEMOBLT-UHFFFAOYSA-N 0.000 description 2
- ZZLVWYATVGCIFR-UHFFFAOYSA-N cyclohexane-1,1,2-triamine Chemical compound NC1CCCCC1(N)N ZZLVWYATVGCIFR-UHFFFAOYSA-N 0.000 description 2
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 2
- PKRGYJHUXHCUCN-UHFFFAOYSA-N cyclohexanehexone Chemical compound O=C1C(=O)C(=O)C(=O)C(=O)C1=O PKRGYJHUXHCUCN-UHFFFAOYSA-N 0.000 description 2
- MCFZBCCYOPSZLG-UHFFFAOYSA-N cyclopent-4-ene-1,3-dione Chemical compound O=C1CC(=O)C=C1 MCFZBCCYOPSZLG-UHFFFAOYSA-N 0.000 description 2
- GHAUROKXNSHBAG-UHFFFAOYSA-N cyclopentane-1,1-diamine Chemical compound NC1(N)CCCC1 GHAUROKXNSHBAG-UHFFFAOYSA-N 0.000 description 2
- LOGSONSNCYTHPS-UHFFFAOYSA-N cyclopentane-1,3-dione Chemical compound O=C1CCC(=O)C1 LOGSONSNCYTHPS-UHFFFAOYSA-N 0.000 description 2
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 2
- 239000011152 fibreglass Substances 0.000 description 2
- XBOHKUPCELBZPH-UHFFFAOYSA-N furan-2,3-diamine Chemical compound NC=1C=COC=1N XBOHKUPCELBZPH-UHFFFAOYSA-N 0.000 description 2
- AHIXHWRUDZFHEZ-UHFFFAOYSA-N furan-2,3-dicarbaldehyde Chemical compound O=CC=1C=COC=1C=O AHIXHWRUDZFHEZ-UHFFFAOYSA-N 0.000 description 2
- 229940015043 glyoxal Drugs 0.000 description 2
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000004761 kevlar Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 2
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 2
- 239000002491 polymer binding agent Substances 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 2
- GVWYIGSUECJNRM-UHFFFAOYSA-N pyridine-2,5-dicarbaldehyde Chemical compound O=CC1=CC=C(C=O)N=C1 GVWYIGSUECJNRM-UHFFFAOYSA-N 0.000 description 2
- PMWXGSWIOOVHEQ-UHFFFAOYSA-N pyridine-2,6-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=N1 PMWXGSWIOOVHEQ-UHFFFAOYSA-N 0.000 description 2
- KFISEQOLPGMMBB-UHFFFAOYSA-N pyridine-3,5-dicarbaldehyde Chemical compound O=CC1=CN=CC(C=O)=C1 KFISEQOLPGMMBB-UHFFFAOYSA-N 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 2
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 2
- BFLIRPGEXPAQAW-UHFFFAOYSA-N thiophene-2,3-diamine Chemical compound NC=1C=CSC=1N BFLIRPGEXPAQAW-UHFFFAOYSA-N 0.000 description 2
- WSEJZRIZDQWMKQ-UHFFFAOYSA-N thiophene-2,3-dicarbaldehyde Chemical compound O=CC=1C=CSC=1C=O WSEJZRIZDQWMKQ-UHFFFAOYSA-N 0.000 description 2
- OTMRXENQDSQACG-UHFFFAOYSA-N thiophene-2,5-dicarbaldehyde Chemical compound O=CC1=CC=C(C=O)S1 OTMRXENQDSQACG-UHFFFAOYSA-N 0.000 description 2
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461951613P | 2014-03-12 | 2014-03-12 | |
| US61/951,613 | 2014-03-12 | ||
| PCT/US2015/020292 WO2015138804A1 (en) | 2014-03-12 | 2015-03-12 | Novel covalently cross-linked malleable polymers and methods of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017512244A JP2017512244A (ja) | 2017-05-18 |
| JP2017512244A5 true JP2017512244A5 (https=) | 2018-04-19 |
Family
ID=54068217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016557017A Pending JP2017512244A (ja) | 2014-03-12 | 2015-03-12 | 共有結合で架橋された可鍛性ポリマーおよび使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9453099B2 (https=) |
| EP (1) | EP3116935B1 (https=) |
| JP (1) | JP2017512244A (https=) |
| KR (1) | KR102317792B1 (https=) |
| ES (1) | ES2983111T3 (https=) |
| WO (1) | WO2015138804A1 (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105647111B (zh) * | 2016-04-12 | 2017-10-10 | 吉林大学 | 一种通过亚胺键共价连接的聚亚胺复合材料及其制备方法 |
| WO2018000242A1 (zh) * | 2016-06-29 | 2018-01-04 | 南京大学 | 自修复材料在3d打印中的应用 |
| US10829612B2 (en) | 2016-07-01 | 2020-11-10 | Georgia Tech Research Corporation | Methods of recycling and reshaping thermosetting polymers and composites thereof |
| WO2019013814A1 (en) | 2017-07-14 | 2019-01-17 | Hewlett-Packard Development Company, L.P. | 3D PRINTING |
| JP6942000B2 (ja) * | 2017-08-01 | 2021-09-29 | 株式会社日立製作所 | 繊維強化樹脂及びその製造方法 |
| JP2019025841A (ja) * | 2017-08-01 | 2019-02-21 | 株式会社日立製作所 | 繊維強化樹脂複合体及びその製造装置 |
| DE102017010165A1 (de) | 2017-11-02 | 2019-05-02 | Friedrich-Schiller-Universität Jena | Selbstheilende Polymere und deren Verwendung |
| WO2019099944A1 (en) | 2017-11-16 | 2019-05-23 | The Regents Of The University Of California | Recyclable and reconfigurable high-performance polymer networks and uses thereof |
| WO2019100069A1 (en) * | 2017-11-20 | 2019-05-23 | The Regents Of The University Of Colorado, A Body Corporate | Dynamic covalent thermoset nanocomposites and uses thereof |
| CN108530590B (zh) * | 2018-03-22 | 2020-09-25 | 西北工业大学 | 一种含有类共轭、刚性结构的Vitrimer的制备方法 |
| MX2021002659A (es) * | 2018-09-06 | 2021-08-11 | Mallinda | Rutas anhidras hacia polimeros y combinaciones de redes covalentes altamente procesables. |
| JP7394575B2 (ja) * | 2018-10-04 | 2023-12-08 | 星和電機株式会社 | 共有結合性有機構造体組成物、その焼成体、およびこれらの製造方法 |
| WO2020106815A1 (en) | 2018-11-21 | 2020-05-28 | The Regents Of The University Of California | Decomposable and recyclable epoxy thermosetting resins |
| CN110563904B (zh) * | 2019-08-05 | 2020-12-22 | 厦门大学 | 一种聚合物包覆碳纳米管复合材料、制备方法和应用 |
| US12359032B2 (en) * | 2019-08-14 | 2025-07-15 | The Regents Of The University Of Colorado, A Body Corporate | Rapid fabrication and/or repair of fiber reinforced covalent adaptable network composites |
| EP4241541A4 (en) * | 2020-11-05 | 2025-01-08 | The Regents of the University of Colorado, a body corporate | SELF-HEALING, RECYCLABLE AND RECONFIGURABLE PORTABLE ELECTRONIC DEVICE |
| WO2022187451A1 (en) | 2021-03-03 | 2022-09-09 | Mallinda | Vitrimers containing additives |
| CN113121953B (zh) * | 2021-03-24 | 2022-08-12 | 云南大学 | 三维整体石墨烯气凝胶-聚亚胺复合材料及其制备方法 |
| US11713370B1 (en) * | 2021-07-15 | 2023-08-01 | Hrl Laboratories, Llc | Adaptable thermoset polymers with internal dynamic bonds, and methods of making and using the same |
| CN113698561B (zh) * | 2021-09-01 | 2024-04-09 | 中国科学院宁波材料技术与工程研究所 | 主链降解型金属离子络合聚席夫碱防污树脂、制法与应用 |
| CN115819699A (zh) * | 2023-01-03 | 2023-03-21 | 江苏海洋大学 | 一种含有大体积侧基的共聚型聚亚胺动态高分子薄膜的制备方法 |
| KR102850463B1 (ko) * | 2023-02-28 | 2025-08-25 | 한국화학연구원 | X선 산란을 이용한 비트리머의 토폴로지 동결 전이 온도 측정 방법 |
| CN116836385B (zh) * | 2023-07-14 | 2025-11-28 | 北京化工大学 | 一种含席夫碱型动态共价键的可修复热固性材料及其制备方法和应用 |
| CN118755036B (zh) * | 2024-07-23 | 2025-12-09 | 华中科技大学 | 低温合成高玻璃化转变温度聚亚胺的制备方法及其应用 |
| CN118772357B (zh) * | 2024-07-23 | 2025-12-09 | 华中科技大学 | 耐热耐水聚亚胺的制备方法及其在天然植物纤维复合材料中应用 |
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| US3372086A (en) * | 1965-04-14 | 1968-03-05 | Union Carbide Corp | Water-soluble polyalkylenepolyamine/dialdehyde resins and application thereof in production of wet strength paper |
| CA2051497A1 (en) * | 1991-01-18 | 1992-07-19 | John Reale Jr. | Membrane process |
| JP2603058B2 (ja) * | 1993-07-27 | 1997-04-23 | 荒川化学工業株式会社 | 芳香族ポリイミンおよびその製法，ならびに該芳香族ポリイミンに用いられる芳香族ポリイミンオリゴマーおよびその製法 |
| JPH10168148A (ja) * | 1996-12-06 | 1998-06-23 | Arakawa Chem Ind Co Ltd | 芳香族ポリイミンオリゴマーおよびその製造方法、ならびに芳香族ポリイミンおよびその製造方法 |
| WO2004003044A2 (en) * | 2002-06-28 | 2004-01-08 | Jean-Marie Lehn | Dynamers: polymeric materials exhibiting reversible formation and component exchange |
| DE102004035542A1 (de) * | 2004-07-22 | 2006-02-09 | Henkel Kgaa | Zwei-Komponenten-Bindemittel |
| KR20080031349A (ko) * | 2005-06-30 | 2008-04-08 | 미쓰이 가가쿠 가부시키가이샤 | 생분해성 폴리머, 그의 제조방법, 및 그의 성형물 및 용도 |
| FR2943559B1 (fr) * | 2009-03-30 | 2011-04-08 | Centre Nat Rech Scient | Membrane polymere dynamique autosupportee,procede de preparation et utilisations. |
| EP2740755A1 (en) | 2012-12-07 | 2014-06-11 | Fonds de l'ESPCI - Georges Charpak | Processable semi-crystalline polymer networks |
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2015
- 2015-03-12 ES ES15760804T patent/ES2983111T3/es active Active
- 2015-03-12 KR KR1020167028279A patent/KR102317792B1/ko active Active
- 2015-03-12 EP EP15760804.3A patent/EP3116935B1/en active Active
- 2015-03-12 WO PCT/US2015/020292 patent/WO2015138804A1/en not_active Ceased
- 2015-03-12 JP JP2016557017A patent/JP2017512244A/ja active Pending
- 2015-03-12 US US14/656,684 patent/US9453099B2/en active Active
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