Research progress in gas⁃separation membrane materials of hyperbranched polymer

doi:10.19491/j.issn.1001-9278.2022.11.013

Abstract

Abstract:

In this paper， the research progress in the hyperbranched polymer⁃based gas⁃separation membrane materials was reviewed. Different types of hyperbranched polymers were introduced， and their synthetic technologies were described， such as traditional hyperbranched polymers and large π⁃conjugated hyperbranched polymers. The mechanisms and functions of azo⁃hyperbranched polymers， polyamide⁃hyperbranched polymers， and blend hyperbranched polymers in the preparation of separation membranes were introduced in detail. The future research directions of hyperbranched polymers in the field of gas⁃separation membranes were prospected.

Key words: hyperbranched polymer, gas?separation membrane, synthesis, research progress

CLC Number:

TQ325

ZHAO Wenwen, XU Shuangping, JIA Hongge, WANG Xing, XU Jingyu. Research progress in gas⁃separation membrane materials of hyperbranched polymer[J]. China Plastics, 2022, 36(11): 84-93.

Figures/Tables 11

Fig.1. Synthesis routes of carbazole⁃ and phthalazinone⁃based porous organic polymers through hyper cross⁃linking and oxidation coupling reaction

Fig.2. Schematic diagram of synthesis procedure and application of AZOPOP/PPESK composite membrane

Fig.3. Schematic diagram of structure of HBP⁃PAZ⁃SiO9 （Degree of polymerization=15）

Fig.4. Schematic diagrams of structure of 6FDA，TAPB and BNDA

Fig.5. Schematic diagrams of HBPI⁃CL

Fig.6. Schematic diagram of crossing⁃linking structures of three different MN⁃PI membranes

Fig.7. Schematic diagram of the synthesis of PHA （6FAHP⁃BTC）

Fig.8. Schematic diagram of the preparation of HPEI⁃GO/CS⁃PVAm/PS membrane

Fig.9. Schematic diagram of HPEI⁃GO/TMC composite membrane

Fig.10. Synthesis of HBPI

Fig.11. Schematic diagram of structure of PEI⁃g⁃ZIF⁃8 nanoparticles

References 51

1	Geng C， Sun Y， Zhang Z， et al. Mitigated aging in a defective metal⁃organic framework pillared polymer of an intrinsic porosity hybrid membrane for efficient gas separation［J］. ACS Sustainable Chemistry & Engineering， 2022， 10（11）： 3 643⁃3 650.
2	Widakdo J， Chiao Y H， Lai Y L， et al. Mechanism of a self⁃assembling smart and electrically responsive PVDF⁃graphene membrane for controlled gas separation［J］. ACS applied materials & interfaces， 2020， 12（27）： 30 915⁃30 924.
3	Chakrabarty T， Giri A K， Sarkar S. Mixed‐matrix gas separation membranes for sustainable future： A mini review［J］. Polymers for Advanced Technologies， 2022， 33（6）： 1 747⁃1 761.
4	Yang R， Chen M Y， Li P. Carbon molecular sieve hollow fiber composite membrane derived from PMDA⁃ODA polyi⁃mide for gas separation［J］. High Performance Polymers， 2022， 34（4）： 444⁃454.
5	Hou R， Smith S J D， Konstas K， et al. Synergistically improved PIM⁃1 membrane gas separation performance by PAF⁃1 incorporation and UV irradiation［J］. Journal of Materials Chemistry A， 2022， 10（18）： 10 107⁃10 119.
6	Zhao Y， Zhou C， Kong C， et al. Ultrathin reduced graphene oxide/organosilica hybrid membrane for gas separation［J］. JACS Au， 2021， 1（3）： 328⁃335.
7	Chen M， Yang R， Li P. Preparation of defect⁃free hollow fiber membranes derived from PMDA⁃ODA polyimide for gas separation［J］. Chemical Engineering Research and Design， 2022， 179： 154⁃161.
8	Wang J， Zhou M， Lu D， et al. Virtual screening of nanoporous materials for noble gas separation［J］. ACS Applied Nano Materials， 2022， 5（3）： 3 701⁃3 711.
9	Fakoori M， Azdarpour A， Abedini R， et al. Effect of Cu⁃MOFs incorporation on gas separation of Pebax thin film nanocomposite （TFN） membrane［J］. Korean Journal of Chemical Engineering， 2021， 38（1）： 121⁃128.
10	Xin Q， Zhao M， Guo J， et al. Light⁃responsive metal⁃organic framework sheets constructed smart membranes with tunable transport channels for efficient gas separation［J］. RSC advances， 2022， 12（1）： 517⁃527.
11	Memon F H， Rehman F， Lee J， et al. Transition metal dichalcogenide⁃based membranes for water desalination， gas separation， and energy storage［J］. Separation & Purification Reviews， 2022： 1⁃15.
12	Bi X， Zhang Y， Zhang F， et al. MOF nanosheet⁃based mixed matrix membranes with metal⁃organic coordination interfacial interaction for gas separation［J］. ACS Applied Materials & Interfaces， 2020， 12（43）： 49 101⁃49 110.
13	Jiang S， Shi X， Sun F， et al. Fabrication of crystalline microporous membrane from 2D MOF nanosheets for gas separation［J］. Chemistry⁃An Asian Journal， 2020， 15（15）： 2 371⁃2 378.
14	Nie J， Yoshizawa N， Tanaka K. Effect of chemical vapor deposition of toluene on gas separation performance of carbon molecular sieve membranes［J］. Journal of Porous Materials， 2022， 29（2）： 393⁃404.
15	Ashtiani S， Khoshnamvand M， Číhal P， et al. Fabrication of a PVDF membrane with tailored morphology and properties via exploring and computing its ternary phase dia⁃gram for wastewater treatment and gas separation applications［J］. RSC advances， 2020， 10（66）： 40 373⁃40 383.
16	Lv X， Li D， Ma Y， et al. From gas separation to ion transport in the cavity of hyperbranched polyamides based on triptycene aimed for electrochromic and memory devices［J］. Polymer Chemistry， 2022， 13（6）： 808⁃818.
17	Zhao M， Ban Y， Yang K， et al. A highly selective supramolecule array membrane made of zero‐dimensional molecules for gas separation［J］. Angewandte Chemie， 2021， 133（38）： 21 145⁃21 151.
18	Farha O K， Spokoyny A M， Hauser B G， et al. Synthesis， Properties， and Gas Separation Studies of a Robust Diimide⁃Based Microporous Organic Polymer［J］. Chemi⁃stry of Materials， 2009， 21（14）：3 033⁃3 035.
19	Liou G S， Lin H Y， Yen H J. Synthesis and characterization of electroactive hyperbranched aromatic polyamides based on A2B⁃type triphenylamine moieties［J］. Joural of Materials Chemistry， 2009， 19（41）： 7 666⁃7 673.
20	Vanjinathan M， Shanavas A， Nasar A S， et al. Synthesis and properties of hyperbranched polyurethanes， hyperbranched polyurethane copolymers with and without ether and ester groups using blocked ssocyanate monomers［J］. Journal of Polymer Science Part A： Polymer Chemistry， 2007， 45（17）： 3 877⁃3 893.
21	Kim Y H， Webster O W. Hyperbranched polyphenylenes［J］. Macromolecules， 1992， 25（21）： 5 561⁃5 572.
22	Kushakova N S， Shapovalov A V， Rud D A， et al. Synthesis of hyperbranched polyphenylenes by suzuki reaction and their spectral characteristics［J］. Polymer Science Series B， 2008， 51（9/10）： 409⁃415.
23	Wen G A， Xin Y， Peng B， et al. Hyperbranched triazine⁃containing polyfluorenes： Efficient blue emitters for polymer light⁃emitting diodes （PLEDs）［J］. Polymer， 2007， 48（7）： 1 824⁃1 829.
24	Zhu B， Han Y， Sun M H， et al. Water⁃soluble dendronized polyfluorenes with an extremely high quantum yield in water［J］. Macromolecules， 2007， 40（13）： 4 494⁃4 450.
25	Yu M H， Liu L B， Wang S. Water⁃soluble dendritic⁃conjugated polyfluorenes： Synthesis， characterization， and interactions with DNA［J］. Journal of Polymer Science Part A： Polymer Chemistry， 2008， 46（22）： 7 462⁃7 472.
26	Malenfant P R L， Fréchet J M J. Dendrimers as solubili⁃zing groups for conducting polymers： Preparation and chara⁃cterization of polythiophene functionalized exclusively with aliphatic ether convergent dendrons［J］. Macromolecules， 2000， 33（10）： 3 634⁃3 640.
27	Zhao Hongyong， Qian Xie， Ding Xiaoli， et al. High performance post⁃modified polymers of intrinsic microporosity （PIM⁃1） membranes based on multivalent metal ions for gas separation［J］. Journal of Membrane Science， 2016， 514： 305⁃312.
28	Patel Hasmukh A， Sang Hyun Je， Joonho Park， et al. Unprecedented high⁃temperature CO₂selectivity in N₂⁃phobic nanoporous covalent organic polymers［J］. Nature Communications， 2013， 4（1）：1⁃8.
29	Cheng Liu， Li Yuemin， Zhang Manxia， et al. Hierarchical porous organic hyper⁃cross⁃linked polymers containing phthalazinone and carbazole moieties for gas uptake and fluorescence properties［J］. European Polymer Journal， 2020， 130：109674.
30	Wang J， Xiong S， Tao J， et al. An azo⁃bridged polymer of intrinsic microporosity modified poly（phthalazinone ether sulfone ketone） membrane for efficient O₂/N₂ separation［J］. Separation and Purification Technology， 2020， 248：117044.
31	Huang L， Guo W， Mondal H， et al. Effect of branch length on the structural and separation properties of hyperbranched poly（1， 3⁃dioxolane）［J］. Macromolecules， 2021， 55（1）： 382⁃389.
32	Zhang G， Tran T N， Huang L， et al. Thin⁃film composite membranes based on hyperbranched poly（ethylene oxide） for CO₂/N₂ separation［J］. Journal of Membrane Science， 2022， 644： 120184.
33	Liang Xu， Lei Tianyang， Jing Boyu， et al. Synthesis of soluble oligsiloxane⁃end⁃capped hyperbranched polyazomethine and their application to CO₂/N₂ separation membranes［J］. Designed Monomers & Polymers， 2018， 21（1）： 99⁃104.
34	Deng G， Luo J， Liu S， et al. Low⁃temperature synthesis and gas transport properties of novel contorted hyperbranched polyimides containing binaphthyl structures［J］. Separation and Purification Technology， 2020， 248： 117088.
35	Fang J， Kita H， Okamoto K I. Gas permeation properties of hyperbranched polyimide membranes［J］. Journal of Membrane science， 2001， 182（1/2）：245⁃256.
36	Peter J， Khalyavina A， Kríz J， et al. Synthesis and gas transport properties of ODPA⁃TAP⁃ODA hyperbranched polyimides with various comonomer ratios［J］. European Polymer Journal， 2009， 45（6）：1 716⁃1 727.
37	刘善友. （A_2+B_4）型超支化聚酰亚胺的分子设计及性能研究［D］. 吉林：吉林大学， 2016..
38	ZHANG L， MA T. Progress of membrane preparation usging hyperbranched polymers as key materials［J］.China Sciencepaper，2018，13（24）：2 747⁃2 753.
39	Song N， Ma T， Wang T， et al. Crosslinked microporous polyimides with polar substituent group for efficient CO₂ capture［J］. Microporous and Mesoporous Materials， 2020， 293：109809.
40	袁晓旭. 超支化聚酰亚胺的合成与气体分离性能研究［D］.天津：天津理工大学 2019.
41	Liu S， Luo J， Deng G， et al. From a hyperbranched polyi⁃mide to a microporous network polyimide via reaction temperature change and its application in gas separation membranes［J］. Polymers for Advanced Technologies， 2021， 32（4）： 1 866⁃1 876.
42	Marek Lanč， Petr Sysel， Marek Šoltys， et al. Synthesis， preparation and characterization of novel hyperbranched 6FDA⁃TTM based polyimide membranes for effective CO₂ separation： effect of embedded mesoporous silica particles and siloxane linkages［J］. Polymer， 2018， 144： 33⁃42.
43	Yang T， Pang H， Chen Z， et al. Synthesis and enhanced CO₂/CH₄ selectivity of hyperbranched copolyimide membranes［J］. High Performance Polymers， 2021， 33（6）： 675⁃684.
44	Suzuki T， Miki M， Yamada Y. Gas transport properties of hyperbranched polyimide/hydroxy polyimide blend membranes［J］. European Polymer Journal， 2012， 8（8）： 1 504⁃1 512.
45	Suzuki T， Yamada Y. Effect of thermal treatment on gas transport properties of hyperbranched polyimide⁃silica hybrid membranes［J］. Journal of Membrane Science， 2012， 417/418： 193⁃200.
46	Suzuki T， Takenaka M， Yamada Y. Synthesis and gas transport properties of hyperbranched polybenzoxazole⁃silica hybrid membranes［J］. Journal of Membrane Scien⁃ce， 2017， 521：10⁃17.
47	Shen Y， Wang H， Liu J D， et al. Enhanced performance of a novel polyvinyl amine/chitosan/graphene oxide mixed matrix membrane for CO₂ capture［J］. ACS Sustainable Chemistry & Engineering， 2015， 3（8）：1 819⁃1 829.
48	Dong G， Zhang Y， Hou J， et al. Graphene oxide nanosheets based novel facilitated transport membranes for efficient CO₂ capture［J］. Industrial & Engineering Chemi⁃stry Research， 2016， 55（18）： 5 403⁃5 414.
49	Sim Y H， Wang H， Li F Y， et al. High performance carbon molecular sieve membranes derived from hyperbranched polyimide precursors for improved gas separation applications［J］. Carbon， 2013， 53： 101⁃111.
50	Gao Y， Qiao Z， Zhao S， et al. In situ synthesis of polymer grafted ZIFs and application in mixed matrix membrane for CO₂ separation［J］. Journal of Materials Chemistry A， 2018， 6（7）： 3 151⁃3 161.
51	Fakhar A， Dinari M， Lammertink R， et al. Enhanced CO₂ capture through bulky poly （urethane⁃urea）⁃based MMMs containing hyperbranched triazine based silica nanoparticles［J］. Separation and Purification Technology， 2020， 241： 116734.

[1]	YANG Yan, WANG Jie, LI Zongyu, WANG Yiming, WANG Yunnan, LI Shuijuan, LEI Liangcai, LI Haiying. A review for synthetic methods of hyperbranched ionic liquid polymers [J]. China Plastics, 2022, 36(8): 159-165.
[2]	FENG Kai, LI Yongqing, MA Xiuqing, HAN Ying. Research progress and application in toughening modification of polyoxymethylene [J]. China Plastics, 2022, 36(7): 157-164.
[3]	FENG Xiu, SHEN Ying, XU Sheng. Synthesis and application of pentavalent organic bismuth for polyurethane [J]. China Plastics, 2022, 36(5): 104-109.
[4]	SUN Qi, GAO Xing, CUI Xuemei, LIAN Huiqin, CUI Xiuguo, WANG Xiaodong. Research progress in development and applications of black phosphorene for flame retardancy of polymers [J]. China Plastics, 2022, 36(5): 133-139.
[5]	CHEN Wenjing, YANG Xiaolong, HAN Shuntao, HAN Ying, MA Xiuqing. Research progress in modification methods of polyacrylonitrile materials [J]. China Plastics, 2022, 36(4): 158-165.
[6]	JIANG Sen, WANG Liyan, CHEN Yanming, ZHANG Le, ZHAI Guifa. Synthesis thermal performance of PBS copolyester modified with MPO [J]. China Plastics, 2022, 36(4): 24-29.
[7]	LI Jinglin, ZHENG Yi, ZHAO Liya, WANG Pan, YANG Xinyu, REN Lianhai. Research progress in biosynthesis of polyhydroxyalkanoates from kitchen waste [J]. China Plastics, 2022, 36(3): 110-119.
[8]	YANG Qinjie, LI Jiawen, LI Ming, CHEN Gang, LI Guangzhao, Peng Biyou, HAN Rui. Research progress in fused deposition modeling 3D printing equipment [J]. China Plastics, 2022, 36(2): 157-171.
[9]	YU Zhengfa, ZHAN Yue, CUI Yongyan. Synthesis of new silicon boron phosphorus flame retardant and its application for fire retardant coatings [J]. China Plastics, 2022, 36(10): 117-124.
[10]	WU You, WANG Bohua, SUN Jianjian, JIN Yujuan. Study on Modification of PPC/PBS Blends with Epoxy⁃terminated Hyperbranched Polymer [J]. China Plastics, 2021, 35(4): 5-11.
[11]	HUANG Xubo, LIU Zhaogang, ZHAO Jingang, YANG Yuxuan, CHEN Mingguang, WU Jinxiu, HU Yanhong, FENG Fushan. Effect of lanthanum 2⁃benzoyl benzoate on thermal stability of PVC [J]. China Plastics, 2021, 35(12): 94-101.
[12]	SONG Kunpeng, WANG Yinjie, FANG Zhuqing, LIU Jiping, RUAN Fang. Controllable Preparation and Characterizations of ZIF⁃67/Polyphosphazene Composite Microspheres [J]. China Plastics, 2021, 35(1): 1-7.
[13]	TANG Wei, QIAN Lijun, QIU Yong, CHEN Yajun, XU Bo, ZHAO Zhen. Research Progress in Halogen⁃free Flame Retardant Technology for Polypropylene [J]. China Plastics, 2021, 35(1): 136-149.
[14]	Wei ZHAI, Jianjian SUN, Bohua WANG, Chong TENG, Shiyu XIE, Fenghao HAO, Yujuan JIN. Study on Toughening Modification of PLA/PPC Blends with Hyperbranched Ethylenediamine Trazine Polymer [J]. China Plastics, 2020, 34(6): 27-33.
[15]	ZHANG Xin, ZHOU Wen, QIN Wenbo, LIU Jinglong, GUO Bin, HUANG Yanan. Research Progress in Applications of Forestry Chemicals in Plastics and Composites [J]. China Plastics, 2020, 34(11): 102-108.