芴基、酰亚胺基和萘基聚合物气体分离膜的研究进展

doi:10.16085/j.issn.1000-6613.2023-0661

化工进展 ›› 2024, Vol. 43 ›› Issue (4): 1897-1911.DOI: 10.16085/j.issn.1000-6613.2023-0661

• 材料科学与技术 • 上一篇

芴基、酰亚胺基和萘基聚合物气体分离膜的研究进展

范文轩¹^,²^,³(), 徐双平¹^,²(), 贾宏葛¹^,², 张明宇¹^,², 蘧延庆¹^,²

^1.齐齐哈尔大学材料科学与工程学院，黑龙江齐齐哈尔 161006
^2.黑龙江省聚合物基复合材料重点实验室，黑龙江齐齐哈尔 161006
^3.齐齐哈尔大学化学与化学工程学院，黑龙江齐齐哈尔 161006

收稿日期:2023-04-23 修回日期:2023-05-29 出版日期:2024-04-15 发布日期:2024-05-13
通讯作者: 徐双平
作者简介:范文轩（1995—），男，硕士研究生，研究方向为桥接聚硅氧烷气体分离膜的制备。E-mail：18340780380@163.com。
基金资助:
国家自然科学基金青年基金(52203093);黑龙江省省属高等学校基本科研业务费科研项目(145109117)

Research progress on polymeric membranes containing fluorenyl, imide and naphthyl groups for gas separation

FAN Wenxuan¹^,²^,³(), XU Shuangping¹^,²(), JIA Hongge¹^,², ZHANG Mingyu¹^,², QU Yanqing¹^,²

^1.School of Materials Science and Engineering, Qiqihar University, Qiqihar 161006, Heilongjiang, China
^2.Heilongjiang Provincial Key Laboratory of Polymeric Composite Materials, Qiqihar 161006, Heilongjiang, China
^3.School of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar 161006, Heilongjiang, China

Received:2023-04-23 Revised:2023-05-29 Online:2024-04-15 Published:2024-05-13
Contact: XU Shuangping

摘要/Abstract

摘要：

聚合物链间距和链刚度是影响聚合物膜对气体渗透性能的决定因素，刚性基团（如芴基、酰亚胺基及萘基）引入聚合物链中，基于其大体积和扭曲结构能够有效阻碍分子链堆积，从而降低分子链堆积密度，使聚合物具有较高的自由体积，能有效改善膜对气体的渗透选择性。本文综述了近5年含芴基、酰亚胺基和萘基聚合物在气体分离中的研究，按结构分类，详细介绍了三类聚合物的合成以及膜对气体的选择性，分析了影响气体选择性的主要因素。最后，综合现有刚性聚合物的特点，从改性高气体渗透性低选择性材料、改性生物基材料及制备复合混合基质膜等角度出发，展望了此类材料的未来发展趋势，为制备高性能气体分离膜提供参考。

关键词: 芴, 酰亚胺, 萘, 气体分离膜

Abstract:

The inter-polymer chain spacing and polymer chain stiffness are the determining factors for gas permeation properties, the introduction of rigid groups (fluorenyl, imide and naphthyl) into the polymer chain can effectively improve gas permselectivity due to the presence of large volume and rigid twisted groups in polymers can inhibit interchain stacking of relatively rigid chains (i.e., increase free volume fraction) and reduce rotational mobility around flexible links (i.e., increase stiffness). In this paper, the recent five years studies on membranes based on polymer containing fluorenyl, imide and naphthyl group materials in the field of gas separation were reviewed. These researches were classified by the structure of polymer materials that make up the membranes and introduced in terms of synthesis, gas selectivity and the main factor affecting the selectivity. Finally, based on the characteristics of rigid polymers, the application of rigid polymer materials should be expanded in terms of the modification of existing materials with high gas permeability and low selectivity, the modification of bio-based materials and the preparation of composite membranes, providing a reference for the preparation of gas separation membranes with high performance in the future.

Key words: fluorenyl, imide, naphthyl, gas separation membrane

中图分类号:

TQ325

范文轩, 徐双平, 贾宏葛, 张明宇, 蘧延庆. 芴基、酰亚胺基和萘基聚合物气体分离膜的研究进展[J]. 化工进展, 2024, 43(4): 1897-1911.

FAN Wenxuan, XU Shuangping, JIA Hongge, ZHANG Mingyu, QU Yanqing. Research progress on polymeric membranes containing fluorenyl, imide and naphthyl groups for gas separation[J]. Chemical Industry and Engineering Progress, 2024, 43(4): 1897-1911.

图/表 28

图1 三种双(苯基)芴聚酰亚胺(PI)的结构式[36]

图2 二酐MMBMDA、二胺FDBDA单体和两种双(苯基)芴PIM-PI的结构式[37]

图3 6FDA-APAF0.5-Cardo0.5共聚酰亚胺结构式[38]

图4 PIM-1和Cardo-PIM-1的结构式[44]

图5 线型多孔有机聚合物的合成[45]

图6 PIM-SBF 1~7的合成方案[46]

图7 热重排芴基聚醚苯并𫫇唑的结构式[51-52]

图8 Am-PAFEK-x共聚物的结构式[53]

图9 Ph-PEEKs、PEEKs的结构式[54]

表1 含芴基聚合物膜气体渗透选择性

聚合物	渗透性/Barrer				选择性			参考文献
聚合物	CO₂	CH₄	O₂	N₂	CO₂/CH₄	CO₂/N₂	O_2/N₂	参考文献
6FDA-FBPF	61.82	2.43	20.00	5.20	25.42	11.89	3.85	[36]
MMBMDA-FDBDA	876	34	172	38	26.2	23.2	4.56	[37]
7.5% f-MWCNTs	5300	—	180	—	—	11.0	—	[44]
PIM-SBF-2	22300	2020	3820	1150	11.0	19.4	3.2	[46]
PEBO-6FDA	245.04	—	60.73	10.58	—	23.16	5.74	[51]
TRCP-4∶6	269.0	4.60	46.8	5.20	58.48	51.73	9.00	[52]
Am-PAFEK-60%	4.67	0.14	0.55	0.15	33.36	31.13	3.67	[53]
Ph-PEEK-3	17.14	1.18	4.08	1.05	14.59	16.35	3.89	[54]
PEEK-3	14.08	1.06	3.50	1.01	13.30	14.00	3.48	[54]

图10 酰亚胺桥接聚甲基氢硅氧烷（PMHS-I）的合成[60]

图11 酰亚胺桥接聚五甲基三硅氧烷的合成[61]

图12 无规嵌段共聚物 PIS 的化学结构式[62]

图13 相容性聚合物/聚倍半硅氧烷共混物的结构[63]

图14 PI和PI-CL的合成示意图[64]

图15 微孔聚酰亚胺CF3-PI-CL的结构式[65]

图16 PMDA-DAT聚酰亚胺的合成路线[66]

图17 TB-PI聚合物前体的化学结构[67]

图18 不同类型的TR-PBOI膜的结构式[68]

图19 聚合物TR-PBOI的结构式[69]

图20 含三蝶烯TRI-PBO膜的结构式[70]

表2 含酰亚胺基聚合物气体渗透选择性

聚合物	渗透性/Barrer				选择性			参考文献
聚合物	CO₂	CH₄	O₂	N₂	CO₂/CH₄	CO₂/N₂	O₂/N₂	参考文献
PMHS-I	—	—	31.00	6.98	—	—	4.44	[60]
IBPPMS	—	—	47.1	6.62	—	—	7.11	[61]
UV-PIS-4	69	1.1	21.5	3.25	61.0	21.2	6.6	[62]
CMS PILPSQ-20	2465	44.02	—	—	56	—	—	[63]
PMDA-DAT	51.4	1.6	9.4	1.5	32.1	34.27	6.3	[66]
TB-CMS-800	4200	12.5	342	38	112	37	9.0	[67]
m-TR400-2	29.7	0.97	7.8	1.7	30.62	17.47	4.62	[68]
A₄₀B₄₀-TR-420	92	1.68	—	—	54.7	—	—	[69]
TPI-PBO-0.75	505	18	107	25	28	20.2	4.3	[70]

图21 NTDA-TrMPD/BTFBz的合成方案[73]

图22 联萘聚酰亚胺的合成[74]

图23 联萘醚基PIs结构式[75]

图24 微孔萘基PIs的合成[76]

图25 微孔聚酰亚胺的结构式[77]

表3 含萘基聚合物气体渗透选择性

聚合物	渗透性/Barrer				选择性			参考文献
聚合物	CO₂	CH₄	O₂	N₂	CO₂/CH₄	CO₂/N₂	O₂/N₂	参考文献
NT-TR/BT (1/1)	930	43.1	164	45.5	21.6	20.4	3.6	[73]
XS10	25.9	0.41	4.89	0.78	63.2	33.2	6.3	[75]
PI-3F	845	55.3	99.8	53.8	15.4	15.7	1.9	[76]
TNTDA-DAT	728	24	159	32	29.7	22.6	4.93	[77]

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芴基、酰亚胺基和萘基聚合物气体分离膜的研究进展

Research progress on polymeric membranes containing fluorenyl, imide and naphthyl groups for gas separation

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