Preparation and Performance of Thermally Rearranged Gas Separation Membranes Containing Tetraarylimidazole Structure

Pin-ru Li; Guo-yong Xiao; Yuan-lin Chen; Yun-hua Lu; Lin Li; Tong-hua Wang

doi:10.11777/j.issn1000-3304.2023.23178

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Preparation and Performance of Thermally Rearranged Gas Separation Membranes Containing Tetraarylimidazole Structure

Research Article | 更新时间：2024-01-19

- Preparation and Performance of Thermally Rearranged Gas Separation Membranes Containing Tetraarylimidazole Structure
- Acta Polymerica Sinica Vol. 55, Issue 2, Pages: 212-221(2024)
- 作者机构：
  
  1.辽宁科技大学化工学院鞍山 114051
  2.大连理工大学化工学院精细化工国家重点实验室碳素实验室大连 116024
- 作者简介：
  
  Guo-yong Xiao, E-mail: xiaoguoyong@ustl.edu.cn
  Yun-hua Lu, E-mail: luyunhua@ustl.edu.cn
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2023.23178
  CLC：
- Published：20 February 2024，
  
  Published Online：31 October 2023，
  
  Received：06 July 2023，
  
  Accepted：18 August 2023
- 稿件说明：
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李品儒, 肖国勇, 陈元林, 鲁云华, 李琳, 王同华. 含四芳基咪唑结构的热重排气体分离膜的制备与性能研究. 高分子学报, 2024, 55(2), 212-221

Li, P. R.; Xiao, G. Y.; Chen, Y. L.; Lu, Y. H.; Li, L.; Wang, T. H. Preparation and performance of thermally rearranged gas separation membranes containing tetraarylimidazole structure. Acta Polymerica Sinica, 2024, 55(2), 212-221
李品儒, 肖国勇, 陈元林, 鲁云华, 李琳, 王同华. 含四芳基咪唑结构的热重排气体分离膜的制备与性能研究. 高分子学报, 2024, 55(2), 212-221 DOI： 10.11777/j.issn1000-3304.2023.23178.

Li, P. R.; Xiao, G. Y.; Chen, Y. L.; Lu, Y. H.; Li, L.; Wang, T. H. Preparation and performance of thermally rearranged gas separation membranes containing tetraarylimidazole structure. Acta Polymerica Sinica, 2024, 55(2), 212-221 DOI： 10.11777/j.issn1000-3304.2023.23178.

摘要

合成了一种新型含四芳基咪唑结构的二胺单体4

4'-(4

5-二苯基-(3-羟基-4-氨基苯氧基)苯基)咪唑(PMAPPP)，然后分别与5种二酐单体聚合，经热酰亚胺化处理得到含羟基聚酰亚胺(HPI)薄膜. 接着，对这些薄膜进行450 ℃热处理，得到相应的热重排(TR)膜材料，并对薄膜进行了结构与性能表征. 结果表明，刚性大体积四芳基咪唑结构的引入使HPI膜表现出优异的热性能和力学性能，玻璃化转变温度在263~361 ℃，拉伸强度在98.4~118.3 MPa. 热重排后，TR膜的气体分离性能得到了显著提高. 其中，TR(PMAPPP-6FDA)的气体渗透性能最佳，即H

(269.31 Barrer)、CO

(284.25 Barrer)、O

(62.75 Barrer)和N

(10.67 Barrer)，CO

和O

的理想选择性分别为25.24和5.88，且O

的分离性能超过2008 Robeson上限. 因此，将四芳基咪唑结构引入到HPI分子结构中，可以获得一类气体分离性能优异的TR膜材料.

Abstract

In recent years

the thermal rearrangement (TR) membrane materials derived from hydroxyl-containing polyimides (HPI) as precursors have received extensive attention in the field of gas separation. In this study

the dihydroxy compound 4

‍4'-(4

‍5-diphenyl-(4-hydroxyphenyl))imidazole (PMOPPP) containing rigid and bulky tetraarylmidazole structure was first synthesized

and then reacted with 5-fluoro-2-nitrophenol to produce a dinitro compound 4

‍4'-(4

‍5-diphenyl-(3-hydroxy-4-nitrophenoxy)phenyl)imidazole (PMNPPP). After reduction treatment

a new kind of diamine monomer 4

‍4'-‍(4

5-diphenyl-‍(3-hydroxy-4-aminophenoxy)phenyl)imidazole (PMAPPP) was obtained. Then

the diamine PMAPPP was separately polymerized with five kinds of dianhydride monomers

followed by thermal imidization treatment to obtain HPI membranes. Subsequently

these membranes were further thermally treated at 450 ℃ for 1 h to obtain the corresponding TR membranes

and the structure and performance of these membrane materials were characterized. The testing results showed that the introduction of rigid and large volume tetraarylimidazole structure resulted in excellent thermal and mechanical properties of five HPI membranes

and the glass transition temperatures (

) were in the range of 263‒361 ℃ and the tensile strength ranged from 98.4 MPa to 118.3 MPa. Compared to HPI membrane materials

the gas separation performances of TR membranes were significantly improved. Among them

the TR(PMAPPP-6FDA) exhibited the highest gas permeabilities

namely H

(269.31 Barrer)

(284.25 Barrer)

(62.75 Barrer) and N

(10.67 Barrer). Moreover

the ideal selectivities of CO

and H

were 25.24

5.88 and 26.64

respectively

and the O

separation performance was beyond the 2008 Robeson upper bound.

关键词

四芳基咪唑结构聚酰亚胺热重排气体分离膜

Keywords

Tetraarylimidazole structurePolyimideThermal rearrangementGas separation membranes

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