Research Progress of Synthesis, Structure, and Performance of Main-chain Liquid Crystalline Aromatic Polyesteramides

LI Ya-dong; BAO Feng; WANG Ming-liang; ZHU Cai-zhen; ZHENG Zhao-hui; DING Xiao-bin; XU Jian

doi:10.14028/j.cnki.1003-3726.2024.23.252

您当前的位置：

首页 >

文章列表页 >

Research Progress of Synthesis, Structure, and Performance of Main-chain Liquid Crystalline Aromatic Polyesteramides

更新时间：2024-02-06

- Research Progress of Synthesis, Structure, and Performance of Main-chain Liquid Crystalline Aromatic Polyesteramides
- Polymer Bulletin Vol. 37, Issue 3, Pages: 281-296(2024)
- 作者机构：
  
  1..深圳大学化学与环境工程学院，低维材料基因工程研究院，深圳 518060
  2..中国科学院成都有机化学研究所，成都 610041
- 作者简介：
- 基金信息：
- DOI：10.14028/j.cnki.1003-3726.2024.23.252
  CLC：
- Received：18 July 2023，
  
  Accepted：24 August 2023，
  
  Published：20 March 2024
- 稿件说明：
移动端阅览
李亚东, 鲍锋, 王明良, 朱才镇, 郑朝晖, 丁小斌, 徐坚. 主链型液晶聚芳酯酰胺的合成、结构与性能研究进展. 高分子通报, 2024, 37(3), 281–296

Li, Y. D.; Bao, F.; Wang, M. L.; Zhu, C. Z.; Zheng, Z. H.; Ding, X. B.; Xu, J. Research progress of synthesis, structure, and performance of main-chain liquid crystalline aromatic polyesteramides. Polym. Bull. (in Chinese), 2024, 37(3), 281–296
李亚东, 鲍锋, 王明良, 朱才镇, 郑朝晖, 丁小斌, 徐坚. 主链型液晶聚芳酯酰胺的合成、结构与性能研究进展. 高分子通报, 2024, 37(3), 281–296 DOI： 10.14028/j.cnki.1003-3726.2024.23.252.

Li, Y. D.; Bao, F.; Wang, M. L.; Zhu, C. Z.; Zheng, Z. H.; Ding, X. B.; Xu, J. Research progress of synthesis, structure, and performance of main-chain liquid crystalline aromatic polyesteramides. Polym. Bull. (in Chinese), 2024, 37(3), 281–296 DOI： 10.14028/j.cnki.1003-3726.2024.23.252.

摘要

主链型液晶聚合物(main-chain liquid crystalline polymers，MCLCPs)分子链易取向的特性赋予其优异的性能，在航空、电子等领域具有不可替代的地位。其中芳香族聚酯酰胺(aromatic polyesteramides，APEAs)作为重要的一类，解决了单一化学结构的聚芳酯须在较高温度下加工、聚芳酰胺分子间氢键带来的刚性过大、易吸水等问题，具有可观的应用前景。目前相关研究中的分子链结构与聚合方法繁多，但缺少系统性的梳理。本文按照酯键与酰胺键的生成次序，将APEAs的合成分为同时生成、易生成无规链结构的一步缩聚法与先后分别制备、可得到有规序列的两步缩聚法。另外，不同结构单体的反应特性决定了适用的聚合方法与条件不同，因此本文一并整理了其聚合反应的影响因素。在此基础上，梳理了主链结构与性能的关系，展望未来的发展方向，以期为新型APEAs的合成提供借鉴与参考。

Abstract

Main-chain liquid crystalline polymer (MCLCPs) possess excellent performance due to its readily orientable molecular chain

making it irreplaceable in fields such as aerospace and electronics. Specifically

aromatic polyesteramides (APEAs) address the issues of processing at high temperatures required by both single aromatic polyesters and aromatic polyamides

the excessive rigidity caused by hydrogen bonding between characteristic groups of aromatic polyamides

and susceptibility to water absorption. However

despite the plethora of studies on APEAs’ molecular chain structures and synthesis methods

there remains a lack of systematic overview. Based on the order of ester and amide bond formation

the synthesis is categorized into two distinct approaches: one-step condensation method that simultaneously generates bonds

resulting in random chain structures; and two-step condensation method that sequentially produces bonds

yielding ordered sequences. Moreover

the suitability of various monomer structures affects the polymerization methods and conditions

and hence

an assessment of the factors influencing the polymerization reaction is presented. Building upon this foundation

the relationship between main-chain structure and properties is comprehensively reviewed

and future development directions are proposed to provide guidance and references for the synthesis of novel APEAs.

关键词

Keywords

references

S. J. Picken, ; D. J. Sikkema, ; H. Boerstoel, ; T. J. Dingemans, ; S. van der Zwaag, Liquid crystal main-chain polymers for high-performance fibre applications . Liq. Cryst. , 2011 , 38 ( 11-12 ), 1591 – 1605 .

孔海娟 , 张蕊 , 周建军 , 马禹 , 滕翠青 , 余木火 . 芳纶纤维的研究现状与进展 . 中国材料进展 , 2013 , 32 ( 11 ), 676 – 684 .

解孝林 , 杨成 , 唐旭东 , 吴大诚 . 热致液晶性聚酯酰胺的研究进展 . 化学研究与应用 , 1996 , 8 ( 2 ), 159 – 164 .

S. Zhou, ; X. L. Wang, ; W. Zhang, ; M. Y. Zhang, ; X. L. Zhang, ; N. Zhao, ; R. G. Liu, ; J. A. Xu, ; Z. H. Shen, ; X. H. Fan, Facile preparation and characterization of soluble aramid . J. Appl. Polym. Sci. , 2018 , 135 ( 23 ), 4634159 .

S. Zhou, ; M. Y. Zhang, ; R. Wang, ; J. Ping, ; X. L. Zhang, ; N. Zhao, ; J. Xu, ; Z. H. Shen, ; X. H. Fan, Synthesis and characterization of new aramids based on o -( m -triphenyl)-terephthaloyl chloride and m -( m -triphenyl)-isophthaloyl chloride . Polymer , 2017 , 109 , 49 – 57 .

P. W. Morgan, Linear condensation polymers from phenolphthalein and related compounds . J. Polym. Sci. A , 1964 , 2 ( 1 ), 437 – 459 .

G. C. East, ; V. Kalyvas, ; J. E. McIntyre, ; A. H. Milburn, Factors affecting the formation of high molecular weight aromatic polyesteramides by solution polycondensation . Polymer , 1989 , 30 ( 3 ), 558 – 563 .

S. M. M. Morsi, ; H. A. Mohamed, ; S. H. El-Sabbagh, Polyesteramidesulfone as novel reinforcement and antioxidant nanofiller for NBR blended with reclaimed natural rubber . Mater. Chem. Phys. , 2019 , 224 , 206 – 216 .

J. Preston, Self-regulating polycondensations: ordered aromatic polyamide-esters . J. Polym. Sci. A-1 Polym. Chem. , 1970 , 8 ( 11 ), 3135 – 3144 .

Y. Imai, ; S. Abe, ; M. Ueda, Preparation and properties of aromatic polyamide-esters from aminophenols and aromatic diacid chlorides . J. Polym. Sci. A Polym. Chem. , 1981 , 19 ( 12 ), 3285 – 3291 .

S. B. Oswal, ; N. I. Malek, ; A. K. Pandya, Interfacial polymerization of linear aromatic poly(ester amide)s . Int. J. Polym. Mater. , 2009 , 58 ( 4 ), 202 – 216 .

F. Higashi, ; A. Hoshio, ; J. Kiyoshige, Preparation of aromatic polyester-amides by direct polycondensation with diphenyl chlorophosphate as activator . Makromol. Chem. , Rapid Commun. , 1983 , 4 ( 6 ), 371 – 374 .

F. Higashi, ; A. Hoshio, ; H. Ohtani, Synthesis of high-molecular-weight poly(amide-ester)s by direct polycon-densation with diphenyl chlorophosphate . J. Polym. Sci. A Polym. Chem. , 1984 , 22 ( 12 ), 3983 – 3988 .

F. Higashi, ; M. Ozawa, ; A. Mochizuki, Synthesis of soluble aromatic polyesteramides by stepwise copolycondensation of bisphenols and aromatic diamines with diphenyl chlorophosphate in pyridine . J. Polym. Sci. A Polym. Chem. , 1986 , 24 ( 4 ), 637 – 643 .

C. P. Chen, ; T. C. Studies on thermotropic liquid crystalline polymers. XVI. Chang, Synthesis and properties of fully aromatic poly(amide-ester)s with naphthalene structures . J. Polym. Sci. A Polym. Chem. , 1996 , 34 ( 14 ), 2857 – 2865 .

Y. Ji, ; Y. Bai, ; X. B. Liu, ; K. Jia, Progress of liquid crystal polyester (LCP) for 5G application . Adv. Ind. Eng. Polym. Res. , 2020 , 3 ( 4 ), 160 – 174 .

S. X. Cheng, ; T. S. Chung, Effect of a fluorine lateral moiety on the liquid crystallinity of wholly aromatic polyester-amides . Polymer , 2002 , 43 ( 26 ), 7433 – 7441 .

E. W. Choe, ; M. Borzo, Synthesis and randomization of well-defined sequence, wholly aromatic copolyester/esteramides . J. Appl. Polym. Sci. , 1994 , 53 ( 5 ), 621 – 632 .

Y. F. Tang, ; L. Yuan, ; G. Z. Liang, ; A. J. Gu, Reprocessable triple-shape-memory liquid crystalline polyester amide with ultrahigh thermal resistance . Ind. Eng. Chem. Res. , 2020 , 59 ( 31 ), 14015 – 14024 .

I. Sava, ; I. Ronova, ; M. Bruma, Synthesis of poly(1,3,4-oxadiazole-amide-ester)s and study of the influence of conformational parameters on their physical properties . Polym. J. , 2006 , 38 ( 9 ), 940 – 948 .

I. Sava, New aromatic polyesteramides: synthesis and properties . Polimery , 2011 , 56 ( 4 ), 263 – 270 .

G. P. Zhang, ; G. R. Peng, ; X. T. Bi, Electrochemical polymerization of pyrrole in polyesteramide matrix . Synth. Met. , 1993 , 55 ( 2-3 ), 1123 – 1128 .

张广平 , 彭光荣 , 毕先同 . 两种新型溶致型液晶芳香聚酯酰胺的合成与表征 . 功能高分子学报 , 1993 , 6 ( 3 ), 211 – 217 .

傅清红 , 刘德山 , 周其庠 . 热致规则全芳液晶聚酯酰胺的合成和液晶相转变 . 合成纤维工业 , 1990 , 13 ( 1 ), 25 – 30 .

H. Ebadi, ; S. Mehdipour-Ataei, Heat-resistant, pyridine-based polyamides containing ether and ester units with improved solubility . Chinese. J. Polym. Sci. , 2010 , 28 ( 1 ), 29 – 37 .

N. Yamazaki, ; M. Niwano, ; J. Kawabata, ; F. Higashi, Studies on reactions of N-phosphonium salts of pyridines. 12. Preparation of peptides and active esters by a hydrolysis-dehydration reaction with phosphonites, and application of reaction to polymer synthesis . Tetrahedron , 1975 , 31 ( 7 ), 665 – 670 .

Y. D. Liu, ; S. Zhou, ; N. Zhao, ; J. Xu, ; Z. H. Shen, ; X. H. Fan, ; Q. F. Zhou, Facile synthesis and characterization of soluble aramid containing polar hydroxyl side group . Polymer , 2022 , 238 , 124411 .

S. H. Hsiao, ; W. T. Leu, ; W. Guo, Synthesis and properties of novel aromatic poly(ester amide)s bearing naphthalene-2,7-diyl units . Polym. J. , 2002 , 34 ( 12 ), 925 – 935 .

S. H. Hsiao, ; W. T. Leu, Synthesis and properties of novel aromatic poly(ester amide)s derived from 1,5-bis(4-aminobenzoyloxy)naphthalene and aromatic dicar-boxylic acids . Eur. Polym. J. , 2004 , 40 ( 11 ), 2471 – 2480 .

W. Guo, ; W. T. Leu, ; S. H. Hsiao, Synthesis and properties of ortho -linked aromatic poly(ester-amide)s and poly(ester-imide)s bearing 2,3-bis(benzoyloxy)naphthalene units . J. Polym. Res. , 2007 , 14 ( 5 ), 359 – 372 .

S. M. Aharoni, Dilute and concentrated solution properties of zigzag polymers comprising long rodlike segments with freely rotating joints . Macromolecules , 1987 , 20 ( 4 ), 877 – 884 .

S.E. Mallakpour, ; A.R. Hajipour, ; R. Vahabi, Synthesis and characterization of novel poly(amide-ester-imide)s based on bis( p -amidobenzoyl chloride)-N-trimellitylimido-L-leucine . Iran. Polym. J. , 2001 , 10 ( 5 ), 321 – 330 .

Y. Imai, ; S. Abe, ; T. Takahashi, ; M. Ueda, Preparation and properties of ordered and random polyamide-esters from 4-(4-amino- α , α -dimethylbenzyl)phenol and aromatic diacyl chlorides . J. Polym. Sci. Polym. Chem. Ed. , 1982 , 20 ( 3 ), 683 – 689 .

S. Mehdipour-Ataei, ; P. Einollahy, Novel diols containing ester and amide groups and resulting poly(ester amide ester)s . J. Appl. Polym. Sci. , 2004 , 93 ( 6 ), 2699 – 2703 .

S. Mallakpour, ; M. Kolahdoozan, Preparation and characterization of novel optically active poly(amide-ester-imide)s based on bis( p -aminobezoic acid)- N -trimellitylimido-S-valine via direct polyesterification . Iran. Polym. J. , 2006 , 15 ( 4 ), 307 – 315

K. Y. Sandhya, ; C. K. S. Pillai, ; K. Sree Kumar, New liquid-crystalline poly(ester amide)s: the role of nitro groups in the phase behavior . J. Polym. Sci. B , 2004 , 42 ( 7 ), 1289 – 1298 .

J. G. Lynch, ; G. D. Stimuli-responsive polymers. 10. Jaycox, Photo-regulation of optical rotations in azobenzene modified poly(ester-amide)s containing highly structured, atropisomeric backbone geometries . Polymer , 2014 , 55 ( 16 ), 3564 – 3572 .

S. Mehdipour-Ataei, ; P. Einollahy, Synthesis, charac-terization and properties of novel poly(ester-amide-urethane)s . Macromol. Symp. , 2004 , 214 ( 1 ), 339 – 350 .

周其凤 . 液晶高分子的分子工程 . 功能高分子学报 , 1992 , 5 ( 2 ), 93 – 101 .

S. L. Oswal, ; A. K. Pandya, Synthesis and characterization of linear aromatic polyester-amides from diacid chlorides and aminophenols . Iran. Polym. J. , 2004 , 13 ( 3 ), 205 – 212 .

I. Sava, Influence of conformational parameters on physical properties of some poly(amide-ester)s . Rev. Roum. Chim. , 2006 , 51 ( 7-8 ), 753 – 758 .

H. Li, Seino, ; K. Yonetake, ; M. Ueda, Synthesis and characterization of ordered poly(amide-ester)s from isophthaloyl chloride and 4-(2-aminoethyl)phenol . Macromolecules , 1999 , 32 ( 12 ), 3851 – 3858 .

G. S. Liou, ; S. H. Hsiao, Synthesis and properties of aromatic poly(ester amide)s with pendant phosphorus groups . J. Polym. Sci. A Polym. Chem. , 2002 , 40 ( 4 ), 459 – 470 .

W. Guo, ; W. T. Leu, ; S. H. Hsiao, ; G. S. Liou, Thermal degradation behaviour of aromatic poly(ester-amide) with pendant phosphorus groups investigated by pyrolysis-GC/MS . Polym. Degrad. Stab. , 2006 , 91 ( 1 ), 21 – 30 .

S. Mehdipour-Ataei, ; R. Malekimoghaddam, ; M. Nami, Novel pyridine-based ether ester diamine and resulting thermally stable poly(ether ester amide)s . Eur. Polym. J. , 2004 , 40 ( 11 ), 2523 – 2529 .

S. S. Ankushrao, ; V. N. Kadam, ; Y. S. Patil, ; V. P. Ubale, ; N. N. Maldar, ; A. A. Ghanwat, Synthesis and characterization of processable heat resistant co-poly(ester-amide)s containing cyclopentylidene moiety . J. Macromol. Sci. A , 2017 , 54 ( 2 ), 124 – 132 .

M. Bruma, ; I. Negulescu, ; F. Mercer, ; W. Daly, ; J. Fitch, ; P. Cassidy, Fluorene-containing polyesters and poly(ester-amide)s . J. Macromol. Sci. A , 1995 , 32 ( 8-9 ), 1521 – 1530 .

S. H. Hsiao, ; Y. C. Liao, Synthesis and properties of novel organosoluble and light-colored poly(ester-amide)s and poly(ester-imide)s with triptycene moiety . J. Polym. Res. , 2018 , 25 ( 2 ), 52 .

Views

1148

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

No data

Related Author

No data

Related Institution

No data

⁰