氟取代聚芳醚酮低温合成及其结构研究

董大林; 宾月珍; 蹇锡高

doi:10.11777/j.issn1000-3304.2021.21260

您当前的位置：

首页 >

文章列表页 >

氟取代聚芳醚酮低温合成及其结构研究

研究论文 | 更新时间：2024-10-08

- 氟取代聚芳醚酮低温合成及其结构研究
- Synthesis of Fluorine-substituted Poly(aryl ether ketone)s under Low Temperature and Its Structure
- 高分子学报 2022年53卷第3期页码：261-272
- 作者机构：
  
  1.大连理工大学高分子材料系
  2.辽宁省高性能树脂工程技术研究中心大连 116024
- 作者简介：
  
  Yue-zhen Bin, E-mail: binyz@dlut.edu.cn
- 基金信息：
  
  国家自然科学基金(基金号 ┣21374014);U1663226┫
- DOI：10.11777/j.issn1000-3304.2021.21260
  中图分类号：
- 纸质出版日期：2022-03-20，
  
  网络出版日期：2021-12-23，
  
  收稿日期：2021-09-02，
  
  录用日期：2021-11-26
- 稿件说明：
移动端阅览
董大林,宾月珍.氟取代聚芳醚酮低温合成及其结构研究[J].高分子学报,2022,53(03):261-272.

Dong Da-lin,Bin Yue-zhen.Synthesis of Fluorine-substituted Poly(aryl ether ketone)s under Low Temperature and Its Structure[J].ACTA POLYMERICA SINICA,2022,53(03):261-272.
董大林,宾月珍.氟取代聚芳醚酮低温合成及其结构研究[J].高分子学报,2022,53(03):261-272. DOI： 10.11777/j.issn1000-3304.2021.21260.

Dong Da-lin,Bin Yue-zhen.Synthesis of Fluorine-substituted Poly(aryl ether ketone)s under Low Temperature and Its Structure[J].ACTA POLYMERICA SINICA,2022,53(03):261-272. DOI： 10.11777/j.issn1000-3304.2021.21260.

摘要

通过傅克酰基化反应合成4

4'-二(4-氟苯甲酰基)二苯醚、4

4'-二(五氟苯甲酰基)二苯醚、4

4'-二(4-氟苯甲酰基)二苯硫醚以及4

4'-二(五氟苯甲酰基)二苯醚4种长链双卤单体，并进一步制备了含二氮杂萘酮聚芳醚酮聚合物. 通过多氟取代双卤单体在含二氮杂萘酮聚芳醚酮聚合物主链中引入氟原子. 多氟取代双卤单体具有多个反应位点，低温反应以及两步投料的聚合路线保证了溶液缩聚反应在多氟取代双卤单体的指定位点进行，保证了氟取代含二氮杂萘酮聚芳醚酮聚合物的线形结构并具有一定的分子量. 讨论了氟原子的引入对于含二氮杂萘酮聚芳醚酮聚合物合成路线、分子结构、数均分子量、热性能以及序列结构的影响.

Abstract

Poly(aryl ether ketone)s are high performance engineering plastics with excellent comprehensive performance. They are usually prepared by solution polycondensation at high temperature with bisphenol monomers and dihalogen monomer. Polycondensation at high temperature makes it difficult to prepare and raises production costs. As a result

preparation of poly(aryl ether ketone)s at low temperature is significant in scientific research and industrial production. On the other hand

introduction of fluorine atoms into poly(aryl ether ketone)s with phthalazinone can optimize comprehensive properties. Here

fluorine atoms are introduced in dihalogen monomers to prepare fluorine substituted poly(aryl ether ketone)s at low temperature. Long-chain dihalogenated monomers are obtained by Friedel-Crafts acylation reaction with pentafluorobenzoic acid instead of p-fluorobenzoic acid. Fluorine substituted long-chain dihalogenated monomers are used in preparation of poly(aryl ether ketone)s with phthalazinone at low temperature. Fluorine atoms were introduced into main chain of poly(aryl ether ketone)s containing phthalazinone. Polyfluorosubstituted dihalogenated monomers have multiple reaction sites. Low temperature reaction and two-step feeding polymerization route ensure that solution polycondensation reaction is carried out at certain position of polyfluorosubstituted dihalogenated monomers and that fluorine substituted poly(aryl ether ketone)s with phthalazinone are linear polymers. The introduction of fluorine atoms has an impact on synthetic route

molecular structure

number average molecular weight

thermal properties and sequence structure of poly(aryl ether ketone)s with phthalazinone. Two kinds of fluorine substituted poly(aryl ether ketone)s with phthalazinone synthesised with long-chain dihalogenated monomers are amorphous polymers. With the introduction of fluorine atoms

glass transition temperatures of the corresponding poly(aryl ether ketone)s with phthalazinone are improved; while number-average molecule weight and thermal decomposition temperature of fluorine substituted poly(aryl ether ketone)s with phthalazinone are reduced

due to the low-temperature reaction. Otherwise

fluorine substituted poly(aryl ether ketone)s with phthalazinone have potential for further post functionalization. It's expected that this study could provide reference for other researchers.

关键词

二氮杂萘酮聚芳醚酮氟取代序列结构

Keywords

PhthalazinonePoly(aryl ether ketone)Fluoro-substitutionSequence structure

references

Chen G, Chen P, Zeng L X, Xu J J, Liu P Q. J Macromol Sci B, 2019, 58(12): 934-946. doi:10.1080/00222348.2019.1677298http://dx.doi.org/10.1080/00222348.2019.1677298

Dong Dalin(董大林), Bin Yuezhen(宾月珍), Jian Xigao(蹇锡高). Acta Polymerica Sinica(高分子学报), 2020, 51(12): 1321-1334. doi:10.11777/j.issn1000-3304.2020.20130http://dx.doi.org/10.11777/j.issn1000-3304.2020.20130

Luan J S, Zhang S L, Geng Z, Wang G B. Polym Eng Sci, 2013, 53(10): 2254-2260. doi:10.1002/pen.23613http://dx.doi.org/10.1002/pen.23613

Wu T, Liu P Q, Wang X, Zeng L X, Ye G D, Xu J J. J Appl Polym Sci, 2013, 128(2): 1110-1116. doi:10.1002/app.38338http://dx.doi.org/10.1002/app.38338

Li R S, Wu T, Zeng L X, Xu J J, Liu P Q. J Appl Polym Sci, 2014, 131(16): 40595. doi:10.1002/app.40595http://dx.doi.org/10.1002/app.40595

Zeng L X, Li R S, Chen P, Xu J J, Liu P Q. J Appl Polym Sci, 2016, 133(32): 43800. doi:10.1002/app.43800http://dx.doi.org/10.1002/app.43800

Dong D L, Bin Y Z, Jian X G. High Perform Polym, 2021, 33(3): 276-284. doi:10.1177/0954008320958048http://dx.doi.org/10.1177/0954008320958048

Bao Feng(鲍锋), Liu Cheng(刘程), Song Yuanyuan(宋媛媛), Wu Zuoqiang(邬祚强), Wang Jinyan(王锦艳), Jian Xigao(蹇锡高). Acta Polymerica Sinica(高分子学报), 2018, (6): 692-699. doi:10.11777/j.issn1000-3304.2017.17http://dx.doi.org/10.11777/j.issn1000-3304.2017.17

Scholes C A, Kanehashi S, Stevens G W, Kentish S E. Sep Purif Technol, 2015, 147: 203-209. doi:10.1016/j.seppur.2015.04.023http://dx.doi.org/10.1016/j.seppur.2015.04.023

Fang M F, Okamoto Y, Koike Y, He Z J, Merkel T C. J Fluorine Chem, 2016, 188: 18-22. doi:10.1016/j.jfluchem.2016.05.013http://dx.doi.org/10.1016/j.jfluchem.2016.05.013

Mirchandani G, Samanta S, Raghavendra V B, Chaudhary S, Baustkar S, Shyamroy S, Singha N K. Prog Org Coat, 2021, 152: 1-12. doi:10.1016/j.porgcoat.2020.106106http://dx.doi.org/10.1016/j.porgcoat.2020.106106

Han D J, Kim S, Heo H J, Park I J, Kang H S, Lee S G, Lee J C, Sohn E H. ACS Appl Polym Mater, 2020, 2(9): 3957-3965. doi:10.1021/acsapm.0c00625http://dx.doi.org/10.1021/acsapm.0c00625

Liu J C, Wang K, Xie Y Z, Gao F, Zeng Q T, Yuan Y, Liu R, Liu X Y. J Coat Technol Res, 2017, 14(6): 1325-1334. doi:10.1007/s11998-017-9931-8http://dx.doi.org/10.1007/s11998-017-9931-8

Hajdok I, Bona A, Werner H J, Kerres J. Eur Polym J, 2014, 52: 76-87. doi:10.1016/j.eurpolymj.2013.12.003http://dx.doi.org/10.1016/j.eurpolymj.2013.12.003

Zhao Z H, Ma X H, Zhang A X, Song N H. J Polym Sci, Part A: Polym Chem, 2011, 49(11): 2423-2433. doi:10.1002/pola.24673http://dx.doi.org/10.1002/pola.24673

Ding J F, Qi Y H. Macromolecules, 2008, 41(3): 751-757. doi:10.1021/ma071669uhttp://dx.doi.org/10.1021/ma071669u

Kimura K, Tabuchi Y, Yamashita Y, Cassidy P E, Fitch J W, Okumura Y. Polym Adv Technol, 2000, 11(8-12): 757-765. doi:10.1002/1099-1581(200008/12)11:8/12<757::aid-pat54>3.0.co;2-zhttp://dx.doi.org/10.1002/1099-1581(200008/12)11:8/12<757::aid-pat54>3.0.co;2-z

Kimura K, Nishichi A, Yamashita Y. Polym Adv Technol, 2004, 15(6): 313-319. doi:10.1002/pat.476http://dx.doi.org/10.1002/pat.476

Ding J F, Liu F T, Li M, Day M, Zhou M. J Polym Sci, Part A: Polym Chem, 2002, 40(23): 4205-4216. doi:10.1002/pola.10504http://dx.doi.org/10.1002/pola.10504

Ding J F, Day M, Robertson G P, Roovers J. Macromol Chem Phys, 2004, 205(8): 1070-1079. doi:10.1002/macp.200400016http://dx.doi.org/10.1002/macp.200400016

Schonberger F, Chromik A, Kerres J. Polymer, 2010, 51(19): 4299-4313. doi:10.1016/j.polymer.2010.07.022http://dx.doi.org/10.1016/j.polymer.2010.07.022

Li W W, Wang S B, Zhang X F, Wang W P, Xie X F, Pei P C. Int J Hydrogen Energy, 2014, 39(25): 13710-13717. doi:10.1016/j.ijhydene.2014.03.133http://dx.doi.org/10.1016/j.ijhydene.2014.03.133

Guo H X, Wang Z F, Liu Y, Huo P F, Gu J Y, Zhao F B. J Membr Sci, 2020, 611: 118337. doi:10.1016/j.memsci.2020.118337http://dx.doi.org/10.1016/j.memsci.2020.118337

Liu G S, Shang Y M, Xie X F, Wang S B, Wang J H, Wang Y W, Mao Z Q. Int J Hydrogen Energy, 2012, 37(1): 848-853. doi:10.1016/j.ijhydene.2011.04.047http://dx.doi.org/10.1016/j.ijhydene.2011.04.047

Li C P, Zhang S M, Wang S B, Xie X F, Deng C S, Pei P C. Int J Hydrogen Energy, 2014, 39(26): 14362-14369. doi:10.1016/j.ijhydene.2014.03.049http://dx.doi.org/10.1016/j.ijhydene.2014.03.049

Liu Q, Zhang S H, Wang Z Q, Chen Y N, Jian X G. Polymer, 2020, 198: 122525. doi:10.1016/j.polymer.2020.122525http://dx.doi.org/10.1016/j.polymer.2020.122525

Hoque M E, Hassan M M M, Chattopadhyay B. J Am Chem Soc, 2021, 143(13): 5022-5037. doi:10.1021/jacs.0c13415http://dx.doi.org/10.1021/jacs.0c13415

Chauveau E, Marestin C, Mercier R, Espuche E, Morin A. J Polym Sci, Part B: Polym Phys, 2017, 55(10): 771-777. doi:10.1002/polb.24330http://dx.doi.org/10.1002/polb.24330

Lee S C, Guo L, Yue H F, Liao H H, Rueping M. Synlett, 2017, 28(19): 2594-2598

Ge X C, Xu Y, Xiao M, Meng Y Z, Hay A S. Eur Polym J, 2005, 42(5): 1206-1214. doi:10.1016/j.eurpolymj.2005.11.013http://dx.doi.org/10.1016/j.eurpolymj.2005.11.013

Liu Qian(刘乾), Yang Yuxue(杨玉雪), Zhang Shouhai(张守海), Xue Rendong(薛仁东), Jian Xigao(蹇锡高). Acta Polymerica Sinica(高分子学报), 2018, (5): 581-587. doi:10.11777/j.issn1000-3004.2017.17211http://dx.doi.org/10.11777/j.issn1000-3004.2017.17211

Li X, Jiang J W, Yu L M, Liu X L, Sheng S R. High Perform Polym, 2015, 27(2): 200-206. doi:10.1177/0954008314543119http://dx.doi.org/10.1177/0954008314543119

Cheng L, Han K, Xu K, Gadinski M R, Wang Q. Polym Chem-UK, 2013, 4(8): 2436-2439. doi:10.1039/c3py00174ahttp://dx.doi.org/10.1039/c3py00174a

浏览量

110

下载量

CSCD

文章被引用时，请邮件提醒。

提交

工具集

关联资源

不同序列结构的二氧化碳/环氧丙烷/邻苯二甲酸酐三元共聚物的可控合成及性能研究

聚芳醚酮可纺性和结构优化的研究进展

主链含芳基均三嗪环结构杂萘联苯共聚芳醚腈的结构与性能

呋喃杂环聚芳醚酮聚合物的合成与性能