Citation: He Qin-zheng, Wang Jin-yan, Song Lei, Jian Xi-gao. Synthesis, Curing and Properties of Poly (phthalazione ether sulfone ketone) Copolymers Crosslinked by Click Chemistry[J]. Chinese Journal of Polymer Science, ;2016, 34(10): 1208-1219. doi: 10.1007/s10118-016-1835-z shu

Synthesis, Curing and Properties of Poly (phthalazione ether sulfone ketone) Copolymers Crosslinked by Click Chemistry

Department of Polymer Science & Materials, Dalian University of Technology, Dalian 116024, China

Corresponding author: Wang Jin-yan, wangjinyan@dlut.edu.cn
Received Date: 15 March 2016
Revised Date: 31 May 2016
Accepted Date: 6 June 2016

Fund Project: the National Natural Science Foundation of China 51273029

Functionalized poly(phthalazinone ether sulfone ketone) was synthesized by successive chloromethylation and azidation, followed by curing reaction with the propargyl end-groups of various molecular weight crosslinking agents in the presence of Cu(I) catalyst via the azide-alkyne click reaction. The influences of the chain length of crosslinking agents on the poly(phthalazinone ether sulfone ketone) system were studied. FTIR and DSC tests demonstrated certain crosslinking by azide-alkyne reaction with the formation of triazole ring. DSC results showed that curing temperature shifted to lower temperatures considerably in the presence of Cu(I) catalyst. TGA showed cured polymers were of much higher thermal stability, including higher thermal decomposition temperatures and higher char-yielding properties. After being cured, the polymers became insoluble in organic solvents and the gel fraction of the cured polymers exceeded 71%. Wide-angle X-ray diffraction results indicated there was a short distance order in the poly(ether sulfone) (PES) main chain except for the azido methyl poly(phthalazinone ether sulfone ketone) and 4,4'-bis(2-propynyloxy) biphenyl ( AMPPESK-BP) system.
- Poly(arylene ether sulfone),
- Crosslinking,
- Click chemistry
1. [1]
  Kurosawa, T., Higashihara, T. and Ueda, M., Polym. Chem., 2013, 4(1): 16
2. [2]
  Shi, J.L., Hu, H.S., Xia, Y.G. and Liu, Z.P., J. Mater. Chem. A., 2014, 2(24): 9134
3. [3]
  Yu, G.P., Liu, C., Wang, J.Y., Li, G.H., Han, Y.J. and Jian, X.G., Polymer, 2010, 51: 100
4. [4]
  Li, W.W., Tang, H.Y., Chen, X.F., Fan, X.H. and Zhou, Q.F., Polymer, 2008, 49: 4080
5. [5]
  Fache, B., Gallot, B., Gelin, M.P., Milano, J.C. and Pham, Q.T., J. Appl. Polym. Sci., 2013, 127(5): 3798
6. [6]
  Sava, M., J. Appl. Polym. Sci., 2009, 112(3): 1399
7. [7]
  Wang, Y., Wang, S.J., Bian, C., Zhong, Y.H. and Jing, X.L., Polym. Degrad. Stab., 2015, 111: 239 doi: 10.1016/j.polymdegradstab.2014.11.016
8. [8]
  Kimura, H., Matsumoto, A. and Ohtsuka, K., J. Appl. Polym. Sci., 2009, 112(3): 1762
9. [9]
  Qian, L.J., Qiu, Y.,Wang, J.Y. and Xi, W., Polymer, 2015, 68: 262
10. [10]
  Tu, J.W., Tucker, S.J., Christensen, S., Sayed, A.R., Jarrett, W.L. and Wiggins, J.S., Macromolecules, 2015, 48(6): 1748
11. [11]
  Chen, F., Yuan, L., Gu, A.J., Lin, C. and Liang, G,Z., Polym. Eng. Sci., 2013, 9(53): 1871
12. [12]
  CheOhashi, S., Kilbane, J., Heyl, T. and Ishida, H., Macromolecules, 2015, 48(23): 8412
13. [13]
  Dumas, L., Bonnaud, L., Olivier, M., Poorteman, M. and Dubois, P., Eur. Polym. J., 2016, 75: 486 doi: 10.1016/j.eurpolymj.2016.01.021
14. [14]
  Chang, H.C., Lin, H.T. and Lin, C.H., Polym. Chem., 2012, 3(4): 970
15. [15]
  Harrison, W.L., Hickner, M.A., Kim, Y.S. and McGrath, J.E., Fuel cells, 2005, 5(2): 201
16. [16]
  Ren, J.N., Zhang, S.L., Liu, Y., Wang, Y., Pang, J.H. and Wang, Q.H., J. Membr. Sci., 2013, 434: 161
17. [17]
  Yang, S., Wang, J., Huo, S.Q., Wang, J.P. and Tang, Y.S., Polym. Degrad. Stab., 2016, 126: 9 doi: 10.1016/j.polymdegradstab.2016.01.011
18. [18]
  Saba, N., Jawaid, M. and Paridah, M.T., Polym. Adv. Technol., 2016, 126: 11
19. [19]
  Wang, X.S., Pang, H.C. and Lin, Y., Polym. Degrad. Stab., 2016, 98: 2609
20. [20]
  Mercado, L.A., Galia, M. and Cadiz, V., J. Appl. Polym. Sci., 2006, 44(5): 1676
21. [21]
  Kiuchi, Y., Iji, M. and Shukichi, T., Polym. Degrad. Stab., 2014, 109: 336 doi: 10.1016/j.polymdegradstab.2013.05.013
22. [22]
  Lin, C.H., Wang, Y.R., Feng, Y.R. and Juang, T.Y., Polymer., 2014, 54: 1612
23. [23]
  Wang, L.L., Luo, F., Dang, L.L. and Luo, M.B., J. Mater. Chem., 2015, 3: 13724
24. [24]
  Guan, Z., Huang, Y.M. and Wang, W.D., Anal. Chim. Acta., 2008, 627(2): 225
25. [25]
  Lin, C.H., Chen, J.C., Huang, C.M., Jehng, J.M., Chang, H.C. and Su, W.C., Polymer, 2013, 54: 6936
26. [26]
  Czech, Z. and Wojciechowicz, M., Eur. Polym. J., 2006, 42: 2153
27. [27]
  Smitha, C., Sukumaran, K. and Reghunadhan, N., J. Appl. Polym. Sci., 2013, 130(2): 1289 doi: 10.1002/app.39295
28. [28]
  Kolb, H.C., Finn, M.G. and Sharpless, K.B., Angew. Chem. Int. Ed., 2001, 40: 2004
29. [29]
  Hvilsted, S., Polym. Int., 2012, 61(4): 485 doi: 10.1002/pi.v61.4
30. [30]
  Dohler, D., Michael, P. and Wolfgang, H.B., Macromolecules, 2012, 45: 3335 doi: 10.1021/ma300405v
31. [31]
  Sumerlin, S., Tsarevsky, N.V. and Louche, G., Macromolecules, 2005, 38: 7540 doi: 10.1021/ma0511245
32. [32]
  Tsarevsky, N.V. and Matyjaszewski, K., Macromolecules, 2007, 40: 4439 doi: 10.1021/ma070705m
33. [33]
  Zhou, H.X., Liu, C., Wang, J.Y. and Jian, X.G., Chinese J. Polym. Sci., 2011, 29(5): 719
1. [1]
  Yang Liu , Minglu Li , Jianxun Ding , Xuesi Chen . Glycoengineering-assistant biomineralization for tumor blockade therapy. Chinese Chemical Letters, 2025, 36(5): 110146-. doi: 10.1016/j.cclet.2024.110146
2. [2]
  Fangzhou Li , Liang Gao , Linping Wang , Ben-Lin Hu . Unlocking the elasticity in ferroelectrics by slight crosslinking. Chinese Journal of Structural Chemistry, 2025, 44(3): 100443-100443. doi: 10.1016/j.cjsc.2024.100443
3. [3]
  Yifei Zhang , Yuncong Xue , Laiwei Gao , Rui Liao , Feng Wang , Fei Wang . Merging non-covalent and covalent crosslinking: En route to single chain nanoparticles. Chinese Chemical Letters, 2024, 35(6): 109217-. doi: 10.1016/j.cclet.2023.109217
4. [4]
  Xingyu Ma , Yi-Xin Chen , Zi Ye , Chong-Jing Zhang . Isotope-labeled click-free probes to identify protein targets of lysine-targeting covalent reversible molecules. Chinese Chemical Letters, 2025, 36(5): 110203-. doi: 10.1016/j.cclet.2024.110203
5. [5]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
6. [6]
  Peiwen Liu , Fang Zhao , Jing Zhang , Yunpeng Bai , Jinxing Ye , Bo Bao , Xinggui Zhou , Li Zhang , Changlu Zhou , Xinhai Yu , Peng Zuo , Jianye Xia , Lian Cen , Yangyang Yang , Guoyue Shi , Lin Xu , Weiping Zhu , Yufang Xu , Xuhong Qian . Micro/nano flow chemistry by Beyond Limits Manufacturing. Chinese Chemical Letters, 2024, 35(5): 109020-. doi: 10.1016/j.cclet.2023.109020
7. [7]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
8. [8]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Qiang Sun , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Li Wang . Recent progress on surface chemistry Ⅱ: Property and characterization. Chinese Chemical Letters, 2025, 36(1): 110100-. doi: 10.1016/j.cclet.2024.110100
9. [9]
  Yingxiao Zong , Yangfei Wei , Xiaoqing Liu , Junke Wang , Huanfang Guo , Junli Wang , Zhuangzhi Shi , Tao Tu , Cheng Yang , Chongyang Wang , Leyong Wang . The 4^th CCL Organic Chemistry Forum held in Zhangye. Chinese Chemical Letters, 2024, 35(8): 109743-. doi: 10.1016/j.cclet.2024.109743
10. [10]
  Haiying Lu , Weijie Li . The electrolyte solvation and interfacial chemistry for anode-free sodium metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(11): 100334-100334. doi: 10.1016/j.cjsc.2024.100334
11. [11]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
12. [12]
  Bingwei Wang , Yihong Ding , Xiao Tian . Benchmarking model chemistry composite calculations for vertical ionization potential of molecular systems. Chinese Chemical Letters, 2025, 36(2): 109721-. doi: 10.1016/j.cclet.2024.109721
13. [13]
  Junmeng Luo , Qiongqiong Wan , Suming Chen . Chemistry-driven mass spectrometry for structural lipidomics at the C=C bond isomer level. Chinese Chemical Letters, 2025, 36(1): 109836-. doi: 10.1016/j.cclet.2024.109836
14. [14]
  Jie Yang , Xin-Yue Lou , Dihua Dai , Jingwei Shi , Ying-Wei Yang . Desymmetrized pillar[8]arenes: High-yield synthesis, functionalization, and host-guest chemistry. Chinese Chemical Letters, 2025, 36(1): 109818-. doi: 10.1016/j.cclet.2024.109818
15. [15]
  Haojie Song , Laiyu Luo , Siyu Wang , Guo Zhang , Baojiang Jiang . Advances in poly(heptazine imide)/poly(triazine imide) photocatalyst. Chinese Chemical Letters, 2024, 35(10): 109347-. doi: 10.1016/j.cclet.2023.109347
16. [16]
  Xiao Zhu , Yanbing Mo , Jiawei Chen , Gaopan Liu , Yonggang Wang , Xiaoli Dong . A weakly-solvated ether-based electrolyte for fast-charging graphite anode. Chinese Chemical Letters, 2024, 35(8): 109146-. doi: 10.1016/j.cclet.2023.109146
17. [17]
  Jing Wang , Zenghui Li , Xiaoyang Liu , Bochao Su , Honghong Gong , Chao Feng , Guoping Li , Gang He , Bin Rao . Fine-tuning redox ability of arylene-bridged bis(benzimidazolium) for electrochromism and visible-light photocatalysis. Chinese Chemical Letters, 2024, 35(9): 109473-. doi: 10.1016/j.cclet.2023.109473
18. [18]
  Dongsheng Yang , Zixin Li , Yaoyao Lian , Ziyao Fu , Tianjiao Li , Pengtao Ma , Guoping Yang . A novel square-shaped Zr-substituted polyoxotungstate for the efficient catalytic oxidation of sulfide to sulfone. Chinese Chemical Letters, 2025, 36(3): 109717-. doi: 10.1016/j.cclet.2024.109717
19. [19]
  .
  CCS Chemistry 综述推荐│绿色氧化新思路：光/电催化助力有机物高效升级
  . CCS Chemistry, 2025, 7(10.31635/ccschem.024.202405369): -.
20. [20]
  .
  CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
  . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(889)
HTML views(18)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142