Citation: Qing-Zhong Guo, Yi Du, Jun-Fang Guo, Liang Li, Jiang-Yu Wu, Guo-Ping Yan. Synthesis and ring-opening copolymerization of cyclic aryl ester dimers[J]. Chinese Chemical Letters, ;2013, 24(10): 897-900. shu

Synthesis and ring-opening copolymerization of cyclic aryl ester dimers

  • Corresponding author: Jun-Fang Guo, 
  • Received Date: 1 April 2013
    Available Online: 20 May 2013

    Fund Project: The work described in this paper was supported by grants from the National Natural Science Foundation of China (Nos. 21001085, 20904045) (Nos. 21001085, 20904045) the Natural Science Foundation of Hubei Province (No. 2010CDB11104) (No. 2010CDB11104)Doctoral Program Foundation of Wuhan Institute of Technology (No. 11105032). (No. 11105032)

  • Two kinds of cyclic aryl ester dimers have been synthesized by reaction of phthaloyl dichloride with bisphenols via interfacial polycondensation. The cyclic dimers readily undergo anionic ring-opening polymerization or copolymerization in the melt by using sodium benzoate as the initiator, producing linear, high molecular weight polyesters. The contents of cyclic dimers in the homopolymers P1, P2, and copolymer P12 are 13.7%, 10.2%, 2.9%, respectively, which indicates that ring-opening copolymerization of cyclic dimers may impel the conversion of cyclic dimers and decrease the content of cyclic dimers in the resulting copolymer. Moreover, the isothermal chemorheology of the ring-opening copolymerization of cyclic dimers indicates that the reactivemoltenmixture has low shear viscosity and the viscosity increases slowly in the initial stage of ring-opening polymerization.
  • 加载中
    1. [1]

      [1] D.J. Brunelle, E.P. Boden, T.G. Shannon, Remarkably selective formation of macrocyclic aromatic carbonates: versatile new intermediates for the synthesis of aromatic polycarbonates, J. Am. Chem. Soc. 112 (1990) 2399-2402.

    2. [2]

      [2] P. Hodge, S.D. Kamau, A. Ben-Haida, R.T. Williams, Cyclo-depolymerizations of polycarbonates in solution: use of the macrocyclic oligomers obtained in entropically-driven ring-opening polymerizations and copolymerizations to give carbonate-carbonate and carbonate-carboxylate ester copolymers, React. Funct. Polym. 11 (2012) 868-877.

    3. [3]

      [3] Q.Z. Guo, H.H. Wang, J.Y. Wu, D. Guo, T.L. Chen, Synthesis and ring-opening polymerization of macrocyclic aryl ketone oligomers, Polym. Adv. Technol. 21 (2010) 290-295.

    4. [4]

      [4] H.H. Wang, J.Y. Ding, T.L. Chen, Cyclic oligomers of phenolphthalein polyarylene ether sulfone (ketone): preparation through cyclo-depolymerisation of corresponding polymers, Chin. Chem. Lett. 15 (11) (2004) 1377-1379.

    5. [5]

      [5] N. González-Vidal, A.M.D. Ilarduya, S. Muñoz-Guerra, Poly(ethylene-co-1,4-cyclohexylenedimethylene terephthalate) copolyesters obtained by ring opening polymerization, J. Polym. Sci. Part A: Polym. Chem. 47 (2009) 5954-5966.

    6. [6]

      [6] K. Pang, R. Kotec, A. Tonelli, Ring-opening polymerization of the cyclic dimer of poly(trimethylene terephthalate), J. Polym. Sci. Part A: Polym. Chem. 44 (2006) 6801-6809.

    7. [7]

      [7] H.L. Chen, W. Yu, C.X. Zhou, Entropically-driven ring-opening polymerization of cyclicbutylene terephthalate: rheology and kinetics, Poly. Eng. Sci.52 (2012) 91-101.

    8. [8]

      [8] D.J. Brunelle, Cyclic oligomer chemistry, J. Polym. Sci. Part A: Polym. Chem. 46 (2008) 1151-1164.

    9. [9]

      [9] H.L. Chen, C.W. Huang, W. Yu, C.X. Zhou, Effect of thermally reduced graphite oxide (TrGO) on the polymerization kinetics of poly(butylene terephthalate) (pCBT)/TrGO nanocomposites prepared by in situ ring-opening polymerization of cyclic butylene terephthalate, Polymer 54 (2013) 1603-1611.

    10. [10]

      [10] H.Y. Jiang, T.L. Chen, J.P. Xu, Synthesis, structure, and ring-opening polymerization of macrocyclic aromatic esters: a new route to high-performance polyarylates, Macromolecules 30 (1997) 2839-2842.

    11. [11]

      [11] Q.Z. Guo, C. Liu, H. Lu, S.F. Hu, Synthesis, characterization and ring-opening polymerization of cyclic aryl ester dimer containing hexafluoroisopropylidene unit, J. Wuhan Inst. Technol. 33 (5) (2011) 41-44.

  • 加载中
    1. [1]

      Yue SunLiming YangYaohang ChengGuanghui AnGuangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250

    2. [2]

      Qinghong ZhangQiao ZhaoXiaodi WuLi WangKairui ShenYuchen HuaCheng GaoYu ZhangMei PengKai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167

    3. [3]

      Jiakun Bai Junhui Jia Aisen Li . An elastic organic crystal with piezochromic luminescent behavior. Chinese Journal of Structural Chemistry, 2024, 43(6): 100323-100323. doi: 10.1016/j.cjsc.2024.100323

    4. [4]

      Yuan LiuBoyang WangYaxin LiWeidong LiSiyu Lu . Understanding excitonic behavior and electroluminescence light emitting diode application of carbon dots. Chinese Chemical Letters, 2025, 36(2): 110426-. doi: 10.1016/j.cclet.2024.110426

    5. [5]

      Peiyan ZhuYanyan YangHui LiJinhua WangShiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533

    6. [6]

      Yi LiuPeng LeiYang FengShiwei FuXiaoqing LiuSiqi ZhangBin TuChen ChenYifan LiLei WangQing-Dao Zeng . Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers. Chinese Chemical Letters, 2024, 35(10): 109571-. doi: 10.1016/j.cclet.2024.109571

    7. [7]

      Junxin LiChao ChenYuzhen DongJian LvJun-Mei PengYuan-Ye JiangDaoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732

    8. [8]

      Hongdao LIShengjian ZHANGHongmei DONG . Magnetic relaxation and luminescent behavior in nitronyl nitroxide-based annuluses of rare-earth ions. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 972-978. doi: 10.11862/CJIC.20230411

    9. [9]

      Yan ZouYin-Shuang HuDeng-Hui TianHong WuXiaoshu LvGuangming JiangYu-Xi Huang . Tuning the membrane rejection behavior by surface wettability engineering for an effective water-in-oil emulsion separation. Chinese Chemical Letters, 2024, 35(6): 109090-. doi: 10.1016/j.cclet.2023.109090

    10. [10]

      Siwei WangWei-Lei ZhouYong Chen . Cucurbituril and cyclodextrin co-confinement-based multilevel assembly for single-molecule phosphorescence resonance energy transfer behavior. Chinese Chemical Letters, 2024, 35(12): 110261-. doi: 10.1016/j.cclet.2024.110261

    11. [11]

      Shulei HuYu ZhangXiong XieLuhan LiKaixian ChenHong LiuJiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408

    12. [12]

      Xiaohui FuYanping ZhangJuan LiaoZhen-Hua WangYong YouJian-Qiang ZhaoMingqiang ZhouWei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688

    13. [13]

      Hailong HeWenbing WangWenmin PangChen ZouDan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534

    14. [14]

      Bing NiuHonggao HuangLiwei LuoLi ZhangJianbo Tan . Coating colloidal particles with a well-defined polymer layer by surface-initiated photoinduced polymerization-induced self-assembly and the subsequent seeded polymerization. Chinese Chemical Letters, 2025, 36(2): 110431-. doi: 10.1016/j.cclet.2024.110431

    15. [15]

      Zhenzhen Zhao Meichen Jiao Jiejie Ling Han Jiang Yan Gao Hao Xu Hai-Qing Li Jingang Jiang Peng Wu Le Xu . Toward the microporous zeolite family with tunable large-medium cage and pore opening. Chinese Journal of Structural Chemistry, 2024, 43(9): 100336-100336. doi: 10.1016/j.cjsc.2024.100336

    16. [16]

      Wenling YuanFengli LiZhe ChenQiaoxin XuZhenhua GuanNanyu YaoZhengxi HuJunjun LiuYuan ZhouYing YeYonghui Zhang . AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement. Chinese Chemical Letters, 2024, 35(5): 108788-. doi: 10.1016/j.cclet.2023.108788

    17. [17]

      Jing-Qi TaoShuai LiuTian-Yu ZhangHong XinXu YangXin-Hua DuanLi-Na Guo . Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade. Chinese Chemical Letters, 2024, 35(6): 109263-. doi: 10.1016/j.cclet.2023.109263

    18. [18]

      Qiuyun LiYannan ZhuYining WangGang QiWen-Juan HaoKelu YanBo Jiang . Catalytic CH activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones. Chinese Chemical Letters, 2024, 35(9): 109494-. doi: 10.1016/j.cclet.2024.109494

    19. [19]

      Wenyu GaoLiming ZhangChuang ZhaoLixiang LiuXingran YangJinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447

    20. [20]

      Xue ZhaoMengshan ChenDan WangHaoran ZhangGuangzhi HuYingtang Zhou . Ultrafine nano-copper derived from dopamine polymerization & synchronous adsorption achieve electrochemical purification of nitrate to ammonia in complex water environments. Chinese Chemical Letters, 2024, 35(8): 109327-. doi: 10.1016/j.cclet.2023.109327

Metrics
  • PDF Downloads(0)
  • Abstract views(695)
  • HTML views(10)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return