Access to new carbohydrate-functionalized polylactides via organocatalyzed ring-opening polymerization

被引:48
|
作者
Miao, Yong [1 ,2 ,3 ,4 ,5 ]
Rousseau, Cyril [4 ,5 ]
Mortreux, Andre [1 ,2 ,3 ,4 ]
Martin, Patrick [4 ,5 ]
Zinck, Philippe [1 ,2 ,3 ,4 ]
机构
[1] Univ Lille Nord France, F-59000 Lille, France
[2] ENSCL, UCCS, CCM, F-59652 Villeneuve Dascq, France
[3] USTL, UCCS, CCM, F-59655 Villeneuve Dascq, France
[4] CNRS, UMR8181, F-59652 Villeneuve Dascq, France
[5] UCCS, IUT Bethune, F-62400 Bethune, France
关键词
Organocatalysis; Star polymers; cyclodextrin; EPSILON-CAPROLACTONE; D-GLUCOSE; LACTIDE; CYCLODEXTRINS; ROUTE; NANOPARTICLES; INITIATORS; ACTIVATION; COPOLYMERS; CATALYSTS;
D O I
10.1016/j.polymer.2011.08.040
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The 4-dimethylaminopyridine (DMAP) catalyzed ring-opening polymerization of lactide using various carbohydrate initiators has been assessed for the functionalization of polylactide. Selectively protected glucose derivatives bearing a free primary alcohol (Gic-1r) and a free secondary alcohol (Glc-2r), glucose and cyclodextrin diol derivatives (Glc-diol and CD-diol), methyl-alpha-D-glucopyranoside (Glc-Me) and native beta-cyclodextrin (CD) were used as initiators. According to the solubility of the carbohydrate derivative, the polymerizations were conducted in chlorinated solvents and in the bulk. Relatively narrow distributions are obtained in high yields in the absence of side reactions, affording a 100% functionalization efficiency. The catalytic synthesis of new carbohydrate link-functionalized polylactides and carbohydrate core star polylactides is reported. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5018 / 5026
页数:9
相关论文
共 50 条
  • [21] PLA via Enzymatic Ring-Opening Polymerization
    不详
    JOURNAL OF APPLIED POLYMER SCIENCE, 2009, 111 (04) : A5 - A5
  • [22] Continuous flow ring-opening polymerization and ring-opening metathesis polymerization
    Liu, Yihuan
    Ou, Shi
    Wu, Jiaqi
    Zhao, Rongji
    Hou, Ruixiang
    Li, Xiaomin
    Sun, Yongxiang
    Li, Yuguang
    Hu, Xin
    Zhu, Ning
    Guo, Kai
    EUROPEAN POLYMER JOURNAL, 2024, 216
  • [23] Access to Poly-β-Peptides with Functionalized Side Chains and End Groups via Controlled Ring-Opening Polymerization of β-Lactams
    Zhang, Jihua
    Kissounko, Denis A.
    Lee, Sarah E.
    Gellman, Samuel H.
    Stahl, Shannon S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (04) : 1589 - 1597
  • [24] Biomaterials from sugars: ring-opening polymerization of a carbohydrate lactone
    Tang, Min
    White, Andrew J. P.
    Stevens, Molly M.
    Williams, Charlotte K.
    CHEMICAL COMMUNICATIONS, 2009, (08) : 941 - 943
  • [25] Ring-opening polymerization
    Penczek, Stanislaw
    Pretula, Julia
    Slomkowski, Stanislaw
    CHEMISTRY TEACHER INTERNATIONAL, 2021, 3 (02) : 33 - 57
  • [26] Functionalized Polyesters via Stereoselective Electrochemical Ring-Opening Polymerization of O-Carboxyanhydrides
    Zhong, Yongliang
    Feng, Quanyou
    Wang, Xiaoqian
    Chen, Jia
    Cai, Wenjun
    Tong, Rong
    ACS MACRO LETTERS, 2020, 9 (08) : 1114 - 1118
  • [27] New polyolefins via ring-opening metathesis polymerization for biomedical applications
    Wang, Yanzhao
    Hillmyer, Marc
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [28] Cyclic Alternating Ring-Opening Metathesis Polymerization (CAROMP). Rapid Access to Functionalized Cyclic Polymers
    Song, Airong
    Parker, Kathlyn A.
    Sampson, Nicole S.
    ORGANIC LETTERS, 2010, 12 (17) : 3729 - 3731
  • [29] EXPLORATORY RING-OPENING POLYMERIZATION - RING-OPENING POLYMERIZATION OF VINYLKETENE CYCLIC ACETAL
    CHO, I
    KIM, SK
    JOURNAL OF POLYMER SCIENCE PART C-POLYMER LETTERS, 1990, 28 (13) : 417 - 421
  • [30] Epoxy functionalized cycloolefin polymers by ring-opening metathesis polymerization
    So, Jongho
    Cho, Eun Seon
    Kim, Sang Youl
    POLYMER CHEMISTRY, 2022, 13 (33) : 4752 - 4756