Citation: Fang Zhang, Hang-tian Zhang, Tian Yang, Bo Kong, An-ru Guo, Qi Zhang, Yi-xian Wu. Synthesis and Property of Novel Functionalized Polytetrahydrofuran-b-polyisobutylene-b-polytetrahydrofuran Triblock Copolymers[J]. Acta Polymerica Sinica, ;2020, 51(1): 98-116. doi: 10.11777/j.issn1000-3304.2020.19151 shu

Synthesis and Property of Novel Functionalized Polytetrahydrofuran-b-polyisobutylene-b-polytetrahydrofuran Triblock Copolymers

State Key Laboratory of Chemical Resource Engineering, Beijing Laboratory of Biomedical Materials, Beijing University of Chemical Technology, Beijing 100029

Corresponding author: Yi-xian Wu, wuyx@mail.buct.edu.cn
Received Date: 10 August 2019
Revised Date: 9 September 2019

The functionalized polyisobutylenes (PIBs) carrying allyl-Br or allyl-NH₂ with different molecular weights and narrow molecular weight distribution, could be successfully synthesized via controlled/living cationic polymerization of isobutylene (IB) in n-hexane/CH₂Cl₂ mixed solvents at −80 °C. Controlled/Living cationic ring-opening polymerization (ROP) of tetrahydrofuran (THF) was achieved with Allyl-Br/AgClO₄ initiating system at 0 °C. Two kinds of novel functionalized PTHF-b-PIB-b-PTHF triblock copolymers were designed and synthesized via combination with controlled/living cationic polymerization of IB and controlled/living cationic ROP of THF. Terminal hydroxyl functionalized HO-PTHF-b-PIB-b-PTHF-OH triblock copolymers (expressed as FIBF-OH) were successfully synthesized by using the PIBs with difunctional allyl-Br terminal groups (Br-PIB-Br) as macroinitiators to initiate living cationic ROP of THF in the presence of AgClO₄ to create living PTHF⁺-b-PIB-b-PTHF⁺ chains and then terminating by H₂O molecules. On the other hand, PTHF-b-HN-PIB-NH-b-PTHF triblock copolymers containing hydrogen bonds at the connection point of PTHF and PIB segments (expressed as FIBF-NH) were also successfully synthesized via efficient nucleophilic substitution reaction between living PTHF⁺ chains and amine groups in H₂N-PIB-NH₂. Due to the dynamic incompatibility between polar PTHF segments and nonpolar PIB segments and the crystallization of PTHF segments, PTHF-b-PIB-b-PTHF triblock copolymers exhibit an obvious microphase separation micromorphology. It is recognized that the chemical structure in the PTHF-b-PIB-b-PTHF triblock copolymers makes a great contribution to the formation of hydrogen bonding and thus the supramolecular network. The crystallization of PTHF segments could be improved even in FIBF-NH with relatively short PTHF segments, e.g. M_n,PTHF = 0.7 kg·mol⁻¹. FIBF-NH could be completely self-healing at 25 °C for 10 min after cutting on its surface. However, the cutting on FIBF-OH surface was difficult to heal even at 30 °C for 3 days. Moreover, the PTHF-b-PIB-b-PTHF triblock copolymers could be used as drug carrier by interactions between PTHF segment and drug. The drug carrier microspheres exhibit pH-sensitive drug-release rate in PBS with different pH values. The novel functionalized PTHF-b-PIB-b-PTHF triblock copolymers combined the respective good properties from PIB and PTHF segments would have their potential applications as biomedical and smart-healing functional materials.
- Polyisobutylene,
- Polytetrahydrofuran,
- Block copolymer,
- Living cationic polymerization,
- Supramolecular network
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沈阳化工大学材料科学与工程学院沈阳 110142