Reinvestigation of the ring-opening polymerization of ε-caprolactone with 1,8-diazacyclo[5.4.0]undec-7-ene organocatalyst in bulk

被引：11

作者：

Chen, Yang ^{[1
]}

Zhang, Jie ^{[1
]}

Xiao, Wenhao ^{[1
]}

Chen, Anfu ^{[1
]}

Dong, Zhixian ^{[1
]}

Xu, Jinbao ^{[1
]}

Xu, Wenhua ^{[2
]}

Lei, Caihong ^{[1
]}

机构：

[1] Guangdong Univ Technol, Sch Mat & Energy, Guangdong Prov Key Lab Funct Soft Condensed Matte, Guangzhou 510006, Peoples R China

[2] Northwest Univ, Coll Chem & Mat Sci, Key Lab Synthet & Nat Funct Mol Chem, Minist Educ, Xian 710069, Peoples R China

来源：

EUROPEAN POLYMER JOURNAL | 2021年 / 161卷

基金：

中国国家自然科学基金;

关键词：

CL; DBU; Controlled; living ROP; End-functionality; CATALYSTS; DBU; BUTYROLACTONE; OPPORTUNITIES; CHALLENGES; CHEMISTRY; INITIATOR; COPOLYMER; ENZYMES; BASES;

D O I：

10.1016/j.eurpolymj.2021.110861

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) was used as organocatalyst to reinvestigate the ring-opening polymerization (ROP) of epsilon-caprolactone (CL) with benzyl alcohol (BnOH) initiator in bulk at 90 degrees C considering the unsuccessful ROP of CL at RT in previously reported publications. Kinetic study indicates that the PCLs could be well-designed with a controlled/living character of polymerization. The use of functional initiators, such as 2hydroxyethyl methacrylate (HEMA), propargyl alcohol (PGA), 6-azido-1-hexanol (AHA) and methoxy poly (ethylene glycol) (mPEG) leads to end-functionalized PCLs. Accordingly, the block copolymerization of CL with delta-valerolactone (VL), trimethylene carbonate (TMC) and lactide (LA) successfully proceeded to give PCL-b-PVL, PCL-b-PTMC and PCL-b-PLA copolymers. Finally, the reaction mechanism was studied with DFT calculations and NMR measurements.

引用

页数：10

共 74 条

[61] Synthesis of Poly(ε-caprolactone-co-methacrylic acid) Copolymer via Phosphazene-Catalyzed Hybrid Copolymerization [J].

Xu, Jinbao ;

Yang, Hongjun ;

Zhang, Guangzhao .

MACROMOLECULAR CHEMISTRY AND PHYSICS, 2013, 214 (03) :378-385

[62] Tuning the H-bond donicity boosts carboxylic acid efficiency in ring-opening polymerization [J].

Xu, Songquan ;

Zhu, Hui ;

Li, Zhenjiang ;

Wei, Fulan ;

Gao, Yu ;

Xu, Jiaxi ;

Wang, Haixin ;

Liu, Jingjing ;

Guo, Tianfo ;

Guo, Kai .

EUROPEAN POLYMER JOURNAL, 2019, 112 :799-808

[63] Bifunctional phosphazene-thiourea/urea catalyzed ring -opening polymerization of cyclic esters [J].

Yuan, Ruiting ;

Xu, Guangqiang ;

Lv, Chengdong ;

Zhou, Li ;

Yang, Rulin ;

Wang, Qinggang .

MATERIALS TODAY COMMUNICATIONS, 2020, 22

[64] Preparation of Biodegradable Cationic Polycarbonates and Hydrogels through the Direct Polymerization of Quaternized Cyclic Carbonates [J].

Yuen, Alexander Y. ;

Lopez-Martinez, Elena ;

Gomez-Bengoa, Enrique ;

Cortajarena, Aitziber L. ;

Aguirresarobe, Robert H. ;

Bossion, Amaury ;

Mecerreyes, David ;

Hedrick, James L. ;

Yang, Yi Yan ;

Sardon, Haritz .

ACS BIOMATERIALS SCIENCE & ENGINEERING, 2017, 3 (08) :1567-1575

[65] A review on degradation mechanisms of polylactic acid: Hydrolytic, photodegradative, microbial, and enzymatic degradation [J].

Zaaba, Nor Fasihah ;

Jaafar, Mariatti .

POLYMER ENGINEERING AND SCIENCE, 2020, 60 (09) :2061-2075

[66] Organocatalytic polymerization [J].

Zhang, Cheng-Jian ;

Zhang, Xing-Hong .

SCIENCE CHINA-CHEMISTRY, 2019, 62 (09) :1087-1089

[67] Ring-opening polymerization of ε-caprolactone with recyclable and reusable squaric acid organocatalyst [J].

Zhang, Jie ;

Xu, Liguo ;

Xiao, Wenhao ;

Chen, Yang ;

Dong, Zhixian ;

Xu, Jinbao ;

Lei, Caihong .

EUROPEAN POLYMER JOURNAL, 2021, 157

[68] Tunable hydantoin and base binary organocatalysts in ring-opening polymerizations [J].

Zhang, Lei ;

Zhou, Fangyuan ;

Li, Zhenjiang ;

Liu, Bo ;

Yan, Rui ;

Li, Jie ;

Hu, Yongzhu ;

Zhang, Chan ;

Luo, Zikun ;

Guo, Kai .

POLYMER CHEMISTRY, 2020, 11 (35) :5669-5680

[69] Preparation and characterization of DBU-loaded MCM-41 for adsorption of CO2 [J].

Zhang, Lu ;

Li, Yuan ;

Zhou, Hongcang .

ENERGY, 2018, 149 :414-423

[70] Imidodiphosphorimidate (IDPi) as an efficient organocatalyst for controlled/living ring-opening polymerization of lactones [J].

Zhang, Xun ;

Jiang, Yu ;

Ma, Qiang ;

Hu, Siping ;

Wang, Qinggang ;

Liao, Saihu .

EUROPEAN POLYMER JOURNAL, 2020, 123

← 1 2 3 4 5 6 7 8 →