Highly crystalline, heat resistant and biodegradable copolyesters from fully bio-based bis(pyrrolidone) monomer
Hanxu Zhu,
Han Hu,
Qingyang Luan,
Chen Lin,
Juanfang Xu,
Jinggang Wang,
Wu Bin Ying,
Jin Zhu
Affiliations
Hanxu Zhu
Key Laboratory of Bio-based Polymeric Materials Technology and Application of Zhejiang Province, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, PR China; University of Chinese Academy of Sciences, Beijing 100049, PR China
Han Hu
Key Laboratory of Bio-based Polymeric Materials Technology and Application of Zhejiang Province, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, PR China; Corresponding authors.
Qingyang Luan
Key Laboratory of Bio-based Polymeric Materials Technology and Application of Zhejiang Province, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, PR China; University of Chinese Academy of Sciences, Beijing 100049, PR China
Chen Lin
Key Laboratory of Bio-based Polymeric Materials Technology and Application of Zhejiang Province, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, PR China
Juanfang Xu
Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, PR China
Jinggang Wang
Key Laboratory of Bio-based Polymeric Materials Technology and Application of Zhejiang Province, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, PR China; Corresponding authors.
Wu Bin Ying
School of Electrical Engineering (EE), Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, South Korea
Jin Zhu
Key Laboratory of Bio-based Polymeric Materials Technology and Application of Zhejiang Province, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, PR China; Corresponding authors.
Improving the heat resistance of bio-based and biodegradable polyesters is of great significance to extend their applications. Herein, N,N’-trans-1,4-cyclohexane-bis(pyrrolidone-4-methyl carboxylate) (T-CBPMC) was prepared through efficient Michael-addition reaction between dimethyl itaconate and trans-1,4-cyclohexanediamine. The obtained T-CBPMC was copolymerized into aliphatic poly(butylene succinate) (PBS), and a series of PBSPs copolymers with T-CBPMC (BP) molar percentages between 41−80 mol % and weight average molecular weight (Mw) values ranging between 5.77*104 and 6.67*104 g/mol were prepared. BP units efficiently facilitated the melting temperature (203-251 °C) and isothermal-crystallization rate (t1/2 < 20 s) of PBSPs, endowing the highest heat resistance among commercial biodegradable polyesters, which helps maintain stable in pasteurization, high-temperature disinfection, and microwave environments. Moreover, these copolymers displayed remarkable mechanical, gas barrier properties and degradability. PBSP40-PBSP60 obtained high elastic modulus (335–872 MPa) and tensile strength (24.7–31.5 MPa), and good toughness simultaneously. Multiple-ring structures and large steric hindrance of BP units resulted in superior O2 barrier performance than that of non-degradable PET films. Importantly, the PBSP copolyesters showed obvious degradation in water environments and relatively better enzymatic degradation. It was interesting to find that even with 70 % of the BP units, the PBSP copolyesters still retained hydrolysis ability. The resulting PBSP copolyesters open the way for alternative candidates of biodegradable packaging materials with rapid crystallization, high heat-resistance and gas barrier.
