1 : 1 alternating and 1 : 2 sequence-controlled radical copolymerization of 1,3-pentadiene isomers with maleic anhydride/ N -phenylalkyl maleimide

The competition between the Diels–Alder cycloaddition and the sequence-controlled radical copolymerization of maleic anhydride/ N -phenylalkyl maleimide (MAH/NPMI) with 1,3-pentadiene (PD) isomers was investigated. The copolymerization behavior significantly depended on the isomer conformation as we...

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Bibliographic Details
Published in:Polymer chemistry 2020-01, Vol.11 (3), p.675-681
Main Authors: Liu, Kun, Sun, Min, Xie, Fengli, Hu, Cainan, Yang, Zan, Li, An, Xia, JinKui, Qiu, Xu, Wang, Xu, Deng, Haoyun
Format: Article
Language:English
Subjects:
Copolymerization
Copolymers
Cycloaddition
Isomers
Maleic anhydride
NMR
Nuclear magnetic resonance
Polymer chemistry
Reaction kinetics
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Summary:The competition between the Diels–Alder cycloaddition and the sequence-controlled radical copolymerization of maleic anhydride/ N -phenylalkyl maleimide (MAH/NPMI) with 1,3-pentadiene (PD) isomers was investigated. The copolymerization behavior significantly depended on the isomer conformation as well as the feeding ratio, leading to the formation of AB-alternating and AAB-periodic (2 : 1 sequence-controlled) copolymers with M n values up to 10 5 g mol −1 under mild conditions. The sequence-controlled radical copolymerization mechanism was discussed based on the “bond-forming initiation theory” via the key tetramethylene-intermediate, which is in agreement with the results of the kinetics analysis and the microstructure analysis determined by NMR. The suggested mechanism involved the formation of a π-allyl-2-hexene 1,6-diradical formed by the reaction of s- trans PD with MAH, which initiates the MAH-CP alternating copolymerization.
ISSN:1759-9954
1759-9962
DOI:10.1039/C9PY01642B