Synthesis of polyarylates and aliphatic polyesters by divalent acyl-1,2,4-triazole: a route to metal-free synthesis at low temperature

Aromatic, semiaromatic, and aliphatic polyesters were synthesized at moderate temperatures (25–80 °C) by the polymerization of divalent acyl-1,2,4-triazoles using 4-(dimethylamino)pyridine as a catalyst. The monomers were prepared from divalent acyl chloride in high yields, although some of them req...

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Bibliographic Details
Published in:Polymer journal 2021-08, Vol.53 (8), p.887-893
Main Authors: Kohsaka, Yasuhiro, Mori, Ichiro, Homma, Kazumasa, Akae, Yosuke, Matsuura, Daisuke, Kimura, Yoshikazu
Format: Article
Language:English
Subjects:
140/131
639/638/455/941
639/638/455/959
Acetyl chloride
Acrylic resins
Aliphatic compounds
Biomaterials
Bioorganic Chemistry
Catalysts
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Crystal structure
Crystallinity
Diols
Lager
Low temperature
Monomers
Original Article
Polyarylates
Polyester resins
Polymer Sciences
Polymerization
Solution polymerization
Surfaces and Interfaces
Thin Films
Toluene
Transesterification
Triazoles
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Summary:Aromatic, semiaromatic, and aliphatic polyesters were synthesized at moderate temperatures (25–80 °C) by the polymerization of divalent acyl-1,2,4-triazoles using 4-(dimethylamino)pyridine as a catalyst. The monomers were prepared from divalent acyl chloride in high yields, although some of them required that toluene and pyridine be used as solvents due to their high crystallinity. Melt polymerization in diphenyl ether was effective in affording semiaromatic and aliphatic polyesters. However, this method was not suitable for aromatic polyesters, as the reaction system became heterogeneous at 80 °C. Nevertheless, solution and interfacial polymerization reactions were effective in obtaining aromatic polyesters. The novel monomers provided polyester synthesis at moderate temperature without the use of any metal catalyst or halide monomers. The polymerization of divalent acyl-1,2,4-triazoles and diols/bisphenols afforded a series of aromatic, semiaromatic, and aliphatic polyesters. Compared with polymerization by transesterification, this polymerization proceeded irreversibly at relatively low temperature (
ISSN:0032-3896
1349-0540
DOI:10.1038/s41428-021-00484-0