High‐performance epoxy hybrid non‐isocyanate polyurethanes prepared from diol‐cyclocarbonation bisphenol A dicyclocarbonate

A new synthesis route different from convenient epoxy/CO2 method was established to synthesize a five‐membered dicyclocarbonate of bisphenol A (BisA‐5dCC), and its hybrid non‐isocyanate polyurethanes with epoxy resins (HNIPUs) were reported. Bisphenol A was first reacted with 3‐chloro‐1,2‐propanedio...

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Bibliographic Details
Published in:Polymer engineering and science 2023-09, Vol.63 (9), p.3025-3036
Main Authors: Liu, Xiang-nan, Wang, Yuan-meng, Li, Xiang-yuan, Zhang, Jun-ying, Zhao, Jing-bo
Format: Article
Language:English
Subjects:
Bisphenol A
Butanediol
Carbonates
Dynamic mechanical analysis
Epoxy resins
Fourier transforms
Infrared analysis
Isocyanates
Mechanical properties
Phenols
Polyurethane
Polyurethanes
Production processes
Synthesis
Tensile strength
Tensile tests
Thermodynamic properties
Thermogravimetric analysis
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Summary:A new synthesis route different from convenient epoxy/CO2 method was established to synthesize a five‐membered dicyclocarbonate of bisphenol A (BisA‐5dCC), and its hybrid non‐isocyanate polyurethanes with epoxy resins (HNIPUs) were reported. Bisphenol A was first reacted with 3‐chloro‐1,2‐propanediol to prepare a bisphenol A tetraol (BisA‐4OH), and then was reacted with excess diethyl carbonate to obtain BisA‐5dCC. Three polyhydroxyurethanes with H2N‐terminal groups (PHUs) were synthesized from the aminolysis polyaddition of BisA‐5dCC and excess hexanediamine. The PHUs were crosslinked with 1,4‐butanediol diglycidyl ether and bisphenol A diglycidyl ether, respectively, and different HNIPUs were prepared. The structures of BisA‐4OH, BisA‐5dCC, and PHUs were confirmed, and the HNIPUs were characterized by Fourier transform infrared, differential scanning calorimetry, dynamic mechanical analysis, thermogravimetric analysis, and tensile tests. HNIPUs prepared from aromatic epoxy showed higher Tg (up to 81°C) and better tensile strength (as high as 60 MPa) than those from aliphatic epoxy. High‐performance HNIPUs with excellent thermal and mechanical properties were successfully synthesized.HighlightsDicyclocarbonate of bisphenol A (BisA‐5dCC) was prepared from a BisA tetraol.H2N‐terminated PHUs were synthesized further from the aminolysis of BisA‐5dCC.Hybrid non‐isocyanate polyurethanes (HNIPUs) were obtained from PHUs and epoxys.HNIPUs prepared from aromatic epoxy showed high Tg up to 81°C.They showed excellent tensile strength as high as 60 MPa.
ISSN:0032-3888
1548-2634
DOI:10.1002/pen.26425