Synthesis of Multi‐Functionalized N–Cl Hydantoin Polyurethane for Chemical Warfare Agent Decomposition with High N–Cl Stability

• Published in: Macromolecular chemistry and physics Vol. 220; no. 16
• Main Authors: Bae, Kihyeon, Gwak, Nohoon, Park, Myung Kyu, Lee, Bumjae, Lee, Kyung Jin
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 01.08.2019
• Subjects: Alkynes; azide–alkyne click reaction; Biological & chemical weapons; Catalysis; Chemical reactions; Chemical warfare; chemical warfare agents; Decomposition; Fluorination; Hydantoin; Mustard gas; N‐halamine; Organic chemistry; Polyethylene glycol; Polyurethane resins; Stability; thermoplastic polyurethane; Urethane thermoplastic elastomers
• ISSN: 1022-1352; 1521-3935
• DOI: 10.1002/macp.201900213

N‐chlorinated hydantoin thermoplastic polyurethane (N–Cl HD‐TPU) is synthesized via azide–alkyne click reaction of the azido TPU polymers followed by chlorination in order to develop catalytic polymer materials for decomposition of chemical warfare agents. The N–Cl HD‐TPU shows good decomposition efficacy of 2‐chloroethyl ethyl sulfide (simulant of mustard gas) over 90% and 60% in the form of porous membrane and fiber, respectively. However, stability of N–Cl moiety is significantly decreased by moisture and UV from environments within 24 h. The several different types of additional moieties such as decyne, polyethylene glycol, and fluorinated alkyl chain are co‐functionalized to HD‐TPU backbone in order to improve N–Cl stability. When decyne moiety is co‐functionalized, the N–Cl HD‐TPU shows enhanced stability under maintaining their decomposition efficiency. The N‐chlorinated hydantoin thermoplastic polyurethane‐based non‐solvent induced phase separation membrane and electrospun fiber for decomposition of chemical warfare agent as catalytic functional polymer are successfully obtained. In order to achieve good decomposition efficiency and N–Cl stability simultaneously, the multi‐functionalized TPU with additional chemical groups such as decyne, polyethyleneglycol acetylene, and perfluoro octane acetylene is synthesized and tested.