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Synthesis of Polyacrylate‐Based Polyurethane by Organocatalyzed Group Transfer Polymerization and Polyaddition
Author(s) -
Liu Yujian,
Jia Qun,
Ding Yuansheng,
Chen Yougen
Publication year - 2020
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.202000217
Subject(s) - polymer chemistry , acrylate , polyurethane , chemistry , acrylate polymer , methyl acrylate , ethyl acrylate , polymerization , copolymer , polymer , organic chemistry
The current work describes the synthesis of novel polyacrylate‐based polyurethanes through the polyaddition of hexamethylene diisocyanate (HDI) with α,ω ‐hydroxyl end‐functionalized polyacrylates (HO‐PA‐OHs), including α,ω ‐hydroxyl end‐functionalized poly( n ‐butyl acrylate) (HO‐P n BA‐OH), poly( n ‐octyl acrylate) (HO‐P n OA‐OH), and poly( n ‐lauryl acrylate) (HO‐P n LA‐OH), respectively. HO‐PA‐OHs are prepared by the N‐ (trimethylsilyl)bis(trifluoromethanesulfonyl)imide (Me 3 SiNTf 2 )‐catalyzed group transfer polymerizations (GTPs) of n ‐butyl acrylate ( n BA), n ‐octyl acrylate ( n OA), and n ‐lauryl acrylate ( n LA) in toluene at room temperature using the functional 1‐(2‐triisopropylsiloxyethoxy)‐1‐triisopropylsiloxy‐2‐methyl‐1‐propene as an initiator and the low ceiling temperature acrylate, 2‐(triisopropylsiloxy)ethyl α‐phenylacrylate, as a terminator, followed by the desilylation of the resulting α,ω ‐triisopropylsiloxy end‐functionalized polyacrylates ( i Pr 3 SiO‐PA‐OSi i Pr 3 s) using tetra‐ n ‐butylammonium fluoride (TBAF). The polyaddition reactions between HO‐PA‐OHs and HDI are carried out in toluene using 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) as the catalyst to afford the target polyacrylate‐based polyurethanes. The polymer structures are characterized by 1 H NMR spectroscopy and FT‐IR measurements. The thermal properties of the resulting polyacrylate‐based polyurethanes are investigated by differential scanning calorimeter.