TY - JOUR
T1 - Ketene-Based Route to rigid Cyclobutanediol Monomers for the Replacement of BPA in High Performance Polyesters
AU - Burke, DJ
AU - Kawauchi, T
AU - Kade, MJ
AU - Leibfarth, FA
AU - McDearmon, B
AU - Wolffs, M
AU - Kierstead, PH
AU - Moon, B
AU - JonHawker, Craig
PY - 2012
Y1 - 2012
N2 - Recently, polyesters based on the diol monomer 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCBDO) have been shown to exhibit excellent thermal stability, mechanical properties, and optical clarity. In particular, the ability of TMCBDO to replace bisphenol A as a diol monomer in polycarbonates and polyesters has resulted in significant commercial and academic interest in these types of monomers. Herein, we report a versatile synthetic strategy based on the dimerization of ketenes derived from the thermal treatment of Meldrum's acid for the synthesis of structurally diverse cyclobutanediol (CBDO) monomers. This strategy allows a library of CBDO monomers amenable to standard polyester polymerization procedures to be prepared and the structural diversity of these CBDO monomers provides polymers with tunable physical properties, such as glass transition temperature ranging from 120 to 230 degrees C. The versatility and modularity of this Meldrum's acid based approach to substituted cyclobutan
AB - Recently, polyesters based on the diol monomer 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCBDO) have been shown to exhibit excellent thermal stability, mechanical properties, and optical clarity. In particular, the ability of TMCBDO to replace bisphenol A as a diol monomer in polycarbonates and polyesters has resulted in significant commercial and academic interest in these types of monomers. Herein, we report a versatile synthetic strategy based on the dimerization of ketenes derived from the thermal treatment of Meldrum's acid for the synthesis of structurally diverse cyclobutanediol (CBDO) monomers. This strategy allows a library of CBDO monomers amenable to standard polyester polymerization procedures to be prepared and the structural diversity of these CBDO monomers provides polymers with tunable physical properties, such as glass transition temperature ranging from 120 to 230 degrees C. The versatility and modularity of this Meldrum's acid based approach to substituted cyclobutan
M3 - Article
SN - 2161-1653
JO - AMER CHEMICAL SOC
JF - AMER CHEMICAL SOC
ER -