TY - JOUR
T1 - Polymer grafting onto polyurethane backbone via Diels-Alder reaction
AU - Agar, Soykan
AU - Durmaz, Hakan
AU - Gunay, Ufuk Saim
AU - Hizal, Gurkan
AU - Tunca, Umit
N1 - Publisher Copyright:
© 2014 Wiley Periodicals, Inc.
PY - 2014/12/2
Y1 - 2014/12/2
N2 - The aliphatic polyurethane with pendant anthracene moieties (PU-anthracene) was prepared from polycondensation of anthracen-9-yl methyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate (anthracene diol), 1 with hexamethylenediisocyanate in the presence of dibutyltindilaurate in CH2Cl2 at room temperature for 10 days. Thereafter, the PU-anthracene (Mn,GPC = 12,900 g/mol, Mw/Mn = 1.87, relative to PS standards) was clicked with a linear α-furan protected-maleimide terminated-poly(methyl methacrylate) (PMMA-MI) (Mn,GPC = 2500 g/mol, Mw/Mn = 1.33), or -poly(ethylene glycol) (PEG-MI) (Mn,GPC = 550 g/mol, Mw/Mn = 1.09), to result in well-defined PU-graft copolymers, PU-g-PMMA (Mn,GPC = 23800 g/mol, Mw/Mn = 1.65, relative to PS standards) or PU-g-PEG (Mn,GPC = 11,600 g/mol, Mw/Mn = 1.45, relative to PS standards) using Diels-Alder reaction in dioxane/toluene at 105 °C. The Diels-Alder grafting efficiencies were found to be over 93-99% using UV spectroscopy. Moreover, the structural analyses and the thermal transitions of all copolymers were determined via 1H NMR and DSC, respectively.
AB - The aliphatic polyurethane with pendant anthracene moieties (PU-anthracene) was prepared from polycondensation of anthracen-9-yl methyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate (anthracene diol), 1 with hexamethylenediisocyanate in the presence of dibutyltindilaurate in CH2Cl2 at room temperature for 10 days. Thereafter, the PU-anthracene (Mn,GPC = 12,900 g/mol, Mw/Mn = 1.87, relative to PS standards) was clicked with a linear α-furan protected-maleimide terminated-poly(methyl methacrylate) (PMMA-MI) (Mn,GPC = 2500 g/mol, Mw/Mn = 1.33), or -poly(ethylene glycol) (PEG-MI) (Mn,GPC = 550 g/mol, Mw/Mn = 1.09), to result in well-defined PU-graft copolymers, PU-g-PMMA (Mn,GPC = 23800 g/mol, Mw/Mn = 1.65, relative to PS standards) or PU-g-PEG (Mn,GPC = 11,600 g/mol, Mw/Mn = 1.45, relative to PS standards) using Diels-Alder reaction in dioxane/toluene at 105 °C. The Diels-Alder grafting efficiencies were found to be over 93-99% using UV spectroscopy. Moreover, the structural analyses and the thermal transitions of all copolymers were determined via 1H NMR and DSC, respectively.
KW - DSC
KW - Diels-Alder reaction
KW - GPC
KW - NMR
KW - TGA
KW - aliphatic polyurethane (PU)
KW - anthracene
KW - click reaction
KW - diisocyanate
KW - diol
KW - furan-protected maleimide terminated-poly(ethylene glycol) (PEG-MI)
KW - furan-protected maleimide terminated-poly(methyl methacrylate) (PMMA-MI)
KW - polycondensation; UV
UR - http://www.scopus.com/inward/record.url?scp=84921459688&partnerID=8YFLogxK
U2 - 10.1002/pola.27466
DO - 10.1002/pola.27466
M3 - Article
AN - SCOPUS:84921459688
SN - 0887-624X
VL - 53
SP - 521
EP - 527
JO - Journal of Polymer Science, Part A: Polymer Chemistry
JF - Journal of Polymer Science, Part A: Polymer Chemistry
IS - 4
ER -