TY - JOUR
T1 - A bifunctional monomer derived from lactide for toughening polylactide
AU - Jing, Feng
AU - Hillmyer, Marc A.
PY - 2008/10/22
Y1 - 2008/10/22
N2 - (6S)-3-Methylene-6-methyl-1,4-dioxane-2,5-dione was synthesized from l-lactide and used as the dienophile to prepare spiro[6-methyl-1,4-dioxane-2,5-dione-3,2′-bicyclo[2.2.1]hept[5]ene] via an exoselective and diastereofacial-selective Diels-Alder reaction. Polymerizations of this bifunctional lactide derivative were successfully carried out under ring-opening and ring-opening metathesis polymerization conditions to yield high molecular weight and high Tg polymers. We further demonstrated that by incorporating a small percentage of spiro[6-methyl-1,4-dioxane-2,5-dione-3,2-bicyclo[2.2.1]hept[5]ene] into poly(1,5-cyclooctadiene) and copolymerizing it with dl-lactide, novel polymeric alloys of PLA can be created that have tremendous improvements in toughness over PLA and the corresponding binary blend of PLA and poly(1,5-cyclooctadiene).
AB - (6S)-3-Methylene-6-methyl-1,4-dioxane-2,5-dione was synthesized from l-lactide and used as the dienophile to prepare spiro[6-methyl-1,4-dioxane-2,5-dione-3,2′-bicyclo[2.2.1]hept[5]ene] via an exoselective and diastereofacial-selective Diels-Alder reaction. Polymerizations of this bifunctional lactide derivative were successfully carried out under ring-opening and ring-opening metathesis polymerization conditions to yield high molecular weight and high Tg polymers. We further demonstrated that by incorporating a small percentage of spiro[6-methyl-1,4-dioxane-2,5-dione-3,2-bicyclo[2.2.1]hept[5]ene] into poly(1,5-cyclooctadiene) and copolymerizing it with dl-lactide, novel polymeric alloys of PLA can be created that have tremendous improvements in toughness over PLA and the corresponding binary blend of PLA and poly(1,5-cyclooctadiene).
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U2 - 10.1021/ja804357u
DO - 10.1021/ja804357u
M3 - Article
C2 - 18821759
AN - SCOPUS:54249095629
SN - 0002-7863
VL - 130
SP - 13826
EP - 13827
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 42
ER -