A bifunctional monomer derived from lactide for toughening polylactide.
(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).
Jing
Feng
F
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455-0431, USA.
Hillmyer
Marc A
MA
D004146:Dioxanes / Q000138:chemical synthesis* / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D011091:Polyesters / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C533789:3-methylene-6-methyl-1,4-dioxane-2,5-dione; D004146:Dioxanes; D007783:Lactones; D011091:Polyesters; D013141:Spiro Compounds; C533790:spiro(6-methyl-1,4-dioxane-2,5-dione-3,2'-bicyclo(2.2.1)hept(5)ene); C033616:poly(lactide); C091880:dilactide