Comparison of salicylate-based poly(anhydride-esters) formed via melt-condensation versus solution polymerization.
Salicylate-based poly(anhydride-esters) were synthesized via two different methods, melt-condensation and solution polymerization, and the resulting polymers were compared. Acetylsalicylic acid was used as a model compound to mimic the active polymer chain-ends during melt-condensation, and formed a low-molecular-weight (<1500) polymer when subjected to melt-condensation polymerization conditions. The polymers and model compounds were analyzed by NMR ((1)H and (13)C) and IR spectroscopies to elucidate the structures. Spectroscopic analysis revealed the formation of a thermodynamically stable salicylate ester via salicylate-anhydride rearrangement during melt-condensation polymerization, which did not occur during solution polymerization. The salicylate-based poly(anhydride-esters) undergo a thermodynamic rearrangement during melt-condensation polymerization that is not observed for solution polymerization.
Schmeltzer
Robert C
RC
Department of Chemistry and Chemical Biology, Rutgers University, Piscataway, NJ 08854, USA.
Johnson
Michelle
M
Griffin
Jeremy
J
Uhrich
Kathryn
K
D000812:Anhydrides / Q000737:chemistry*; D000818:Animals; D002460:Cell Line; D051379:Mice; D044367:Phase Transition; D011091:Polyesters / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D012459:Salicylates / Q000737:chemistry*; D012996:Solutions; D013696:Temperature
D000812:Anhydrides; D011091:Polyesters; D012459:Salicylates; D012996:Solutions