title: Photo-cross-linked poly(thioether-co-carbonate) networks derived from the natural product quinic acid.
abstract: Polycarbonate networks derived from the natural product quinic acid that can potentially return to their natural building blocks upon hydrolytic degradation are described herein. Solvent-free thiol-ene chemistry was utilized in the copolymerization of tris(alloc)quinic acid and a variety of multifunctional thiol monomers to obtain poly(thioether-co-carbonate) networks with a wide range of achievable thermomechanical properties including glass transition temperatures from -18 to +65 °C and rubbery moduli from 3.8 to 20 MPa. The network containing 1,2-ethanedithiol expressed an average toughness at 25 and 63 °C of 1.08 and 2.35 MJ/m(3), respectively, and an order-of-magnitude increase in the average toughness at 37 °C of 15.56 MJ/m(3).
authors.affiliation: Department of Chemistry, ‡Department of Chemical Engineering, §Department of Materials Science and Engineering, and ⊥Department of Biomedical Engineering, Texas A&M University , College Station, Texas 77842-3012, United States.
authors.forename: Lauren A
authors.initials: LA
authors.lastname: Link
authors.forename: Alexander T
authors.initials: AT
authors.lastname: Lonnecker
authors.forename: Keith
authors.initials: K
authors.lastname: Hearon
authors.forename: Cameron A
authors.initials: CA
authors.lastname: Maher
authors.forename: Jeffery E
authors.initials: JE
authors.lastname: Raymond
authors.forename: Karen L
authors.initials: KL
authors.lastname: Wooley
mesh_terms: D001688:Biological Products / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D055119:Elastic Modulus; D008027:Light; D011076:Polycarboxylate Cement / Q000737:chemistry*; D011091:Polyesters / Q000737:chemistry*; D011801:Quinic Acid / Q000737:chemistry*; D013314:Stress, Mechanical; D013440:Sulfides / Q000737:chemistry*; D013696:Temperature
chemical_list: D001688:Biological Products; D003432:Cross-Linking Reagents; D011076:Polycarboxylate Cement; D011091:Polyesters; D013440:Sulfides; D011801:Quinic Acid; C005506:polycarbonate
keywords: photo-cross-linking; polycarbonates; quinic acid; renewable polymers; thiol−ene chemistry