Enzymatic one-pot route to telechelic polypentadecalactone epoxide: synthesis, UV curing, and characterization.
In an enzymatic one-pot procedure immobilized lipase B from Candida antarctica was used to synthesize semicrystalline diepoxy functional macromonomers based on glycidol, pentadecalactone, and adipic acid. By changing the stoichiometry of the building blocks, macromonomers of controlled molecular weight from 1400 to 2700 g mol(-1) could be afforded. The enzyme-catalyzed reaction went to completion (conversion >or=95%) within 24 h at 60 degrees C. After removal of the enzyme, the produced macromonomers were used for photopolymerization without any purification. The macromonomers readily copolymerized cationically with a cycloaliphatic diepoxide (Cyracure UVR-6110; CA-dE) to high conversion. The cross-linked copolymers formed a durable film with a degree of crystallinity depending on the macromonomer size and amount of CA-dE used, without CA-dE the macromonomers homopolymerized only to a low degree. Combined with CA-dE conversions of 85-90% were determined by FT-Raman spectroscopy. The films became more durable once reinforced with CA-dE, increasing the cross-link density and reducing the crystallinity of the PDL segments in the films.
Eriksson
Magnus
M
Department of Biochemistry, School of Biotechnology, KTH, Royal Institute of Technology, Stockholm, Sweden.
Fogelström
Linda
L
Hult
Karl
K
Malmström
Eva
E
Johansson
Mats
M
Trey
Stacy
S
Martinelle
Mats
M
D002626:Chemistry, Pharmaceutical / Q000379:methods*; D057075:Enzyme Assays / Q000379:methods*; D005656:Fungal Proteins; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry / Q000528:radiation effects; D008049:Lipase / Q000378:metabolism; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D014466:Ultraviolet Rays
D005656:Fungal Proteins; D007783:Lactones; D011108:Polymers; D008049:Lipase; C431349:lipase B, Candida antarctica