1,4-Dioxane-2,5-dione-type monomers derived from l-ascorbic and d-isoascorbic acids. Synthesis and polymerisation.
l-Ascorbic and d-isoascorbic acids have been used as the starting materials for the preparation of (3R,4'S)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1,4-dioxane-2,5-dione (IPTA), (3R and S, 4'S,6R)-3-methyl-6-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1,4-dioxane-2,5-dione (IPTP) and (3R,4'R)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1,4-dioxane-2,5-dione (IPEA), three novel 1,4-dioxane-2,5-dione-type monomers. Ring-opening homopolymerisation and copolymerisation of the IPTA monomer, derived from l-ascorbic acid, with d,l-lactide have been performed. The polymers were characterised by elemental microanalysis, as well as IR and (1)H and (13)C NMR spectroscopies. GPC was used to estimate product molecular weights, and thermal studies (DSC and TGA) revealed that all the polymers were amorphous, being stable up to 250 degrees C under nitrogen.
Bueno
Manuel
M
Departamento de Química Orgánica y Farmacéutica, Universidad de Sevilla, Spain.
Molina
Inmaculada
I
Galbis
Juan A
JA
D001205:Ascorbic Acid / Q000737:chemistry*; D004146:Dioxanes / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry*
D004146:Dioxanes; D011108:Polymers; C005056:isoascorbic acid; D001205:Ascorbic Acid