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Saccharide polymers, 3. Synthesis and polymerization of a 5,6‐unsaturated fructofuranoid derivative
Author(s) -
Wick Stefan,
Yaacoub EmileJoseph
Publication year - 2000
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/(sici)1521-3935(20000101)201:1<93::aid-macp93>3.0.co;2-1
Subject(s) - polymer chemistry , polymerization , derivative (finance) , polymer , chemistry , polymer science , materials science , organic chemistry , financial economics , economics
A new exo‐fructofuranoid monomer 5 was synthesized through a four‐step reaction. This unsaturated sugar monomer has been successfully tested in radical polymerization. Homo‐ and copolymerizations were carried out in solution under various conditions. The corresponding saccharide polymers were isolated as white powder and well characterized. Polymer compositions were determined by elemental analysis (C, H, N) and 1 H and 13 C NMR. Polymerization parameters were determined for the binary system 1,2,3,4‐tetra‐ O ‐benzoyl‐6‐deoxy‐ α ‐ D ‐threo‐5‐eno‐hexofuranose‐2‐uloside ( 5 )/MA giving the reactivity ratios r 1 = 0.47 for 5 and r 2 = 1.13 for MA. The thermal behaviour of saccharide polymers was investigated showing a linear relationship between the glass transition temperature ( T g ) of the saccharide polymers and the sugar content. The saccharide polymers also showed optical activity and exhibit negative optical rotation. Both T g and the specific optical rotations ([ α ] 20 D ) increase with increasing sugar content.