Macrocycles.: 13.: Stannylenated glucose glycosides as cyclic initiators of ε-caprolactone and the synthesis of biodegradable networks

被引:34
作者
Kricheldorf, HR [1 ]
Stricker, A [1 ]
机构
[1] Univ Hamburg, Inst Tech & Makromol Chem, D-20146 Hamburg, Germany
关键词
D O I
10.1021/ma9909915
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The tetraacetates of alpha- and beta-methylglycosides of D-glucose were reacted with dibutyltin dimethoxide in hot toluene with elimination of methyl acetate. The stannylenated glucose derivatives having a five- and six-membered tin-containing ring were isolated in a crystalline form. The soluble a-glycoside was used as cyclic initiator for the polymerization of epsilon-caprolactone at 80 degrees C. It was found by H-1 NMR spectroscopy that the insertion of the lactone exclusively occurs into the six-membered ring at the Sn-O bond of C-6. At prolonged reaction times the stannylenated glucose began to degrade at 80 degrees C. However, at short reaction times (t less than or equal to 2 h) the molecular weight of the macrocyclic polylactone could be controlled by the monomer/initiator ratio (M/I). When sebacoyl chloride was added at the end of the polymerization, all four Sn-O bonds of the active chain end reacted, and swellable, biodegradable networks were obtained. The volume expansion upon swelling depended on the M/I ratio of the ring-opening polymerization and on the solvent.
引用
收藏
页码:696 / 701
页数:6
相关论文
共 21 条