ISSN:
0887-624X
Keywords:
glycidyl methacrylate
;
poly(glycidyl methacrylate)
;
carbon disulfide
;
cyclic dithiocarbonate
;
polymer reaction
;
aminolysis
;
thiol
;
auto-oxidation
;
cross-linking
;
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
5-(Methacryloyloxy)methyl-1,3-oxathiolane-2-thione (3) was synthesized from glycidyl methacrylate (GMA) and carbon disulfide in the presence of lithium bromide in 93% yield. The radical polymerization of 3 in DMSO initiated by AIBN at 60°C afforded corresponding polymethacrylate 4 quantitatively. Copolymerization of 3 with MMA was also carried out. 5-Phenoxymethyl-1,3-oxathiolane-2-thione (6), model dithiocarbonate, reacts with benzylamine at room temperature to afford O-(1-mercapto-3-phenoxy-2-propyl)N-benzyl-thiocarbamate (7) and 1,1′-dithiobis[3-phenoxy-2-(benzylaminothiocarbonyloxy)-propane] (8) in 89% and 7% yield, respectively. Polymer 4 reacted with butylamine or dipropylamine to afford a corresponding polymethacrylate bearing thiol group, which immediately turned to insoluble gel by facile auto-oxidation of the thiol group. © 1995 John Wiley & Sons, Inc.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/pola.1995.080330701
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