Journal of Applied Polymer Science, Vol.72, No.13, 1775-1782, 1999
Polymerization of cyclic monomers. VII. Synthesis and radical polymerization of 1,3-bis[(1-alkoxycarbonyl-2-vinylcyclopropane-1-yl)carboxy]benzenes
1,3-Bis [(1-alkoxycarbonyl-2-vinylcyclopropane-1-yl)carboxy]benzenes 1 [RO: CH3O (a), C2H5O (b)] were synthesized by the esterification of the corresponding 1-alkoxycarbonyl-2-vinylcyclopropane-1-carboxylic acids with resorcinol. The structure of the new vinylcyclopropanes was confirmed by elemental analysis and infrared (IR), H-1 nuclear magnetic resonance (H-1-NMR), and C-13 nuclear magnetic resonance (C-13- NMR) spectroscopy. The radical polymerization of difunctional. 2-vinyl-cyclopropanes in bulk with 2,2'-azoisobutyronitrile (AIBN) results in hard, transparent, crosslinked polymers. During the bulk polymerization of the crystalline bis [(1-methoxycarbonyl-2-vinylcyclopropane-1-yl)carboxy]benzene la, an expansion in volume of about 1% took place. The radical solution polymerization of la resulted in a soluble polymer with pendant 2-vinylcyclopropane groups.
Keywords:radical polymerization;ring-opening polymerization;2-vinylcyclopropanes;low-shrinking monomers;crosslinking monomers