Synthesis of a novel dendronized polyacrylamide triester and its water soluble derivatives with amino and bis(quaternary ammonium) functional groups

POLY 165

Changde Zhang, czhang9@lsu.edu, Macromolecular Studies Group and Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804 and William H. Daly, chdaly@lsu.edu, Department of Chemistry, Louisiana State University, 712 Choppin Hall, Baton Rouge, LA 70803-1804.
Selected quaternized dendrimers show excellent antibacterial properties. The polymerization of acrylamide dendron derived from Behara's amine (BA), di-tert-butyl 4-[2-(tert-butoxycarbonyl)ethyl]-4-aminoheptanedicarboxylate, provides an alternative affordable way to make scaffolds with concentrated functional groups in local microenvironment. The acrylamide of BA, prepared from BA and acryloyl chloride, was polymerizated under free radical conditions. PolyacrylBA was elaborated to form a water soluble polyacrylBADMPDA by first hydrolyzing the tert-butyl esters with formic acid followed by reaction of the resultant polycarboxylated intermediate with N, N-dimethyl-1,3-propanediamine (DMPDA) in the presence of dicyclohexyl carbodiimide (DCC) and 1-hydroxybenzotriazole. Treatment of polyacrylBADMPDA with 3-chloro-2-hydroxypropyl trimethylammonium chloride (Quat 188) formed the quaternized derivative (PolyacrylBADMPDA-Quat188). The chemical structures of these dendronized polymers were confirmed by their NMR spectra, FTIR spectra, and TGA spectra. The MW of the above novel dendronized polymers will be further characterized with GPC-MALS. The quaternized dendronized polymers are expected to exhibit good antibacterial property.
 

General Papers: Synthesis and Characterization
6:00 PM-8:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Polymer Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006