DESIGNED MONOMERS AND POLYMERS, cilt.7, sa.3, ss.291-300, 2004 (SCI-Expanded)
A new acrylate monomer with phosphonic acid ester groups was synthesized from the reaction of the acid chloride derivative of the ether dimer of tert-butyl alpha-(hydroxymethyl) acrylate with diethyl hydroxymethyl phosphonate. Bulk polymerization of this monomer at 75-77degreesC with 2,2'-azobisisobutyronitrile (AIBN) gave soluble cyclopolymers. The T-g value of the cyclopolymer was 44degreesC, and produced a char yield of 36% at 580degreesC. The phosphonate monomer was copolymerized with the ether dinner of tert-butyl alpha-(hydroxymethyl) acrylate in different ratios. The T-g of the copolymers decreased with increasing amounts of the phosphonate monomer in the copolymers, with the values of 148, 105 and 93degreesC for the copolymers containing 10, 30 and 50 mol% phosphonate monomer in feed, respectively. The char residues of the copolymers increased with the incorporation of the phosphonate monomer. The selective hydrolysis of the phosphonate monomer with trimethylsilyl bromide (TMSBr) gave a monomer with two phosphonic acid groups. The polymerization of this monomer at 70-75degreesC with AIBN was unsuccessful; however, this monomer was copolymerized with the ether dimer of tert-butyl alpha-(hydroxymethyl) acrylate and its carboxylic acid derivative.