Novel acrylamido monomers with higher hydrophilicity and improved hydrolytic stability: II. Properties of N-acryloylaminopropanol

The physico-chemical properties and the electrophoretic behavior of the novel set of monomers reported by (Simò-Alfonso et al., Electrophoresis 1996, 17, 723-731) have been evaluated. Of utmost importance was the combination of high hydrophilicity and extreme hydrolytic stability, most desired properties for any electrophoretic matrix, especially for protein fractionation. One of these monomers (N-acryloylaminopropanol, AAP) was found indeed to be extremely hydrophilic (with a partition coefficient P of only 0.10, vs. P = 0.13 for N-acryloylaminoethoxyethanol and P = 0.20 for acrylamide) and to possess excellent stability to alkaline hydrolysis. Its hydrolysis constant (0.008 L mol^-1 min^-1), as a free monomer, in an alkaline milieu, was found to be about one order of magnitude lower than conventional acrylamide (0.05 L mol^-1 min^-1). In the polymer state, the resistance to hydrolysis of poly(AAP) was assessed as 500 times greater than a conventional poly(acrylamide) matrix.