ALPHA,OMEGA-DIFUNCTIONAL OLIGO(OXYETHYLENE)-BASED CROSS-LINKED RESINSAS SOLID-LIQUID PHASE-TRANSFER CATALYSTS

Crosslinked resins were prepared from alpha,omega-diglydicyl and alpha ,omega-dimethacryloyl oligo(ethylene oxide)s by anionic polymerization with triethylenediamine/n-pentanol initiating system or by free-radic al polymerization, respectively. Their activity as solid-liquid phase transfer catalysts was proved in the reaction of 1-bromobutane with po tassium phenoxide, and compared with the activity of similar resins sy nthesized from alpha,omega-diglycidyl oligo(ethylene oxide)s and triet hylenetetramine (TETA). The catalytic activity of dimethacryloyl resin s was higher than that of diglycidyl resins for oligomer chains longer than 6-7 oxyethylene units, whereas the opposite was true for resins of shorter chain lengths. These differences were explained by an unlik e graft content of the resins in the former case, and by a different a bility to complex the potassium cation into the meshes of the resin la ttice, in the latter. In order to improve the catalytic activity of th e resins two methods were developed consisting in the increase of the number of grafts either by decreasing the ratio of TETA/epoxy end grou ps used to the crosslinking of diglycidyl oligomers or by adding 2-mer captoethanol as a transfer agent to the free-radical crosslinking proc ess of dimethacryloyl oligo(ethylene oxide)s.