Hydrobromination of residual vinyl groups on divinylbenzene polymer particles followed by atom transfer radical surface graft polymerization

Abstract

Rigid and monodisperse spherical polymer particles with 2.36 AE 0.18 lm diameter containing residual surface vinyl groups were prepared by photoinitiated precipitation polymerization of divinylbenzene. Anti-Markovnikov addition of HBr to the surface vinyl groups yielded a 2-bromoethyl functionality that was used as macroinitiator for atom transfer radical polymerization (ATRP), providing the possibility for further functionalization by controlled ''grafting from'' processes. This was demonstrated by grafting of glycidyl methacrylate brushes from the particle surface, using an ATRP system based on CuBr and pentamethyl diethylenetriamine. Existence of a methacrylic overlayer was verified by FTIR and XPS measurements, and the grafted particles were easily dispersed in water, confirming conversion of the particle surface from hydrophobic to hydrophilic. Hydrobromination of residual vinyl groups yields a macroinitiator that can be used for grafting of glycidyl methacrylate by ATRP.

Functionalization of Poly(divinylbenzene) Microspheres by Combination of Hydrobromination and Click Chemistry Processes: A Model Study

“…2.5 µm) spherical PDVB beads were prepared by precipitation polymerization technique and the residual double bonds on the surface were activated to primary bromine by anti-Markovnikov addition of hydrogen bromide according to the procedure described in the literature [54]. After the reaction, the brominated particles with 1.46 mmol/g of bromine (estimated by titration method [55]) were obtained.…”

“…Hydrobromination was performed according to a procedure as described in the literature [54]. PDVB microspheres (2 g) were suspended using 80 ml n-heptane in a 250-ml round-bottom flask, and dibenzoyl peroxide (0.18 g, 0.74 mmol) was added to the mixture under magnetic stirrer.…”

Optical percolation and oxygen diffusion in poly(divinylbenzene) doped poly(methyl methacrylate) latex flms

“…The residual double bonds on the surface were nearly monodisperse (∼2.5 μm) (see Fig. 1b), PDVB microspheres were activated to primary bromine [28, 29] and then converted into azide functions by condensation with NaN 3 . Finally, fluorescence labeled PDVB microspheres were obtained by the click reaction [26] with propargyl pyrene [30] through azide functions.…”

Modification of Polydivinylbenzene Microspheres by a Hydrobromination/Click‐Chemistry Protocol and their Protein‐Adsorption Properties

“…Hydrobromination was performed according to a procedure described in the literature 41. PDVB microspheres (2 g) were suspended using 80 mL of n‐heptane in a 250 mL round‐bottom flask; dibenzoyl peroxide (0.18 g, 0.74 mmol) was added to the mixture under stirring with a magnetic stirrer.…”