+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Near-monodisperse poly(2-(methacryloyloxy)ethyl phosphorylcholine)-based macromonomers prepared by atom transfer radical polymerization and thiol-ene click chemistry: novel reactive steric stabilizers for aqueous emulsion polymerization



Near-monodisperse poly(2-(methacryloyloxy)ethyl phosphorylcholine)-based macromonomers prepared by atom transfer radical polymerization and thiol-ene click chemistry: novel reactive steric stabilizers for aqueous emulsion polymerization



Langmuir 28(5): 2928-2936



Poly(2-(methacryloyloxy)ethyl phosphorylcholine) (PMPC) macromonomers have been prepared by the atom transfer radical polymerization (ATRP) of 2-(methacryloyloxy)ethyl phosphorylcholine (MPC) using a bifunctional disulfide-based initiator. To attach a terminal polymerizable methacrylate group, the central disulfide bond was cleaved and the resulting thiols were conjugated to 3-(acryloyloxy)-2-hydroxypropyl methacrylate using tris(2-carboxyethyl)phosphine (TCEP) in water. Here TCEP serves as both the disulfide cleavage agent and also the catalyst for the subsequent Michael addition, which is highly selective for the acrylate group. The resulting methacrylate-terminated macromonomers were used as a reactive steric stabilizer for the aqueous emulsion polymerization of styrene, yielding near-monodisperse PMPC-stabilized polystyrene (PS) latexes of around 100-200 nm in diameter. As a comparison, the disulfide-containing PMPC homopolymer precursor and the intermediate thiol-functional PMPC homopolymer (PMPC-SH) were also evaluated as potential steric stabilizers. Interestingly, near-monodisperse latexes were also obtained in each case. These three sterically-stabilized latexes, prepared using either PMPC macromonomer, disulfide-based PMPC homopolymer, or PMPC-SH homopolymer as a reactive steric stabilizer, remained colloidally stable after both freeze-thaw experiments and the addition of an electrolyte, indicating that a coronal layer of PMPC chains prevented flocculation in each case. In contrast, both a charge-stabilized PS latex prepared in the absence of any steric stabilizer and a PS latex prepared in the presence of a nonfunctional PMPC homopolymer exhibited very poor colloidal stability when subjected to a freeze-thaw cycle or the addition of an electrolyte, as expected.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 054560024

Download citation: RISBibTeXText

PMID: 22191694

DOI: 10.1021/la204083z


Related references

Synthesis of biomimetic poly[2-(methacryloyloxy)ethyl phosphorycholine]-coated magnetite nanoparticles via surface-initiated atom transfer radical polymerization. Journal of Nanoscience and Nanotechnology 11(10): 8469-8473, 2012

Synthesis of Biomimetic Poly[2-(methacryloyloxy)ethyl phosphorycholine]-Coated Magnetite Nanoparticles via Surface-Initiated Atom Transfer Radical Polymerization. Journal of Nanoscience and Nanotechnology 11(10): 8469-8473, 2011

Localized surface plasmon resonance nanosensing of C-reactive protein with poly(2-methacryloyloxyethyl phosphorylcholine)-grafted gold nanoparticles prepared by surface-initiated atom transfer radical polymerization. Analytical Chemistry 86(11): 5587-5594, 2015

Synthesis and self-assembly of thermoresponsive PEG-b-PNIPAM-b-PCL ABC triblock copolymer through the combination of atom transfer radical polymerization, ring-opening polymerization, and click chemistry. Journal of Physical Chemistry. B 115(50): 14947-14955, 2011

Synthesis and in situ atomic force microscopy characterization of temperature-responsive hydrogels based on poly(2-(dimethylamino)ethyl methacrylate) prepared by atom transfer radical polymerization. Langmuir 23(1): 241-249, 2006

Preparation of well-defined poly(2-hydroxyethyl methacrylate) macromonomers via atom transfer radical polymerization. Macromolecular Rapid Communications 35(2): 242-248, 2014

Polymeric phosphorylcholine-camptothecin conjugates prepared by controlled free radical polymerization and click chemistry. Bioconjugate Chemistry 20(12): 2331-2341, 2010

Room temperature, aqueous post-polymerization modification of glycidyl methacrylate-containing polymer brushes prepared via surface-initiated atom transfer radical polymerization. Langmuir 26(23): 18219-18230, 2011

Stimuli-responsive multifunctional membranes of controllable morphology from poly(vinylidene fluoride)-graft-poly[2-(N,N-dimethylamino)ethyl methacrylate] prepared via atom transfer radical polymerization. Langmuir 24(24): 14151-8, 2009

A combination of "thiol-ene" click chemistry and surface initiated atom transfer radical polymerization: Fabrication of boronic acid functionalized magnetic graphene oxide composite for enrichment of glycoproteins. Talanta 180: 54-60, 2018

Induction heating vs conventional heating for the hydrothermal treatment of nitinol and its subsequent 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate coating by surface-initiated atom transfer radical polymerization. Acs Applied Materials and Interfaces 3(10): 4059-4066, 2012

Reactive surfactants in heterophase polymerization. Part XXIIincorporation of macromonomers used as stabilizers in styrene dispersion polymerization. Polymers for Advanced Technologies 8(10): 608-615, 1997

Surface-functionalized and surface-functionalizable poly(vinylidene fluoride) graft copolymer membranes via click chemistry and atom transfer radical polymerization. Langmuir 27(6): 2936-2945, 2011

Poly(ε-caprolactone) modification via surface initiated atom transfer radical polymerization with bio-inspired phosphorylcholine. Materials Science and Engineering. C, Materials for Biological Applications 77: 45-51, 2018

Nanostructured hybrid hydrogels prepared by a combination of atom transfer radical polymerization and free radical polymerization. Biomaterials 30(29): 5270-5278, 2009