Generation and Surface Functionalization of Electro Photographic Toner Particles for Biomaterial Applications
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The surface functionalization of the developed microparticles gives rise to further interesting applications [1]. Basic hydrolysis of the poly(methacrylic) surface provides a simple route to highly surface functionalized microparticles via post-synthesis modification without altering their bulk properties. In this article, we provide the investigation about the surface functionalization of acrylic microparticles and the subsequent carbodiimide-mediated coupling of numerous functional amines onto the generated carboxylic groups. Various chemically valuable functionalities, comprising of thiol, alkyne and azide, were bound onto the particles’ surface and allow for further versatile modifications via huisgen cycloaddition as well as thiolene reaction [2]. EXPERIMENT Propargylamine (98 %), cysteamine (95 %), 11-azido-3,6,9-trioxaundecan-1-amine (90 %), N-(3-dimethylaminopropyl)-N -ethylcarbodiimide hydrochloride (EDC, 98 %), 2-(Nmorpholino)ethanesulfonic acid (MES, 98 %), 2,2 -azobis(2-methylpropionitrile) (AIBN, 98 %), dimethyl sulfoxide (99.9 %), ), propidium iodide (94%) and fluorescein diacetate were purchased from Sigma-Aldrich GmbH (Steinheim, Germany) and used without further purification. Chloroform (99.8 %, Avantor Performance Materials, Griesheim, Germany), acetone (99.3 %, Avantor Performance Materials, Griesheim, Germany), methanol (99.9 %, Avantor Performance Materials, Griesheim, Germany), resazurin sodium salt (AlamarBlue®, Invitrogen Life Technologies GmbH, Darmstadt, Germany), endothelial cell growth medium (Invitrogen Life Technologies GmbH, Darmstadt, Germany) and poly(diallyldimethylammonium chloride) (molecular weight 1,07 x 105 g mol-1, BTG Instruments GmbH, Herrsching, Germany) were used as received. Pyrogenic silica (HDK N20 Pharma®) was provided by Wacker Chemie AG (München, Germany). Aqueous sodium hydroxide solutions were created from solid sodium hydroxide pellets (> 99 %, AppliChem GmbH, Darmstadt, Germany) in water (Milli-Q®, Millipore GmbH, Schwalbach, Germany). Methyl methacrylate (Sigma-Aldrich GmbH, Steinheim, Germany) was dried over calcium sulfate for 16 h and distilled under reduced pressure prior to use. Polymer synthesis The polymeric microparticles were synthesized by an UV-initiated suspension polymerization of methyl methacrylate. The monomer (107 mL, 1000 equivalents) and the initiator 2,2 azobis(2-methylpropionitrile) (AIBN, 2,45 g, 15 equivalents) were dispersed at 800 rounds per minute in an aqueous silica suspension (0.4 wt.-% SiOx, 900 mL) with a disc turbine stirrer (six blades, outer diameter = 6 cm) in a 1 L-glass reaction vessel (H.W.S. Labortechnik, Mainz, Germany). The polymerization proceeded for 24 h at 20 °C under UV-radiation by a watercooled medium-pressure mercury lamp (TQ150, UV Consulting Peschl, Mainz, Germany). The synthesized P(MMA) particles were purified by filtration and redispersion in hydrochloric acid (0.1 M) in a methanol/H2O-solution (volume ratio 1:1) for three times and subsequent washing in phosphate buffer (100 mM, pH 7.0) as well as pure wat
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