Synthesis and characterization of particles consisting of a biodegradable poly(l-lactide) core and a functional hydrophilic shell

Kipping, Martin; Krahl, Franziska; Döring, Artjom; Adler, Hans-Jürgen P.; Kuckling, Dirk

doi:10.1016/j.eurpolymj.2009.10.008

Cited by 12 publications

(9 citation statements)

References 31 publications

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“…N ‐Isopropyl acrylamide (NIPAAm, Sigma‐Aldrich) was recrystallized from n ‐hexane before use. The synthesis of 2‐(((dodecylthio)carbonothioyl)thio)‐2‐methylpropanoic acid (CTA 3) was carried out according to the literature from Lai et al SKA was synthesized according to the literature …”

Section: Methodssupporting

confidence: 77%

Synthesis of Amphiphilic Block Copolymers Based on SKA by RAFT Polymerization

Picker

Schneider

et al. 2017

Macro Chemistry & Physics

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Temperature‐sensitive amphiphilic block copolymers of 2,2‐dimethyl‐1,3‐dioxolan‐4‐yl‐methyl acrylate (solketal acrylate, SKA) and N‐isopropyl acrylamide (NIPAAm) have been prepared via reversible addition‐fragmentation chain transfer radical polymerization (RAFT). A kinetics study of SKA polymerization is performed in order to find a compatible RAFT chain transfer agents (CTA) and versatile polymerization conditions for the synthesis of well‐defined poly(2,2‐dimethyl‐1,3‐dioxolan‐4‐yl‐methyl acrylate) (PSKA). Depending on the RAFT‐CTA and the reaction time, PSKA with molar masses up to 5700 g mol−1 and dispersity values as low as 1.1 could be prepared. Additionally, the end group distribution of PSKA is investigated via electrospray ionization‐ion mobility separation–mass spectrometry. The chain extensions of the homopolymers for the second block of NIPAAm are analyzed with size‐exclusion chromatography. Amphiphilic block copolymers are obtained after hydrolysis of hydrophobic PSKA block to target hydrophilic poly(2,3‐dihydroxypropyl acrylate) block.

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Section: Methodssupporting

confidence: 77%

Synthesis of Amphiphilic Block Copolymers Based on SKA by RAFT Polymerization

Picker

Schneider

et al. 2017

Macro Chemistry & Physics

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“…Deprotection of the solketal group was done according to a literature-known procedure [ 57 ]. A mass of 0.5 g of the PSKA- b -P(NIPAAm- co -VDMA-prolinamide) block copolymer was dissolved in a mixture of 10 mL THF and 15 mL glacial acetic acid.…”

Section: Methodsmentioning

confidence: 99%

Micellar Organocatalysis Using Smart Polymer Supports: Influence of Thermoresponsive Self-Assembly on Catalytic Activity

Herberg

Kuckling

2020

Polymers

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Micellar catalysts with a switchable core are attractive materials in organic synthesis. However, little is known about the role of the shell forming block on the performance of the catalyst. Thermoresponsive block copolymers based on poly(N-isopropylacrylamide-co-vinyl-4,4-dimethylazlactone) attached to different permanently hydrophilic blocks, namely poly(ethylene glycol), poly(N,N-dimethylacrylamide), and poly(2,3-dihydroxypropyl acrylate), were successfully synthesized via reversible addition/fragmentation chain transfer radical polymerization (RAFT). Post-polymerization attachment of an amino-functionalized L-prolineamide using the azlactone ring-opening reaction afforded functionalized thermoresponsive block copolymers. Temperature-induced aggregation of the functionalized block copolymers was studied using dynamic light scattering. It was shown that the chemical structure of the permanently hydrophilic block significantly affected the size of the polymer self-assemblies. The functionalized block copolymers were subjected to an aldol reaction between p-nitrobenzaldehyde and cyclohexanone in water. Upon temperature-induced aggregation, an increase in conversion was observed. The enantioselectivity of the polymer-bound organocatalyst improved with an increasing hydrophilic/hydrophobic interface as a result of the different stability of the polymer aggregates.

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“…Linear diblock and triblock copolymers were prepared using solketal or glycerol carbonate (meth)acrylates. Diblock copolymers combining a biodegradable core and a hydrophilic shell were synthesized [43]. In such case, two polymerization techniques are involved, with the ring opening polymerization (ROP) of the lactic acid (LLA) first followed by the ATRP of the solketal acrylate (SolA).…”

Section: Controlled/living Radical Polymerizationmentioning

confidence: 99%

Various radical polymerizations of glycerol‐based monomers

Pham

Monge

Lapinte

et al. 2013

Euro J Lipid Sci & Tech

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This review aims at making the state of the art of the radical polymerizations of glycerolbased monomers, especially (meth)acrylate and vinylic/allylic derivatives. Acrylate and methacrylate derivatives bearing numerous secondary groups like ester, cyclocarbonate, acetal and urethane were involved in free radical polymerization and radical controlled polymerizations as well as in the photopolymerization. Glycerol-based monomers bearing a vinylic or an allylic polymerizable group polymerize by acceptor-donor process and produce alternating copolymers. From all these monomers, the synthesis of functionalized polymers was possible, leading to various valuable applications.

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Synthesis and characterization of particles consisting of a biodegradable poly(l-lactide) core and a functional hydrophilic shell

Cited by 12 publications

References 31 publications

Synthesis of Amphiphilic Block Copolymers Based on SKA by RAFT Polymerization

Synthesis of Amphiphilic Block Copolymers Based on SKA by RAFT Polymerization

Micellar Organocatalysis Using Smart Polymer Supports: Influence of Thermoresponsive Self-Assembly on Catalytic Activity

Various radical polymerizations of glycerol‐based monomers

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