Synthesis and characterization of new pH- and thermo-responsive hydrogels based on N-isopropylacrylamide and 2-oxazolines

Rueda, Juan Carlos; Campos, Estuardo; Komber, Hartmut; Zschoche, Stefan; Häußler, Liane; Voit, Brigitte

doi:10.1080/15685551.2013.840471

Cited by 19 publications

(28 citation statements)

References 35 publications

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“…It allows, after polymerization, the introduction of both functional groups via a one‐step modification reaction. The polymerization kinetics of this monomer with various 2‐alkyl‐2‐oxazoline comonomers has been reported by Bouten et al, and this monomer has also been copolymerized with P(NIPAM) and postmodified forming temperature‐ and pH‐responsive polymers . In this respect, MestOx seems to be an ideal monomer for the synthesis of more polar and stimuli‐responsive n PropOx‐based copolymers.…”

Section: Introductionmentioning

confidence: 55%

Synthesis of pH‐ and thermoresponsive poly(2‐n‐propyl‐2‐oxazoline) based copolymers

Boerman

Laan

Bender³

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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Polymers that possess lower critical solution temperature behavior such as poly(2-alkyl-2-oxazoline)s (PAOx) are interesting for their application as stimulus-responsive materials, for example in the biomedical field. In this work, we discuss the scalable and controlled synthesis of a library of pHand temperature-sensitive 2-n-propyl-2-oxazoline P(nPropOx) based copolymers containing amine and carboxylic acid functionalized side chains by cationic ring opening polymerization and postpolymerization functionalization strategies. Using turbidimetry, we found that the cloud point temperature (CP) is strongly dependent on both the polymer concentration and the polymer charge (as a function of pH). Furthermore, we observed that the CP decreased with increasing salt concentration, whereas the CP increased linearly with increasing amount of carboxylic acid groups. Finally, turbidimetry studies in PBSbuffer indicate that CPs of these polymers are close to body temperature at biologically relevant polymer concentrations, which demonstrates the potential of P(nPropOx) as stimulusresponsive polymeric systems in, for example, drug delivery applications. V C 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 1573-1582

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Section: Introductionmentioning

confidence: 55%

Synthesis of pH‐ and thermoresponsive poly(2‐n‐propyl‐2‐oxazoline) based copolymers

Boerman

Laan

Bender³

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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“…The latter was ascribed to the quarternization of the amide function of the POx, however, this assumption was not proven. 52 Macro monomers consisting of MeOx and a methoxy carbonyl subsituted 2-oxazoline were synthesized using iodomethyl styrene as initiator. 48 To produce α,ω-functionalized POx the authors did not use a bis-functional initiator but initiated the polymerization with iodomethyl styrene and introduced the second styrene group by end-capping with a styrene modified piperazine.…”

Section: Hydrogels By Pox Macro Monomersmentioning

confidence: 99%

Covalently cross-linked poly(2-oxazoline) materials for biomedical applications – from hydrogels to self-assembled and templated structures

2015

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REVIEW This journal isCovalently cross-linked polymeric materials play an important role in life science. Hydrogels produced from multifunctional polymers can be utilized in numerous (bio)applications, such as drug delivery, tissue engineering and (bio)sensing. Also nano-/micro-scaled assemblies benefit from a covalent linkage for instance to prevent premature disassembly or to generate a passive tissue specifity when used as drug delivery agent. In both cases there is a need for biocompatible polymers with manifold (orthogonal) functionalization possibilities. By using the cationic ring-opening polymerization of 2-oxazolines it is possible to accomplish both tasks. In this review we summerize covalantly cross-linked structures consisting of poly(2-oxazoline)s including three dimensional scaffolds, micellar systems as well as multilayer capsules. We focus on the cross-linking chemistry and the impact of the addressed systems regarding biological application.

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“…PEtOx and poly(2‐propyl‐2‐oxazoline) (PPropOx) show lower critical solution (LCST) behavior with better reversibility as compared to the gold standard poly( N ‐isopropylacrylamide) . The properties of PAOx can be easily tuned by variation of the side chain substituent, also enabling the incorporation of (protected) side chain functionalities …”

Section: Introductionmentioning

confidence: 99%

Synthesis of poly(2‐oxazoline)s with side chain methyl ester functionalities: Detailed understanding of living copolymerization behavior of methyl ester containing monomers with 2‐alkyl‐2‐oxazolines

Bouten

Hertsen

Vergaelen

et al. 2015

J. Polym. Sci., Part A: Polym. Chem.

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Poly(2-oxazoline)s with methyl ester functionalized side chains are interesting as they can undergo a direct amidation reaction or can be hydrolyzed to the carboxylic acid, making them versatile functional polymers for conjugation. In this work, detailed studies on the homo-and copolymerization kinetics of two methyl ester functionalized 2-oxazoline monomers with 2-methyl-2-oxazoline, 2-ethyl-2-oxazoline, and 2-npropyl-2-oxazoline are reported. The homopolymerization of the methyl ester functionalized monomers is found to be faster compared to the alkyl monomers, while copolymerization unexpectedly reveals that the methyl ester containing monomers significantly accelerate the polymerization. A computational study confirms that methyl ester groups increase the electrophilicity of the living chain end, even if they are not directly attached to the terminal residue. Moreover, the electrophilicity of the living chain end is found to be more important than the nucleophilicity of the monomer in determining the rate of propagation. However, the monomer nucleophilicity can be correlated with the different rates of incorporation when two monomers compete for the same chain end, that is, in copolymerizations.

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Synthesis and characterization of new pH- and thermo-responsive hydrogels based on N-isopropylacrylamide and 2-oxazolines

Cited by 19 publications

References 35 publications

Synthesis of pH‐ and thermoresponsive poly(2‐n‐propyl‐2‐oxazoline) based copolymers

Synthesis of pH‐ and thermoresponsive poly(2‐n‐propyl‐2‐oxazoline) based copolymers

Covalently cross-linked poly(2-oxazoline) materials for biomedical applications – from hydrogels to self-assembled and templated structures

Synthesis of poly(2‐oxazoline)s with side chain methyl ester functionalities: Detailed understanding of living copolymerization behavior of methyl ester containing monomers with 2‐alkyl‐2‐oxazolines

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