Poly(2-ethyl-2-oxazoline--propylethylene imine)s by controlled partial reduction of poly(2-ethyl-2-oxazoline): synthesis, characterization and cytotoxicity

The partial reduction of poly(2-ethyl-2-oxazoline) was investigated. A series of poly(2-ethyl-2-oxazoline- co-N -propylethylene imine)s were synthesized by direct reduction using lithium aluminum hydride or borane/dimethylsulfide (BH 3 /DMS), respectively. It is shown that the degree of reduction ca...

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Bibliographic Details
Published in:Polymer chemistry 2021-02, Vol.12 (5), p.68-688
Main Authors: Halupczok, Sebastian, Pfister, Maria, Ringhand, Annemarie, Fetsch, Corinna, Cubukova, Alevtina, Appelt-Menzel, Antje, Luxenhofer, Robert
Format: Article
Language:English
Subjects:
Aluminum hydrides
Biocompatibility
Biomedical materials
Cationic polymerization
Chemical synthesis
Direct reduction
Glass transition temperature
Lithium aluminum hydrides
Material properties
Metal hydrides
NMR spectroscopy
Polyethyloxazoline
Polymer chemistry
Polymers
Reaction time
Stoichiometry
Titration
Toxicity
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Summary:The partial reduction of poly(2-ethyl-2-oxazoline) was investigated. A series of poly(2-ethyl-2-oxazoline- co-N -propylethylene imine)s were synthesized by direct reduction using lithium aluminum hydride or borane/dimethylsulfide (BH 3 /DMS), respectively. It is shown that the degree of reduction can be readily controlled either by the reaction time when using an excess of LiAlH 4 or by the stoichiometry of BH 3 /DMS, as was demonstrated by 1 H-NMR spectroscopy. Differential scanning calorimetry revealed that the glass transition temperature of the products decreased with increasing degree of reduction up to 25% of reduction, above which no glass transition could be detected. Moreover, acid-base titration showed a very pronounced, reduction degree dependent buffering capacity of these polymers between pH 4 and 8, which is of great interest, e.g. in the context of endosomal escape. This control over the reduction allows to tailor the synthesis of partially cationic polymers on the basis of poly(2-oxazoline)s, which, in combination over the hydrophilic/lipophilic balance through the side chain length allows a tight control over materials properties. Such materials may be interesting, inter alia , for biomaterials or organic electronics. Cationic polymers obtained via partial reduction of poly(2-ethy-2-oxazoline)s were studied on their cytocompatibility and their buffer capacity in acidic environment.
ISSN:1759-9954
1759-9962
DOI:10.1039/d0py01258k