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Fabricating Degradable Thermoresponsive Hydrogels on Multiple Length Scales via Reactive Extrusion, Microfluidics, Self-assembly, and Electrospinning

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Thermoresponsive poly(2-oxazine)s.

Meta M Bloksma¹, Renzo M Paulus, Huub P C van Kuringen

¹Laboratory of Macromolecular Chemistry and Nanoscience, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven, The Netherlands.

Macromolecular Rapid Communications

|November 29, 2011

Summary

New poly(2-oxazine)s exhibit tunable thermoresponsive behavior. These polymers show lower critical solution temperatures (LCST) and enhanced water solubility compared to related poly(2-oxazoline)s, offering versatile applications.

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Preparation of Thermoresponsive Nanostructured Surfaces for Tissue Engineering

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Area of Science:

Polymer Chemistry
Materials Science
Organic Synthesis

Background:

Poly(2-oxazoline)s are a well-established class of polymers with tunable properties.
The synthesis and characterization of poly(2-oxazine)s, isomers of poly(2-oxazoline)s, are less explored.
Understanding the structure-property relationships of poly(2-oxazine)s is crucial for developing novel functional materials.

Purpose of the Study:

To synthesize novel monomers: 2-methyl-2-oxazine (MeOZI), 2-ethyl-2-oxazine (EtOZI), and 2-n-propyl-2-oxazine (nPropOZI).
To investigate the living cationic ring-opening polymerization (CROP) of these monomers under microwave-assisted conditions.
To characterize the thermoresponsive behavior and water solubility of the resulting poly(2-oxazine)s and compare them with poly(2-oxazoline) isomers.

Main Methods:

Monomer synthesis of MeOZI, EtOZI, and nPropOZI.
Living cationic ring-opening polymerization (CROP) utilizing microwave irradiation.
Thermogravimetric analysis and cloud point temperature (T(CP)) determination to assess thermoresponsiveness.
Solubility studies in aqueous media.

Main Results:

Successful synthesis and microwave-assisted CROP of MeOZI, EtOZI, and nPropOZI.
Poly(EtOZI) (pEtOZI) and poly(nPropOZI) (pnPropOZI) demonstrated thermoresponsive behavior with lower critical solution temperatures (LCST).
The T(CP) of pEtOZI and pnPropOZI were lower than those of analogous poly(2-oxazoline)s.
Poly(2-oxazine)s exhibited higher water solubility than their poly(2-oxazoline) counterparts, indicating a stronger influence of the side chain on solubility.

Conclusions:

Variations in both side chains and main chains of poly(cyclic imino ether)s allow for the creation of distinct homopolymers.
The synthesized poly(2-oxazine)s offer tunable cloud point temperatures (T(CP)) and enhanced water solubility.
These findings provide a foundation for designing novel thermoresponsive polymers with tailored properties for various applications.