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Preparation of Epoxides

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

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

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Poly(2-oxazoline) hydrogel monoliths via thiol-ene coupling.

Tim R Dargaville¹, Rebecca Forster, Brooke L Farrugia

¹Institute of Health and Biomedical Innovation, Queensland University of Technology, Kelvin Grove, Queensland 4059, Australia. t.dargaville@qut.edu.au

Macromolecular Rapid Communications

|August 14, 2012

Summary

New poly(2-oxazoline)s form soft gels rapidly via UV crosslinking. These tunable, degradable hydrogels show promise for advanced biomaterial applications.

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Area of Science:

Polymer Chemistry
Materials Science
Biomaterials

Background:

Cationic ring-opening polymerization (CROP) is a versatile method for synthesizing poly(2-oxazoline)s (POx).
Hydrogels are water-swollen polymer networks with broad applications in biomedicine.
Developing efficient crosslinking strategies for POx is crucial for creating functional hydrogels.

Purpose of the Study:

To synthesize novel copoly(2-oxazoline)s with pendant alkene groups.
To investigate the UV-initiated crosslinking of these copolymers into homogeneous networks.
To explore the tunable properties and degradability of the resulting hydrogels for biomaterial applications.

Main Methods:

Cationic ring-opening polymerization of 2-(dec-9-enyl)-2-oxazoline with 2-methyl-2-oxazoline or 2-ethyl-2-oxazoline.
UV-initiated thiol-ene crosslinking using dithiol molecules.
In situ photo-rheology for monitoring network formation.
Swelling studies to assess water uptake and tunability.
Preparation of degradable hydrogels using hydrolytically cleavable crosslinkers.

Main Results:

Homogeneous poly(2-oxazoline) networks were formed rapidly (within minutes) via UV crosslinking.
Photo-rheology confirmed the swift gelation process.
Hydrogel swelling behavior was tunable by adjusting macromer hydrophilicity and alkene content.
Degradable hydrogels were successfully synthesized by incorporating cleavable crosslinkers.

Conclusions:

The rapid synthesis of alkene-functionalized POx macromers and their efficient UV crosslinking enable fast hydrogel formation.
The developed hydrogels exhibit tunable swelling properties and can be designed for degradability.
These poly(2-oxazoline) hydrogels represent promising candidates for future biomaterial applications due to their mild synthesis and processing conditions.