Poly(2‐oxazoline)s based on fatty acids

Abstract

Poly(2-oxazoline)s are an interesting class of synthetic poly(amide) s that can be prepared by living cationic ring-opening polymerization. The properties of poly(2-oxazoline) s can be tuned by variation of the 2-substituent of the 2-oxazoline monomer. In this contribution the utilization of fatty acids as side chains for poly(2-oxazoline) s is highlighted. The incorporation of such long aliphatic side-chains results in hydrophobic crystalline poly(2-oxazoline) s that are often applied for the preparation of amphiphilic structures as well as for low surface energy and low adhesive coatings. The most popular fatty-acid based poly(2-oxazoline) s are the saturated poly(2-nonyl-2-oxazoline) and poly(2-undecyl-2-oxazoline) as well as the unsaturated poly(2-decenyl-2-oxazoline) and poly(2-"soy alkyl''-2-oxazoline)

How to Modulate the Chemical Structure of Polyoxazolines by Appropriate Functionalization

“…2‐(9‐Decenyl)‐2‐oxazoline was modified by thiol‐ene coupling in the presence of 2‐mercaptoethanol giving polyols for polyurethane formulations 110. The unsaturated parts of the soy‐based 2‐oxazoline monomer have been employed to crosslink the cores of micelles under UV‐irradiation 114, 115. The same strategy has been used with tetrathiol in order to elaborate novel photoresists 116.…”

Bioinspired Poly(2-oxazoline)s

“…Aspects of advanced macromolecular engineering of polyoxazolines, including side-and end-chain functionalization, synthesis and properties of block and random copolymers, etc., have very recently been assorted by Hoogenboom [9,10], Schlaad et al [11], and Makino and Kobayashi [12]. The use of fatty acid based monomers for the preparation of sustainable poly(2-oxazoline)s was also recently highlighted by Hoogenboom [13].…”

“…Not considered are other emerging applications of poly(2-oxazoline)s, for instance in the fields of biomedicine and life sciences, where POXylation is being successfully introduced as an alternative to PEGylation [14], which has very recently been reviewed elsewhere [15]. Rather than trying to present a comprehensive overview of the literature as was done in other recent articles [9][10][11][12][13], it is aimed to introduce the importance and potential of bioinspired poly(2-oxazoline)s based on selected key references from the last decade.…”

A Green Approach for the Synthesis and Thiol‐ene Modification of Alkene Functio1489lized Poly(2‐oxazoline)s

“…[2,3] The chemical versatility of fatty acids, i.e., different chain length and amount of double bonds, has been exploited for the fabrication of various monomers as basis for the synthesis of well-defined polymers. [4,5] In addition, the double bond functionalities have been utilized for post-modification reactions of the resulting materials, such as cross-linking and thiolene reactions. [6,7] Recently, Turunc and Meier [8] described the synthesis, characterization, and polymerization of monomers derived from methyl 10-undecenoate via a thiol-ene (''click'') approach.…”

“…Up to date, diverse studies have been reported on the use of various saturated fatty acid-based 2-oxazoline monomers for the preparation of well-defined (co)polymers. [4] Moreover, the synthesis and polymerization of 2-''soy-alkyl''-2-oxazoline (SoyOx) [6,18] and 2-(dec-9-enyl)-2-oxazoline (DecEnOx), which are both based on unsaturated fatty acids, has been reported. The synthesis and polymerization of DecEnOx was first described by Cai and Litt.…”