NDLI: Lipoates as building blocks of sulfur-containing branched macromolecules

Content Provider	Royal Society of Chemistry (RSC)
Author	Tsarevsky, Nicolay V. Tang, Houliang
Copyright Year	2015
Abstract	The radical copolymerization of cyclic disulfide-type monomers (ethyl lipoate or lipoic acid) with ethyl acrylate (1 : 1 molar feed ratio) yielded copolymers containing a significant fraction of backbone disulfide groups, which were degradable upon reduction. A compound containing two types of radically polymerizable groups (cyclic disulfide (1,2-dithiolane) and vinyl), 2-acryloyloxyethyl lipoate (AOELp), was synthesized and demonstrated to be a useful precursor for highly branched sulfur-containing polymers. Under radical polymerization conditions, AOELp served as a crosslinker, but up to moderate to high conversions and prior to gelation, soluble highly branched polymers were produced containing reductively degradable disulfide moieties, originating from the attack of a sulfur-centered radical on a 1,2-dithiolane group from AOELp or the polymer (pendant group), or the coupling of two sulfur-centered radicals. Alternatively, the reduction of AOELp afforded the corresponding dithiol acrylate (an AB2-type monomer), which participated in radical or ionic step-growth thiol–ene reactions, yielding highly branched reductively non-degradable polymers with thioether-type sulfur atoms in the backbones.
Starting Page	6936
Ending Page	6945
Page Count	10
File Format	HTM / HTML PDF
ISSN	17599954
Volume Number	6
Issue Number	39
Journal	Polymer Chemistry
DOI	10.1039/c5py01005e
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Lipoic acid Dithiolane Carboxylic acid Molar mass Acrylate Disulfide Radical polymerization Polymer Monomer Organosulfur compounds
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Bioengineering Biomedical Engineering Polymers and Plastics

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