title: Tailored thiol-functional polyamides: synthesis and functionalization.
abstract: In this article, a synthetic concept for the preparation of polyamides with functional side groups is described. First, the synthesis of a bis(thiolactone) monomer is shown in a concise three-step route from itaconic acid and DL-homocysteine thiolactone. The reactivity of the resulting bis(thiolactone) toward hexyl amine is examined. Next, the bis(thiolactone) is reacted as A,A-type monomer with different B,B-type comonomers (1,12-diaminododecane and 1,3-bis(aminopropyl)tetramethyldisiloxane). Ring opening of the thiolactones by the diamines leads to polyamides with pendant thiol groups. Using two diamines in different ratios, the properties of the resulting polyamides are tuned (thermal properties are determined) and different molecular weights are acquired. Subsequently, the thiol groups are reacted with methyl acrylate via Michael addition to functionalize the polyamides. Functionalization of thiol-functional polyamides using poly(ethylene glycol) monomethyl ether (mPEG) acrylates (Mn = 480 and 1700 g mol(-1) ) results in water-soluble amphiphilic poly-amides with molecular weights higher than 10,000 g mol(-1) .
authors.affiliation: DWI - Leibniz-Institute for Interactive Materials, Forckenbeckstr. 50, D-52056, Aachen, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Mommer
authors.forename: Helmut
authors.initials: H
authors.lastname: Keul
authors.forename: Martin
authors.initials: M
authors.lastname: Möller
mesh_terms: D009757:Nylons / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D009757:Nylons
keywords: Michael addition; polyamides; postpolymerization modification; thermal properties; thiols