Premium
Tailored Thiol‐Functional Polyamides: Synthesis and Functionalization
Author(s) -
Mommer Stefan,
Keul Helmut,
Möller Martin
Publication year - 2014
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201400377
Subject(s) - thiolactone , polymer chemistry , polyamide , monomer , ethylene glycol , thiol , acrylate , surface modification , ether , materials science , chemistry , organic chemistry , polymer
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 (M ¯ n= 480 and 1700 g mol −1 ) results in water‐soluble amphiphilic polyamides with molecular weights higher than 10 000 g mol −1 .