Qu Taoguang, West Kevin N, Rupar Paul A
Department of Chemistry & Biochemistry, The University of Alabama Tuscaloosa Alabama 35487-0336 USA
Department of Chemical & Biomolecular Engineering, The University of South Alabama Mobile Alabama 36688-0001 USA.
RSC Adv. 2023 Jul 28;13(33):22928-22935. doi: 10.1039/d3ra03478j. eCollection 2023 Jul 26.
Poly(ester amide)s (PEAs) bearing various side chains were synthesized by post-polymerization modification of PA-1, a vinylidene containing PEA. The thiols 1-dodecanethiol (1A-SH), 2-phenylethanethiol (1B-SH), 2-mercaptoethanol (1C-SH), thioglycolic acid (1D-SH), furfuryl mercaptan (1E-SH) and sodium-2-mercaptoethanesulfonate (1F-SH) were reacted with PA-1 to form PEAs PA-1A through PA-1F respectively. PEAs containing non-polar thiol side chains (PA-1A, PA-1B, PA-1E), showed little change in solubility compared to PA-1, while PEAs with more polar side chains improved solubility in more polar solvents. PA-1F, functionalized with sodium-2-mercaptoethanesulfonate, became water-soluble. The introduction of pendant functional groups impacted the thermal behaviors of PEAs in a wide range. The PEAs were thermally stable up to 368 °C, with glass transition temperatures () measured between 117 to 152 °C. Moreover, to demonstrate the versatility of the PEAs, thermal reprocessable networks and polyurethanes were successfully fabricated by reacting with a bismaleimide (1,6-bis(maleimido)hexane, 1,6-BMH) and a diisocyanate (4,4'-diphenylmethane diisocyanate, 4,4'-MDI), respectively. This study paves the way for the facile synthesis of functional poly(ester amide)s with great potential in many fields.
通过对含偏二乙烯基的聚（酯酰胺）PA-1进行后聚合改性，合成了带有各种侧链的聚（酯酰胺）（PEA）。硫醇1-十二烷硫醇（1A-SH）、2-苯乙硫醇（1B-SH）、2-巯基乙醇（1C-SH）、巯基乙酸（1D-SH）、糠硫醇（1E-SH）和2-巯基乙磺酸钠（1F-SH）分别与PA-1反应，形成PEA PA-1A至PA-1F。含有非极性硫醇侧链的PEA（PA-1A、PA-1B、PA-1E）与PA-1相比，溶解度变化不大，而具有更多极性侧链的PEA在极性更强的溶剂中的溶解度有所提高。用2-巯基乙磺酸钠官能化的PA-1F变得可溶于水。侧基官能团的引入在很大范围内影响了PEA的热行为。PEA在高达368℃时具有热稳定性，玻璃化转变温度（）在117至152℃之间。此外，为了证明PEA的多功能性，分别通过与双马来酰亚胺（1,6-双（马来酰亚胺基）己烷，1,6-BMH）和二异氰酸酯（4,4'-二苯基甲烷二异氰酸酯，4,4'-MDI）反应，成功制备了热可再加工网络和聚氨酯。本研究为在许多领域具有巨大潜力的功能性聚（酯酰胺）的简便合成铺平了道路。
