Styrenated urethane oil synthesis via CuAAC "click" chemistry approach

Yazgan-Birgi P., Alemdar N., Erciyes A. T.

PROGRESS IN ORGANIC COATINGS, vol.84, pp.107-114, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 84
  • Publication Date: 2015
  • Doi Number: 10.1016/j.porgcoat.2015.02.018
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.107-114
  • Istanbul Technical University Affiliated: Yes


In this study, a novel route for the modification of sunflower oil-based partial triglycerides with styrene (St) was described. For this purpose, in the first step, copolymers of St and 4-chloromethyl styrene (P(St-co-CMS)) were synthesized by free radical polymerization (FRP) and controlled/living radical polymerization (nitroxide mediated radical polymerization (NMRP)) methods. In the second step, chloro groups of these samples were transformed into azido groups by using NaN3/DMF and then azido groups were coupled with propargyl alcohol to achieve hydroxyl functional polystyrene chain (PSt-OH) via Cu(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition (CuAAC) "click" chemistry approach. Finally, alcohol groups of PSt-OH and the partial glyceride (PG) were combined by the reaction with toluene 2,4-diisocyanate (TDI). As a result, styrenated urethane oil (PG-TDI-PSt) was obtained as an oil-based binder. The structures were determined by FT-IR, H-1 NMR and GPC analyses, and film properties of the products were examined according to the related standards. (PG-TDI-PSt) gave good film properties, and therefore could be considered as an applicable oil-based binder. (C) 2015 Elsevier B.V. All rights reserved.