POS1-0147
Synthesis and Amphiphilic Property of Substituted Acrylic Acid Polymer with Octadecyl Group
Topic
S1. Polymer Synthesis
When and Where
Sep 29, 2026
08:30 - 09:30
Room 301 (Grand Ballroom)
Session Chairs
Hae Jung SON
Boseok KANG
Presenter(s)
Syamim Syufiana Binti Sazali (Mie University)
Co-Author(s)
Abstract
Amphiphilic polymers are composed of hydrophilic and hydrophobic parts. The combination of interfacial activity and self-organization makes them useful as surfactants, drug delivery systems, and tissue engineering materials. Amphiphilic homopolymers have also attracted much attention because they form diverse aggregates and exhibit stimuli-responsive behavior through interactions between hydrophilic and hydrophobic moieties.
Amphiphilic monomers based on substituted acrylic acid with a long alkyloxy segment at the α-position have attracted considerable interest. Recently, the preparation and properties of poly(α-dodecyloxymethylacrylic acid) (Poly-1) were investigated. Poly-1 forms reverse micelles and extracts water-soluble Rhodamine B into a hexane layer.
The purpose of this research is to synthesize a new amphiphilic homopolymer, poly(α-octadecyloxymethylacrylic acid) (Poly-2), bearing a longer alkyl chain at the α-position to explore materials with higher extraction ability. The synthesis of the new monomer, α-octadecyloxymethylacrylic acid (2), was examined using tert-butyl acrylate as a starting material. First, a hydroxymethyl group was introduced at the α-position of tert-butyl acrylate by the Morita–Baylis–Hillman reaction to afford tert-butyl α-hydroxymethylacrylate. The hydroxymethyl group was converted to a bromomethyl group with phosphorus tribromide, followed by introduction of an octadecyl group via Williamson ether synthesis using triethylamine and 4-dimethylaminopyridine. Finally, the tert-butyl group was hydrolyzed to obtain the target monomer 2. Poly-2 was obtained by radical polymerization of 2 in CHCl₃ at 60°C using 2,2′-azobisisobutyronitrile (AIBN) as an initiator. Poly-2 shows extraction ability toward Rhodamine B similar to that of Poly-1.
Amphiphilic monomers based on substituted acrylic acid with a long alkyloxy segment at the α-position have attracted considerable interest. Recently, the preparation and properties of poly(α-dodecyloxymethylacrylic acid) (Poly-1) were investigated. Poly-1 forms reverse micelles and extracts water-soluble Rhodamine B into a hexane layer.
The purpose of this research is to synthesize a new amphiphilic homopolymer, poly(α-octadecyloxymethylacrylic acid) (Poly-2), bearing a longer alkyl chain at the α-position to explore materials with higher extraction ability. The synthesis of the new monomer, α-octadecyloxymethylacrylic acid (2), was examined using tert-butyl acrylate as a starting material. First, a hydroxymethyl group was introduced at the α-position of tert-butyl acrylate by the Morita–Baylis–Hillman reaction to afford tert-butyl α-hydroxymethylacrylate. The hydroxymethyl group was converted to a bromomethyl group with phosphorus tribromide, followed by introduction of an octadecyl group via Williamson ether synthesis using triethylamine and 4-dimethylaminopyridine. Finally, the tert-butyl group was hydrolyzed to obtain the target monomer 2. Poly-2 was obtained by radical polymerization of 2 in CHCl₃ at 60°C using 2,2′-azobisisobutyronitrile (AIBN) as an initiator. Poly-2 shows extraction ability toward Rhodamine B similar to that of Poly-1.
