Macromolecular Research

  • 제13권6호
  • /
  • Pages.467-476
  • /
  • 2005
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  • 1598-5032(pISSN)
  • /
  • 2092-7673(eISSN)
한국고분자학회 (The Polymer Society of Korea)
권호 표지

Synthesis and pH-Dependent Micellization of Sulfonamide-Modified Diblock Copolymer

  • Pal Ravindra R. (Department of Polymer Science and Engineering, Sungkyunkwan University) ;
  • Kim Min Sang (Department of Polymer Science and Engineering, Sungkyunkwan University) ;
  • Lee Doo Sung (Department of Polymer Science and Engineering, Sungkyunkwan University)
  • 발행 : 2005.12.01
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초록

The main objective of this study was to develop and characterize pH-sensitive biodegradable polymeric materials. For pH-sensitivity, we employed three kinds of moieties: 2-amino-3-(lH-imidazol-4-yl)-propionic acid (H), N-[4-( 4,6-dimethyl-pyrimidin-2ylsulfamoyl)-phenyl]succinamic acid (SM), and 2- {3-[ 4-( 4,6-dimethyl-pyrim­idin- 2-ylsulfamoyl)-phenylcarbamoyl]-propionylamino} -3-(3 H - imidazol-4-yl)-propionic acid (SH). The pH -sensitive diblock copolymers were synthesized by ring opening polymerization and coupling reaction from poly(ethylene glycol) (MPEG), $\varepsilon$-caprolactone (CL), D,L-lactide (LA) and pH-sensitive moieties. The pH-sensitive SH molecule was synthesized in a two-step reaction. The first step involved the synthesis of SHM, a methyl ester derivative of SH, by coupling reaction of SM and L-histidine methyl ester dihydrochloride, whereas the second step involved the hydrolysis of the same. The synthesized SM, SHM and SH molecules were characterized by FTIR, $^{1}H$-NMR and $^{13}C$-NMR spectroscopy, whereas diblock copolymers and pH-sensitive diblock copolymer were characterized by $^{1}H$-NMR and GPC analysis. The critical micelle concentrations were determined at various pH conditions by fluorescence technique using pyrene as a probe. The micellization and demicellization studies of pH-sensitive diblock copolymers were also done at different pH conditions. The pH-sensitivity was further established by acid-based titration and DLS analysis.

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