Design of controlled releasing system: Synthesis of an amphiphilic copolymer endowed with acid-labile side chains based on quaternarization of amine-containing prepolymer with benzyl halide having acetal moiety
2009
Morinaga, Hisatoyo | Morikawa, Hiroshi | Sudo, Atsushi | Endo, Takeshi
A methacrylate having a hydrophilic poly(ethylene glycol) chain and 2-(N,N-dimethylamino)ethyl methacrylate were radically copolymerized to obtain a statistical hydrophilic copolymer having tertiary amino groups in the side chains. The obtained polymeric amine was quantitatively quaternarized by a benzyl chloride-type molecule having an acetal moiety derived from geraniol, which is a hydrophobic alcohol widely used as a fragrance ingredient. The resulting copolymer, which had PEG chain and the quaternary ammonium moieties as hydrophiles and the acetal moieties as hydrophobes, exhibited amphiphilicity to form stable associates in water. The acetal moieties were stable for 30 days at pH 9, while they were gradually hydrolyzed at pH 4 to release geraniol continuously at least for 30 days, confirming the potential applicability of the copolymer to a controlled releasing system of functional molecules.
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