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

Abstract

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. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 3241–3247, 2009

A new water‐soluble branched poly(ethylene imine) derivative having hydrolyzable imidazolidine moieties and its application to long‐lasting release of aldehyde

“…In addition, this strategy with using polymer scaffolds offers other advantages: Especially, in fragrance applications, immobilization of highly volatile fragrance molecules onto polymers can prevent their rapid evaporation to allow long‐lasting of their scent. Freedom in designing polymer scaffold with optimized parameters such as molecular weight and composition is also an attractive feature of the strategy, by which miscibility and aggregation behaviors of the polymers can be controlled 9, 10…”

Effect of glass transition temperature on heat‐responsive gas bubbles formation from polymers containing tert‐butoxycarbonyl moiety

“…It was revealed that the T d 5 and T max values decreased to 130 and 143 °C in the addition of TsOH, respectively. Acid‐catalyzed deprotection was reported for the decomposition of polymers including BOC group 27–31 as well as other groups such as tert ‐butyl esters and acetal‐protected groups …”

Treatment of aortoiliac chronic total occlusions: Guidelines and reality

“…Development of polymeric profragrances can overcome these drawbacks (1) and (2). 1, 18–20 When the polymeric profragrances are synthesized by copolymerization of hydrophilic and hydrophobic monomers, varying their feed ratio enables adjustment of properties such as hydrophilicity.…”