620627-85-2Relevant academic research and scientific papers
A versatile route to functionalized dilactones as monomers for the synthesis of poly(α-hydroxy) acids
Leemhuis, Mark,Van Steenis, Jan Hein,Van Uxem, Michelle J.,Van Nostrum, Cornelus F.,Hennink, Wim E.
, p. 3344 - 3349 (2007/10/03)
A synthetic pathway to functionalized six-membered dilactones structurally analogous to lactide is described. Through the use of orthogonal protecting groups, the synthesis of functionalized dilactones was performed in a straightforward way by cyanuric chloride-mediated cyclization of the corresponding linear α-hydroxy acid dimers. The synthesis of three different dilactones - methylglycolide, benzyloxymethylglycolide, and 2-benzyloxymethyl-5-methylglycolide - by the same procedure demonstrated the versatility of this route. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Degradation mechanism and kinetics of thermosensitive polyacrylamides containing lactic acid side chains
Neradovic,Van Steenbergen,Vansteelant,Meijer,Van Nostrum,Hennink
, p. 7491 - 7498 (2007/10/03)
Diblock copolymers of poly(N-isopropylacrylamide-co-N-(2-hydroxypropyl)methacrylamide lactate) (poly(NIPAAm-co-HPMAm-lactate)) as a thermosensitive block and poly(ethylene glycol) (PEG) as a hydrophilic block form polymeric micelles above the cloud point (CP) of the temperature-sensitive block. Destabilization of these micelles occurs upon hydrolysis of the lactate side chains. Here we report on the degradation kinetics of the HPMAm-mono(di)lactate monomers and their copolymers with NIPAAm. The degradation of the monomers and polymers in their soluble state (thus below their CP) followed normal ester hydrolysis behavior: the degradation rate increased with temperature, pH (from pH 7.5 to 11), and dielectric constant of the medium. Above the CP, where the polymers are in a precipitated state, a significant retardation of the polymer degradation occurred due to a decrease of dielectric constant of the local environment of the precipitated polymer. This study shows that it is possible to predict the rate of formation of HPMAm in NIPAAm-co-HPMAm-lactate copolymers with results in an increase of the overall hydrophilicity of the polymers and destabilization of polymeric micelles based on poly(NIPAAm-co-HPMAm-lactate).
