Zespół Innowacji, Technologii i Analiz

Projekty z zakresu ochrony zdrowia

Projekty z zakresu ochrony zdrowia


pH-Sensitive biodegradable hydrogels

Nazwa projektu

pH-Sensitive biodegradable hydrogels based on functional poly(caprolactone)

Kierownik projektu 

Dr inż. Michał Kawalec

Okres realizacji 


Wartość projektu 

268 333,000

Cel projektu 

Functional synthetic polymers have received considerable scientific interest and attention in recent years for their potential as promising novel materials enhancing properties of well-known polymers. The availability of functional pendant groups is highly desirable for the fine tuning of properties like crystallinity, glass transition temperature, hydrophilicity and chemical reactivity in view of, e.g., drug delivery systems, improvement of biocompatibility, modification of bioadhesion. However, majority of commercially available functional monomers are (meth)acrylates which form respective polymers known to be non-degradable. Apparently, dormant character of the materials is not always desired, especially when temporary biomedical application is intended. In this field one of the most often investigated polymers are aliphatic polyesters comprising of lactides, glycolide and ε- caprolactone units. The polymers own their popularity to the biodegradable and biocompatible character as well as commercial availability of the monomers which, in conjunction with developed polymerization techniques, gives access to materials of desired properties. However, functionalization of such molecules is extremely limited. In general, a few strategies were reported in literature. First strategy assumes enolization of poly(caprolactone) (PCL) with lithium diisopropyl amide and reaction of such-formed carboanions with various electrophiles (benzaldehyde, naphthoyl chloride, benzyl chloroformate, and iodomethane). [S. Ponsart, J. Coudane, M. Vert Biomacromolecules 2000, 1, 275] However, the degree of substitution depended on experimental conditions while PCL itself, suffered main chain scission during the enolization. The same procedure was applied later on to produce α-iodo-ε-caprolactone. [S. El Habnouni, V. Darcos, J. Coudane Macromol. Rapid Commun. 2009, 30, 165] Homopolymerization of α-iodo-ε-caprolactone and its copolymerization with ε-caprolactone, catalyzed by tin compounds resulted in polymers with expected molar masses and compositions. Several γ-substituted-ε-caprolactones were also synthesized like 5-ethylene ketal ε-caprolactone [D. Tian, Ph. Dubois, C. Grandfils, R. Jerome Macomolecules 1997, 30, 406] 4-(t-butyldimethylsilyloxy)-ε-caprolactone [G. Pitt, Z.W. Gu, P. Ingram, R.W. Hendren J Polym Sci Polym Chem 1987, 25, 955]) or γ-(2-bromo-2-methylpropionyl)-ε- caprolactone (D. Mecerreyes, B. Atthoff, K.A. Boduch, M. Trollsas, J.L. Hedrick Macromolecules 1999, 32, 5175] among which first and third were shown to polymerize in “living” manner. Noteworthy, relatively simple strategy of α-chloro-ε-caprolactone preparation was developed via one step oxidation of commercially available α-chloro-cyclohexanone with m-chloroperbenzoic acid.

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