A novel well-defined linear poly(methacrylic acid) macromonomers for biomaterial applications: The synthesis and characterization

A novel well-defined linear poly(methacrylic acid) macromonomers for biomaterial applications: The synthesis and characterization

Audiovisual work

Low molecular weight alpha-allyl terminated poly(tert-butyl methacrylate) (poly(t-BMA)) macromonomers with narrow polydispersities (Mw/Mn = 1.16) were synthesized via controlled atom transfer radical polymerization (ATRP) using Cu(I)Br/hexamethyltriethylenetetraamine catalyst system in conjunction with an allyl-2-bromoisobutyrate as the functional initiator. The polymerizations exhibited a linear increase of molecular weight in direct proportion to the monomer conversion and a first-order kinetics with respect to monomer concentration (GPC and GC analysis). No significant difference was found between using polar or non-polar solvents (tetrahydrofuran or benzene, respectively). Optimization of reaction conditions with a view to obtain the highest degree of active terminal bromine is discussed. Quenching the ATRP reaction with allyltributyltin afforded alpha,omega-allyl terminated poly(t-BMA) macromonomers by replacing of the terminal bromine for omega-allyl functional group. Successful synthetic steps were confirmed by 1H NMR, FT-IR and MALDI-TOF analyses. Well-defined alpha,omega-allyl terminated poly(methacrylic acid) macromonomers were obtained by deprotection of tert-butyl group from alpha,omega-allyl terminated poly(t-BMA) macromonomers, which are candidates for further polymerization to form end-linked hydrogels useful in biomaterial/tissue engineering applications.

Low molecular weight alpha-allyl terminated poly(tert-butyl methacrylate) (poly(t-BMA)) macromonomers with narrow polydispersities (Mw/Mn = 1.16) were synthesized via controlled atom transfer radical polymerization (ATRP) using Cu(I)Br/hexamethyltriethylenetetraamine catalyst system in conjunction with an allyl-2-bromoisobutyrate as the functional initiator. The polymerizations exhibited a linear increase of molecular weight in direct proportion to the monomer conversion and a first-order kinetics with respect to monomer concentration (GPC and GC analysis). No significant difference was found between using polar or non-polar solvents (tetrahydrofuran or benzene, respectively). Optimization of reaction conditions with a view to obtain the highest degree of active terminal bromine is discussed. Quenching the ATRP reaction with allyltributyltin afforded alpha,omega-allyl terminated poly(t-BMA) macromonomers by replacing of the terminal bromine for omega-allyl functional group. Successful synthetic steps were confirmed by 1H NMR, FT-IR and MALDI-TOF analyses. Well-defined alpha,omega-allyl terminated poly(methacrylic acid) macromonomers were obtained by deprotection of tert-butyl group from alpha,omega-allyl terminated poly(t-BMA) macromonomers, which are candidates for further polymerization to form end-linked hydrogels useful in biomaterial/tissue engineering applications.

macromonomers, biomaterials

macromonomers, biomaterials

Vojtová, L., Koberstein, J. T., Turro, N. T.

10.09.2002

Brno University of Technology

Brno

0009-2770

Chem. Listy, Symposia 2002

1

S227

5