Publication detail

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

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

Original Title

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

English Title

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

Type

presentation

Language

en

Original Abstract

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.

English abstract

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.

Keywords

macromonomers, biomaterials

Released

10.09.2002

Publisher

Brno University of Technology

Location

Brno

ISBN

0009-2770

Book

Chem. Listy, Symposia 2002

Edition

1

Edition number

1

Pages from

S227

Pages count

5

BibTex


@misc{BUT63347,
  author="Lucy {Vojtová} and Jeffrey T. {Koberstein} and Nicholas {Turro}",
  title="A novel well-defined linear poly(methacrylic acid) macromonomers for biomaterial applications: The synthesis and characterization",
  annote="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.",
  address="Brno University of Technology",
  booktitle="Chem. Listy, Symposia 2002",
  chapter="63347",
  edition="1",
  institution="Brno University of Technology",
  year="2002",
  month="september",
  pages="S227",
  publisher="Brno University of Technology",
  type="presentation"
}