Controlled polymerisation of sulfonate-containing monomers via Atom Transfer Radical Polymerisation

Darren Campbell, Arun Sohdi, Brian Tighe

Research output: Contribution to conferenceAbstract

Abstract

Anti-fouling is a key element in the development of biomedical materials. Poly(ethyleneglycol) is commonly used as an integral part of biomaterials for this very purpose. However polyethers can be problematic as they can autooxidise relatively rapidly, especially in the presence of oxygen and transition metal ions, present in most biochemically-relevant solutions. Zwitterionic-based materials have shown potential as biomaterials. For example
phosphorylcholine-based polymers, such as - methacryloyloxyethylphosphorylcholine (MPC), have been used to produce commercial biocompatible materials. However, MPC has been
reported as difficult to synthesise and handle. Another class of zwitterionic monomer used in the literature is based on the sulfobetaine moiety. The resulting polysulfobetaines have also been reported as having low protein absorption and as being easier to handle, they therefore have potential for biomaterial applications. One such sulfobetaine monomer is N,Ndimethyl-
N-(2-acryloylethyl)-N-(3-sulfopropyl) ammonium betaine (SPDA). Very few studies have been carried out on the controlled polymerisation of SPDA in aqueous media. However there have been a number of studies on N-(3-sulfopropyl)-N-(methacryloxyethyl)-N,N dimethylammonium betaine (Figure 1), also known as sulfobetaine methacrylate (SBMA), which is the methacrylate analogue of SPDA. Zhang et al.2, 4 grafted two zwitterionic
polymers, PSBMA and poly(carboxybetaine methacrylate), from glass and gold substrates via Atom Transfer Radical Polymerisation (ATRP). The initiators were immobilised to the substrates using 2-bromo-2-methyl-N-3-[(triethoxysilyl)propyl]propanamide (BrTMOS). The catalyst system for polymerisation was CuBr with 2,2’-bipyridine (bpy). These studies were carried out in a degassed solvent of pure water and methanol (1:1 volume ratio). The PSBMA grafts were demonstrated to have high resistance to protein absorption, as effective as PEG and MPC-based polymers.
Original languageEnglish
PagesC10_P35
Publication statusUnpublished - 2010
Event43rd IUPAC World Polymer Congress - Glasgow, United Kingdom
Duration: 11 Jul 201016 Jul 2010
http://www.rsc.org/ConferencesAndEvents/RSCConferences/Macro2010/

Congress

Congress43rd IUPAC World Polymer Congress
Abbreviated titleMACRO 2010
CountryUnited Kingdom
CityGlasgow
Period11/07/1016/07/10
OtherThe 43rd IUPAC World Polymer Congress, 'Macro2010', was the latest in the series of the biennial meetings of the IUPAC Polymer Division. The series has been running for several decades and is the largest international multi-symposium conference dedicated to all aspects of polymer science and engineering.

Macro2010 was organised by the Royal Society of Chemistry (RSC) and hosted by the Pure and Applied Macromolecular Chemistry Group (Macro Group UK), a joint interest group of the RSC and the Society of Chemical Industry (SCI).
Internet address

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Atom transfer radical polymerization
Biocompatible Materials
Methacrylates
Monomers
Polymerization
Betaine
Polymers
Polyethers
Substrates
Fouling
Ammonium Compounds
Grafts
Gold
Polyethylene glycols
Transition metals
Metal ions
Methanol
Proteins
Oxygen
Glass

Cite this

Campbell, D., Sohdi, A., & Tighe, B. (2010). Controlled polymerisation of sulfonate-containing monomers via Atom Transfer Radical Polymerisation. C10_P35. Abstract from 43rd IUPAC World Polymer Congress, Glasgow, United Kingdom.
Campbell, Darren ; Sohdi, Arun ; Tighe, Brian. / Controlled polymerisation of sulfonate-containing monomers via Atom Transfer Radical Polymerisation. Abstract from 43rd IUPAC World Polymer Congress, Glasgow, United Kingdom.
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Campbell, D, Sohdi, A & Tighe, B 2010, 'Controlled polymerisation of sulfonate-containing monomers via Atom Transfer Radical Polymerisation' 43rd IUPAC World Polymer Congress, Glasgow, United Kingdom, 11/07/10 - 16/07/10, pp. C10_P35.

Controlled polymerisation of sulfonate-containing monomers via Atom Transfer Radical Polymerisation. / Campbell, Darren; Sohdi, Arun; Tighe, Brian.

2010. C10_P35 Abstract from 43rd IUPAC World Polymer Congress, Glasgow, United Kingdom.

Research output: Contribution to conferenceAbstract

TY - CONF

T1 - Controlled polymerisation of sulfonate-containing monomers via Atom Transfer Radical Polymerisation

AU - Campbell, Darren

AU - Sohdi, Arun

AU - Tighe, Brian

PY - 2010

Y1 - 2010

N2 - Anti-fouling is a key element in the development of biomedical materials. Poly(ethyleneglycol) is commonly used as an integral part of biomaterials for this very purpose. However polyethers can be problematic as they can autooxidise relatively rapidly, especially in the presence of oxygen and transition metal ions, present in most biochemically-relevant solutions. Zwitterionic-based materials have shown potential as biomaterials. For examplephosphorylcholine-based polymers, such as - methacryloyloxyethylphosphorylcholine (MPC), have been used to produce commercial biocompatible materials. However, MPC has beenreported as difficult to synthesise and handle. Another class of zwitterionic monomer used in the literature is based on the sulfobetaine moiety. The resulting polysulfobetaines have also been reported as having low protein absorption and as being easier to handle, they therefore have potential for biomaterial applications. One such sulfobetaine monomer is N,Ndimethyl-N-(2-acryloylethyl)-N-(3-sulfopropyl) ammonium betaine (SPDA). Very few studies have been carried out on the controlled polymerisation of SPDA in aqueous media. However there have been a number of studies on N-(3-sulfopropyl)-N-(methacryloxyethyl)-N,N dimethylammonium betaine (Figure 1), also known as sulfobetaine methacrylate (SBMA), which is the methacrylate analogue of SPDA. Zhang et al.2, 4 grafted two zwitterionicpolymers, PSBMA and poly(carboxybetaine methacrylate), from glass and gold substrates via Atom Transfer Radical Polymerisation (ATRP). The initiators were immobilised to the substrates using 2-bromo-2-methyl-N-3-[(triethoxysilyl)propyl]propanamide (BrTMOS). The catalyst system for polymerisation was CuBr with 2,2’-bipyridine (bpy). These studies were carried out in a degassed solvent of pure water and methanol (1:1 volume ratio). The PSBMA grafts were demonstrated to have high resistance to protein absorption, as effective as PEG and MPC-based polymers.

AB - Anti-fouling is a key element in the development of biomedical materials. Poly(ethyleneglycol) is commonly used as an integral part of biomaterials for this very purpose. However polyethers can be problematic as they can autooxidise relatively rapidly, especially in the presence of oxygen and transition metal ions, present in most biochemically-relevant solutions. Zwitterionic-based materials have shown potential as biomaterials. For examplephosphorylcholine-based polymers, such as - methacryloyloxyethylphosphorylcholine (MPC), have been used to produce commercial biocompatible materials. However, MPC has beenreported as difficult to synthesise and handle. Another class of zwitterionic monomer used in the literature is based on the sulfobetaine moiety. The resulting polysulfobetaines have also been reported as having low protein absorption and as being easier to handle, they therefore have potential for biomaterial applications. One such sulfobetaine monomer is N,Ndimethyl-N-(2-acryloylethyl)-N-(3-sulfopropyl) ammonium betaine (SPDA). Very few studies have been carried out on the controlled polymerisation of SPDA in aqueous media. However there have been a number of studies on N-(3-sulfopropyl)-N-(methacryloxyethyl)-N,N dimethylammonium betaine (Figure 1), also known as sulfobetaine methacrylate (SBMA), which is the methacrylate analogue of SPDA. Zhang et al.2, 4 grafted two zwitterionicpolymers, PSBMA and poly(carboxybetaine methacrylate), from glass and gold substrates via Atom Transfer Radical Polymerisation (ATRP). The initiators were immobilised to the substrates using 2-bromo-2-methyl-N-3-[(triethoxysilyl)propyl]propanamide (BrTMOS). The catalyst system for polymerisation was CuBr with 2,2’-bipyridine (bpy). These studies were carried out in a degassed solvent of pure water and methanol (1:1 volume ratio). The PSBMA grafts were demonstrated to have high resistance to protein absorption, as effective as PEG and MPC-based polymers.

M3 - Abstract

SP - C10_P35

ER -

Campbell D, Sohdi A, Tighe B. Controlled polymerisation of sulfonate-containing monomers via Atom Transfer Radical Polymerisation. 2010. Abstract from 43rd IUPAC World Polymer Congress, Glasgow, United Kingdom.