Synthesis and characterization of styrene – maleic anhydride copolymer derivatives
Date
2009-12
Authors
Mpitso, Khotso
Journal Title
Journal ISSN
Volume Title
Publisher
Stellenbosch : University of Stellenbosch
Abstract
ENGLISH ABSTRACT:
In this study, a functional styrene – maleic anhydride copolymer (SMA) was synthesized via
reversible addition-fragmentation chain transfer mediated polymerization (RAFT). The
obtained copolymer had an alternating structure with well controlled molecular weight. The
structure of the copolymer was found to alternating when characterized by NMR and
MALDI-Tof-MS.
SMA copolymer is functional polymer due to the presence of reactive maleic anhydride
moiety in its backbone. The SMA copolymer was used as a starting material for synthesis of
other three copolymers with potential anti-viral activity. These three copolymers are referred
to as SMA copolymer derivatives because they were synthesized by reacting either maleic
anhydride or styrene moieties with certain chemical compounds. The three derived
copolymers are; styrene-maleimde copolymer (SMI), styrene sulfonate-maleic anhydride
copolymer (SSMA) and styrene sulfonate– maleimide copolymer (SSMI).
SMI was synthesized by reacting 4-aminomethylbenzene sulfonamide compound with
maleic anhydride moieties on the backbone of SMA copolymer. The reaction proceeded in
the presence of co-catalysts triethylamine and dimethylamino pyridine to from amide
linkages. The copolymer was characterized by NMR spectroscopy, SEC and FTIR
spectroscopy.
SSMA copolymer was successfully synthesized by reacting styrene moieties of the SMA
copolymers with chlorosulfonic acid. The SSMA copolymer was further reacted with amine
compound to synthesize SSMI copolymer. The synthesis of SSMI was achieved by reacting
the maleic anhydride moieties in the backbone of the SSMA copolymer with N1,N1-
dimethylpropane-1,3-diamine. Both copolymers were successfully characterized by FTIR
spectroscopy.
AFRIKAANSE OPSOMMING: 'n Funksionele stireen-maleïensuuranhidried (SMA) kopolimeer is berei d.m.v. omkeerbare addisie-fragmentasie ketting-oordrag-beheerde (OAFO) polimerisasie. Die polimere het 'n wissellende struktuur en goed beheerde molekulêre massa gehad. Die wisselende struktuur is bevestig d.m.v. KMR en MALDI-ToF analise. Die SMA kopolimeer is funksioneel a.g.v. die teenwoordigheid van reaktiewe anhidriedgroepe in die polimeerrugraat. Hierdie SMA kopolimeer is gebruik as uitgangstof vir die bereiding van drie ander kopolimere met potensiele teenvirale-aktiwiteit: stireenmaleïimied kopolimeer (SMI), stireensulfonaat-maleïensuuranhidried kopolimeer (SSMA) en stireensulfonaat-maleïimied kopolimeer (SSMI). Hiedie kopolimere staan bekend as SMA-kopolimeerderivate omdat hulle berei is deur d.m.v. die reaksie van of maleïensuuranhidried of stireengroepe. SMI is suksesvol berei d.m.v. die reaksie van 4-aminobenseensulfonamied met maleïensuuranhidriedeenhede op die polimeerruggraat in die teenwoordigheid van die kokataliste trietielamien of dimetielaminopiridien, om sodoende amiedbindings te vorm. Die kopolimere is gekarakteriseer m.b.v. grootte-uitsluitings-chromatografie (SEC), KMR en FTIR. Die SMMA kopolimeer is suksesvol gesintetiseer d.m.v. die reaksie van die stireeneenhede van die SMMA kopolimeer met chlorosulfoonsuur. Die SSMA kopolimeer is verder gereageer met amienverbindings om die SSMI kopolimeer te lewer. SMMI kopolimere is berei d.m.v. die reaksie van die maleïensuuranhidriedgroepe in die ruggraat van die SSMA kopolimeer met N',N'-dimetielpropaan-1,3-diamien. Albei kopolimere is suksesvol gekarakteriseer m.b.v. KMR en FTIR.
AFRIKAANSE OPSOMMING: 'n Funksionele stireen-maleïensuuranhidried (SMA) kopolimeer is berei d.m.v. omkeerbare addisie-fragmentasie ketting-oordrag-beheerde (OAFO) polimerisasie. Die polimere het 'n wissellende struktuur en goed beheerde molekulêre massa gehad. Die wisselende struktuur is bevestig d.m.v. KMR en MALDI-ToF analise. Die SMA kopolimeer is funksioneel a.g.v. die teenwoordigheid van reaktiewe anhidriedgroepe in die polimeerrugraat. Hierdie SMA kopolimeer is gebruik as uitgangstof vir die bereiding van drie ander kopolimere met potensiele teenvirale-aktiwiteit: stireenmaleïimied kopolimeer (SMI), stireensulfonaat-maleïensuuranhidried kopolimeer (SSMA) en stireensulfonaat-maleïimied kopolimeer (SSMI). Hiedie kopolimere staan bekend as SMA-kopolimeerderivate omdat hulle berei is deur d.m.v. die reaksie van of maleïensuuranhidried of stireengroepe. SMI is suksesvol berei d.m.v. die reaksie van 4-aminobenseensulfonamied met maleïensuuranhidriedeenhede op die polimeerruggraat in die teenwoordigheid van die kokataliste trietielamien of dimetielaminopiridien, om sodoende amiedbindings te vorm. Die kopolimere is gekarakteriseer m.b.v. grootte-uitsluitings-chromatografie (SEC), KMR en FTIR. Die SMMA kopolimeer is suksesvol gesintetiseer d.m.v. die reaksie van die stireeneenhede van die SMMA kopolimeer met chlorosulfoonsuur. Die SSMA kopolimeer is verder gereageer met amienverbindings om die SSMI kopolimeer te lewer. SMMI kopolimere is berei d.m.v. die reaksie van die maleïensuuranhidriedgroepe in die ruggraat van die SSMA kopolimeer met N',N'-dimetielpropaan-1,3-diamien. Albei kopolimere is suksesvol gekarakteriseer m.b.v. KMR en FTIR.
Description
Thesis (MSc (Chemistry and Polymer Science))--University of Stellenbosch, 2009.
Keywords
RAFT polymerization, Styrene -- Maleic anhdride, Copolymers, Addition polymerization, Dissertations -- Polymer science, Theses -- Polymer science