Synthesis and characterization of styrene – maleic anhydride copolymer derivatives

• Main Author: Mpitso, Khotso
• Other Authors: Klumperman, L.
• Language: en_ZA
• Published: Stellenbosch : University of Stellenbosch 2009
• Subjects: RAFT polymerization; Styrene > Maleic anhdride; Copolymers; Addition polymerization; Dissertations > Polymer science; Theses > Polymer science; Chemistry and Polymer Science
• Online Access: http://hdl.handle.net/10019.1/1972

Thesis (MSc (Chemistry and Polymer Science))--University of Stellenbosch, 2009. === 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.