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Synthesis, polymerisation and characterisation of a novel olefin-modified acrylate monomer, 1-methyl-1-propyl-hexel acrylate

Mange, Siyabonga (2005-03)

Thesis (PhD)--Stellenbosch University, 2005.


ENGLISH ABSTRACT: Finding use for byproducts from the chemical industry holds many advantages for a country's economy. Synthesis of new monomers from such byproducts adds value to otherwise otherwise low-value material. The synthesis of a new olefin-modified acrylate monomer, 1-methyl-1-propyl-hexyl acrylate (1-MPHA), derived from 1-pentene, is reported. Homopolymerisation of the monomer 1-MPHA was carried out in both benzene and in toluene. The products of full-conversion of the homopolymer poly-(1-MPHA) were characterised by GPC, NMR, TGA and DMA. Kinetic studies of the homopolymerisation process of 1- MPHAwere also undertaken. The monomer 1-methyl-1-propyl-hexyl acrylate (1-MPHA) was copolymerised with methyl methacrylate (MMA). Samples obtained from full conversion copolymerisations at various 1-MPHAIMMAfeed ratios were characterised by GPC, NMR, TGA and DMA. Reactivity ratios of the two monomers were obtained from in situ 1H NMR kinetic studies. 1-MPHA was also copolymerised with vinyl acetate (VAc). Samples obtained from full conversion copolymerisation with a 1-MPHA content ranging from 2 to 16 wt% were characterised by GPC, NMR, TGA and DMA. The solubility parameter and the hydrophobicity of the VAc/1-MPHA copolymers were also determined. Reactivity ratios of the two monomers were obtained from in situ 1HNMR kinetic studies. Further copolymerisation studies with styrene and glycidyl methacrylate as comonomers were undertaken. The chemical analysis and thermogravimetric analysis of the copolymers are reported. In conclusion, the use of 1-methyl-1-propyl-hexyl acrylate as a comonomer results in a reduction in the glass transition temperature, better thermal stability, increased hydrophobicity with an insignificant loss in stiffness of the copolymers. These properties are due to the long and branched chain structure of the 1-MPHA monomer.

AFRIKAANSE OPSOMMING: Gebruik van byprodukte van die chemiese nywerheid hou groot voordele in vir die land se ekonomie. Sintese van nuwe monomere vanuit sulke byprodukte dra by tot waardetoevoeging tot andersins lae-waarde byprodukte. Die sintese van 'n nuwe olefien-gewysigde akrilaatmonomeer afkomstig van 1-penteen, naamlik 1-metiel-1-propiel-heksielakrilaat (1-MPHA), word hier beskryf. Homopolimerisasie van die monomeer 1-MPHA is uitgevoer in beide benseen en tolueen. Die produkte van die volledige omskakeling van die homopolimeer is met behulp van GPC, KMR, TGA en DMA gekarakteriseer. Die reaksiekinetika van die homopolimerisasie van 1-MPHA is ook ondersoek. Die monomeer 1-MPHA is met metielmetakrilaat (MMA) gekopolimeriseer. Monsters van die volledig omgeskakelde kopolimere met verskeie 1- MPHNMMA voerverhoudings is m.b.v. GPC, KMR,' TGA en DMA gekarakteriseer. Die reaktiwiteitsverhoudings van die twee monomere is vanaf 1HKMR-studies bepaat. 1-MPHA is ook met vinielasetaat (VAc) gekopolimeriseer. Monsters van die produk van die volledige kopolimerisasie met 1-MPHA , met 'n inhoud van 2- 16 massa 0/0, is ook m.b.v. GPC, KMR, TGA en DMA gekarakteriseer. Die 1- MPHA het die hidrofobisiteit van VAc/1-MPHA aansienlik verhoog. Die reaktiwiteitsverhoudings van die twee monomere is vanaf in situ 1H KMRstudies bepaal. Verdere kopolimerisasiestudies met stireen en glisidielmetakrilaat as komonomere is onderneem. Chemiese- en termogravimetriese analises van die kopolimere is gedoen en gerapporteer. Ter afsluiting, die gebruik van 1-metiel-1-propiel-heksielakrilaat as komonomeer het 'n verlaging in die glasoorgangstemperatuur, verhoogde termiesestabiliteit, verhoogde hidrofobisiteit, en 'n klein verlies in die stewigheid (Eng. stiffness) van die kopolimeer tot gevolg. Hierdie eienskappe is as gevolg van die lang, vertakte kettingstruktuur van die 1-MPHA monomeer.

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