Synthesis of Oligomers of 12-Acryloyloxydodecanoic Acid via Reversible Addition Fragmentation Transfer (RAFT) Polymerisation

Lilian Tichagwa, Ron D. Sanderson, Harald Pasch


A long chain fatty acid carrying an acryloyl functionality, 12-acryloyloxydodecanoic acid (12-ADA), was prepared
from 11-hydroxydodecanoic acid and acryloyl chloride and used as monomer in the synthesis of oligomers of 12-ADA
via the RAFT controlled polymerisation process. Reversible Addition Fragmentation Transfer (RAFT) reagents were
prepared and used to control the polymerisation process and produced an oligomeric product with few monomeric units
instead of a high molecular weight polymer of 12-ADA. The transfer reagents were prepared from Grignard
intermediates from a reaction of dithioacids with free radical initiators 2,2-azobisisobutyronitrile (AIBN) and
4,4-azobis(4-cyanopropanoic acid) (ACP). It was found that short-chain oligomers in the form of dimers and trimers
characterized by Electrospray Mass Spectrometry, ESMS and Gel Permeation chromatography, GPC were the major
products obtained when RAFT reagents had been used in the controlled polymerisation. As a control, polymerisation
was carried out in the absence of RAFT reagents and high molecular-weight polymers were obtained. This confirmed
the effectiveness of the prepared RAFT reagents as polymerisation controllers and provided a way for the synthesis of
oligomers. Here, the preparation of oligomers of 12-ADA using AIBN-RAFT reagents is reported. The method is
expected to provide one way of preparing oligomers of controlled chain length/molecular mass which also carry a
carboxylic acid functional group at one end.

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International Journal of Chemistry   ISSN 1916-9698 (Print)   ISSN 1916-9701 (Online)

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