Institute of Organic Chemistry

EPOXIDIZED Plukenetia conophora oil BASED THIOL –

ENE COATINGS
Akintayo Cecilia Olufunke, Michael A. R. Meier
Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, 76131 Karlsruhe, Germany E-mail: m.a.r.meier@kit.edu

Introduction
The reaction of multifunctional thiols and enes is an established radical reaction and can lead to the rapid
production of films and thermoset plastics with excellent mechanical and physical properties[1]. Plukenetia
conophora based thiols and enes were synthesized through the Lewis acid catalysed ring opening reaction of
epoxidized Plukenetia conophora oil with multifunctional thiols or hydroxyl functional allyl compounds,
respectively. The functional group conversions were determined by Fourier transform infrared spectroscopy
(FTIR) and 1H NMR. Thiol-ene functionalized products were then reacted at different mole ratios and at different
temperature (60, 90 and 100 °C) without initiators to form highly crosslinked polymers. The coating and thermal
properties of the resulting polymers were studied and characterized using DMTA, DSC, TGA, and GPC.

Experimentals and results

Plukenetia conophora based multifunctional thiols and enes were synthesized by reacting epoxidized PKCO with thiols
( trimethylol-Propane tri-3-mercaptopropionate (TMPTM),pentaerythritol tetra-3-mercaptopropionate (PTM) or enes (allyl
alcohol (AA) and tri-metylolpropane-di allyl ether (TAE)at room temperature.

Polymerization was carried out at 60,90 and 100oC without initiator , the reactant mole ratio 1:1 (thiol : ene)
Fig. 2: FTIR spectra of PKCO,EPKCO and PKCAA

PKCO

O
HO
O O
O
HO
O
Novozyme 435 OH O OH
H2O2(35%) / Toluene O O
1 16hrs / 40oC
n BF3, acetone
O O
O O
O O
PKCAA
O O
O O O OH
O O O
SH O HO O
O
O OH
HO O O OH
R
O
SH n HS OH O
SH
HS BF3, acetone EPKCO
R

HS
S
SH
R OH
OH R SH
HS S
S

HO
SH
HS
HS
O R HS
R
O OH SH
HS O S R
S HO S
O
O OH
HO S O OH
S SH
OH S SH
R

R R
SH
HS
SH
PKCAA
HS

EPKCO

PKCO

Fig. 1: Synthesis of thiol and ene functionalized EPKCO through reaction of

epoxy ring opening by (a) multifunctional thiols; and (b) hydroxyl functional Fig.3: NMR spectra of PKCO,EPKCO and PKCAA
enes

Acknowledgement
We thank the Alexander von Humboldt Foundation for a Georg Forster Research Fellowship for C.O. Akintayo

KIT – University of the State of Baden-Wuerttemberg and

National Research Center of the Helmholtz Association