2259
Full Paper
Macromolecular
Chemistry and Physics
wileyonlinelibrary.com DOI: 10.1002/macp.201300385
Reverse Iodine Transfer Polymerization (RITP)
of 1,1,2,2-Tetrahydroperfluorodecyl Acrylate
in Supercritical Carbon Dioxide
Cécile Bouilhac,* Mathieu Chirat, Christine Joly-Duhamel,
Patrick Lacroix-Desmazes*
Reverse iodine transfer polymerization (RITP) of 1,1,2,2-tetrahydroperfluorodecyl acrylate (FDA)
is successfully performed in supercritical carbon dioxide (scCO
2
) at 70 °C under a CO
2
pressure of
300 bar. PolyFDA (PFDA) of increasing molecular weights (from 10 000 to 100 000 g mol
−1
) is syn-
thesized with good agreement between theoretical,
1
H NMR spectroscopy and and size exclu-
sion chromatography/refractive index/right-angle laser-light scattering/differential viscometer
(SEC/RI/RALLS/DV)-estimated molecular weights (M
n
). Furthermore, the increase of M
n
goes with
a decrease of the dispersity of the polymers ( Ð
from 2.06 to 1.33), which is consistent with a
controlled radical polymerization (CRP). Lastly,
the structure of final PFDA and therefore the
RITP process are confirmed by matrix-assisted
laser desorption ionization time-of-flight mass
spectrometry (MALDI-TOF MS) analyses.
Dr. C. Bouilhac
Institut Charles Gerhardt Montpellier UMR5253 CNRS-
UM2-ENSCM-UM1, Equipe Ingénierie et Architectures
Macromoléculaires, Université Montpellier II cc1702, Place
Eugène Bataillon, 34095, Montpellier Cedex 5, France
E-mail: cecile.bouilhac@univ-montp2.fr
Dr. M. Chirat, Dr. C. Joly-Duhamel, Dr. P. Lacroix-Desmazes
Institut Charles Gerhardt Montpellier UMR5253 CNRS-
UM2-ENSCM-UM1, Equipe Ingénierie et Architectures
Macromoléculaires, Ecole Nationale Supérieure de Chimie de
Montpellier, 8 Rue de l’Ecole Normale, 34296, Montpellier
Cedex 5, France
E-mail: patrick.lacroix-desmazes@enscm.fr
the utilization of supercritical carbon dioxide (scCO
2
) has
attracted considerable interest in various fields, including
in polymerization.
[2–4]
Indeed, scCO
2
presents the advan-
tage of being inexpensive, environmentally benign, non-
toxic, non-flammable and its critical temperature and
pressure are easy to reach ( T
C
= 31 °C, P
C
= 73 bar). More-
over, scCO
2
has a very low viscosity and a high diffusion
coefficient along with densities similar to common sol-
vents. The ability to tune these physical properties by
slight variations of pressure or temperature is unique to
supercritical fluids.
The solubility of many homopolymers and copoly-
mers has been studied in scCO
2
.
[5–8]
Thus, polymers
can be categorized into either “CO
2
-philic” (such as
poly(fluoroalkyl(meth)acrylate)s and silicone-based poly-
mers
[9]
or “CO
2
-phobic” materials (conventional organic
polymers, either hydrophilic such as poly( N-vinyl pyr-
rolidone) or lipophilic such as polystyrene). Except a few
examples (e.g., Beuermann et al.
[10]
have successfully
synthesized polystyrene in scCO
2
via homogeneous free-
radical polymerization, although they worked at rela-
tively high pressure, up to 1500 bar, and the monomer
1. Introduction
In recent years, “green chemistry” has been emerging as
a concept going against, among others, the introduction
of persistent organic pollutants into the ecosystem.
[1]
In
this context, chemists are paying more and more atten-
tion to the replacement of conventional organic solvents
by environmentally friendly compounds. In particular,
Macromol. Chem. Phys. 2013, 214, 2259−2265
© 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim