Supporting Information for
Journal of Applied Polymer Science
Solubilization and Polymer Analogous Reactions of
Poly(epichlorohydrin) in Ionic Liquids
Byoung Gak Kim1,2, Eun-Ho Sohn1, Jae Seung Chung1, Seung-Yeop Kwak2,*, and Jong-Chan Lee1,*
Department of Chemical and Biological Engineering, Seoul National University, Shilim-9Dong, Gwanak-Gu, Seoul 151-744, Korea, and Department of Materials Science and
Engineering, Seoul National University, Shilim-9-Dong, Gwanak-Gu, Seoul 151-744, Korea
* To whom correspondence should be addressed. E-mail: jongchan@snu.ac.kr. Fax: +82 2 888 1604
1
Department of Chemical and Biological Engineering, Seoul National University.
2
Department of Materials Science and Engineering, Seoul National University.
1
Preparation of poly[oxy[[2-(perfluorooctyl)ethyl]thiomethyl]ethylene] (H2F8TP).
H2F8TP synthesized in DMAc at 70 oC was contain byproducts more than 50 mol-%
but H2F8TP synthesized in ionic liquid, [bmim][Cl], does not contain any byproduct
and get higher conversion (100 mol-%) and yield (80 wt.-%) (Figure S1). 1H NMR of
sodium
1H,1H,2H,2H-perfluorodecanthiolate
(CDCl3
/
1,1,2-
trichlorotrifluoroethanemixture): δ= 2.53 (m, 2H), 2.88 (m, 2H). 1H NMR of H2F8TP
(CDCl3 / 1,1,2-trichlorotrifluoroethanemixture): δ= 2.39 (m, 2H), 2.73 (m, 2H), 2.81 (m,
2H), 3.64 (m, 3H).
Recycle of ionic liquid.
1H,1H,2H,2H-perfluorodecanthiol (464 mg, 0.97 mmol) was added to a stirred
solution of sodium methoxide (58 mg, 1.07 mmol) in methanol (10 mL). After stirring
at room temperature for 30 min, the mixture was transferred into a solution of
poly(epichlorohydrin) (76 mg, 0.82 mmol) in [hmim][Cl] (10 mL). The reaction mixture
was stirred at 70 oC for 15 min, then centrifuged at 12,150 g (10,000 rpm) for 2 h, a
transparent yellow liquid phase, identified as pure ionic liquid by NMR (Figure S2),
was separated from lower gel phase containing both small amount of ionic liquid and
product polymer. The gel phase was highly viscous and we can separate the ionic liquid
2
easily and successively to recycle. Figure S3 shows photographs of ionic liquid and
product. This process was repeated successfully 3 times.
3
Figure S1. NMR spectra of H2F8TP using: (A) DMAc; (B) ionic liquid [bmim][Cl].
4
Figure S2. NMR spectra of (A) [hmim][Cl] before use and (B) [hmim][Cl] recycled 3
times.
5
Figure S3. Photographs of ionic liquid and product: (A) before centrifuge; (B) after
centrifuge.
6