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Citation: LI Cong, HU Fangyu, JIANG Liming, CHENG Xinchai, CHEN Yaozu. Synthesis of New Fluorinated Epoxides and Preliminary Investigations on Their UV-curing Properties[J]. Chinese Journal of Applied Chemistry, ;2011, 28(2): 177-181. doi: 10.3724/SP.J.1095.2011.00244 shu

Synthesis of New Fluorinated Epoxides and Preliminary Investigations on Their UV-curing Properties

1.
a MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027;
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b Zhejiang Chehe Chemical Engineering Co.Ltd., Suichang

Corresponding author: JIANG Liming,
Received Date: 27 April 2010
Available Online: 5 July 2010
Fund Project: 浙江省重点科技专项(2009C11129)资助项目 (2009C11129)

Perfluoroalkyoxy-substituted cyclohexene oxides(EFPO1 and EFPO2) were obtained by two-step reactions using the dimer and trimer of hexafluoropropylene oxide and 4-cyclohexene-1,2-dimethanol as main raw materials.The structures of as-synthesized products were confirmed by spectroscopy analyses including FT-IR and ¹H NMR.These fluoro-epoxides are compatible with the prepolymers such as bisphenol-A diglycidyl ether and ethylene glycol diglycidyl ether,thereby endowing the coatings composed of them with improved hydrophobicity as evidenced by the photoinitiated curing experiments.The preliminary investigation of their UV-curing performance shows that the hydrophobicity increases linearly with increasing fluoro-epoxide content in the composition.As expected,the hydrophobic effect is more pronounced for EFPO2 than EFPO1 at the same conditions,because the former has a longer ferfluoroalkyoxy group.For example,upon addiing 1% mass fraction of EFPO2,the water contact angle of the UV-cured films was 99° and was higher 14° than that found for the films without the fluoro-component,whereas the value for EFPO1-modified films was 87°.When containing 5% EFPO2,high hydrophobic surface was achieved with a water contact angle of 113 for the UV-cured films.In addition,it should be pointed out that the hydrophobic surface can be further improved by heating the UV-cured films at 110℃ for 6 h.For the coatings containing 1%~5% EFPO2,the post-heating treatment resulted in a change of the water contact angles from the range 99°~113° to 113°~118°,while the changes were from 87°~100° to 99°~110° for EFPO1 analogs.The thermal migration of fluoro-chains and aggregation on the film surface seems to be responsible for the enhancement in hydrophobicity.Consequently,this new type of fluorine-containing epoxy monomers is expected as the surface modifier used in coatings,inks and release materials.
- fluorinated epoxides,
- UV-curing,
- hydrophobicity,
- coating
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