Presentation Title

Synthesis of a Unique Fluoropolymer Material for Light-Cured 3D Printing and Aerospace Surface Protectants

Format of Presentation

Poster to be presented Friday March 31, 2017

Abstract

Technological advances in aerospace, automotive, electronics and other high-technology industries continue to increase the demand for improved materials capable of performance under extreme environmental conditions. Due to the low polarizability, high electronegativity and small atomic radius of the fluorine atom, the replacement of hydrogen with fluorine on carbon-based polymeric materials imparts exceptional thermal, oxidative and chemical stability, with resistance to weathering, friction and aging. These fluoropolymer materials – such as poly(hexafluoropropylene oxide), which is marketed under the Du Pont trade name of Krytox® – have already been used ubiquitously since the 1960s in applications such as automotive fluids, aerospace elastomers (e.g. rocket seals and O-rings), and microelectronics (e.g. core and cladding of optical fibers). However, to obtain the desired properties demanded by new applications, structural modification of these materials is required based on empirical precedent and theoretical properties. In this research, a poly(hexafluoropropylene oxide) (pHFPO) building block is specifically tailored to incorporate a perfluoroisopropenyl endgroup that would couple the monomer’s high-performance properties with the ability to polymerize (i.e. solidify) upon exposure to light or radical conditions. The resulting material is anticipated to be important in new fluoropolymer markets, including applications in anti-reflective and self-cleaning surfaces, energy storage devices, protective coatings for optical fibers and photo-induced 3D printing. Although perfluoroisopropenyl endgroups are highly valued for these applications, their inclusion in a fluoropolymer by an ether linkage is extremely challenging and essentially unexplored. Here, a unique pHFPO analogue is synthesized in which the material is obtained at over 95% conversion.

Department

Chemistry

Faculty Advisor

Chadron Mark Friesen

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Synthesis of a Unique Fluoropolymer Material for Light-Cured 3D Printing and Aerospace Surface Protectants

Technological advances in aerospace, automotive, electronics and other high-technology industries continue to increase the demand for improved materials capable of performance under extreme environmental conditions. Due to the low polarizability, high electronegativity and small atomic radius of the fluorine atom, the replacement of hydrogen with fluorine on carbon-based polymeric materials imparts exceptional thermal, oxidative and chemical stability, with resistance to weathering, friction and aging. These fluoropolymer materials – such as poly(hexafluoropropylene oxide), which is marketed under the Du Pont trade name of Krytox® – have already been used ubiquitously since the 1960s in applications such as automotive fluids, aerospace elastomers (e.g. rocket seals and O-rings), and microelectronics (e.g. core and cladding of optical fibers). However, to obtain the desired properties demanded by new applications, structural modification of these materials is required based on empirical precedent and theoretical properties. In this research, a poly(hexafluoropropylene oxide) (pHFPO) building block is specifically tailored to incorporate a perfluoroisopropenyl endgroup that would couple the monomer’s high-performance properties with the ability to polymerize (i.e. solidify) upon exposure to light or radical conditions. The resulting material is anticipated to be important in new fluoropolymer markets, including applications in anti-reflective and self-cleaning surfaces, energy storage devices, protective coatings for optical fibers and photo-induced 3D printing. Although perfluoroisopropenyl endgroups are highly valued for these applications, their inclusion in a fluoropolymer by an ether linkage is extremely challenging and essentially unexplored. Here, a unique pHFPO analogue is synthesized in which the material is obtained at over 95% conversion.