Diels−Alder Trapping of Photochemically Generated o-Quinodimethane Intermediates: An Alternative Route to Photocured Polymer Film Development

Content Provider	Semantic Scholar
Author	Tyson, Daniel S. Ilhan, Faysal Meador, Mary Ann B. Smith, Dee Dee Scheiman, Daniel A. Meador, Michael A.
Copyright Year	2005
Abstract	Photolysis of o-methylphenyl ketones generates o-quinodimethane intermediates that can be trapped in situ by dienophiles through Diels−Alder cycloadditions. This well-known photochemical process is applied to a series of six new photoreactive monomers containing bis(o-methylphenyl ketone) functionalities combined with diacrylate and triacrylate esters for the development of acrylic ester copolymer blends. Irradiation of cyclohexanone solutions of the bis(o-methylphenyl ketone)s and acrylate esters produce thin polymer films. Solid state 13C NMR data indicated 47−100% reaction of the bis(o-methylphenyl ketone)s, depending on experimental conditions, to yield the desired products. DSC and TGA analyses were performed to determine the glass transition temperature, Tg, and onset of decomposition, Td, of the resulting polymer films. A statistical “design of experiments” approach was used to obtain a systematic understanding of the effects of experimental variables on the extent of polymerization and the final p...
Starting Page	3638
Ending Page	3646
Page Count	9
File Format	PDF HTM / HTML
Volume Number	38
Alternate Webpage(s)	https://ntrs.nasa.gov/archive/nasa/casi.ntrs.nasa.gov/20050198873.pdf
Alternate Webpage(s)	https://doi.org/10.1021/ma048291%2B
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article