NEMOTO Fujito Neos Co., Central Research Institute, Manager, 中央研究所, 所長
KUROSAWA Hideo Osaka University, Faculty of Engineering, Associate Professor, 工学部, 助教授 (40029343)
|Budget Amount *help
¥2,500,000 (Direct Cost : ¥2,500,000)
Fiscal Year 1991 : ¥500,000 (Direct Cost : ¥500,000)
Fiscal Year 1990 : ¥2,000,000 (Direct Cost : ¥2,000,000)
Since the fluorine-containing compounds are valuable as organic materials, studies on the synthesis of novel compounds, their utilization, and their properties are becoming more active. One of the most important uses of those compounds are concering the surface improvement of solid and liquid, because of the extreme low surface trnsion or surface energy of perfluoroalkyl-containig compounds.
In the present study, one isomer of perfluoropropyrene dimers, perfluoro-2-methyl-2-pentene, which is industrially produced but is stiff not valuable from the view point of utilization is focussed to the synthesis of fluorine-containing heterocyclic compounds and to the utilization to surface improvement.
As the results, it is clarified that 6-membered heterocyclic compounds, pyrimidines with various substituent at 2-position were obtained in good yields. It is also recognized that these compounds showed the peculiar reactivity. In spite of the aromatic compounds, their fluorine atom substituted at 4
-position can be replaced by various nucleophile by the influence of vivo perfluoroalkyl substituents on the aromatic ring. When perfluoroalkyl-containing compounds are utilized as surface improve, a certain spacer are usually introduced between hydrophilic and lipophilic moieties, otherwise those surface improve without such spacer ar-e difficult to exhibit their inherently excelent properties due to the rigidity of perfluoroalkyl group. In the present study, developed is the method to link the rigid tertiary perfluoroalkyl moiety and the chemically or physically active group, which can be easily derivatized to hydrophilic moiety, with the flexible oxymethylene spacer. Tbus, in dimethylformamide, perfluoro-2-methyl-2-pentene reacted with various chloromethyl ethers in the presence of potassium fluoride to afford (tertiary-perfluoroalkyl) methyloxy compounds. Industrially important is that this active group can consist of alkyl, allyl, aryl, aralkyl, haloalkyl, or ether group, and that these compounds can be easily derived to surface improver. Less