Fluorinated compounds have many excellent properties including water and oil repellency, high lubricativity and stain protectivity as represented by poly (tetrafluoroethylene). Many kinds of silane coupling agents and hybrid surfactants having a fluorocarbon chain were prepared as surface modifiers, and the properties and applications were studied. Silane coupling agents prepared, F (CF₂) ₁₀CH₂CH₂SiX₂ (X = Cl, OCH₃, NCO), were studied on the application to dentistry. Novel fluorinated silane coupling agents with a biphenyl structure, F (CF₂) _n- (C₆H₄) ₂-CH₂CH₂Si (OCH₃) ₃, were synthesized. Modified glass surface with these compounds indicated the properties of highly heat-resistance up to 350t, oxidation-resistance, and acid-resistance. New types of surfactants having both a fluorocarbon chain and a hydrocarbon chain in their molecules, namely hybrid surfactants, were prepared. Hybrid surfactants would be prospective chemicals in industrial, medical and dental fields.

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A liquid unsaturated fatty alcohol containing only slight amount of conjugated diene impurities was obtained by the selective hydrogenation of industrial oleyl alcohol, originally taken from palm kernel oil through the use of a copper-chromium-mangane oxide catalyst, followed by fractional distillation and steam distillation. The liquid unsaturated alcohol thus obtained was improved with respect to suppression of odor and color impairment possibly arising from degradation. Additionally, the cloud point was kept low.

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Marine organisms contain carotenoids with unique structure, and highly unsaturated fatty acids (HUFA) with health beneficial effects. Fucoxanthin, from the edible seaweed Undaria pinnatifida, induced apoptosis in human leukemia and colon cancer cells. Furthermore, the activities of apoptosis induction by halocynthiaxanthin and fucoxanthinol isolated from the sea squirt Halocynthia roretzi as metabolites of fucoxanthin were higher than that of fucoxanthin. In addition, dietary fucoxanthin attenuated the weight gain of white adipose tissue and decreased blood glucose in obese/diabetic mice. These results show multi-functional properties of fucoxanthin and its metabolites. On the other hand, to extend the application of HUFAs, enzymatic preparation of phospholipid (PL) binding HUFA and bioconversion of HUFA to hydroxyl cyclic fatty acid have been attempted. Phospholipase A₂ and Lipozyme IM show specificities on sn-2 and sn-1 position of PL, respectively, in esterification and acidolysis. Utilization of water mimics was effective in increasing the reaction yield of HUFA-PL. Further, tetrahydrofuranyl hydroxyl and diepoxy bicyclic fatty acids were converted from HUFA by Bacillus megateriurn ALA2.

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