Studies on synthesis of dyes having fluoroalkyl groups and water-repellent dying

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Dyes having fluoroalkyl groups to function as water- and oil repellent agents have hardly reported owing to the difficulties of syntheses. In this work, novel fluoroalkylated anilines were synthesized by (1) the reaction of perfluoroalkanoyl peroxides with acetoanilide, or (2) the coupling of perfluoroalkyl iodide and iodoaniline. By the diazo-coupling reaction, acid and direct dyes having fluoroalkyl group on the aromatic ring were easily prepared.I selected the acid dyes, applied to the dyeing of nylon, and basically studied the novel water-repellent dying system from the viewpoint of surface free energies, contact angles, and ESCA surface analysis.At the same amount of dye exhaustion, water contact angles increased in the order of RィイD2fィエD2 = CFィイD23ィエD2 < CィイD23ィエD2FィイD27ィエD2 << CィイD26ィエD2FィイD213ィエD2 【approximately equal】 CィイD28ィエD2FィイD217ィエD2, in the latter two cases, nylon surface could be changed apparently to water-repelled. Based on the ESCA measurements, the peak area ratio on FィイD21sィエD2 to NィイD2lsィエD2 was taken as a new measure of fluorine concentration at the surface. Those FィイD21sィエD2/NィイD21sィエD2 peak ratios were highly correlated to the water contact angles. The difference that was observed depending on RィイD2fィエD2 could be interpreted in terms of the diffusion of dyes into the bulk.