| This dissertation is concerned with the design and synthesis of novel azo disperse dyes capable of imparting water repellency as well as color to textile fibers. In this study, 20 azo disperse dyes were synthesized by incorporating a fatty alkyl group or a perfluoro alkyl group into the structures of two commercial dyes, C.I. Disperse Red 1 and C.I. Disperse Blue 106 and by using diazo and coupling components containing these types of hydrophobic groups. The structures of the developed dyes were confirmed by 1H NMR spectroscopy, elemental analysis, and mass spectrometry.; The new disperse dyes were applied to polyester fabrics and the effects of built-in hydrophobic groups on color, dyeing, fastness properties, and water repellency were determined. It was found that the incorporation of a fatty alkyl group or a perfluoro alkyl group into the structures of the two commercial dyes led to a hypsochromic shift and that increasing the chain length of the hydrophobic group had no effect on λmax but did lower the percent exhaustion and K/S values.; There was no significant difference in the fastness properties of polyester dyed with C.I. Disperse Red 1 analogs and a C.I. Disperse Blue 106 analog versus the commercial parent dyes. In general, dyes containing a perfluoro alkyl group had better lightfastness than those containing a fatty alkyl group. All tested dyes exhibited good washfastness.; It was found that the water repellency ratings obtained using AATCC Test Method 22-1989 were surprisingly lower than expected and that ESCA (Electron Spectroscopy for Chemical Analysis) showed only a small amount of fluorine (1.5–2.3%) on the surface of polyester dyed with dyes containing a built-in perfluoro alkyl group. However, there was definitely a reduction in the wettability of fabrics dyed with the new dyes, as indicated by an increase in wetting times (AATCC Test Method 39-1977) compared to the undyed fabric. |
