Synthesis and Spectral Properties of Fluorescent Phthalimidylhydrazone Disperse Dyes and their Application to Poly(ethylene terephthalate) Dyeing

• Published in: Fibers and polymers pp. 2567 - 2578
• Main Authors: 염기철, SANTOSH KUMAR, 고준석
• Format: Journal Article
• Language: English
• Published: 한국섬유공학회 01.09.2022
• Subjects: 섬유공학
• ISSN: 1229-9197; 1875-0052

A series of fluorescent phthalimidylhydrazone disperse dyes based on pyrrolinone esters were synthesized andcharacterized using Fourier-transform infrared spectroscopy, proton nuclear magnetic resonance (1H-NMR) spectroscopy,and elemental analysis. The synthesized dyes were confirmed to be keto-hydrazone tautomers and were found to be mixturesof Z/E isomers, with the Z form being predominant, via 1H-NMR spectroscopy. Although the effect of N-alkylation inphthalimide on the absorption spectra and color properties of the dyed poly(ethylene terephthalate) (PET) was negligible,dyes that contained a longer N-alkyl substituent achieved higher color yields on the PET fabrics, owing to their increasedhydrophobicity. The synthesized dyes exhibited a reasonably intense fluorescence in the solution state, with a quantum yieldof 0.109-0.122, as well as in the dyed fabric. The phthalimidylhydrazone disperse dyes exhibited excellent color fastness aftera mild alkaline treatment instead of the conventional reduction clearing, which causes environmental problems due to thehigh biochemical oxygen demand and alkalinity in dyehouse effluents. KCI Citation Count: 0