High Light-Fastness Acid Dyes Synthesized from Corresponding Anthraquinone Chromophore Utilizing a Sulfonation Reaction. I. Dye Synthesis and Characterization

• Published in: Fibers and polymers Vol. 19; no. 9; pp. 1791 - 1798
• Main Authors: Lee, Eui-Jae, Kim, Kyung-Won, Kim, Geun-Hyeong, Park, Chae-Eun, Choi, Jae-Hong
• Format: Journal Article
• Language: English
• Published: Seoul The Korean Fiber Society 01.09.2018; Springer Nature B.V; 한국섬유공학회
• Subjects: Acid dyes; Acids; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chromophores; Dyeing; Dyes; Light fastness; NMR; Nuclear magnetic resonance; Polyamide resins; Polymer Sciences; Sulfonic acid; 섬유공학; Polyamide; Sulfonation; Light fastness; Anthraquinone; Acid dye
• ISSN: 1229-9197; 1875-0052
• DOI: 10.1007/s12221-018-7947-z

As the diameter of polyamide fibers decreased to finer denier, the dyeing fastness tends to be deteriorated due to the increase of their surface area, particularly both light fastness and wash fastness. In this study, three acid dyes were synthesized utilizing a sulfonation reaction starting from corresponding hydrophobic dye (for yellow and red dye) and dye intermediate containing a sulfonic acid group (for blue dye), those featured by high light fastness property. A Gaussian structural prediction model was used to determine the structure of the acid dyes prior to dye synthesis, and the optimal structures of three acid dyes were analyzed. Dye structures prepared were confirmed by 1 H-NMR, mass spectroscopy, and elemental analysis. By using a UV-vis spectrophotometer, the absorption maxima and molar extinction coefficient were also measured for three acid dyes comparing to that of the corresponding disperse dye or blue dye intermediate. Judging from spectroscopic data, the introduction of sulfonyl groups led to increase of molar extinction coefficient and a bathochromic shift.