Title Page
Contents
ABSTRACT 11
Ⅰ. Introduction 13
Ⅱ. Experimental 17
2.1. Materials 17
2.2. Synthesis of Dye Intermediates 17
2.3. Synthesis of Spiroindolinonaphthoxazine Dyes (5 and 6) 18
2.3.1. SNO (5, Trimethylspiroindoline-2,3'-3H-naphth[2,1-b][1,4]oxazine) 18
2.3.2. SNO-OH 19
2.4. Instrumental Analysis 20
2.5. Computation of log P and Dipole Moment 21
2.6. Dyeing 21
2.7. Photochromic Performance Assessment 23
2.8. Photocoloration Behavior and Photofatigue Resistance Assessment 23
2.9. Color Fastness Test 24
Ⅲ. Results and Discussion 25
3.1. Characterization of Dyes 25
3.2. Spectral Properties of the Synthesized Dyes 28
3.3. Dyeing Properties 29
3.3.1. Temperature and pH 29
3.3.2. Effect of 1,4-diazabicyclo[2.2.2]octane 37
3.3.3. Time 40
3.3.4. Build-up 41
3.4. Photo-coloration and fading Behavior 43
3.5. Photofatigue Resistance 44
3.5.1. Repeated photo-coloration-fading cycles 44
3.5.2. Repeated washings 46
3.6. Color Fastness Properties 48
Ⅳ. Conclusion 51
References 52
Abstract (in Korean) 55
Table 1. Chemical structure and yield of the synthesized spironaphthoxazine dyes 20
Table 2. FT-IR data of the synthesized dyes 5 and 6 26
Table 3. ¹H-NMR data of the synthesized dyes 5 and 6 26
Table 4. Elemental analysis data for the synthesized dyes 5 and 6 26
Table 5. Melting points, dipole moment, and log P values of the synthesized spironaphthoxazine dyes 27
Table 6. Absorption maxima of the synthesized dyes in solution after UV irradiation 28
Table 7. Rendering images of the dyed nylon with SNO before and after UV irradiation 30
Table 8. Rendering images of the dyed nylon with SNO-OH before and after UV irradiation 34
Table 9. Color fastness to washing for the nylon fabric dyed with the synthesized dyes 48
Table 10. Color fastness to dry heat at 150 °C for the nylon fabric dyed with the synthesized dyes 49
Table 11. Color fastness to light for the nylon fabric dyed with the synthesized dyes 49
Figure 1. K/S spectra of SNO at different pHs and temperatures before (dashed line) and after (solid line) UV irradiation for 5 min 31
Figure 2. Photochromic efficiency of nylon fabric dyed with SNO at various dyeing temperatures and pHs: (a) background color strength (ƒk,s) before UV...[이미지참조] 32
Figure 3. K/S spectra of SNO-OH at different pHs and temperatures before (dashed line) and after (solid line) UV irradiation for 5 min 35
Figure 4. Photochromic efficiency of nylon fabric dyed with SNO-OH at various dyeing temperatures and pHs: (a) background color strength (ƒk,s)...[이미지참조] 36
Figure 5. DABCO effect on photochromic efficiency of nylon fabric dyed with (a) SNO and (b) SNO-OH at various dyeing temperatures 39
Figure 6. Photochromic behaviors of nylon fabric dyed with 1.0 %omf of (a) SNO at 80 °C and (b) SNO-OH at 90 °C for various dyeing times 41
Figure 7. Photochromic color buildup properties of nylon fabric dyed with SNO and SNO-OH before and after UV irradiation 42
Figure 8. (a) Photocoloration and (b) fading (after UV exposure for 20 min) behavior of nylon fabric dyed with SNO and SNO-OH 44
Figure 9. Photofatigue behavior of nylon fabric dyed with SNO during 11 cycles of photocoloration-fading: (a) color difference changes; (b) CIELAB a*... 45
Figure 10. Photofatigue behavior of nylon fabric dyed with SNO-OH during 11 cycles of photocoloration-decoloration: (a) color difference changes; (b)... 46
Figure 11. Photocoloration-fading behavior of nylon fabric dyed with (a) SPO and (b) SPO-OH during 10 repeated washings 47
Scheme 1. Phototransformation of spiroindolinonaphthoxazine: MM2 geometry-optimized structures of spirooxazine (closed form) and its ring-... 14
Scheme 2. Synthesis of 1-nitroso-2,7-dihydroxynaphthalene (2) 18
Scheme 3. Synthesis of trimethylspiroindoline-2,3'-3H-naphth[2,1-b][1,4]oxazine (5) 19
Scheme 4. Synthesis of 9'-Hydroxy-1,3,3-trimethyl-spiro{indoline-2, get 3'[3H]naphtho[2,1-b][1,4]oxazine} (6) 20
Scheme 5. Photoproducts generation pathway of spiroindolinonaphthoxazine 37