Characteriza*on of Ligh1ast Dyes for Digital Prin*ng Applica*ons
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1 Characteriza*on of Ligh1ast Dyes for Digital Prin*ng Applica*ons Harold S. Freeman College of Tex*les, orth Carolina State University 1
2 Outline Background Research Plan Red Dye Characteriza*on Blue Dye Characteriza*on Summary and Acknowledgements 2
3 BACKGROUD Disperse Dyes Range widely in hue, brilliance and color strength Used for hydrophobic fibers (PET) Thermal fixa*on and wash-off process CH 2 CH 2 OH O 2 O H H O 2 O H 2 OC 6 H 12 OH SO 2 H OH O OH O OH C.I. Disperse Yellow 42 C.I. Disperse Blue 27 C.I. Disperse Red 91 O 2 Cl AcH O 2 (CH 2 CH 2 OCOCH 3 ) 2 OCH 3 OH C.I. Disperse Red 167:1 C.I. Disperse Orange 29 3
4 BACKGROUD Photostabilizers (UV Absorbers) US Patent , 1995; US Patent ,
5 BACKGROUD Jablonski Diagram 5
6 BACKGROUD Genera*on I Disperse Dye Analogs H O 2 SO 2 H H O 2 HO O OCH 3 C.I. Disperse Yellow 42 SO 2 H O 2 Cl AcH (CH 2 CH 2 OCOCH 3 ) 2 C.I. Disperse Red 167:1 R H O Cl O H O 2 C 2 H 5 CH 2 CH 2 C Dyes and Pigments, 20(3), 147 (1992) Dyes and Pigments, 42, 53 (1999) 6
7 CF 3 H 3 C C BACKGROUD Other Ligh1ast Disperse Dye Analogs O 2 H H O 2 CF 3 H 3 C C H H S C H 3 C S C H 3 C RH C HR O H O O 2 O H OH O H OH O OH O 2 O OH US 2004/ A1; 2006/ A1 7
8 Analy*cal Methods Column chromatography RESEARCH PLA Characteriza*on of Disperse Dyes for Digital Prin*ng Molecular nature Excited state proper*es High-performance liquid chromatography Mass spectrometry MR Absorp*on and emission spectroscopy Fluorescence measurements X-ray crystallography 8
9 Project Overview Target Dyes o Yellow, Red, Blue Experimental Methods o Absorp*on & Fluorescence Spectra o Singlet Oxygen o GSOP, E0-0, ESOP o Pump-probe, Triplet State o Single Crystal X-ray Synthe*c Work Structure Property Correla*ons
10 RESULTS AD DISCUSSIO Analogs of 1 Dyes TLC Analysis Generation 1 Generation 2 Generation 3 300h h h Yellow Red Blue Scarlet Dye # Dye Designation Generation 1 Disperse Yellow 42 Generation 1 2 Disperse Yellow 86 Generation 1 3 Yellow II Generation 2 4 Yellow III Generation 3 5 Disperse Red 60 Generation 1 6 Red II Generation 2 7 Red III Generation 3 8 Disperse Blue 56 Generation 1 9 Blue II Generation 2 10 Blue III Generation 3 11 Scarlet II Generation 2 12 Scarlet III Generation 3 13 Violet-Blue III Generation 3 14 Cyan III Generation 3 15 Black III Generation 3 TLC analysis of the three genera@on of dyes, using CHCl 3 as eluent 10
11 RESULTS AD DISCUSSIO for II Scarlet dye HPLC Analysis 11
12 RESULTS AD DISCUSSIO for II Scarlet dye MS Analysis Mass spectrum of the Sc1 component (518). Proposed molecular structure for the Sc1 component. 12
13 RESULTS AD DISCUSSIO for II Scarlet dye MS and MR Analysis _Y4 # RT: AV: 48 L: 6.04E7 T: FTMS + p ESI Full ms [ ] m/z MS of Sc2 scan at min (442). Proposed molecular structure for Sc2. 13
14 RESULTS AD DISCUSSIO for II Scarlet dye MS and MR Analysis _Y5 # RT: AV: 33 L: 5.69E7 T: FTMS + p ESI Full ms [ ] m/z MS for the Sc3 peak at min (442). Proposed molecular structure for Sc3. 14
15 RESULTS AD DISCUSSIO for II Scarlet dye X-ray Crystallographic Analysis: Scarlet 3 Cell for Sc3 Donor-H Acceptor-H Donor-Acceptor Angle 6--H6A--O (14) 2.189(14) (9) 160.5(12) 6--H6B (13) 2.512(13) (9) 128.6(11) 7--H (12) 1.933(12) (8) 136.9(10) 15
16 RESULTS AD DISCUSSIO for II Scarlet DyeS Absorbance Emission Spectra Sc1 Absorbance Sc1 Emission Emission intensity (CPS) Wavelength (nm) 0 Absorbance Sc2 Absorbance Sc2 Emission Emission intensity (CPS) Absorbance 1.0 Sc3 Absorbance Sc3 Emission Emiission intensity (CPS) Wavelengh (nm) Wavelenght (nm) 16
17 RESULTS AD DISCUSSIO TLC Analysis Generation 1 Generation 2 Generation 3 300h h h Yellow Red Blue Scarlet Dye # Dye Designation Generation 1 Disperse Yellow 42 Generation 1 2 Disperse Yellow 86 Generation 1 3 Yellow II Generation 2 4 Yellow III Generation 3 5 Disperse Red 60 Generation 1 6 Red II Generation 2 7 Red III Generation 3 8 Disperse Blue 56 Generation 1 9 Blue II Generation 2 10 Blue III Generation 3 11 Scarlet II Generation 2 12 Scarlet III Generation 3 13 Violet-Blue III Generation 3 14 Cyan III Generation 3 15 Black III Generation 3 TLC analysis of the three genera@on of dyes, using CHCl 3 as eluent 17
18 RESULTS AD DISCUSSIO for II Blue Dyes HPLC Analysis 18
19 RESULTS AD DISCUSSIO for II Blue Dyes MS Analysis _B4 # RT: AV: 32 L: 8.13E7 T: FTMS + p ESI Full ms [ ] _B5 # RT: AV: 35 L: 2.66E7 T: FTMS + p ESI Full ms [ ] m/z Blue 4 scan min m/z Blue 5 scan min Mass for Blue 4&5:
20 RESULTS AD DISCUSSIO for II Blue Dye X-ray Crystallographic Analysis: Blue Å Donor-H Acceptor-H Donor- Angle Acceptor O1-H1...O (15) 1.725(15) (8) 151.5(14) O5-H5...O (15) 1.675(15) (9) 152.7(13) 2-H2...O (13) 2.635(13) (9) 143.4(11) 2-H2...O (13) 1.964(14) (9) 134.1(12) 20
21 RESULTS AD DISCUSSIO for II Blue Dye X-ray Crystallographic Analysis: Blue 5 Donor-H Acceptor-H Donor- Angle Acceptor O3-H3... O4 0.91(5) 1.75(5) 2.560(4) 147.(5) O3-H3... O4 0.91(5) 2.31(5) 2.763(4) 110.(4) O5-H5... O3 0.84(5) 2.45(5) 3.094(4) 134.(4) O5-H5... O4 0.84(5) 1.84(5) 2.572(4) 146.(5) 2-H2... O6 1.00(4) 1.75(4) 2.594(5) 140.(4) 21
22 RESULTS AD DISCUSSIO for II Blue dye Emission Spectra 0.4 Blue 4 Blue Absorbance Emission intensity (CPS) Wavelength 0 22
23 Transient Absorption Spectra Blue nm 650nm 23
24 Transient Absorption Spectra Blue nm Mixture 24
25 RESULTS AD DISCUSSIO Other Molecular Structures Violet III Dye Red II-3 Dye Yellow II-1 Dye 25
26 SUMMARY AD COCLUSIO Summary o Genera*on 2 Dyes Dye mixtures used to improve the light fastness ESIPT o Genera*on 3 Dyes Simplified systems especially for red and blue o Photochemistry/Photophysics Emission Spectra Weak Transient Absorp*ons Low Singlet Oxygen Produc*on one o Mixtures 26
27 Acknowledgements Walmart US Manufacturing Innova*on Fund Faculty Colleagues Profs. Lisa Chapman, Ahmed El-Shafei, Malgorzata Szymczyk Students and Research Associates Drs. Yi Ding, Jihye Lim, ahid Mehraban Analy*cal Facili*es at C State Department of Chemistry 11/20/16 27
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