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Chang and Chao: Preparation of microemulsion based disperse dye inks for thermal bubble ink jet printing Yellow 77 had better compatibility with other ingredients to achieve printability of more than 8h and lightfastness of grade 5. Moreover, the samples of B60-am, R109-am, Y77- bm, and Y99-am in the given microemulsion presented best stability without particle size variation in the storage stability test. Nevertheless, the samples of B79-am and R60-am demonstrated slightly decreased particle size in the microemulsion. After the microemulsions were formulated into inks, the samples of R109-am-7% and Y77-bm-10% could not be printed with thermal bubble ink jet for more than 8h, which is probably due to poor heat resistance of diazo structure or larger particle clogging in the nozzle after the ink has been frequently heated in the thermal bubble print head. When the ink concentration was diluted in half, B60-am-4% and R109-am-3.5% exhibited a particle size increase and slight decrease in lightfastness, which is due to the generation of agglomerates in the unbalanced system with higher amounts of surfactants and solvent. Notably, it was found that anthraquinone dyes yield higher lightfastness than diazo dyes to attain the lightfastness grade of 5. The microemulsion inks of this study had many advantages over other inks containing just the dye dispersions. One advantage was that microemulsion ink was a microheterogeneous system that provided a large interfacial area to accommodate dye content up to 8–10% and low viscosity to effectively meet the demand of ink drop performance without adding other viscosity modifiers. Another advantage was that microemulsion inks produced printed dot sizes that were nearly independent of the surface properties of the medium; they could present good printing quality either on paper or 100% polyester fabric without nozzle clogging and edge feathering. The most important advantage was that dyes in the given microemulsion exhibited smaller particle size than in dispersion formulations and, thereby, good storage stability with very little particle size variation. ACKNOWLEDGMENTS The authors thank S. P. Rwei in our department for helpful discussions. The authors also thank Widetex, Pleasant and Best Chemical, Jintex Co., Pan Asia Chemical, and Sino- Japan Chemical for offering materials. Nevertheless, we gratefully acknowledge Taiwan Textile Research Institute for support. REFERENCES 1 K. J. Lissant, Emulsions and Emulsion Tech., Part III (Marcel Dekker, New York, 1984) pp. 140–162. 2 A. García, M. Llusar, S. Sorli, J. Calbo, M. A. Monros, and G. Page, J. Eur. Ceram. Soc. 23, 1829–1838 (2003). 3 M. Häger et al., Colloids Surf., A 183-185, 247–257 (2001). 4 R. Guo, H. Qi, Y. Chen, and Z. Yang, Mater. Res. Bull. 38, 1501–1507 (2003). 5 C. Mo, M. Zhong, and Q. Zhong, J. Electroanal. Chem. 493, 100–107 (2000). 6 K. Aikawa, K. Kaneko, T. Tamura, M. Fujitsu, and K. Ohbu, Colloids Surf., A 150, 95–104 (1999). 7 R. Guo, H. Qi, Y. Chen, and Z. Yang, Int. J. Inorg. Mater. 18, 645–652 (2003). 8 C. A. Miller, R. N. Huan, W. J. Benton, and T. Fort, Jr., J. Colloid Interface Sci. 61, 554–568 (1977). 9 V. K. Bansal, D. O. Shah, and J. P. O’Connell, J. Colloid Interface Sci. 75, 462–475 (1980). 10 R. Guo, H. Qi, Z. Yang, and Y. Chen, Ceram. Int. 30, 2259–2267 (2004). 11 B. D. Gans, P. C. Duineveld, and U. S. Schubert, Adv. Mater. (Weinheim, Ger.) 16, 203–213 (2004). 418 J. Imaging Sci. Technol. 515/Sep.-Oct. 2007
Journal of Imaging Science and Technology® 51(5): 419–423, 2007. © Society for Imaging Science and Technology 2007 Effects of Molecular Substituents of Copper Phthalocyanine Dyes on Ozone Fading Fariza B. Hasan, Michael P. Filosa and Zbigniew J. Hinz ZINK Imaging Inc., Waltham, Massachusetts 02451 E-mail: fariza.hasan@zink.com Abstract. Copper phthalocyanine dyes, widely used in various imaging systems, are susceptible to fading under ambient conditions. One of the main factors responsible for such fading is the presence of ozone. Addition of suitable antiozonants has been shown to be effective in improving ozone stability. Although the exact mechanism of such stabilization is not fully understood, the electronic structures of the additives have shown to have significant impact on their effectiveness. In order to increase the ozone stability of copper phthalocyanine dyes without any additives, several copper phthalocyanine dyes containing substituents of varying electronic structures were synthesized and tested for ozone stability. The structure of a copper phthalocyanine dye with significantly improved stability to ozone is described in this paper. Possible mechanisms leading to such stability are also discussed. © 2007 Society for Imaging Science and Technology. DOI: 10.2352/J.ImagingSci.Technol.200751:5419 INTRODUCTION Copper phthalocyanine CuPC dyes are extensively used in various imaging systems because of several advantages, including high spectral absorptivity, solubility in various common solvents, and relatively greater lightfastness compared to several other classes of dyes. However, CuPC dyes are also susceptible to ozone fading under various ambient conditions, which can cause deterioration of images. A large number of papers related to the effects of ozone exposure on image stability have been published. Some of the recent publications are referred to in this article. 1–11 Several types of materials commonly used as antiozonants in other industries, such as p-phenylenediamines for reducing degradation of rubber due to exposure to ozone, are not suitable for imaging systems because of the highly colored products formed due to their reactions with ozone. These reactions have been shown to proceed through electron transfer mechanisms. 12 Other methods used for minimizing degradation of rubber due to exposure to ozone, such as coating with impermeable materials, are not easily applicable to imaging products, except in a limited number of imaging systems where polymeric materials can be transferred over the printed images. However, in such systems the efficiency of these materials depends on the continuity of the transferred polymeric layer, and any defect present in this Received Jan. 11, 2007; accepted for publication Mar. 1, 2007. 1062-3701/2007/515/419/5/$20.00. layer would allow ozone to diffuse through and cause degradation of the dyes in images. Several aminoanthraquinone dyes having similar functional groups as p-phenylenediamines are efficient antiozonants, but they do not form highly colored reaction products, due to the presence of electron withdrawing carbonyl groups in the fused ring systems. 13,14 Aminoanthraquinone dyes, as well as p-phenylenediamines, are essentially ozone scavengers and thus reduce the availability of ozone to react with CuPC dyes. It is expected that the presence of molecular substituents, which can act as ozone scavengers would also render the CuPC dye molecules more resistant to fading and discoloration due to exposure to ozone. In order to test this hypothesis, and since the reaction of olefins with ozone is well known, a CuPC dye with allyl substituents was synthesized. To verify the mechanism, two other CuPC dyes with different substituents were also synthesized and tested. EXPERIMENTAL PROCEDURES Substituted Copper Phthalocyanine Dyes The structures of the synthesized CuPC dyes with varying substituents, labeled as CuPC-B, CuPC-C, and CuPC-D, are shown in Figure 1. A commercially available CuPC dye, Solvent Blue 70 (CAS No. 12237-24-0) was used as the control for the tests. Although the exact structure of this dye is not known, it is possibly a mixture of several isomers containing various ring substituents, and can be represented as CuPC-A. Synthesis of Copper Phthalocyanine Dyes The synthetic method used for the substituted copper phthalocyanine dyes is described in Scheme 1. 15 Copper phthalocyaninetetrasulfonic acid tetrasodium salt (Aldrich), containing four −SO 3 Na groups as ring substituents was suspended in a 4:1 mixture of sulfolane and dimethylacetamide. A 32-fold excess of phosphorus oxychloride was added, and the reaction mixture was allowed to reflux for 4h, after which the reaction mixture was cooled to room temperature and poured into rapidly stirring ice water. The blue precipitated solid was collected, washed with water, and dried in a vacuum desiccator at room temperature for 24 h. The crude wet cake, with some water present, was dissolved/suspended in methylene chloride and cooled to 4°C. A large excess of diallyl amine (for CuPC-B), dibutylamine (for CuPC-C) or diethoxyethylamine (for 419
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