The synthesis of some novel derivatives of 4-[N,N-bis(β-hydroxyethyl)- amino]azobenzene is reported, and the effects of ortho-substituents on photoinduced trans→ cis isomerism about the azo group, mass spectral behavior, and the photost ability of these dyes are described. An ortho-nitro group inhibits trans → cis photo- isomerism about the azo group and affords poor photostability. Those ortho-substituted dyes showing a greater tendency to undergo photoinduced trans → cis isomerism and recover quickly are also more photostable and less subject to rupture at the β-nitrogen- carbon bond in the mass spectrometer. The photolysis experiments were done using acetate and triacetate film and fiber, and the mass spectrometric analyses were done by direct probe using the electron-impact technique.
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References
1.
Albini, A., Fasani. E., and Pietra, S., The Photochemistry of Azo Dyes: The Wavelength-dependent Photoreduction of 4-Diethylamino-4'-nitroazobenzene, J. Chem. Soc. Perkin Trans.II (11), 1393-1395 (1982 ).
2.
Aliwarga, H. , and Hallas, G., Synthesis and Electronic Spectra of Some Azo Disperse Dyes Derived From N-2,2,2-Trifluoroethyl-1,2,3,4-tetrahydroquinoline , Dyes Pigments2, 195-203 (1981).
3.
Al-Kassim, S. , and Peters, A.T., New Intermediates andDyes for Synthetic-polymer Fibres—Derivatives of 2-Chloro-4-nitro-4'-[N-β-hydroxylethyl-N-β-cyanoethylamino]azobenzene , J. Soc. Dyers Colour. 89, 359-363 (1973).
4.
Atherton, E. , and Seltzer, I., Some Studies of the Fading of Simple Monoazo Dyes, J. Soc. Dyers Colour.65, 639-649 (1949).
5.
Atherton, E. , and Peters, R.H., SomeFurther Investigations into the Fading Rates of Monoazo Dyes, J. Soc. Dyers Colour. 68, 64-66 (1952).
6.
Ball, P., and Nicholls, C.H., Photochromism of the Azo Tautomer of 4-Phenylazo-1-naphthol and its O-Methyl Ether in Solvents and Polymer Substrates, Dyes Pigments6, 13-25 (1985).
7.
Desai, N.F., and Giles, C.H., TheOxidation of Azo Dyes and Its Relation to Light Fading, J. Soc. Dyers Colour. 65, 639-649 (1949).
8.
Freeman, H.S. , and Hsu, W.N., Photolytic Behavior of Some Popular Disperse Dyes on Polyester and Nylon Substrates, Textile Res. J.57, 223-234 (1987).
9.
McIntosh, S.A., Freeman, H.S., and Singh, P., X-Ray Crystal Structure of the Dyes 2-Nitro-4'-[N,N-Bis(β-Hydroxyethyl)amino]azobenzene and 2-Cyano-4'[N,N-Bis(β-Hydroxyethyl)amino]azobenzene, Textile Res. J. (in press).
10.
Hallas, G., TheEffects of Terminal Groups in 4-Aminoazobenzene and Disperse Dyes Related Thereto, J. Soc. Dyers Colour. 95, 285-294 (1979).
11.
Mehta. H.P. , and Peters, A.T., Electron Impact-induced Fragmentation of 4-Aminoazobenzene Dyes and Relationships with Photochemical Stability, Appl. Spertrosc.28, 241-243(1974).
12.
Mehta, H.P. , and Peters, A.T., Substituent Effects on the Colour, Dyeing and Fastness Properties of 4-N-β-Cyanoethyl-N-β-Hydroxylethylaminoazobenzenes, Part I: Monosubstituted Derivativa. Dyes and Pigments2, 259-269 (1981).
13.
Mehta, H.P. , and Peters, A.T., Substituent Effects on the Colour, Dyeing, and Fastness Properties of 4-N-β-Cyanoethyl-N-β-Hydroxvethylaminoazobenzenes, Part II: Disubstituted Derivatives. Dyes Pigments3, 71-78 (1982).
14.
Muller, C., RecentDevelopments in the Chemistry of Disperse Dyes and Their Intermediates, Am. Dyest. Rep.58 (3), 37-44, (1970).
15.
Nagaraja, S.N. , and Sunthankar, S.V., Cellulose Acetate Dyes, Part IV: Synthesis of para-Arylazopenylaminoacrylates as Dyes for Cellulose AcetateJ. Sci. Ind. Res. 20D, 374-378 (1961).
16.
Nagaraja, S.N. , and Sunthankar, S.V., Cellulose Acetate Dyes, Part V: Synthesis of 6-Arylazoquinolines and Dyes for Cellulose Acetate, J. Sci. Ind. Res. 20D, 407-409 (1961).
17.
Peters, A.T. , Substituent Effects on the Colour. Dyeing, and Fastness Properties of Trisubstituted 4-N-β-Hydroxyethyl-N-β-Cyanoethylaminoazobenzenes , J. Soc. Dyers Colour. 101, (11), 361-367 (1985).
18.
Ross, D.O., and Blanc, J., "Photochromism, Techniques of Chemistry," vol. 3, G. H. Brown, Ed., Wiley-Interscience, New York, 1971 , pp. 471-556.
19.
Schroeder, H.E., and Boyd, S.N., Dyes for the Hydrophobic Fibers , Textile Res. J.27, 275-285 (1957).
20.
Still, W.C. , Kahn, M., and Mitra. A., Rapid Chromatrographic Technique for Preparative Separations with Moderate Resolution, J. Org; Chem.43, 2923-2925 (1978).
21.
Zollinger, H. , "Color Chemistry - Synthesis. Properties, and Applications of Organic Dyes and Pigments," VCH Verlagsgesellschaft . Federal Republic of Germany, 1987, pp. 103-105.
