Cationic Dyes for Paper, Leather, and Other Substrates

Cationic dyes exhibit good affinity for negatively charged wood pulp and unbleached pulp grades. Anionic fixing agents improve their wetfastness. Cat­ionic dyes are chosen because of their brilliance and intensity, which makes them especially valuable for recycled paper grades. Their poor lightfastness is not a maior problem because of the low light stability of the substrate itself. They suffer from poor affinity for bleached, lignin-free pulp grades, which are used, for instance, in the manufacture of table cloths and napkins. Therefore, dyes have been developed for this application that bear several cationic charges linked by substantive moieties, such as urea or triazine [28] (e. g., 30).

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Cationic dyes were the first synthetic organic dyes employed for dyeing leather, initially for dyeing of vegetable-tanned leather. Currently, brilliant cat­ionic dyes are used for enhancing the brilliance of the shades obtained with 1:2 metal-complex dyes.

Because of their coloring strength, cationic dyes are used in the office supplies industry for the manufacture of ink, typewriter ribbon, and copying paper.

Colorless derivatives of the carbinol bases of cationic dyes have recently found application for the manufacture of carbonless copy paper and for special paper used for thermal printers. Examples of such color formers are the crystal violet derivative 31 [29], which develops a blue color, and the black-developing fluorane lactone 32 [30] and benzoxazine33 [31].

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Cationic dyes which absorb in the near-infrared region of the spectrum are used in optical data storage disks, e. g., 34 [32]:

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2.4.2 References

[1] H. A. Staab, Einfuhrung in die TheoretischeOrganische Chemie, 4th ed., Verlag Che — mie, Weinheim, 1964, pp. 236-336, and references cited therein; S. Dahne Z. Chem. 11 (1965)441.

[2] Bayer, FR 1 490 350, 1965.

[3] IG-Farbenind., DE 686 198, 1935 (K. Winter, N. Roh, P. Wolff, G. Schafer).

[4] IG-Farbenind./Bayer, DE 891 120, 1935 (W. Muller, C. Gerres).

[5] Bayer, DE 1 190 126, 1962 (A. Brack, D. Kutzschbach).

[6] Bayer, DE 410487, 1922 (W. Konig); DE 415534, 1923 (A. Blomer); IG Farbenind., DE 641799, 1928 (K. Schmidt).

[7] Bayer, DE 1 083 000, 1957 (R. Raue).

[8] Geigy, DE 1 044 023, 1954, (W. Bossard, J. Voltz, F. Favre); DE 1 050 940, 1954 (W. Bossard, J. Voltz, F. Favre).

[9] O. Fischer, Ber. Dtsch. Chem. Ges. 10 (1877) 1625; 11 (1878) 950; 1881, 14, 2520.

[10] BASF, DE 26016, 27032, 27789, 1883 (Kern, H. Caro); Meister, Lucius und Bruning (today Hoechst AG), DE 34463, 1884.

[11] BASF, DE 44002, 1887 (M. Ceresole). Meister, Lucius und Bruning (today Hoechst AG), DE 48367, 1888.

[12] W. H. Perkin, J. Chem. Soc. 69 (1896) 596, and references cited therein; O. Meth — Cohn, M. Smith, J. Chem. Soc. Perkin Trans. 1 1994, 5.

[13] Hoechst, DE 1 569604, 1966 (G. Schafer, N. Ottawa).

[14] BASF, DE 1886, 1877 (H. Caro).

[15] Du Pont, DE 1 054 616, 1954 (S. N. Boyd, Jr.).

[16] Sandoz, DE 2 118 536, 1970 (R. Entschel, C. Muller, W. Steinemann); BE 756 820, 1970; CH 549 629, 1971 (R. Entschel, C. Muller, W. Steinemann).

[17] Bayer, DE 1 150 652, 1955 (G. Gehrke, L. Nussler).

[18] Allied Chem. Corp., US 3 565 570, 1968 (C. K. Dien).

[19] Ciba, FR 1489 639, 1965.

[20] Hoechst, DE 2 122 975, 1971 (H. Troster, K. Lohe, E. Mundlos, R. Mohr).

[21] Sandoz, DE 2 055 918, 1969 (B. Gertisser, F. Muller, U. Zirngibl).

[22] Eastman Kodak, DE 1 250 947, 1963 (J. G. Fisher, D. J. Wallace, J. M. Straley).

[23] Hoechst, DE 1 941 376, 1969 (K. Lohe).

[24] O. Glenz, W. Beckmann, Melliand Textilber. 38 (1957) 296.

[25] Bayer, DE 2 040 872, 1970 (H.-P. Kuhlthau, R. Raue).

[26] Sandoz, FR 2 013 732, 1969 (R. Entschel, V. Kappeli, C. Muller).

[27] Ciba-Geigy, DE 2 548 009, 1974 (J. Koller, M. Motter, P. Moser, U. Horn, P. Galafassi).

[28] Bayer, DE 2 933 031, 1979 (H. Nickel, F. Muller, P. Mummenhoff).

[29] BASF, DE 1 962 881, 1969 (D. Leuchs, V. Schabacker).

[30] Nisso Kako, JP 5082126, 1971; JP 4862506, 1971; DE 2242693, 1971 (M. Yagahi, T. Suzuki, T. Igaki, S. Kawagoe, S. Horiuchi). Yamamoto Kagaku, JP 51 15445, 1971; JP 5 106561, 1974; DE 2202315, 1971 (Y. Hatano, K. Yamamoto). Nat. Cash Reg., DE 2155 987, 1970 (Ch.-H. Lin). Fuji, DE 2025 171, 1969 (S. Kimura, T. Kobayashi, S. Ishige, M. Kiritani).

[31] Bayer, EP 0 187 329, 1985 (H. Berneth); EP 0 254 858, 1986 (H. Berneth, G. Jabs).

[32] Minnesota Mining and Manufacturing, WO 83/2 027, 1982 (V. L. Bell, I. A. Ferguson, M. J. Weatherley).

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