Dyeing with Azo Dyes

Both the monoamino and the diamino derivatives form intensely colored dyes when diazotized and coupled with phenols and aromatic amines. The dyes formed are fast to light. In the following table silk is given to represent the fabrics used. Wool and cotton were dyed similar shades, though with slight variation. Each silk sample was dyed in acid or alkaline baths as indicated and each bath contained 0.01 gram in twenty cc. solution:

CouplerDiazo.
monoamine		On
silk		Diazo.
diamine		On
silk
Phenoldeep red
(alk)		v. light
yellow		(alk)
deep red		yellow
Dimethylanilineorange
(acid)		light
yellow		orange-red
(acid)		yellow
P-nitranilinelight brown
(acid)		 brownish
(acid)		grayish
brown
P-toluidinelight brown
(acid)		 brownish
(acid)		brownish
Pyrogallic
acid		dark brown
(acid)		grayishdark brown
(alk)		grayish
Salicylic
acid		reddish
(alk)		light brownred
(alk)		brown
B-naphtholdeep red
(alk)		pinkdeep red
(alk)		red
Sulphanilic
acid		light brown
(alk)		brownishbrown
(alk)		brown
A-naphthylaminelight brown
(acid)		brownishyellow
(acid)		yellow
Resorcinolpurple
(alk)		reddark purple
(alk)		deep red

[BIBLIOGRAPHY]

  1. Berzelius, Annales de Physique et Chimie (2) 9, 239, 356 (1818).
  2. Gmelin-Kraut, “Handbuch der Anorg. Chemie” I (1) 705-804; Roscoe and Schorlemmer, “Treatise on Chemistry” I, 467-82 (1920); Browning, “Introduction to the Rarer Elements,” 144-52 (1917).
  3. Victor Lenher, J. Ind. Eng. Chem., 12, 597 (1920).
  4. Le Seleneum et ses applications actuelles, Chimie et Industrie (1919) 245.
  5. C. R. Boggs, U. S. A., 1,249,272; J. Ind. Eng. Chem. 10, 117-8 (1918).
  6. Duhamel & Robiere, Compt. rend. soc. biol. 72, 670 (1913); Am. Chem. Abs. 7, 2624 (1913).
  7. B. G. Duhamel, Compt. rend. soc. biol., 72, 865 (1913); Am. Chem. Abs. 7, 2971 (1913).
  8. Duhamel & Juillard, Compt. rend. soc. biol., 72, 714 (1913); Am. Chem. Abs., 7, 2624 (1913).
  9. B. G. Duhamel, Compt. rend. soc. biol., 82, 724-6 (1919); Am. Chem. Abs. 14, 2383 (1920).
  10. Wassermann, D. R. P., 261,556; 286,950; 287,020.
  11. A. v. Wassermann, Keyser, & M. Wassermann, Duet. Med. Woch., 37, 2389 (1911); Am. Chem. Abs., 6, 650 (1912).
  12. A. v. Wassermann & Hansmann, Berl. klin. Woch., 49, 4, (1911); Am. Chem. Abs., 6, 890 (1912).
  13. Anthraquinone dyes, D. R. P., 256,667.
  14. P. Ehrlich & H. Bauer, Ber., 48, 502 (1915).
  15. Berzelius, Lehrbuch (5 Aufl.) 2, 213; Roscoe and Schorlemmer, “Treatise on Chemistry,” I, 473 (1920).
  16. Bruere, J. Anat. Physiol., Oct., (1891).
  17. T. W. Clarke & W. H. Hurtley, J. Physiol., 36, 62 (1907).
  18. Hugo Bauer, Ber., 47, 1873 (1914).
  19. Ehrlich & Guttmann, Berl. klin. Woch. (1891) 28; U. S. Disp., 20th Edition.
  20. P. Karrer, 49, 597 (1916); Ber., 51, 190 (1918).
  21. Hugo Bauer, Ber., 47, 1873 (1914); D. R. P., 261,969; Friedl., 11, 1124 (1913).
  22. Selenazines, D. R. P., 280,713; 261,793.
  23. U. S. Disp., 20th Edition.
  24. D. R. P., 305,262; 305,263; Am. Chem. Abs., 13,325 (1918).
  25. Bull. soc. chim., 41, 599; Compt. rend., 99, 1154-7 (1885); Brit. Chem. Abs., 50, 376 (1885); A. Ch., (6) 9, 294, 303, 323.
  26. W. Baringer, Ber., 23, 1003 (1889).
  27. P. Spica, Gazz. chim. ital., 7, 90-9 (1877); Brit. Chem. Abs., (1877) II, 189; Compt. rend., 99, 1154 (1884); 100, 1296 (1885); Frerichs, Arch. Pharm., 241, 180, 196; Beil., (1921) III, 295, 261.
  28. C. Paal, Ber., 18, 2255 (1885); Gazz. chim. ital., (I. Zoppellari) 24, II, 399, (1894).
  29. Ida Foa, Gazz. Chim. ital., 39, II, 527, (1909); C-B., (1910) I, 837.
  30. D. R. P., 264,139.
  31. O. Hinsberg, Ber., 22, 862, 2895 (1889); D. R. P., 261,412.
  32. J. prakt. Chem., (1904) II, 69, 509.
  33. E. Abderhalden, Hand. Biol. Chem., III, 2, 954.
  34. Hanzlik & Tarr, Am. Univ. Ezpt. Sta., J. Pharmacol, 14, 221-8 (1919).
  35. Hochst, D. R. P., 299,510.
  36. D. R. P., 264,940; 264,961.
  37. A. Michaelis & M. Stein, Ann., 320, 32 (1902).
  38. Bogert & Hand, J. Am. Chem. Soc., 25, 377 (1902).
  39. B. Bathke, Ann., 152, 210 (1869); Ann., 185, 331; Richter, Organische Chemie, I, 166.
  40. Lesser & Schoeller, Ber., 47, 2293 (1914).
  41. Lesser & Weiss, Ber., 45, 1835 (1912); 46, 2653, (1913).
  42. Wohler & Dean, Ann., 97, 5 (1856); B. Rathke, Ann., 152, 211 (1869).
  43. Cahours, Ann., 61, 92, (1847); 92, 356.
  44. H. Klinger, Ber., 32, 2195, (1899); Ann., 119, 91; 121, 108.
  45. C. A. Joy, Ann., 86, 35, (1853); B. Rathke, Ann., 152, 212, 219 (1869).
  46. Wheeler, Z. Chem., (1867) 436.
  47. Krafft & Lyons, Ber., 27, 1762 (1894); A. Ch., (6), 20, 228.
  48. K. A. Hoffmann, Ber., 27, 2809 (1894).
  49. M. Busch, Ber., 25, 2853, (1892).
  50. Lellmann & Stickel, Ber., 19, 1605 (1886).
  51. B. Rathke, Ann., 152, 201 (1869).
  52. Gabriel & Stelzner, Ber., 29, 1313 (1896).
  53. Bogert, Breneman, & Hand, J. Am. Chem. Soc., 25, 373 (1903).
  54. Am. Chem. Abs., 3, 870 (1903); Bull. Belg. Soc. Chem., 23, 9-11.
  55. Bogert & Hand, J. Am. Chem. Soc., 24, 1035, (1902).
  56. Becker & Meyer, Ber. 37, 2551 (1914).
  57. H. Bauer, Ber. 48, 507 (1915); Lyons & Shinn, J. Am. Chem. Soc. 1902: 1092; Fritz von Konek & O. Schleifer, Ber. 51, 850 (1918); A. Michaelis, Ber. 30, 2827 (1897); Ber. 48, 873 (1915); H. Frerichs, Arch. Pharm. 1902: 240, 656.
  58. Fromm & Martin, Ann., 401, 178 (1913).

[VITA]

Yü-Gwan Chen was born in Nanking, China, March 8, 1893. After graduation from college in 1915, he further studied Chinese classics, 1915-16. He entered Case School of Applied Science, Cleveland, Ohio, as a special student in the Department of Chemistry, 1916-17. He registered at Columbia University to pursue graduate work in chemistry under the Faculty of Pure Science; and was awarded the degree of Master of Arts in 1918. From September 1919 to June 1922, he has been pursuing research in organic chemistry in the research laboratories of Havemeyer Hall, Columbia University.