Synthesis and fastness properties of styryl and azo disperse dyes derived from 6-nitro substituted 3-aryl-2-methyl-4(3H)-quinazolinone
Harjinder Singh Bhatti
Dyes Research Laboratory, University Institute of Chemical Technology, University of Mumbai, Matunga, Mumbai 400019, India.
Ciba India Pvt Ltd, Goregaon(E), Mumbai 400063, India. Email: [email protected]
Search for more papers by this authorSambamurthy Seshadri
Dyes Research Laboratory, University Institute of Chemical Technology, University of Mumbai, Matunga, Mumbai 400019, India.
88, Ashtalakshmi, Bhaudaji Cross Road, Matunga, Mumbai 400019, India. Email: [email protected]
Search for more papers by this authorHarjinder Singh Bhatti
Dyes Research Laboratory, University Institute of Chemical Technology, University of Mumbai, Matunga, Mumbai 400019, India.
Ciba India Pvt Ltd, Goregaon(E), Mumbai 400063, India. Email: [email protected]
Search for more papers by this authorSambamurthy Seshadri
Dyes Research Laboratory, University Institute of Chemical Technology, University of Mumbai, Matunga, Mumbai 400019, India.
88, Ashtalakshmi, Bhaudaji Cross Road, Matunga, Mumbai 400019, India. Email: [email protected]
Search for more papers by this authorAbstract
The synthesis of 6-nitro substituted 3-aryl-2-methyl-4(3H)-quinazolinones from readily available starting materials, such as isatoic anhydride, is described. One of these, 3-phenyl-2-methyl-4(3H)-quinazolinone, has been utilised to prepare a range of styryl disperse dyes for polyester. Novel azo disperse dyes based on 6-nitro-3-(m-diethylaminophenyl)-2-methyl-4(3H)-quinazolinone as coupling component are reported. The application properties of the dyes on polyester and their fastness properties have been evaluated, with the latter being disappointing.
References
- 1 H Yamaguchi and F Ishikawa, J. Heterocycl. Chem., 18 (1981): 67.
- 2 B R Baker, R E Schaub and F J McEvo, J. Org. Chem., 17 (1952): 141.
- 3 H W Grimmel, A Guenther and J F Morgan, J. Am. Chem. Soc., 68 (1946): 542.
- 4 V G Prabhu, R K Browne and J F Zaroslinski, Arch. Int. Pharmacodynamics, 148 (1964) 228; Chem. Abstr., 60 (1964) 15014d.
- 5 J R Vaughan, E Cohen and B Klarberg, J. Am. Chem. Soc., 81 (1959): 5508.
- 6 E Cohen, Arzneim. Forsch., 13 (1963): 660.
- 7 N B Chapman, K Clarke and K Wilson, J. Chem. Soc. (1963): 2256.
- 8 K H Boltze, Arzneim. Forsch., 13 (1963): 688.
- 9 H H Peterson, E Tietz and W Siefken, Angew. Chem., 74 (1962): 855.
- 10 E Yamada, K Sato and M Sugihara, Japan Kokai 74, 04 810 (1974); Chem. Abstr., 81 (1974) 171355W.
- 11 M Okawa, Y Takeda and K Sato, Japan Kokai 73, 00 723 (1973); Chem. Abstr., 78 (1973) 125838w.
- 12 A A Cevasco, DE2209872 (American Cyanamid, USA) 1972.
- 13 R Meinhard, R Neeff and W Mueller, DE2812635 (Bayer, Germany) 1979.
- 14 I J Fletcher, GB2068994 (Ciba-Geigy, Switzerland) 1981.
- 15 R S Pandit and S Seshadri, Indian J. Chem., 11 (1973): 532.
- 16 S B Barnela and S Seshadri, Indian J. Chem., 25B, (1986): 709.
- 17 V Purnaprajna and S Seshadri, Indian J. Chem., 15B (1977): 109.
- 18 S Seshadri and R Rajagopal, Dyes Pigm., 13 (1990): 161.
- 19 S Seshadri and R Rajagopal, Dyes Pigm., 17 (1991): 193.
- 20 V B Piskov, Khim-Farm. Zh., 7 (1973) 8; Chem. Abstr., 79 (1973) 78332k.
- 21 E Chapman and H Stephen, J. Chem. Soc., 127 (1925): 1796.
- 22 E Campaigne and W L Archer, Organic Synthesis, Vol. IV, Ed. N Rabjohn ( New York : John Wiley, 1963) 331.
- 23
M A Kira,
M O Abdel Rehman and
K J Gadalla, Tetrahedron Lett., 14 (1969): 109.
10.1016/S0040-4039(01)88217-4 Google Scholar
- 24 K H Saunders and R L M Allen, Aromatic Diazo Compounds ( London : Arnold, 1985) 11.
- 25 M T Bogert and G A Geiger, J. Am. Chem. Soc., 34 (1912): 524.
- 26 G M Coppola, Synthesis (1980): 505.
- 27 Dictionary Of Organic Compounds, 5th Edn ( New York : Chapman and Hall, 1987).
- 28 H W Grimmel, A Guenther and J F Morgan, J. Am. Chem. Soc., 68 (1946): 542.
- 29 M T Bogert and H S Steines, J. Am. Chem. Soc., 27 (1905): 649.
- 30 E Yamada, K Sato and M Sugihara, Japan Kokai 74, 04 810 (1974); Chem. Abstr., 81 (1974) 171355w.
- 31 M Matsuoka, H Tanii, T Kitao and K Konishi, Kogyo Kagaku Zasshi, 73 (10) (1970): 2195.
- 32 K Hama and T Akamatsu, Japan Kokai 73, 30 655 (1970); Chem. Abstr., 80 (1974) 146974u.
- 33 H Pfitzner and W Dammert, DE2116559 (BASF, Germany) 1972.
- 34 S Pizon and B Pizon, PL73046 (1974); Chem. Abstr., 84 (1976) 19165p.
- 35 A A Fadd, H A Etman, F A Amer, M Bargout and Kh-s Mohamed, J. Chem. Technol. Biotechnol., 62 (2) (1995): 170.
- 36 V A Desai and K R Desai, J. Indian Council Chem., 10 (1) (1994): 25.
- 37 K Hama and T Akamatsu, Japan Kokai 73, 32 562 (1973); Chem. Abstr., 81 (1974) 65367g.
- 38 P H Eerdekens, DE2305172 (AGFA Gevaert, Germany) 1973.
- 39
Standard Methods for the Determination of Colour Fastness of Textile and Leather, 4th Edn and supplements (
Bradford
: SDC, 1978).
10.3403/00068386 Google Scholar