Metal salt azo pigments
Robert M Christie
School of Textiles & Design, Heriot Watt University, Scottish Borders Campus, Galashiels TD1 3HF, UKEmail: [email protected]
Search for more papers by this authorJennifer L Mackay
School of Textiles & Design, Heriot Watt University, Scottish Borders Campus, Galashiels TD1 3HF, UKEmail: [email protected]
Search for more papers by this authorRobert M Christie
School of Textiles & Design, Heriot Watt University, Scottish Borders Campus, Galashiels TD1 3HF, UKEmail: [email protected]
Search for more papers by this authorJennifer L Mackay
School of Textiles & Design, Heriot Watt University, Scottish Borders Campus, Galashiels TD1 3HF, UKEmail: [email protected]
Search for more papers by this authorRobert Christie is Professor in Colour Chemistry & Technology in the School of Textiles & Design, with more than 30 years industrial and academic experience of research in the chemistry and technology of organic pigments. Jennifer Mackay obtained her PhD in 2007 on the basis of a CASE award in collaboration with Ciba Specialty Chemicals (Paisley) and is currently a colour technologist with Thomas Swan & Co. (Consett, Co. Durham).
Abstract
Historically, metal salt azo pigments have evolved from products referred to as ‘lakes’, which were prepared from established water-soluble textile dyes, rendered insoluble by precipitation on to colourless inorganic substrates. The first azo lake pigment, Lithol Red, was reported in 1899. The majority of the current range of industrial metal salt azo pigments no longer contains the insoluble substrate as an integral constituent. Structurally, they may be considered as being derived from sodium salts of anionic azo dyes containing sulphonate and/or carboxylate groups by replacement of the sodium cation, usually with a divalent cation of an alkaline earth (calcium, strontium or barium) or the transition metal manganese. This review provides an account of the historical development of metal salt azo pigments and an overview of the chemical structural types of the current range of commercially important products in relation to their properties and application performance. An overview of the patent literature associated with the development of the products is also given. Importantly, the structural investigations which have been reported on this group of pigments, using a variety of microscopic, spectroscopic and crystallographic techniques, are reviewed.
References
- 1 R M Christie, The Organic and Inorganic Chemistry of Pigments (London: Oil and Colour Chemists’ Association, 2002).
- 2 R M Christie, Pigments: Structures and Synthetic Procedures (London: Oil and Colour Chemists’ Association, 1993).
- 3 J Lenoir, in The Chemistry of Synthetic Dyes, Chapter 6, Vol. 5, Ed. K Venkataraman (London: Academic Press, 1971) 316.
- 4
R M Christie, Colour Chemistry, Vol. 9 (London: Royal Society of Chemistry, 2001).
10.1039/9781847550590 Google Scholar
- 5 H Zollinger, Color Chemistry. Syntheses, Properties, and Applications of Organic Dyes and Pigments, 3rd Edn (Weinheim: Wiley-VCH, 2003).
- 6
W Herbst and
K Hunger, Industrial Organic Pigments. Production, Properties, Applications, 3rd Edn (Weinheim: Wiley-VCH, 2004).
10.1002/3527602429 Google Scholar
- 7 J Lenoir, Peintures Pigm. Vernis, 35 (1959) 303.
- 8 A Siegel and W S Struve, The Chemistry of Organic Pigments. Proceedings of the Perkin Centennial, 1856–1956, Commemorating the Discovery of Aniline Dyes: American Association of Textile Chemists and Colorists, New York (1956) 209.
- 9 T C Patton, in Pigment Handbook Properties and Economics, Vol. 1, Ed. C P Temple (Chichester: Wiley, 1973).
- 10 Colour Index, 3rd Edn, Vol. 9, Pigments and Solvent (Bradford: SDC, 1982); 4th Edn (available at: http://www.colour-index.org).
- 11 T B Reeve, in Treatise on Coatings, Vol. 3, Eds R R Myers and J S Long (New York: Marcel Dekker, 1975) 119.
- 12 R M Christie, R R Mather and R H Wardman, The Chemistry of Colour Application, Chapter 6 (Oxford: Blackwell Science, 2000) 123.
- 13 R Az, B Dewald and D Schnaitmann, Dyes Pigm., 15 (1991) 1.
- 14 R M Christie, C H Chang, H Y Huang and M Vincent, Surf. Coat. Int. Part B, 89 (2006) 77.
- 15 US743071 (Actien Gesellschaft Fur Anilin Fabrikation, 1903).
- 16 R M Christie and S Moss, Dyes Pigm., 8 (1987) 211.
- 17 W Czajkowski, Dyes Pigm., 1 (1980) 17.
- 18
F Xuening,
Z Tianyong and
Z Chunlong, Dyes Pigm., 40 (1999) 199.
10.1016/S0143-7208(98)00053-9 Google Scholar
- 19 G Chisholm, B Hay, K D M Harris, S J Kitchin and K M Morgan, Dyes Pigm., 42 (1999) 159.
- 20 R B McKay, Proc. XVIII FATIPEC Congress, Venice, Italy (1986) 405.
- 21 R B McKay, Prog. Org. Coat., 22 (1993) 211.
- 22 A Whitaker, J.S.D.C., 94 (1978) 431.
- 23 M J Barrow, R M Christie and J E Monteith, Dyes Pigm., 55 (2002) 79.
- 24 M J Barrow, R M Christie, A Lough and P Standring, Dyes Pigm., 45 (2000) 153.
- 25 A Whitaker, J.S.D.C, 104 (1988) 294.
- 26 K Hunger, Rev. Prog. Color., 29 (1999) 71.
- 27 G R Duckett, J R Fryer and T Baird, Inst. Phys. Conf. Ser., 78 (1985) 437.
- 28 R K Harris, P Jonsen and K J Packer, Org. Magn. Reson., 22 (1984) 269.
- 29 R K Harris, P Jonsen, K J Packer and C D Campbell, J. Chem. Soc., Perkin Trans. 2 (1987) 1383.
- 30
A R Kennedy,
C McNair,
W E Smith,
G Chisholm and
S J Teat, Angew. Chem. Int. Ed., 39 (2000) 638.
10.1002/(SICI)1521-3773(20000204)39:3<638::AID-ANIE638>3.0.CO;2-K CAS Web of Science® Google Scholar
- 31 S B Choudhury, D Ray and A Chakravorty, J. Chem. Soc., Dalton Trans. (1992) 107.
- 32 A R Kennedy, J B A Kirkhouse, K M McCarney, O Puissegur, W E Smith, E Staunton, S J Teat, J C Cherryman and R James, Chem. Eur. J., 10 (2004) 4606.
- 33 GB25511 (BASF, 1899).
- 34 US912138 (Actien Gesellschaft Fur Anilin Fabrikation, 1909).
- 35 GB359643 (I G Farben, 1931).
- 36 US2174501 (Calco, 1939).
- 37 US2225665 (DuPont, 1940).
- 38 US2447394 (American Cyanamid, 1948).
- 39 US2598483 (American Cyanamid, 1952).
- 40 US2649383 (DuPont, 1953).
- 41 GB776873 (ICI, 1957).
- 42 US2694055 (Sherwin Williams, 1954).
- 43 US2765300 (American Cyanamid, 1956).
- 44 US2796415 (Sherwin-Williams, 1957).
- 45 US2821525 (American Cyanamid, 1958).
- 46 US2478768 (DuPont, 1949).
- 47 GB120266 (American Cyanamid, 1968).
- 48 GB1114015 (Bayer, 1967).
- 49 GB1169670 (Bayer, 1968).
- 50 US3520870 (American Cyanamid, 1970).
- 51 US352934 (Bayer, 1970).
- 52 GB1312198 (Bayer, 1973).
- 53 US4143036 (DuPont, 1979).
- 54 US5457188 (Bayer, 1995).
- 55 US5747571 (Engelhard, 1998).
- 56 US5997628 (Engelhard, 1999).
- 57 WO00/78872 A1 (Engelhard, 2000).
- 58 US6375733 B1 (Engelhard, 2002).
- 59 WO03/016408 A1 (Clariant, 2003).
- 60 WO02/090444 A1 (Clariant, 2002).
- 61 US2004/0139880 A1 (Clariant, 2004).
- 62 US6902612 B2 (Engelhard, 2005).
- 63 R M Christie and B D Howie, Dyes Pigm., in press.
- 64 US5047517 (Hoechst, 1991).
- 65 US4980458 (Ciba-Geigy, 1990).
- 66 WO 96/22333 (Zeneca, 1995).
- 67 US5744590 (Zeneca, 1998).
- 68 WO02/48266 A2 ( BASF, 2002).
- 69 WO02/059217 A1 (Ciba, 2002).
- 70 US6784286 B2 (BASF, 2004).
- 71 US6913640 B2 (Ciba, 2005).
- 72 WO98/05718 ( Engelhard, 1998).
- 73 GB1516223 (Hoechst, 1978).
- 74 EP0272697 A2 (Dainippon Ink, 1987).
- 75 GB2241502A (Ciba-Geigy, 1990).
- 76 US5102466 (Ciba-Geigy, 1992).
- 77 US5248335 (Toyo Ink, 1993).
- 78 US2013075 (Krebs, 1935).
- 79 GB521509 (ICI, 1940).
- 80 US3841889 (BASF, 1974).
- 81 US5144014 (Toyo Ink, 1992).
- 82 EP0313360B1 (Sun Chemicals, 1989).
- 83 US5243031 (Toyo Ink, 1993).
- 84 EP0848047A1 (Ciba, 1998).
- 85 GB1313147 (Ciba-Geigy, 1973).
- 86 GB2031925 (BASF, 1980).
- 87 US5082498 (BASF, 1992).
- 88 WO93/16137 (Zeneca, 1993).
- 89 US5380363 (Francolor, 1995).
- 90 US4625018 (Inmont, 1986).
- 91 US575843 (Sun Chemicals, 1996).
- 92 US6959055 (Toyo Ink, 2006).
- 93 US4190578 (Ciba-Geigy, 1980).
- 94 US2229049 (Du Pont, 1941).
- 95 US2744027 (Du Pont, 1956).
- 96 US6402828B1 (Ciba, 2002).
- 97 EP1038925A2 (Ciba, 2000).
- 98 US4767844 (Dainippon Ink, 1988).
- 99 EP0480705B1 (Toyo Ink, 1992).
- 100 US4655844 (Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo, 1987).
- 101 US4804415 (Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo, 1989).
- 102 GB1112890 (BASF, 1967).
- 103 US5677435 (Engelhard, 1997).
- 104 US4115377 (Hercules, 1978).
- 105 WO9856859 (Ciba, 1998).
- 106 US4719292 (Hoechst, 1988).
- 107 US6228162, B1 (Clariant, 2001).
- 108 US6146455 (Clariant, 2000).
- 109 US6191263, B2 (Clariant, 2001).
- 110 EP0358810, A1 (Dainippon Ink, 1988).
- 111 US5055564 (Dainippon Ink, 1991).
- 112 US5084106 (Dainippon Ink, 1992).
- 113 US6602342 (Clariant, 2003).
- 114 US2117860 (Du Pont, 1938).
- 115 US4822419 (BASF, 1989).
- 116 US4810302 (Toyo Ink, 1989).
- 117 US5098478 (Sun Chemicals, 1992).
- 118 US5614013 (Ciba-Geigy, 1997).
- 119 US4410617 (Xerox, 1983).
- 120 US5032483 (Fuji Xerox, 1991).
- 121 US6159649 (Clariant, 2000).