Industrial Photochromism

  • Andrew D. Towns
Part of the Lecture Notes in Chemistry book series (LNC, volume 92)


This chapter outlines how industrial photochromic dyes are designed, manufactured and used. It explains the properties that are crucial to their commercial utility and, in doing so, gives a definition of ‘industrial photochromism’. Such colorants possess several key molecular features. This Chapter reveals how these structural elements influence photochromism. Additionally, it describes the typical chemistries employed in dye construction and takes a critical look at the limitations of current commercial colorants. Along the way, the directions that the exploitation of existing types might take in order to improve performance receive attention as do the potential future industrial applications to which photochromic dyes may be put.


Bathochromic Shift Hypsochromic Shift Photochromic Property Photochromic Material Photochromic Behaviour 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.



Thousands of people working during this century and the last within industry, academia and elsewhere in countries across the globe can take a share of the credit for making industrial photochromism what it is. However, the author wishes to acknowledge the contribution to the knowledge, as well as the previously unpublished data, contained within this Chapter of the numerous members of technical staff of Vivimed Labs Europe Ltd (and James Robinson Ltd as was), particularly Dr. D.A. Clarke and Dr. S.M. Partington. In addition, mention must be made of the fruitful collaboration between the organisation with the research groups of Prof. J.D. Hepworth, Dr. B.M. Heron and Dr. C.D. Gabbutt, leading to the creation of insights into the properties of photochromic dyes and its realisation in the form of industrial photochromism.


  1. 1.
    Corns SN, Partington SM, Towns AD (2009) Color Technol 125:249–261Google Scholar
  2. 2.
    Brown GH (ed) (1971) Photochromism. Wiley-Interscience, New YorkGoogle Scholar
  3. 3.
    Dürr H, Bouas-Laurent H (eds) (1990) Photochromism molecules and systems. Elsevier, AmsterdamGoogle Scholar
  4. 4.
    Crano JC, Guglielmetti RJ (eds) (1999) Organic photochromic and thermochromic compounds, vol 1–2. Plenum, New YorkGoogle Scholar
  5. 5.
    Dürr H, Bouas-Laurent H (2001) Pure Appl Chem 73:639–665Google Scholar
  6. 6.
    Zhang J, Zou Q, Tian H (2013) Adv Mater 25:378–399PubMedGoogle Scholar
  7. 7.
    Heller HG, Oliver SN, Whittal J, Johncock W, Darcy PJ, Trundle C (1986) GB2146327B (The Plessey Company plc)Google Scholar
  8. 8.
    Chu NYC, in Ref. 3, Chapter 10, pp 493–509Please provide year, publisher name, and location for Refs. [8, 10, 14, 50, 55, 61, 81, 99].Google Scholar
  9. 9.
    Crano JC, Kwak WS, Welch CN (1992) In: McArdle CB (ed) Applied photochromic polymer systems. Blackie, GlasgowGoogle Scholar
  10. 10.
    Hoffman HJ, in Ref. 3, Chapter 22, pp 822–854Google Scholar
  11. 11.
    Bruneni JL (1997) More than meets the eye: the stories behind the development of plastic lenses. PPG Industries, PittsburghGoogle Scholar
  12. 12.
    Van Gemert B (2000) Mol Cryst Liq Cryst 344:57–62Google Scholar
  13. 13.
    Meslin D (2010) Materials and treatments. Essilor Academy Europe, ParisGoogle Scholar
  14. 14.
    Guglielmetti R, in Ref. 3, Chapter 23, pp 855–878Google Scholar
  15. 15.
    Mortimer RJ, Rosseinsky DR, Monk PMS (eds) (2015) Electrochromic materials and devices. Wiley-VCH, WeinheimGoogle Scholar
  16. 16.
    Österholm AM, Shen DE, Kerszulis JA, Bulloch RH, Kuepfert M, Dyer AL, Reynolds JR (2015) ACS Appl Mater Interfaces 7:1413–1421PubMedGoogle Scholar
  17. 17.
    Little AF, Christie RM (2011) Color Technol 127:275–281; 126 (2010) 164–170; 126 (2010) 157–163Google Scholar
  18. 18.
    Aldib M, Christie RM (2011) Color Technol 127:282–287Google Scholar
  19. 19.
    Lee S-J, Son Y-A, Suh H-J, Lee D-N, Kim S-H (2006) Dyes Pigment 69:18–21Google Scholar
  20. 20.
    Billah SMR, Christie RM, Shamey R (2008) Color Technol 124:223–228Google Scholar
  21. 21.
    Shah MRB, Christie RM, Morgan KM, Shamey R (2005) Mol Cryst Liq Cryst 431:535–539Google Scholar
  22. 22.
    Billah SMR, Christie RM, Shamey R (2012) Color Technol 128:488–492Google Scholar
  23. 23.
    Son Y-A, Park Y-M, Park S-Y, Shin C-J, Kim S-H (2007) Dyes Pigment 73:76–80Google Scholar
  24. 24.
    Peng L, Guo R, Jiang S, Lan J, He Y, Huang X (2015) Fibers Polym 16:1312–1318Google Scholar
  25. 25.
    Billah SMR, Christie RM, Morgan KM (2008) Color Technol 124:229–233Google Scholar
  26. 26.
    Aldib M, Christie RM (2013) Color Technol 129:131–143Google Scholar
  27. 27.
    Aldib M (2015) Color Technol 131:172–182Google Scholar
  28. 28.
    Coimbra P, Gil MH, Duarte CMM, Heron BM, de Sousa HC (2005) Fluid Phase Equilib 238:120–128Google Scholar
  29. 29.
    Cheng T, Lin T, Brady R, Wang X (2008) Fibers Polym 9:301Google Scholar
  30. 30.
    Feczkó T, Samu K, Wenzel K, Neral B, Voncina B (2012) Color Technol 129:18–23Google Scholar
  31. 31.
    van Renesse RL (1998) In: van Renesse RL (ed) Optical document security, 2nd edn. Artech House, Boston, pp 201–224, Chapter 9Google Scholar
  32. 32.
    McCallien DWJ, Bezer M (2000) (John Hogg Technical Solutions Ltd), British Patent 2344599AGoogle Scholar
  33. 33.
    Feringa BL, Browne WR (eds) (2011) Molecular switches, 2nd edn. Wiley-VCH, WeinheimGoogle Scholar
  34. 34.
    Dong H, Zhu H, Meng Q, Gong X, Hu W (2012) Chem Soc Rev 41:1754–1808PubMedGoogle Scholar
  35. 35.
    Irie M, Yokoyama Y, Seki T (eds) (2013) New frontiers in photochromism. Springer Japan, TokyoGoogle Scholar
  36. 36.
    Tsujioka T (2005) Mol Cryst Liq Cryst 431:391–395Google Scholar
  37. 37.
    Barachevsky VA, Strokach YP, Puankov YA, Krayushkin MM (2007) J Phys Org Chem 20:1007–1020Google Scholar
  38. 38.
    Barachevsky VA (2008) J Photochem Photobiol A 196:180–189Google Scholar
  39. 39.
    Tsujioka T (2014) J Mater Chem C 2:3589–3596Google Scholar
  40. 40.
    Raymo FM, Tomasulo M (2005) Chem Soc Rev 34:327–336PubMedGoogle Scholar
  41. 41.
    Yildiz I, Deniz E, Raymo FM (2009) Chem Soc Rev 38:1859–1867PubMedGoogle Scholar
  42. 42.
    Tsujioka T, Irie M (2010) J Photochem Photobiol C 11:1–14Google Scholar
  43. 43.
    Orgiu E, Samori P (2014) Adv Mater 26:1827–1845PubMedGoogle Scholar
  44. 44.
    Andréasson J, Pischel U (2013) Israel J Chem 53:236–246Google Scholar
  45. 45.
    Matsuda K, Irie M (2006) Chem Lett 35:1204–1209; Belser P, De Cola L, Hartl F, Adamo V, Bozic B, Chriqui Y, Iyer VM, Jukes RTF, Kühni J, Querol M, Roma S, Salluce N (2006) Adv Func Mater 16:195–208Google Scholar
  46. 46.
    Fang Y, Sun M (2015) Light Sci Appl 4:e294Google Scholar
  47. 47.
    Yamada M, Kondo M, Mamiya J-I, Yu Y, Kinoshita M, Barrett CJ, Ikeda T (2008) Angew Chem Int Ed 47:4986–4988Google Scholar
  48. 48.
    International Symposium on Photochromism 2013 Book of Abstracts, Berlin, Germany; 2013Google Scholar
  49. 49.
    Irie M (2001) In: Feringa BL (ed) Molecular switches, 1st edn. Wiley-VCH, Weinheim, pp 37–62, Chapter 2Google Scholar
  50. 50.
    Fan M-G, Yu L, Zhao W, in Ref. 4, vol 1, Chapter 4, pp 141–206Google Scholar
  51. 51.
    Whittal J, in Ref. 3, Chapter 9, pp 467–492Google Scholar
  52. 52.
    Heller HG, Koh KSV, Köse M, Rowles N (1999) Photochromics by design: the art of molecular tailoring. In: J Griffiths (ed) Colour science‘98 conference papers. The University of Leeds, HarrogateGoogle Scholar
  53. 53.
    Heller HG, Oliver SN (1981) J Chem Soc Perkin Trans I:197Google Scholar
  54. 54.
    Zollinger H (2003) Color chemistry, 3rd edn. VCHA & Wiley-VCH, ZürichGoogle Scholar
  55. 55.
    Yokoyama Y, Gushiken T, Ubukata T, in Ref. 33, Chapter 3, pp 81–95Google Scholar
  56. 56.
    Kuhn HJ, Braslavsky SE, Schmidt R (2004) Pure Appl Chem 76:2105Google Scholar
  57. 57.
    Kobayakawa T (1999) Third international symposium on photochromism, FukuokaGoogle Scholar
  58. 58.
    Bamfield P, Hutchings MG (2010) Chromic phenomena, 2nd edn. The Royal Society of Chemistry, CambridgeGoogle Scholar
  59. 59.
    Irie M (2000) Chem Rev 100:1685–1716PubMedGoogle Scholar
  60. 60.
    Irie M, Fukaminato T, Matsuda K, Kobatake S (2014) Chem Rev 114:12174–12277PubMedGoogle Scholar
  61. 61.
    Irie M, in Ref. 4, vol 1, Chapter 5, pp 207–222Google Scholar
  62. 62.
    Higashiguchi K, Matsuda K, Tanifuji N, Irie M (2005) J Am Chem Soc 127:8922–8923PubMedGoogle Scholar
  63. 63.
    Morimoto M, Irie M (2005) Chem Commun 3895Google Scholar
  64. 64.
    Irie M (2008) Bull Soc Chem Jpn 81:917Google Scholar
  65. 65.
    Zhao Y, Ikeda T (eds) (2009) Smart light responsive materials: azobenzene-containing polymers and liquid crystals. Wiley, HobokenGoogle Scholar
  66. 66.
    Such G, Evans RA, Yee LH, Davis TP (2003) J Macromol Sci C43:547–579Google Scholar
  67. 67.
    Homola TJ (2000) Mol Cryst Liq Cryst 344:63–68Google Scholar
  68. 68.
    Homola TJ (1999) In: ChemiChromics USA‘99 conference proceedings. Spring Innovations Ltd., New OrleansGoogle Scholar
  69. 69.
    Vázquez-Mera N, Roscini C, Hernando J, Ruiz D, Hernando Campos J (2013) Adv Opt Mater 1:631–636Google Scholar
  70. 70.
    Werkman PJ, Rietjens GH, Bernadus TNM, de Vries GC, Klink SI, Hofstraat JW, Kloosterboer JG (2003) (Koninklijke Philips Electronics NV), World Patent Application 03/001555A1Google Scholar
  71. 71.
    For example: Heft A, Pfuch A, Schimanski A, Grünler B (Innovent e.V.), European Patent 2233545 (2012)Google Scholar
  72. 72.
    For example: Partington SM (Vivimed Labs Europe Ltd.), World Patent Application 2010/020770A1 (2010); Evans RA, Skidmore MA, Yee LH, Hanley TL, Lewis DA (Advanced Polymerik Pty Ltd.), US Patent 7807075 (2010)Google Scholar
  73. 73.
    Evans RA, Hanley TL, Skidmore MA, Davis TP, Such GK, Yee LH, Ball GE, Lewis DA (2005) Nat Mater 4:249PubMedGoogle Scholar
  74. 74.
    Evans RA, Such GK (2005) Aust J Chem 58:825Google Scholar
  75. 75.
    Malic N, Campbell JA, Ali AS, York M, D’Souza A, Evans RA (2010) Macromolecular 43:8488–8501Google Scholar
  76. 76.
    Malic N, Campbell JA, Evans RA (2008) Macromolecular 41:1206Google Scholar
  77. 77.
    Roscini C, Vázquez-Mera N, Ruiz-Molina D (2015) (Consejo Superior de Investigaciones Cientificas), US Patent Application 2015/0024126Google Scholar
  78. 78.
    Amon A, Bretler H, Bleikolm A (1993) (SICPA Holding SA), European Patent 0327788Google Scholar
  79. 79.
    For example, Patel DG, Benedict JB, Kopelman RA, Frank NL (2005) Chem Commun 2208–2210Google Scholar
  80. 80.
    Qin M, Huang Y, Li F, Song Y (2015) J Mater Chem C 3:9265–9275Google Scholar
  81. 81.
    Bertelson RC, in Ref. 4, vol 1, Chapter 1, pp 11–83Google Scholar
  82. 82.
    Klajn R (2014) Chem Soc Rev 43:148–184PubMedGoogle Scholar
  83. 83.
    Van Gemert B (1999) Third international symposium on photochromism, FukuokaGoogle Scholar
  84. 84.
    Van Gemert B in ChemiChromics‘99 conference papers. Spring Innovations, New OrleansGoogle Scholar
  85. 85.
    Wilkinson F, Worrall DR, Hobley J, Jansen L, Williams SL, Langley AJ, Matousek P (1996) J Chem Soc Faraday Trans 92:1331–1336Google Scholar
  86. 86.
    Pottier E, Sergent M, Phan Tan Luu R, Guglielmetti R (1992) Bull Soc Chim Belg 101:719–739Google Scholar
  87. 87.
    York M, Evans RA (2010) Synth Commun 40:3618–3628Google Scholar
  88. 88.
    Van Gemert B, in Ref. 4, Chapter 3, pp 111–140Google Scholar
  89. 89.
    Hepworth JD, Gabbutt CD, Heron BM (1999) Photochromism of Naphthopyrans. In: J Griffiths (ed, Colour science‘98 conference papers. The University of Leeds, HarrogateGoogle Scholar
  90. 90.
    Crano JC, Flood T, Knowles D, Kumar A, Van Gemert B (1996) Pure Appl Chem 68:1395Google Scholar
  91. 91.
    Hepworth JD, Heron BM (2006) In: Kim S-H (ed) Functional dyes. Elsevier, Amsterdam, pp 85–135, Chapter 3Google Scholar
  92. 92.
    Hobley J, Wilkinson F (1996) J Chem Soc Faraday Trans 92:1323–1330Google Scholar
  93. 93.
    For example:Momota J, Kobayakawa Takashi T (Tokuyama Corp.), Japanese Patent 3227062 (2001); Komura Y, Momota J (Tokuyama Corp.), Japanese Patent 2000-026469 (2000); V Krongauz, A Chif, A Aizikovich and V Tchernoivanov (Yeda Research and Development Co. Ltd.), US Patent 6891038 (2005)Google Scholar
  94. 94.
    Partington SM, Towns AD (2014) Dyes Pigment 104:123–130Google Scholar
  95. 95.
    Hovey RJ, Chu NYC, Piusz PG, Fuchsman H (1982) (American Optical Corp.), US Patent 4342668Google Scholar
  96. 96.
    Melzig M, Martinuzzi G (1984) (Optische Werke G Rodenstock), European Patent 0508219Google Scholar
  97. 97.
    Wilkinson F, Hobley J, Naftaly M (1992) J Chem Soc Faraday Trans 88:1511–1517Google Scholar
  98. 98.
    Rickwood M, Marsden SD, Ormsby ME, Staunton AL, Wood DW, Hepworth JD, Gabbutt CD (1994) Mol Cryst Liq Cryst A 246:17–24Google Scholar
  99. 99.
    Malatesta V, in Ref. 4, vol 2, pp 65–166Google Scholar
  100. 100.
    Parry H, Corns N, Towns A (2003) Speciality Chem Mag 23(8):27Google Scholar
  101. 101.
    Clarke DA (1995) Photochromic dyes. In: ChemiChromics‘95 conference papers. Spring Innovations, ManchesterGoogle Scholar
  102. 102.
    Higgins S (2003) Chem Br 39(6):26Google Scholar
  103. 103.
    Gabbutt CD, Hepworth JD, Heron BM, Partington SM, Thomas DA (2001) Dyes Pigment 49:65–74Google Scholar
  104. 104.
    Rickwood M, Smith KE, Gabbutt CD, Hepworth J (1994) (Pilkington Plc), WO 94/22850Google Scholar
  105. 105.
    Gabbutt CD, Gelbrich T, Hepworth JD, Heron BM, Hursthouse MB, Partington SM (2002) Dyes Pigment 54:79–93Google Scholar
  106. 106.
    Gabbutt CD, Heron BM, Instone AC, Horton PN, Hursthouse MB (2005) Tetrahedron 61:463–471Google Scholar
  107. 107.
    Rauzy E, Berro C, Morel S, Herbette G, Lazzeri V, Guglielmetti R (2004) Polym Int 53:455Google Scholar
  108. 108.
    Favaro G, Ortica F, Romani A, Smimmo P (2008) J Photochem Photobiol A 196:190Google Scholar
  109. 109.
    Research Disclosure, 36144 (May 1994) 267Google Scholar
  110. 110.
    Clarke DA, Heron BM, Gabbutt CD, Hepworth JD, Partington SM, Corns SN (2002) (James Robinson Ltd.), European Patent 1117656Google Scholar
  111. 111.
    Clarke DA, Heron BM, Gabbutt CD, Hepworth JD, Partington SM, Corns SN (2011) (Vivimed Labs Europe Ltd.), European Patent 0971914Google Scholar
  112. 112.
    Van Gemert B (1996) (PPG Industries Inc.), World Patent Application 96/14596Google Scholar

Copyright information

© Springer International Publishing Switzerland 2016

Authors and Affiliations

  • Andrew D. Towns
    • 1
    • 2
  1. 1.Lambson Ltd.WetherbyUK
  2. 2.Vivimed Labs Europe Ltd.HuddersfieldUK

Personalised recommendations