Abstract
Photostability is the resistance to change induced by ultraviolet radiation (UVR). Its antonym photolability is the tendency to change under exposure to UVR. Sunscreen photostability and photolability, with its causes, consequences, and solutions, are the subjects of this chapter.
We begin the chapter with a brief history of photostability in the sunscreen industry and explain why photostability will remain a key issue for many years to come. Because sunscreens are photochemical systems, we present a primer on photochemistry to set the stage for the technical sections to follow. In the first of these, we review what has been learned over the past 20 years about the surprisingly complex photochemistry of the UVA filter, avobenzone. Of the 55 or so UV filters approved throughout the world for the use in sunscreens, about half are in common usage. The photostabilities of many of these have been investigated, and we present the results of the most recent studies. We then focus on how various UV filter combinations affect the photostabilities of individual UV filters and the sunscreen product as a whole. We share strategies for improving sunscreen photostability and discuss the dozen or so commercially available photostabilizers and how they function. Lastly, we discuss different approaches to testing photostability.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Similar content being viewed by others
Notes
- 1.
Ï„ KT represents the lifetime of the keto triplet.
References
Polefka TG, Meyer TA, Agin PP, Bianchini RJ (2012) Effects of solar radiation on the skin. J Cosmetic Dermatol 11:134–143
Bonda C, Hu R, Jockusch S (2014) Avobenzone photochemistry: improving photoprotection by stabilizing avobenzone with ethylhexyl methoxycrylene. HPC Today 9:6–10
Dondi D, Albini A, Serpone N (2006) Interactions between different solar UVB/UVA filters contained in commercial suncreams and consequent loss of UV protection. Photochem Photobiol Sci 5:835–843
Turro NJ, Ramamurthy V, Scaiano JC (2009) Principles of molecular photochemistry: an introduction. University Science Books, Sausalito
Schwack W, Rudolph TJ (1995) Photochemistry of dibenzoy methane UVA filters – part 1. Photochem Photobiol B Biol 28:229–234
Andrae I, Bringhen A, Bohm F, Gonzenbach H, Hill T, Mulroy L, Truscott TG (1997) A UVA filter (4-tert-butyl-4’-methoxydibenzoylmethane): photoprotection reflects photophysical properties. J Photochem Photobiol B Biol 37:147–150
Cantrell A, McGarvey DJ (2001) Photochemical studies of 4-tert-butyl-4’ methoxydibenzoylmethane (BM-DBM). J Photochem Photobiol B Biol 64:117–122
Hill TJ (1994) Molecular mechanisms of photoprotection. PhD thesis, Keele University
Huong SP, Rocher E, Fourneron J-D, Charles L, Monnier V, Bun H, Andrieu V (2008) Photoreactivity of the sunscreen butylmethoxydibenzoylmethane (DBM) under various experimental conditions. J Photochem Photobiol A Chem 196:106–112
Bonda CA, Marinelli PM, Trivedi J, Hopper S, Wentworth G (1997) Avobenzone Photostability in Simple Polar and Non-Polar Solvent Systems. Presentation made to the Society of Cosmetic Chemists Annual Scientific Seminar, Seattle
Mturi GJ, Martincigh BS (2008) Photostability of the sunscreening agent 4-tert-butyl-4’-methoxydibenzoylmethane (Avobenzone) in solvents of different polarity and proticity. J Photochem Photobiol A Chem 200:410–420
Yamaji M, Kida M (2013) Photothermal tautamerization of a UV sunscreen (4-tert-butyl-4’-methoxydibenzoylmethane) in acetonitrile studied by steady-state and laser flash photolysis. J Phys Chem A 117:1946–1951
Kikuchi A, Oguchi N, Yagi M (2009) Optical and electron paramagnetic resonance studies of the excited states of 4-tert-butyl-4’-methoxydibanzoylmethane and 4-tert-butyl-4’-methoxydibenzoylpropane. J Phys Chem A 113:13492–13497
Bonda C, Pavlovic A, Hansen K, Bardeen C (2009) Singlet quenching proves faster is better for photostability. Cosm Toil 125:40–48
Tarras-Wahlberg N, Stenhagen G, Larko O, Rosen A, Wennberg A-M, Wennerstrom O (1999) Changes in ultraviolet absorption of sunscreens after ultraviolet irradiation. J Invest Dermatol 113:547–553
Schrader A, Jakupovic J, Baltes W (1994) Photochemical studies on trans-3-methylbutyl 4-methoxycinnamate. J Soc Cosm Chem 45:43–52
Couteau C, Faure A, Fortin J, Paparis E, Coiffard LJM (2007) Study of the photostability of 18 sunscreens in creams by measuring the SPF in vitro. J Pharm Biomed Anals 44:270–273
Herzog B, Wehrle M, Quass K (2009) Photostability of UV absorber systems in sunscreens. Photochem Photobiol 85:869–878
SaNogueira J, Lott DL (2007) Letter to FDA with comments to proposed sunscreen monograph. http://www.regulations.gov/#!documentDetail;D=FDA-1978-N-0018-0652
SaNogueira J, Lott DL (2008) Letter to FDA with supplement to comments to proposed sunscreen monograph. http://www.regulations.gov/#!documentDetail;D=FDA-1978-N-0018-0653
Beasely DG, Meyer TA (2010) Characterization of the UVA protection provided by avobenzone zinc oxide, and titanium dioxide in broad-spectrum sunscreen products. Am J Clin Dermatol 11(6):413–421
Damiani D, Baschong W, Greci L (2007) UV-filter combinations under UV-a exposure: concomitant quantification of over-all spectral stability and molecular integrity. J Photochem Photobiol B Biol 87:95–104
Federal Register/Vol. 64, No. 98/Friday, May 21, 1999/Rules and Regulations/Part 352-Sunscreen drug products for over-the-counter human use/subpart B-active ingredients/§352.20 permitted combinations of active ingredients
Lewicka ZA (2009) The characteristics of nanoscale sunscreen particles. Thesis submitted for Master of Science degree, Rice University
Luttrell T, Halpegamage S, Tao J, Kramer A, Sutter E, Batzill M (2014) Why is anatase a better photocatalyst than rutile? – Model studies on epitaxial TiO2 films. Sci Rep 4:4043
Turci F, Peira E, Corazzari I, Fenoglio I, Trotta M, Fubini B (2013) Crystalline phase modulates the potency of nanometric TiO2 to adhere to and perturb the stratum corneum of porcine skin under indoor light. Chem Res Toxicol 26:1579–1590
Carlotti ME, Ugazio E, Sapino S, Fenoglio I, Greco G, Fubini B (2009) Role of particle coating in controlling skin damage photoinduced by titania nanoparticles. Free Radic Res 43:312–322
Kockler J, Oelgemoller M, Robertson S, Glass BD (2014) Influence of titanium dioxide particle size on the photostability of the chemical UV-filters butyl methoxy dibenzoylmethane and octocrylene in a microemulsion. Cosm 1:128–139
Nguyen U, Schlossman D (2001) Stability study of Avobenzone with inorganic sunscreens. Poster Presentation at the Annual Scientific Meeting of the Society of Cosmetic Chemists, New York
http://www.justaboutskin.com/sun-protection-guide/how-to-evaluate-uva-protection/sunscreen-active-ingredients/sunscreen-photostabilizers/www.merck-performance-materials.com; www.sytheonltd.com; www.personal-care.basf.com
Gonzenbach H, Hill TJ, Truscott TG (1992) The triplet energy levels of UVA- and UVB-sunscreens. J Photochem Photobiol B Biol 16:377–379
Chatelain EB, Gabard B (2001) Photostabilization of butyl methoxydibenzoylmethane (avobenzone) and ethylhexyl methoxycinnamate by bis-ethylhexyloxyphenol methoxyphenyl triazine (tinosorb S), a new broadband filter. Photochem Photobiol 74:401–406
Mendrok-Edinger C, Smith K, Janssen A, Vollhardt J (2009) The quest for stabilizers and sunscreen photostability. Cosm Toil 124(2):47–54
Lin Z-P, Aue WA (1999) Triplet-state energies and substituent effects of excited aroyl compounds in the gas phase. Spectrochimica Acta Part A 56:111–117
Lhiaubet-Vallet V, Marin M, Jimenez O, Gorchs O, Trullas C, Miranda MA (2010) Filter-filter interactions. Photostabilization, triplet quenching and reactivity with singlet oxygen. Photochem Photobiol Sci 9(4):552–558
HallStar Product Information Sheet PC11030 (2011) http://www.in-cosmeticsasia.com/__novadocuments/15139?v=634826419407530000
HallStar Product Information Sheet PC1A054 (2011) http://www.in-cosmeticsasia.com/__novadocuments/15140?v=634826420506970000
HallStar Product Information Sheet PC1H044 http://www.hallstar.com/pis.php?product=1h044
Kikuchi A, Hata Y, Kumasaka R, Yagi M (2013) Photoexcited singlet and triplet states of a UV absorber ethylhexyl methoxycrylene. Photochem Photobiol 89:523–528
Bonda C, Pavlovic A, Hansen K, Bardeen C (2010) Singlet quenching proves faster is better for photostability. Cosme Toil 125:40–48
Bonda CA, Marinelli PJ, Hessefort YZ, Trivedi J, Wentworth G (1999) U.S. Patent No 5,993,789
Bonda C, Steinberg D (2000) A new photostabilizer for full spectrum sunscreens. Cosm Toil 115:37–45
HallStar Product Information Sheet PC11031 (2013) http://www.hallstar.com/pis.php?product=11031
Sytheon brochure for Synoxyl HSS. Available online at http://www.in-cosmetics.com/__novadocuments/46438?v=635285132501130000
Afonso S, Horita K, Silva e Sousa JP, Almeida IF, Lobao PA, Costa PC, Miranda MS, da Esteves Silva JCG, Sousa Lobo JM (2014) Photodegradation of avobenzone: stabilization effect of antioxidants. J Photochem Photobiol B Biol 140:36–40
Rudolph T, Pan J, Scheurich R, Pfluecker F, Graf R, Epstein H (2009) Superior two step approach to completely photoprotect Avobenzone with a designed organic redox pair. SOFW J 135(9):14–19
Massaro RD, Blaisten-Barojas E (2011) Theoretical investigation of the photophysics of methyl salicylate isomers. J Chem Phys 135:164306
http://www.rocheresearchgroup.com/wp-content/uploads/2011/06/DeMayo_ReactionSR.pdf
Kikuchi AM, Yagi M (2011) Direct observation of the intermolecular triplet-triplet energy transfer from UV-a absorber 4-tert-butyl-4’-methoxydibanzoylmethane to UV-B absorber octyl methoxycinnamate. Chem Phys Let 513:63–66
Sayre RM, Dowdy JC, Stanfield JW (2009) In vitro sunscreen transmittance measurement with concomitant evaluation of photostability: evolution of a method. Photochem Photobiol 85(4):1038–1040
Moyal D, Refregier JL, Chardon A (2002) In vivo measurement of the photostability of sunscreen products using diffuse reflectance spectroscopy. Photodermatol Photoimmunol Photomed 18:14–22
Ou-yang HJ, Stanfield JC, Cole CY, Appa Y (2010) An evaluation of ultraviolet a protection and photostability of sunscreens marketed in Australia and New Zealand. Photodermatol Photoimmunol Photomed 26:336–337
Sayre RM, Dowdy JC (2010) The FDA proposed solar simulator versus sunlight. Photochem Photobiol Sci 9:535–539
Sayre RM, Stanfield JW, Bush A, Lott D (2001) Sunscreen standards tested with differently filtered solar simulators. Photoderm Photoimmunol Photomed 17:278–283
Uhlmann B, Mann T, Gers-Berlag H, Sauermann A (1996) Consequences for sun protection factors when solar simulator spectra deviate from the spectrum of the sun. Inter J Cosm Sci 18:13–24
Young A, Boles J, Herzog B, Osterwalder U, Baschong W (2010) A sunscreen’s labeled sun protection factor may overestimate protection at temperate latitudes: a human in vivo study. J Invest Dermatol 130:2457–2462
Lott D (2013) Testing SPF15-100, indoor vs outdoor. Cosm Toil 9:638–647
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2016 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Bonda, C.A., Lott, D. (2016). Sunscreen Photostability. In: Wang, S., Lim, H. (eds) Principles and Practice of Photoprotection. Adis, Cham. https://doi.org/10.1007/978-3-319-29382-0_14
Download citation
DOI: https://doi.org/10.1007/978-3-319-29382-0_14
Published:
Publisher Name: Adis, Cham
Print ISBN: 978-3-319-29381-3
Online ISBN: 978-3-319-29382-0
eBook Packages: MedicineMedicine (R0)