Arzu YILDIRIM, Nur Belinda DEMİR, Berfin AK İZGİ, Büşra Nur ERKOL, Çağla ÖZSU, Gülşah EŞLİK AYDEMİR, Mine MUSTAFAOĞLU, Murat KIZIL, Nubar AYHAN, Sevil EMEN

THE CHEMISTRY MECHANISM OF HAIR DYES

One of the oldest and most well-known cosmetics, hair color has been used by numerous ancient cultures throughout history on both men and women. It involves treating hair with various chemical compounds for changing hair color. According to how long they remain in the hair, these products are primarily divided into two categories: temporary and permanent. This classification is consistent with the types of active substances used in the dyeing process as well as the dyeing method itself, which are referred to as non-oxidative and oxidative hair dye products, respectively. Permanent hair dyes often consist of active chemicals that are not dyed but are oxidized to provide the desired color. As a result, the phrase "oxidative hair dye" was emerged. The precursor part and coupler part are the two main ingredients in formulations for oxidative hair dyes. Quinonediimine intermediates are momentary compounds that are generated when combined with hydrogen peroxide (developer). As a result, the coupler agent and these compounds interact to form the appropriate hair dye molecule. Notably, the entire dyeing process requires both an alkaline medium and an oxidizing agent, often hydrogen peroxide, to ensure that the staining agents reach the cuticle widely. This review's objective is to provide information about hair dye formulations and mechanisms of action as well as repairing damaged hair and new applications.

Keywords:

hair dyes, temporary, semipermanent, permanent, chemical mechanism,

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1. Sudhir SP, Kumarappan A, Vyas LK, Shrivastava D, Deshmukh P, Verma HN. Identification of Nigella sativa seed and its adulterants using DNA Barcode Marker. Am. J. Life Sci. 2016;4: 118-128.
2. Sudhir SP, Kumarappan A, Malakar J, Verma HN. Genetic diversity of Nigella sativa from different geographies using RAPD markers. Am. J. Life Sci. 2016;4:175-180.
3. Sudhir SP, Deshmukh VO, Verma HN. Nigella sativa seed, a novel beauty care ingredient: A review. Int. J. Pharm. Sci. Res. 2016;7:3185-3196.
4. Alam MM, Rahman ML, Haque MZ. Extraction of henna leaf dye and its dyeing effects on textile fibre. Bangladesh J. Scient. Ind. Res. 2007;42:217-222.
5. Jayaganesh S, Jainendra M, Rawat BS, Venkataramana AP. Influence of gamma radiation on microbial and viscosity parameters of henna based hair colour. Int. J. New Technol. Res. 2016;2:11-15.
6. Chisvert A, Chafer A, Salvador A. Hair dyes in cosmetics: regulatory aspects and analytical methods. Analysis of Cosmetic Products. 2018;2:159-173.
7. Sankar J, Rawat BS, Malankar J, Padmanabha VA, Estimation of available oxygen in powder form of oxygen releaser in henna based hair dyes. SSRG Int. J. Applied Chem. 2017;4:34-37.
8. Sankar J, Sawarkar S, Malakar J, Rawat BS, Ali MA. Mechanism of hair dying and their safety aspects: a review. Asian J. Applied Sci. 2017;10 (4):190-196.
9. Draelos ZK. Hair cosmetics. Dermatol Clin 1991; 9:19–27.
10. Bolduc C, Shapiro J. Hair care products. Waving, straightening, conditioning, and coloring. Clin Dermatol 2001; 19:431-6.
11. Harrison S, Sinclair R. Hair colouring, permanent styling and hair structure. Journal of Cosmetic Dermatology. 2004; 2:180-185.
12. Da Franca, Aparecida S, Dario MF, Esteves VB, Baby AR, Velasco MVR. Types of hair dye and their mechanisms of action. Cosmetics. 2015;2: 110-126.
13. Yutaka Shimomura1 and Angela M. Christiano1, 2 (22 September 2010) Annual Review of Genomics and Human Genetics 11:109-132
14. Gillian E Westgate,Natalia V Botchkareva,Desmond J Tobin (30 January 2013) The biology of hair diversity Citations: 35 15. Olivier J. X. Morel‡ and Robert M. Christie*§ ( January 25, 2011) Current Trends in the Chemistry of Permanent Hair Dyeing Chem. Rev. 2011, 111, 4, 2537–2561
16. Célia F. Cruz 1 , Cristiana Costa 1 , Andreia C. Gomes 2 , Teresa Matamá 1,2 and Artur Cavaco-Paulo 1, (20 May 2016; Accepted: 14 July 2016; Published: 25 July 2016 ) Human Hair and the Impact of Cosmetic Procedures: A Review on Cleansing and Shape-Modulating Cosmetics Cosmetics 2016, 3, 26.
17. Kaplan PD, Polefka T, Grove G, Daly S, Jumbelic L, Harper D, Bianchini R. Grey hair: Clinical investigation into changes in hair fibres with loss of pigmentation in a photoprotected population. International Journal of Cosmetic Science. 2011;33(2): 171-182. .
18. Park AM, Khan S, Rawnsley J. Hair biology growth and pigmentation. Facial Plastic Surgery Clinics of North America. 2018;26(4):415-424. .
19. Koch SL, Tridico SR, Bernard BA, Shriver MD, Jablonski NG. The biology of human hair: A multidisciplinary review. Am J Hum Biol. 2020 Mar;32(2): e23316. .
20. Ozeki H, Ito S, Wakamatsu K, Thody AJ. Spectrophotometric characterization of eumelanin and Pheomelanin in hair. Pigment Cell Research, 1996;9(5):265–270. .
21. Shekar SN, Duffy DL, Frudakis T, Montgomery GW, James MR, Sturm RA, Martin NG. Spectrophotometric methods for quantifying pigmentation in human hairinfluence of MC1R genotype and environment. Photochemistry and Photobiology. 2008;84(3):719-726. .
22. Vaughn MR, van Oorschot RAH, Baindur-Hudson S. A comparison of hair colour measurement by digital image analysis with reflective spectrophotometry. Forensic Science International, 2009;183(1–3): 97–101. .
23. Sealy R, Hyde J, Felix C, Menon I, Prota G: Eumelanins and phaeomelanins: Characterization by electron spin resonance spectroscopy. Science. 1982;217: 545–547. .
24. Lasisi T, Ito S, Wakamatsu K, Shaw CN. Quantifying variation in human scalp hair fiber shape and pigmentation. American Journal of Physical Anthropology. 2016;160(2):341-352. .
25. Ito S, Miyake S, Maruyama S, Suzuki I, Commo S, Nakanishi Y, Wakamatsu K. Acid hydrolysis reveals a low but constant level of pheomelanin in human black to brown hair. Pigment Cell & Melanoma Research. 2018;31(3):393-403. .
26. Ito S, Fujita K. Microanalysis of eumelanin and pheomelanin in hair and melanomas by chemical degradation and liquid chromatography. Anal Biochem 1985;144:527–536. .
27. Zviak C, Milléquant J. ‘Hair coloring: non-oxidation coloring’ and ‘Oxidation coloring’, chapters 8 and 9 in The Science of Hair Care , 2nd edition, ed. C Bouillon and J Wilkinson. Taylor and Francis. Boca Raton. 2005.
28. Hefford R. Colourants and dyes for the cosmetics industry. Handbook of Textile and Industrial Dyeing. 2011;2:175-203. .
29. Ballarin B, Galli S, Morigi M. Study of dyeing properties of semipermanent dyestuffs for hair.Int. J. Cosmet. Sci. 2007; 29:49–57.
30. Barel A. O, Paye M, & Maibach H. I (Eds.). Handbook of cosmetic science and technology. CRC Press. 2014; 51.
31. Brown K.C. Hair coloring. hair and hair heater. 2018;191-215.
32. Da França S. A, Dario M. F, Esteves V. B, Baby A. R, & Velasco M. V. R. Types of hair dye and their mechanisms of action, Cosmetics.2015 June; 2(2):110-126.
33. He L, Michailidou F, Gahlon H. L, & Zeng W. Hair dye ingredients and potential health risks from exposure to hair dyeing. American Chemical Society.2022 June; 35(6):901–915.
34. Les colorants Wackherr (LCW). Presentation technique About dyes capillaries; LCW: Saint Paulo, Brazil, 2008. (In Portugal).
35. Lewis D, Mama J, & Hawkes J. A review of aspects of oxidative hair dye chemistry with special reference to N-nitrosamine formation. Materials. 2013 January; 6(2):517-534.
36. Morel O. J, & Christie R. M. Current trends in the chemistry of permanent hair dyeing. Chemical Reviews. 2011;111(4):2537-2561.
37. Robbins C.R. and R.J. Crawford. Cuticle damage and the tensile properties of human hair. J. Soc. Cosmet. Chem. 1991; 42(1):59-67.
38. Sankar J, Sawarkar S, Malankar J, Rawat B. S, & Ali, M. A. Mechanism of hair dying and their safety aspects. Research Journal of Topical and Cosmetic Sciences. 2017;8(2):72-77.
39. Tucker H. H. The coloring of human hair with semipermanent dyes. J. Soc. Cosmet. Chem.1971 May; 22:379-398.
40. Harrison S, Sinclair R, Hair coloring, permanent styling and hair structure. J. Cosmet. Dermatol. 2004, 2, 180–185.
41. Brown K.C. Hair coloring. In Hair and Hair Care; Johnson D H, Marcel Dekker: New York, NY, USA, 1997.35 21 Draelos, Z.K. Hair cosmetics. Dermatol. Clin. 1991, 9, 19–27.
42. Da França S. A, Dario M. F, Esteves V. B, Baby A. R, & Velasco M. V. R. Types of hair dye and their mechanisms of action, Cosmetics.2015 June; 2(2):110-126.
43. More O, Christie R M, Greaves A, Morgan, K.M. Enhanced model for the diffusivity of a dye molecule into human hair fibre based on molecular modelling techniques, Color. Technol. 2008, 124, 301–309.
44. Bolduc C, Shapiro, J. Hair care products: Waving, straightening, conditioning and coloring. Clin. Dermatol. 2001, 19, 431–436.
45. Kojima T, Yamada, H, Yamamoto T, Matsushita Y, Fukushima K. Dyeing regions of oxidative hair dyes in human hair investigated by nanoscale secondary ion mass spectrometry. Colloid Surf. B 2013, 106, 140–144.
46. Wolfram L J, Hair cosmetics. In Handbook of Cosmetic Science and Technology, Barel, A O, Paye M, Maibach H I, Eds. Marcel Dekker: 2001.New York, NY, USA.
47. Les Colorants Wackherr (LCW). Apresentação Técnica Sobre Tinturas Capilares; LCW: São Paulo, Brazil, 2008. (In Portuguese)
48. Scientific Committee on Consumer Products, SCCP/1198/08
49. Lee S. H., Ahn, C. Effect of rinse-off hair conditioner containing argan oil or camellia oil on the recovery of hair damaged by bleaching. Fashion and Textiles. 2022 May;9(1):1-24.
50. Morita T., Kitagawa M., Yamamoto S., Sogabe A., Imura T., Fukuoka T., Kitamoto D. Glycolipid biosurfactants, mannosylerythritol lipids, repair the damaged hair. Journal of Oleo Science. 2010 Jan;59(5):267-272.
51. Kojima T., Tsuji S., Niwa M., Saito K., Matsushita Y., Fukushima K. Distribution analysis of triglyceride having repair effect on damaged human hair by TOF-SIMS. International Journal of Polymer Analysis and Characterization. 2012 Oct;17(1):21-28.
52. Li Z., Xiao J. Repair of damaged hair protein fiber by jointly using transglutaminase and keratin. Scienceasia, 2021;47(2):195-201.
53. Choi W., Son S., Song S. H., Kang N. G., Park S. G. Repairing Damaged Hair Using Pentapeptides of Various Amino Acid Sequences with Crosslinking Reaction. Korea Journal of Cosmetic Science, 2020;2(1):11-19.
54. Fernández E., Martínez-Teipel B., Armengol R., Barba C., Coderch L. Efficacy of antioxidants in human hair. Journal of Photochemistry and Photobiology B: Biology, 2012;117:146-156.
55. Nojiri H., Naito S., Takahasi H., Fujiki M., Kim M. Yolk antibody‑containing hair care products. (US Patent) 5976519. 1999:1‑8.
56. Haveli S. D., Walter P., Patriarche G., Ayache J., Castaing J., Van Elslande E., … Kagan H. B. Hair Fiber as a Nanoreactor in Controlled Synthesis of Fluorescent Gold Nanoparticles. Nano Letters, 2012;12(12):6212–6217.
57. Prasertpol T., Tiyaboonchai W. Nanostructured lipid carriers: A novel hair protective product preventing hair damage and discoloration from UV radiation and thermal treatment. Journal of Photochemistry and Photobiology B: Biology, 2020;204,111769. 58. Da Franca SA, Dario MF, Esteves VB, Baby AR, Velasco MV. Hair Color types and Effect mechanics _ Makeup materials.2015(2):110-126. .
59. Nohyneka GJ, Fautzb R, Kiefferc FB, Toutaina H. Toxicity and human health risk of hair dyes _ food and Chemical Toxicology 42;2004:517–543. .
60. Palisoc S, Causing AM and Natividad M. (2017). Gold nanoparticle / hexaammineruthenium / Nafion ® modified glassy carbon electrodes for trace heavy metal detection in commercial hair dyes _ Analytical Methods . 9(29), 4240-4246. .
61. Concert about hair dye . [ Accessed july 25, 2022]. < URL >.
62. Almeida PJ, Borrego L, Limiñana JM. Age-related sensitization to p-phenylenediamine . Contact dermatitis 2011;64: 172–174. .
63. Patra AP, Shaha KK, Rayamane AP, Dash SK, Mohanty MK, Mohanty S. Paraphenylenediamine containing hair dye : an emerging household poisoning . Am J Forensic Med pathol 2015;36: 167-171. .
64. Chey WY, Kim KL, Yoo TY, Lee AY. Allergic contact dermatitis from hair dye and development of lichen simplex chronicus _ Contact dermatitis 2004;51:5–8. .
65. Prof. Dr. Kirmaz C . Allergic Contact Dermatitis. [Accessed july 25 , 2022] . .
66. Vogel TA, Coenraads PJ, Bijkersma LM, Vermeulen KM, Schuttelaar ML, EDEN Fragrance study Group (2015) real life exposure to p- Phenylenediamine -rate, mode and elicitation reactions in northern Netherlands A case-control study on Contact Dermatitis 72: 355-361. .
67. Goebel C, Coenraads PJ, Rothe H, Kunze G, Kock M, et al. (2010) Allergic Dermatitis 22: 324-331.eliciting immune response to p- phenylenediamine in patients : lay and the role of exposure time. Br J Dermatol 163: 1205-1211. .
68. Yenigün A, Cetemen A, Pektaş E, Karayel E, & Özcan N. (2010). Frequency of respiratory and skin findings in hairdresser's apprentices in Aydın. Asthma Allergy Immunology / Asthma Allergy Immunology. 8:77-87. .
69. Uçar S, Özçelik S & Akyol M. (2011). Allergic contact evaluation of patch test results in cases with dermatitis . Cumhuriyet Medical Journal. 33(3): 299-306. .
70. Jung Y, Kwon S & Kang SY. (2008). Status epilepticus possibly caused by hair dye exposure in a diabetic man. Journal Neurocrit Care. 1:168–170. .
71. Sen BB, Rifaioglu EN, Ekiz Ö, Doğramacı AC, Sen T. (2015). Contact Evaluation of Patch Test Results in Cases with Dermatitis . Bozok Med J 2015;5(2):35-40. .
72. Allergen; Patch Test Standard Series 2018. [Accessed july 26, 2022]. < URL >.
73. Turkish Dermatology Association: Patch Test. [Accessed july 26, 2022]. .
74. Morel, Olivier JX, and Robert M. Christie. Current trends in the chemistry of permanent hair dyeing. Chemical Reviews. 2011;111:2537-2561. .
75. Im, Kyung Min, Tae-Wan Kim, and Jong-Rok Jeon. Metal-chelation-assisted deposition of polydopamine on human hair: a ready-to-use eumelanin-based hair dyeing methodology. ACS Biomaterials Science & Engineering. 2017;3:628-636. .
76. Gao, Zhong Feng, et al. Rapid preparation of polydopamine coating as a multifunctional hair dye. RSC Advances. 2019;9:20492-20496. .
77. Battistella, Claudia, et al. Mimicking natural human hair pigmentation with synthetic melanin. ACS Central Science. 2020;6:1179-1188. .
78. Schlatter, Harald, Timothy Long, and John Gray. An overview of hair dye safety. Journal of Cosmetic Dermatology. 2017; 6:32-36.
79. Towns, Andrew. A review of developments in industrial hair colorant actives for oxidative dyes. Coloration Technology. 2021;137:301-335. .
80. Battistella, Claudia, et al. Bioinspired chemoenzymatic route to artificial melanin for hair pigmentation." Chemistry of Materials. 2020;32:9201-9210. .
81. Sun, Yu, et al. Bioinspired polymeric pigments to mimic natural hair coloring. RSC Advances. 2021;11:1694-1699. . 82. Jia, Weini, et al. Laccase-mediated in situ oxidation of dopamine for dyeing of human hair. Fibers and Polymers. 2021;22:141-148. .
83. Verma, Shivani, and Gunjan Gupta. Natural dyes and its applications: A brief review. International Journal of Research and Analytical Reviews. 2017;4:57-60. .
84. Shahid, Mohammad, and Faqeer Mohammad. Recent advancements in natural dye applications: a review. Journal of Cleaner Production. 2013;53:310-331. .
85. Mihranian, Albert, Natalia Ferraz, and Maria Strømme. Current status and future prospects of nanotechnology in cosmetics. Progress in Materials Science. 2012;57:875-910. .
86. The European Green Deal. ESDN Report, December (2020). .