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The lightfastness and structure of semi-permanent hair dyes, derivatives of o-nitro-N-β-hydroxyethylaniline

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PL
Odporność na działanie światła i budowa barwników typu “semi-permanent”, pochodnych o-nitro-N-β-hydroksyetyloaniliny stosowanych do barwienia włosów
Języki publikacji
EN
Abstrakty
EN
The aim of this study was to examine the substituent effects on lightfastness and spectral properties of o-nitro-N-β-hydroxyethylaniline derivatives, used in semi-permanent hair dyes of HC (Hair Color-Dyes ) type. It has been found that the fading rate of the color of hair dyed depends on the nature of the ED and EA substituents in the o-nitro-N-β-hydroxyethylaniline. The o-nitro-N-β-hydroxyethyl aniline derivatives undergo discoloration according to kinetics of the first order reaction. A negative value of the slope coefficient indicates the oxidative mechanism of the reaction. From the relationship lmax=f(σ) σp─Hammett’s constant were calculated. Using the semi-empirical AM1 quantum chemical method, we calculated the structures of hair dyes The dye structures were optimized using MM +, DM, and AM1.
PL
Celem pracy było zbadanie wpływu podstawników na działanie światła i właściwości spektralne pochodnych o-nitro-N-β-hydroksyetyloaniliny, stosowanych w półtrwałych farbach (semi-permanent) do barwienia włosów. Stwierdzono, że szybkość zaniku barwy włosów zależy od charakteru podstawników ED i EA w o-nitro-N-β-hydroksyetyloanilinie. Pochodne o-nitro-N-β-hydroksyetyloaniliny ulegają odbarwieniu zgodnie z kinetyką reakcji 1-go rzędu. Ujemna wartość współczynnika nachylenia wskazuje na mechanizm utleniający reakcji. Z zależności lmax=f(σ) obliczono stałe σp─Hammetta. Stosując półempiryczną metodę kwantowo-chemiczną AM1, obliczyliśmy budowę barwników pochodnych N-β-hydroksyetyloamino-nitrobenzenu. Struktury barwników optymalizowano przy użyciu MM +, DM oraz AM1. półtrwałe farby do włosów.
Rocznik
Tom
Strony
19--37
Opis fizyczny
Bibliogr. 42 poz., rys., tab., wykr., wz.
Twórcy
  • Łukasiewicz – Łódź Institute of Technology, 73 Zgierska Str., 91-463 Łódź, Poland
  • Institute of Environmental Engineering and Building Installations, Lodz University of Technology, Al. Politechniki 6, 90-924 Łódź, Poland
  • Łukasiewicz – Łódź Institute of Technology, 73 Zgierska Str., 91-463 Łódź, Poland
Bibliografia
  • [1] Ballarin B., Galli, S., Morigi M.: Study of dyeing properties of semipermanant dyestuffs for hair, Int. J. Cosm. Sci. 29, 2007, pp. 49-57.
  • [2] Pohl S., Hnatchenko M. (Clariol Inc.), US4776855 A; 1988.
  • [3] Schrader D., Neuhaus W. (Henkel), US4927627 A; 1990.
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  • [5] Zviak C.: Oxidation Coloring” in “The Science of Hair Care”, ed. C Zviak, E Marcel Dekker, NYork 1986;
  • [6] Tucker H. H.: Coloring of human hair with semipermanent dyes, J. Soc. Cosmet. Chem., 22, 1971, p. 379.
  • [7] Venkataraman K.: „The Chemistry of Synthetic Dyes. Vol. VI”, Academic Press, NYork 1972
  • [8] Draelos Z.K.: Hair cosmetics, Dermatol Clin. 9, 1991, pp. 19-27.
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  • [12] Guthrie J.T., Kazlauciunas A., Rongong L., Rush S.: The Characterization Of Treated And Dyed Hair, Dyes Pigm., 29, 1995), pp. 3-44.
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  • [14] Dario M.F., Baby A.R., Velasco M.V.R., Effects of solar radiation on hair and photoprotection, J. Photochem. Photobiol., B:Biology, 153, 2015, pp. 240-6.
  • [15] Dawber R.: Hair: Its Structure and Response to Cosmetic Preparations, Clinics in Dermatology, 14, 1996, pp. 105-112.
  • [16] O’Donoghue M.N.: Hair care products. In: Olsen EA, editor. Disorders of hair growth. New York: McGraw-Hill, 1994, pp.386-7.
  • [17] Halal J.: Hair Structure and Chemistry Simplified. IV Ed., Milady Thompson Learning, Canada (2002).
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  • [19] Yoshio T., Yoshikaru Y., Kuniaki S.: US4961925; 1995.
  • [20] Szadowski J., Przybylski C.: Relationship Between the Structure of Nitrodiphenylamine Derived Monoazo Acid and their Spectroscopic and Fastness Properties”, Dyes Pigments 5, 1984, 49.
  • [21] Asquith R., Peters A., Wallach F.: Fading of Nitrodiphenylamine Disperse Dyes in Relation to their Structure and Ultraviolet Absorption Spectra, J. Soc. Dyers Colour., 84, 1968, 507.
  • [22] Kuramoto N., Kitao T.: The Photofading Of 1-Arylazo-2-Naphthols In Solution .2. Contribution Of Photo-Reduction To The Anomalous Photofading Of 1-(Para And Ortho-Nitrophenylazo)-2-Naphthols In Alcoholic Solvents, J. Soc. Dyers Colour., 96 , 1980, 529.
  • [23] Skulski L. (doctor thesis), Ed. Technical University of Warsaw, 1966.
  • [24] Lewis D., Mama J., Hawkes J.: A Review of Aspects of Oxidation Hair Dye Chemistry with Special Reference to N-Nitrosoamine Formation, Materials 6, 2013, pp. 517-534.
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  • [29] Heikkinen S., Pitkaniemi J., Sarkeala T., Halila N., Koskenvuo M.: Does Hair Dye Use increase the Risk of Breast Cancer? A Populatio-Based Core-Control Study of Finnish Women, PLoS ONE 8/11/2015, vol.8 (10), pp.1-14.
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  • [36] Dewar M.J.D., Zoebisch E.G., Healy E.F., Stewart J.J.P.: The Development and Use of Quantum-Mechanical Molecular-Models. 76. AM1-A New General-Purpose Quantum-Mechanical Molecular-Model, J.Am.Chem.Soc. 107, 1985, 3902.
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  • [40] K Y Chu, J Griffiths, “ Colour and Constitution of the Nitro- and Dinitro-p-phenylenediamines and their N-Methyl Derivatives”, J.S.C. Perkin I 1978,1194.
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Uwagi
Opracowanie rekordu ze środków MNiSW, umowa nr SONP/SP/546092/2022 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2024).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-64d2e2d6-3789-49cb-8b1d-b4ca0c6da091
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