Facile synthesis of oligo anilines as permanent hair dyes: how chemical modifications impart colour and avoid toxicity

Venkatesan, Gopalakrishnan; Dancik, Yuri; Sinha, Arup; Bigliardi, Mei; Srinivas, Ramasamy; Dawson, Thomas L.; Valiyaveettil, Suresh; Bigliardi, Paul L.

doi:10.1039/c9nj03362a

Cited by 12 publications

(35 citation statements)

References 28 publications

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“…As a permeant we used resorcinol, a common ingredient in cosmetic products. In hair dyes it is used as a coupler to primary intermediates such as p-phenylenediamine to produce the final hair color [44,45], often in concentrations of 1 to 5% [46]. In skin care, it is an ingredient of anti-acne formulations and peels [47].…”

Section: Discussionmentioning

confidence: 99%

Freezing Weakens the Barrier Function of Reconstructed Human Epidermis as Evidenced by Raman Spectroscopy and Percutaneous Permeation

et al. 2020

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The development and characterization of reconstructed human epidermis (RHE) is an active area of R&D. RHE can replace animal tissues in pharmaceutical, toxicological and cosmetic sciences, yielding scientific and ethical advantages. RHEs remain costly, however, due to consumables and time required for their culture and a short shelf-life. Storing, i.e., freezing RHE could help reduce costs but to date, little is known on the effects of freezing on the barrier function of RHE. We studied such effects using commercial EpiSkin™ RHE stored at −20, −80 and −150 °C for 1 and 10 weeks. We acquired intrinsic Raman spectra in the stratum corneum (SC) of the RHEs as well as spectra obtained following topical application of resorcinol in an aqueous solution. In parallel, we quantified the effects of freezing on the permeation kinetics of resorcinol from time-dependent permeation experiments. Principal component analyses discriminated the intrinsic SC spectra and the spectra of resorcinol-containing RHEs, in each case on the basis of the freezing conditions. Permeation of resorcinol through the frozen RHE increased 3- to 6-fold compared to fresh RHE, with the strongest effect obtained from freezing at −20 °C for 10 weeks. Due to the extensive optimization and standardization of EpiSkin™ RHE, the effects observed in our work may be expected to be more pronounced with other RHEs.

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Section: Discussionmentioning

confidence: 99%

Freezing Weakens the Barrier Function of Reconstructed Human Epidermis as Evidenced by Raman Spectroscopy and Percutaneous Permeation

et al. 2020

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“…By an increase in the length of the oligoaniline (up to a certain extent) and by the substitution of electron-donating moieties, a balance between skin sensitization potential and the desired hair nuance properties can be achieved. 251…”

Section: Reviewmentioning

confidence: 99%

Linear and star-shaped π-conjugated oligoanilines: a review on molecular design in syntheses and properties

et al. 2022

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“…Other work has attempted to find oxidation bases that are less sensitising than PPD. One strategy adopted was to examine the propensity to sensitise of alternatives to PPD, TDS or ME‐PPD, which bear bulky alkoxy groups in the 2‐position 164 . As might be expected, they show similarly lowered sensitisation potential to ME‐PPD but exhibited worse dyeing performance in conjunction with peroxide and RL.…”

Section: Alternative Technologiesmentioning

confidence: 99%

A review of developments in industrial hair colorant actives for oxidative dyes

Towns

2021

Coloration Technology

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This paper reviews developments in industrial colorants as active ingredients of commercial products that rely on oxidative chemistry for the coloration of human hair. After outlining the regulatory challenges faced by the industry, which are shaping the landscape of colorant usage, the most commercially important actives utilised in oxidative hair colorant formulations are surveyed from the perspective of their chemistry and economics. Some developments in the form of recently introduced actives are also described.

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Facile synthesis of oligo anilines as permanent hair dyes: how chemical modifications impart colour and avoid toxicity

Abstract: Chemical modification of the hair dye para-phenylenediamine results in colors that avoid in situ oxidation and toxicity.

Cited by 12 publications

References 28 publications

Freezing Weakens the Barrier Function of Reconstructed Human Epidermis as Evidenced by Raman Spectroscopy and Percutaneous Permeation

Freezing Weakens the Barrier Function of Reconstructed Human Epidermis as Evidenced by Raman Spectroscopy and Percutaneous Permeation

Linear and star-shaped π-conjugated oligoanilines: a review on molecular design in syntheses and properties

A review of developments in industrial hair colorant actives for oxidative dyes

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