Oxidative transformation processes and products of para-phenylenediamine (PPD) and para-toluenediamine (PTD)—a review

Meyer, Axel; Fischer, Klaus

doi:10.1186/s12302-015-0044-7

Cited by 57 publications

(44 citation statements)

References 63 publications

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“…However, despite an adequate amount of couplers, not all PPD is converted. The small amount of remaining PPD can still oxidize, especially under alkaline conditions and in the presence of a strong oxidant, as in hair dye products, hence causing sensitization [21].…”

Section: Metabolismmentioning

confidence: 99%

“…Oxidation products of PPD were first studied for the production of azo dyes, which are synthetic colourants used to stain, e.g., clothing, plastics and leather. Later, the toxicological aspects of oxidation products of PPD gained attention [21][22][23][24].…”

Section: Metabolismmentioning

confidence: 99%

“…BQDI can be regarded as the central step in the oxidation of PPD and is one of the first-formed oxidation products. An important side step of this oxidation process is the formation of benzoquinone, another highly protein reactive oxidation product of PPD [21].…”

Section: Metabolismmentioning

confidence: 99%

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Contact Allergy to Hair Dyes

Schuttelaar

Vogel

2016

Cosmetics

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Many strong and extreme sensitizing chemicals, such as para-phenylenediamine (PPD), toluene-2,5-diamine (TDA) and other aromatic amines or cross-reacting substances, are ingredients in hair dye products. The chemistry of hair dyeing and the immunological reactions to the potent sensitizing hair dye components are complex and have not been fully clarified up until now. Recently 2-methoxymethyl-p-phenylenediamine (ME-PPD), a PPD derivate with moderate skin-sensitizing properties, was developed. Although developed for the prevention of sensitization, ME-PPD appears to be tolerated in some PPD/TDA-allergic individuals.

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Section: Metabolismmentioning

confidence: 99%

Section: Metabolismmentioning

confidence: 99%

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Contact Allergy to Hair Dyes

Schuttelaar

Vogel

2016

Cosmetics

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“…It is possible that the strongly π‐donating ‐NH 2 groups in 5 and 6 significantly increase the π‐electron density within the six‐membered metallacyclic rings and this in turn increases sensitivity towards oxygen. It is well known that organic arylamines such as p ‐phenylenediamine slowly degrade in air to form a large number of oxidation products, some via imine intermediates . Related processes may be involved in the reactions of 5 and 6 with oxygen.…”

Section: Resultsmentioning

confidence: 99%

Syntheses of Amino‐Substituted Iridabenzofurans and Subsequent Selective N‐Functionalisation

Frogley

Perera

Wright

2017

Chemistry A European J

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The first examples of amino-substituted fused-ring metallabenzenes, the cationic iridabenzofuran [Ir(C H O{NH -2}{OMe-7})(CO)(PPh ) ][O SCF ] (5) and neutral analogue Ir(C H {NH -2}{OMe-7})Cl(PPh ) (6), can be prepared by reduction of the corresponding nitro-substituted iridabenzofurans with zinc and concentrated hydrochloric acid. N-functionalised derivatives of 5 and 6 are formed through alkylation, sulfonylation or acylation. Thus, consecutive treatments with methyl triflate and base gives the corresponding trimethylammonium-substituted iridabenzofurans while sulfonamide derivatives are formed with p-toluenesulfonyl chloride. N-Acylation of 5 or 6 with acid chlorides, however, selectively form either amide or imide products depending on the charge on the metal and the steric size of the acid chloride. Cationic 5 gives amide substituted products regardless of the conditions whereas neutral 6 rapidly undergoes di-N-acylation with excess benzoyl chloride under mild conditions to give the imide-substituted product Ir(C H O{N[C(O)Ph] -2}{OMe-7})Cl(PPh ) (13). Selective mono-acylation of 6 can be achieved with one equivalent of benzoyl chloride or with excess of the sterically congested pivaloyl chloride.

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“…This strong absorption is due to the formation of trimeric p-PDA product (Bandrowski's base) due to the oxidation of p-PDA by H 2 O 2 (shown in Figure S4). [54][55] The strong absorption strength of the Bandrowski's base and the good overlap with the Ce 3 + emission reduces the probability of energy transfer from Ce 3 + to Tb 3 + ions. The above results imply that To confirm the oxidation of p-PDA molecules attached to the surface of the microrods, FTIR analysis was performed for the mixture of p-PDA capped NaYF 4 microrods and H 2 O 2 (see Figure S5 of supporting information).…”

Section: Resultsmentioning

confidence: 99%

Selective Detection of H₂O₂ Using para‐Phenylenediamine Capped Ce³⁺/Tb³⁺‐Doped NaYF₄ Microrods

et al. 2016

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In this work, we have shown the use of Ln3+‐doped nanomaterials for the selective detection of H2O2 upto nM concentration. This is achieved by capping the Ce3+/Tb3+‐doped NaYF4 microrods using para‐phenylenediamine (p‐PDA). The microrods show strong green emission upon UV excitation due to strong energy transfer from Ce3+ to Tb3+ ions. This strong energy transfer is selectively quenched upon addition of H2O2 leading to reduction in the green emission intensity. This selective quenching of the green emission is due to oxidation of p‐PDA to Bandrowski's base which has strong absorption band close to 310 nm, which falls in 4f5d emission level of Ce3+ ions. The proposed mechanism is also supported by TD‐CAM‐DFT calculations performed on p‐PDA and its oxidized product. The reduction in the emission intensity is found to be very selective which is verified by the addition of other analytes (glucose, glutamic acid, uric acid, urea, tryptophan, aspartic acid and some metal ions, Na+, K+, SO42+, and Mg2+) which normally co‐exist with H2O2 in the body. More than 90% of the initial intensity of the Tb3+ was recovered upon the addition of a NaBH4 solution. The study clearly implies that the resonance energy transfer (RET) using Ln3+‐doped microrods can serve as a tool to selectively detect H2O2 upto the nanomolar concentration.

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Oxidative transformation processes and products of para-phenylenediamine (PPD) and para-toluenediamine (PTD)—a review

Cited by 57 publications

References 63 publications

Contact Allergy to Hair Dyes

Contact Allergy to Hair Dyes

Syntheses of Amino‐Substituted Iridabenzofurans and Subsequent Selective N‐Functionalisation

Selective Detection of H₂O₂ Using para‐Phenylenediamine Capped Ce³⁺/Tb³⁺‐Doped NaYF₄ Microrods

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Oxidative transformation processes and products of para-phenylenediamine (PPD) and para-toluenediamine (PTD)—a review

Cited by 57 publications

References 63 publications

Contact Allergy to Hair Dyes

Contact Allergy to Hair Dyes

Syntheses of Amino‐Substituted Iridabenzofurans and Subsequent Selective N‐Functionalisation

Selective Detection of H2O2 Using para‐Phenylenediamine Capped Ce3+/Tb3+‐Doped NaYF4 Microrods

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Selective Detection of H₂O₂ Using para‐Phenylenediamine Capped Ce³⁺/Tb³⁺‐Doped NaYF₄ Microrods