Chemistry:Pigment Yellow 74

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Pigment Yellow 74
Names
Other names
Hansa Yellow 5GXB
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 228-768-4
UNII
Properties
C18H18N4O6
Molar mass 386.364 g·mol−1
Appearance yellow powder
Density 1.436 g/cm3
Melting point 290 °C (554 °F; 563 K) Decomposes
7.6 µg/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

Pigment Yellow 74 (C.I. 11741) is an azo dye and classified as an arylide yellow. It is an intensely yellow-green solid.[1]

Extraction and presentation

Pigment Yellow 74 is prepared by azo coupling of diazotization 4-nitro-o-anisidine to 2-acetoacetanisidide.[2][3]

Properties

Pigment Yellow 74 is a flammable, hardly flammable, yellow solid that is practically insoluble in water. It decomposes when heated above > 290 °C.[4] It has a triclinic crystal structure with the space group P1 or space group P-1 and the lattice parameters a = 16.06 ± 0.16 Å, b = 7.71 ± 0.08 Å, c = 14.977 ± 0.15 Å. The crystals of the compound are pleochroism. In polarized light, they exhibit an orange glow when the long axis of the crystals is perpendicular to the plane of polarization, as opposed to the case where the long axis of the crystals is parallel to the plane of polarization.[5]

It is a flat molecule, enforced by the hydrogen-bonding via the ketohydrazide group.[6]

Use

Pigment Yellow 74 is used for printing inks and varnishs. The light fastness of fine-grained pigments of the compound is 2 to 3 fastness levels on the blue scale better than that of similar disazo yellow pigments, which is why these are preferably used when high light fastness is required, as is often the case in packaging printing. Similar to the other representatives of this pigment class, the solvent fastnesses are often less satisfactory. Prints with Yellow 74 pigment have poor calendering fastness and are not sterilizable. In contrast, like other monoazo yellow pigments, they are alkali-, acid- and soap-fast.[7][8]

Pigment Yellow 74 is a popular component of artist's paints[9] and tattoo inks.[10]

Regulation

Pigment Yellow 74 is regulated in the course of the CoRAP by Italy.

The use of Pigment Yellow 74 has been limited to 0.1% (1000 mg/kg) in permanent make-up or tattoo ink in the European Union since January 5, 2022.[11]


References

  1. ↑ K. Hunger; W. Herbst (2012). "Pigments, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a20_371. ISBN 978-3-527-30673-2. 
  2. ↑ Joseph V. Koleske, Paint and Coating Testing Manual, pp. 199, ISBN 978-0-8031-7017-9, https://books.google.com/books?id=ri6FkY2xvgcC&pg=PA199 
  3. ↑ Christie, Robert M.; Dryburgh, William T.; Standring, Paul N. (1991). "Some monoazoacetoacetanilide pigments derived from heterocyclic diazo components". Dyes and Pigments 16 (3): 231–240. doi:10.1016/0143-7208(91)85013-x. 
  4. ↑ Record of Pigment Yellow 74 in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  5. ↑ A. Whitaker (1986), "Crystal Data for C.I. Pigment Yellow 74", Journal of the Society of Dyers and Colourists 102 (3): 109–110, doi:10.1111/j.1478-4408.1986.tb01064.x 
  6. ↑ Whitaker, A.; Walker, N. P. C. (1987). "CI Pigment Yellow 74, α-(2-methoxy-4-nitrophenylhydrazono)-α-aceto-2'-methoxyacetanilide". Acta Crystallographica Section C Crystal Structure Communications 43 (11): 2137–2141. doi:10.1107/S0108270187088723. 
  7. ↑ Werner Baumann, Thomas Rothardt (2013), Druckerei-chemikalien, Springer Berlin Heidelberg, pp. 585, ISBN 978-3-642-58474-9, https://books.google.com/books?id=Ps8jBgAAQBAJ&pg=PA585 
  8. ↑ Willy Herbst, Klaus Hunger (2009), Industrielle Organische Pigmente, Wiley-VCH, pp. 265, ISBN 978-3-527-62496-6, https://books.google.com/books?id=zP0JXdYsWP0C&pg=PA265 
  9. ↑ Scherrer, Nadim C.; Stefan, Zumbuehl; Francoise, Delavy; Annette, Fritsch; Renate, Kuehnen (2009). "Synthetic organic pigments of the 20th and 21st century relevant to artist's paints: Raman spectra reference collection". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 73 (3): 505–524. doi:10.1016/j.saa.2008.11.029. PMID 19136293. Bibcode: 2009AcSpA..73..505S. 
  10. ↑ Cui, Yanyan; Spann, Andrew P.; Couch, Letha H.; Gopee, Neera V.; Evans, Frederick E.; Churchwell, Mona I.; Williams, Lee D.; Doerge, Daniel R. et al. (2004). "Photodecomposition of Pigment Yellow 74, a Pigment Used in Tattoo Inks". Photochemistry and Photobiology 80 (2): 175–184. doi:10.1562/2004-04-06-ra-136.1. PMID 15362942. 
  11. ↑ EU-Verordnung 2020 2081, PDF



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