Monoazo (Monohydrazone) pigments based on acetoacetanilides

Robert Christie, Adrian Abel

Research output: Contribution to journalArticlepeer-review

Abstract

The monoazoacetoacetanilide series of pigments, traditionally known as Hansa Yellows, are long-established products that entered the market in the early twentieth century. They are mostly inexpensive products offering bright colors of moderate intensity covering the entire yellow area of the spectrum, good lightfastness, but inferior solvent resistance. The technical properties of the pigments may be explained by their molecular structures, which adopt the ketohydrazone tautomeric form, and their crystal structures. Their good lightfastness is attributed mainly to intramolecular hydrogen-bonding, while their generally inferior fastness to organic solvents is explained by the relatively weak intermolecular interactions in the crystal structure. The monoazoacetanilide pigments are synthesized by the traditional two-stage process of diazotization of a primary aromatic amine, followed by an azo coupling reaction of the resulting diazonium salt with an acetoacetanilide coupling component. Their main use is in decorative paints, although a few products are suitable for printing inks.

Original languageEnglish
Pages (from-to)329-340
Number of pages12
JournalPhysical Sciences Reviews
Volume6
Issue number8
Early online date29 Jun 2021
DOIs
Publication statusPublished - Aug 2021

Keywords

  • azo coupling
  • calcium salt pigments
  • CI Pigment Yellow 1
  • CI Pigment Yellow 111
  • CI Pigment Yellow 3
  • CI Pigment Yellow 6
  • CI Pigment Yellow 65
  • CI Pigment Yellow 73
  • CI Pigment Yellow 74
  • CI Pigment Yellow 97
  • CI Pigment Yellow 98
  • decorative paints
  • diazotization
  • Hansa yellow
  • intramolecular hydrogen-bonding
  • monoazoacetoacetanilide
  • monohydrazone
  • phenylsulfonamide group

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Physics and Astronomy(all)

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