46 Monoazo (Monohydrazone) pigments based on acetoacetanilides
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Robert Christie
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.
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.
Chapters in this book
- Frontmatter I
- Preface V
- Contents VII
- List of contributors XV
- 45 Mixed metal oxide pigments 849
- 46 Monoazo (Monohydrazone) pigments based on acetoacetanilides 859
- 47 Monoazo (Monohydrazone) pigments based on benzimidazolones 871
- 48 Monoazo (Monohydrazone) pigments based on 2-naphthol and derivatives 885
- 49 Naphthopyran dyes 909
- 50 Organic pigments: general principles 925
- 51 Oxonitride pigments 955
- 52 Oxonol dyes 959
- 53 Perylene and perinone pigments 967
- 54 Photochromic dyes 979
- 55 Phthalocyanine blue pigments 1015
- 56 Phthalocyanine green pigments 1029
- 57 Phthalocyanine pigments: general principles 1035
- 58 Pigments: general aspects 1041
- 59 Polymethine dyes 1057
- 60 Quinacridone pigments 1071
- 61 Special effect pigments 1081
- 62 Spirooxazine dyes 1105
- 63 Spiropyran dyes 1125
- 64 Streptocyanine dyes 1153
- 65 Streptomerocyanine dyes 1165
- 66 Titanium dioxide pigments 1177
- 67 Transparent pigments 1195
- 68 Ultramarine pigments 1203
- 69 White pigments 1211
- 70 Zinc oxide pigments 1213
- 71 Zinc sulfide pigments 1219
- Index 1225
Chapters in this book
- Frontmatter I
- Preface V
- Contents VII
- List of contributors XV
- 45 Mixed metal oxide pigments 849
- 46 Monoazo (Monohydrazone) pigments based on acetoacetanilides 859
- 47 Monoazo (Monohydrazone) pigments based on benzimidazolones 871
- 48 Monoazo (Monohydrazone) pigments based on 2-naphthol and derivatives 885
- 49 Naphthopyran dyes 909
- 50 Organic pigments: general principles 925
- 51 Oxonitride pigments 955
- 52 Oxonol dyes 959
- 53 Perylene and perinone pigments 967
- 54 Photochromic dyes 979
- 55 Phthalocyanine blue pigments 1015
- 56 Phthalocyanine green pigments 1029
- 57 Phthalocyanine pigments: general principles 1035
- 58 Pigments: general aspects 1041
- 59 Polymethine dyes 1057
- 60 Quinacridone pigments 1071
- 61 Special effect pigments 1081
- 62 Spirooxazine dyes 1105
- 63 Spiropyran dyes 1125
- 64 Streptocyanine dyes 1153
- 65 Streptomerocyanine dyes 1165
- 66 Titanium dioxide pigments 1177
- 67 Transparent pigments 1195
- 68 Ultramarine pigments 1203
- 69 White pigments 1211
- 70 Zinc oxide pigments 1213
- 71 Zinc sulfide pigments 1219
- Index 1225
