47 Monoazo (Monohydrazone) pigments based on benzimidazolones
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Robert Christie
Abstract
A series of azo pigments containing the benzimidazolone ring were introduced in the mid to late twentieth century as high-performance organic pigments in the yellow, orange, red, and brown shade areas. The structures of the commercial benzimidazolone azo pigments are derived from either the monoazoacetoacetanilide or monoazonaphtharylamide classical azo pigments systems and exist in the ketohydrazone tautomeric forms. The high-performance properties of the pigments have been attributed to a network of intermolecular hydrogen bonds involving the benzimidazolone group, and efficient molecular packing, as demonstrated by X-ray crystal structure determinations. The manufacturing processes leading to the pigments involve traditional diazotization and azo coupling reaction procedures, although they require special conditioning aftertreatments to optimize their performance. Although benzimidazolone azo pigments were initially developed for the coloration of plastics, they have probably had a greater impact on the paint industry. The application properties of the benzimidazolone azo pigments are discussed for individual products.
Abstract
A series of azo pigments containing the benzimidazolone ring were introduced in the mid to late twentieth century as high-performance organic pigments in the yellow, orange, red, and brown shade areas. The structures of the commercial benzimidazolone azo pigments are derived from either the monoazoacetoacetanilide or monoazonaphtharylamide classical azo pigments systems and exist in the ketohydrazone tautomeric forms. The high-performance properties of the pigments have been attributed to a network of intermolecular hydrogen bonds involving the benzimidazolone group, and efficient molecular packing, as demonstrated by X-ray crystal structure determinations. The manufacturing processes leading to the pigments involve traditional diazotization and azo coupling reaction procedures, although they require special conditioning aftertreatments to optimize their performance. Although benzimidazolone azo pigments were initially developed for the coloration of plastics, they have probably had a greater impact on the paint industry. The application properties of the benzimidazolone azo pigments are discussed for individual products.
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
