Disazo (Bishydrazone) pigments based on pyrazolones

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Robert Christie ◽  
Adrian Abel
Keyword(s):  
Tautomeric Form ◽  
Heterocyclic System ◽  
Commercial Product ◽  
Color Strength ◽  
Color Properties ◽  
Organic Pigments ◽  
Printing Ink ◽  
Coupling Components

Abstract The most important classical orange organic pigments are disazopyrazolones, also referred to as diarylide oranges. The first pigment in this series, CI Pigment Orange 13, was discovered in 1910 although it was a further 20 years before it was introduced as a commercial product. Currently, two orange disazopyrazolones are extremely important industrial organic pigments, while two red products are of lesser importance. The products are structurally analogous to the disazoacetoacetanilides (diarylide yellows), which are discussed in a separate chapter. For example, they are symmetrical compounds that exist in the bis-ketohydrazone tautomeric form. The pigments also exhibit similar technical and color properties compared with disazoacetoacetanilide pigments, for example providing high color strength and transparency, features that determine their importance as printing ink pigments. They are manufactured in a process that parallels those used for the disazoacetoacetanilide (diarylide) yellows, but with coupling components containing the pyrazolone heterocyclic system, in place of acetoacetanilides.

Disazo (Bishydrazone) pigments based on acetoacetanilides

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Robert Christie ◽  
Adrian Abel
Keyword(s):  
Crystal Packing ◽  
Molecular Geometry ◽  
Coupling Reactions ◽  
Dominant Group ◽  
Color Strength ◽  
Decomposition Products ◽  
Organic Pigments ◽  
Yellow Pigments ◽  
Structure Investigations ◽  
Coupling Components

Abstract Disazoacetoacetanilide pigments, more commonly known as diarylide yellows, are the most important group of yellow classical organic pigments. They were commercialized in the early 20th century many years after the introduction of the structurally related monazoacetoacetanilides (Hansa yellows). The molecules adopt the bis-ketohydrazone tautomeric form. X-ray single crystal structure investigations have provided an insight into the influence of the molecular geometry and crystal packing arrangements in the solid state on the properties of the pigments in application. The synthesis of diarylide pigments is relatively straightforward, the conditions essentially following those used for the corresponding monoazo pigments, so that the products are economically priced. In the case of these disazo pigments, suitable aromatic amines (1 mol) are bis-diazotized and the resulting bis-diazonium salts reacted with acetoacetanilide coupling components (2 mol), the two azo coupling reactions occurring at the same time. They are by far the dominant group of yellow pigments used in printing inks, well-suited for most standard process yellow inks. They were formerly important in the coloration of plastics but are no longer recommended for polymers processed above 200 °C, under which conditions toxic decomposition products are formed. Diarylide yellow pigments are characterized by high color strength, good to excellent solvent fastness, and good chemical stability, although they generally show inferior lightfastness.

Cationic (Basic) dye complex pigments

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Robert Christie ◽  
Adrian Abel
Keyword(s):  
Water Soluble ◽  
Cationic Dye ◽  
Color Strength ◽  
Organic Pigments ◽  
Basic Dye ◽  
Copper Ferrocyanide ◽  
Printing Inks ◽  
Good Transparency ◽  
Printing Ink

Abstract Cationic (or basic) dye complex pigments are classical organic pigments obtained from water-soluble cationic dyes for textiles, mainly of triarylmethine (arylcarbonium ion) types, which are precipitated using large inorganic counterions, especially those derived from heteropolyacids such as phosphotungstomolybdic acid or, to a certain extent, using the counteranion derived from copper ferrocyanide. This range of pigments includes red, violet, blue and green products, offering brilliant shades, high color strength and good transparency. They are well suited to printing ink applications, although they provide only moderate levels of fastness properties. The pigments are synthesized by treating aqueous solutions of the dyes under highly controlled conditions with solutions of the heteropolyacids, prepared in situ. The copper ferrocyanide salts are obtained by treatment of potassium ferrocyanide with sodium sulfite in water, and subsequently with solutions of the cationic dye and copper (II) sulfate. The pigments are primarily used in inks for packaging and advertising materials. However, they have little use outside printing inks. Reflex or alkali blue pigments are structurally related cationic dye derivatives which are inner salts of the dye structures and are also used in printing inks.

Monoazo (Monohydrazone) pigments based on 2-naphthol and derivatives

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Robert Christie ◽  
Adrian Abel
Keyword(s):  
Metal Salt ◽  
Water Soluble ◽  
Anionic Dyes ◽  
Extensive Discussion ◽  
Synthesis Conditions ◽  
Organic Pigments ◽  
Amide Derivatives ◽  
The Individual ◽  
Coupling Components ◽  
Group 1

Abstract This chapter describes the range of industrial monoazo pigments based on the 2-naphthol (β-naphthol) ring system. This group includes some of the earliest organic pigments introduced commercially and is also numerically the largest group of products currently described in the Colour Index. Most of the pigments within this group are red (with a few oranges), thus complementing the azoacetoacetanilides, which are mostly yellows. Three groups of monoazonaphthol-based pigments may be identified categorized according to the chemical structure of the coupling components used in their synthesis. The first group contains products based on 2-naphthol itself, a second is based on amide derivatives of 3-hydroxy-2-naphthoic acid (naphtharylamides), and the third is a series of metal salt azo pigments. The historical development of these pigments, outlined in an early section of this chapter, originated in the late 19th century with pigments described as ‘lakes’, derived from water-soluble anionic dyes absorbed on to inert colorless substrates, which were the forerunners of products now referred to as metal salt pigments. The non-ionic 2-naphthol-based pigments were introduced soon after. In the early to mid-20th century, a series of monoazonaphtharylamide (Naphthol AS) pigments were developed and introduced commercially. The pigments of this type that are currently manufactured can be sub-divided into products containing a single amide group (group 1) and higher performance products containing more than one amide or sulfonamide groups. Several group 1 pigments have diminished in importance over the years, while some higher performing group 2 pigments have grown in importance. The molecular and crystal structures of the range of pigments are presented and discussed in relation to their performance characteristics. The manufacture of the pigments involves the reaction of a diazotized aromatic amine with the appropriate 2-naphthol-based coupling component, using synthesis conditions typical of phenolic coupling components, followed by conditioning aftertreatments that are typical for azo pigments in general. Finally, there is an extensive discussion of the wide-ranging applications in which the individual pigments are used. While the pigments are especially well-suited to printing ink applications, many products also find use in paints and a few in plastics.

scholarly journals Improvement of Dispersion and Color Effect of Organic Pigments in Polymeric Films via Microencapsulation by the Miniemulsion Technique

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Dongming Qi ◽  
Zhijie Chen ◽  
Lei Yang ◽  
Zhihai Cao ◽  
Minghua Wu
Keyword(s):  
Electron Microscopy ◽  
Fiber Surface ◽  
Adhesive Layer ◽  
Latex Film ◽  
Color Strength ◽  
Adhesive Film ◽  
Organic Pigments ◽  
Transmission Electron ◽  
Digital Microscope ◽  
Fabric Surface

Three primary pigment/poly(n-butyl acrylate-co-styrene) (P(BA+St)) nanocomposites were prepared via encapsulation of the corresponding organic pigments via the miniemulsion technique. The resulting latexes of the P(BA+St)/pigment nanocomposites were filmed in a PTFE mould or printed onto cotton fabric. The morphology of the P(BA+St)/pigment nanocomposites and the dispersion of pigment particles in the latex film and on the printed fabric surface, as well as the adhesion between pigment and adhesive film, were evaluated by transmission electron microscopy (TEM), field emission scanning electron microscopy (FESEM), 3D digital microscope system (3D-POM), and printing results tests. Attributing to the preprotection of adhesive polymer shell, the self-adhesive P(BA+St)/pigment nanocomposites were homogeneously and firmly dispersed both in the thin latex film and in the adhesive layer on the fiber surface. As a result, the color strength, color fastness, and handle of the fabrics printed by the P(BA+St)/pigment nanocomposites latex were significantly improved, compared to the fabrics printed by the conventional pigment blended latex.

scholarly journals Super stretchable chromatic polyurethane driven by anthraquinone chromogen as a chain extender

RSC Advances ◽  
2019 ◽  
Vol 9 (5) ◽  
pp. 2332-2342 ◽  
Author(s):  
Caiyun Zhao ◽  
Chaoxia Wang ◽  
Youjiang Wang ◽  
Donggang Yao
Keyword(s):  
Chain Extender ◽  
Color Strength ◽  
Color Properties ◽  
Washing Fastness ◽  
A Chain

PUEs introducing anthraquinone chromogen as chain extender exhibit superior mechanical and color properties. The improvement of elongation is most significant. BPUE1 and BPUE0.5 display high color strength and supreme rubbing and washing fastness.

The Effect of Commercial Product Soap to the Protein of Epidermis

1974 ◽  
Vol 36 (2) ◽  
pp. 206-209 ◽  
Author(s):  
Ryohei OGURA ◽  
Fuyuhiko NINOMIYA ◽  
Akira KINOSIHTA
Keyword(s):  
Commercial Product
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