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.

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.

Functional Poly(p-Xylylene)s via Chemical Reduction of Poly(p-Phenylene Vinylene)s

2019 ◽  
Author(s):  
Ain Uddin ◽  
Weifan Sang ◽  
Yong Gao ◽  
Kyle Plunkett
Keyword(s):  
Film Formation ◽  
Chemical Reduction ◽  
Water Soluble ◽  
Phenylene Vinylene ◽  
Polymer Modification ◽  
Polymer Backbone ◽  
Crosslinking Process ◽  
Conducting Membranes ◽  
In Situ Crosslinking

The synthesis of poly(p-xylylene)s (PPXs) with sidechains containing alkyl bromide functionality, and their post-polymer modification, is described. The PPXs were prepared by a diimide hydrogenation of poly(p-phenylene vinylene)s (PPVs) that were originally synthesized by a Gilch polymerization. The polymer backbone reduction was carried out with hydrazine hydrate in toluene at 80 °C to provide polymers with the sidechain-containing bromide functionality intact. To demonstrate post-polymer modification of the sidechains, the resulting PPX polymers were modified with trimethylamine to form tetraalkylammonium ion functionality and were evaluated as anion conducting membranes. While PPX homopolymers containing tetralkylammonium ions were completely water soluble and not able to form valuable films, PPX copolymers containing mixed tetraalkylammonium ions and hydrophobic chains were capable of film formation and alkaline stability. In addition, an in situ crosslinking process that used N,N,N',N'-tetramethyl-1,6-hexanediamine during the tetraalkylammonium formation of brominated PPX polymers was also evaluated and gave reasonable films with conductivities of ~10 mS-cm-1.

Functional Poly(p-Xylylene)s via Chemical Reduction of Poly(p-Phenylene Vinylene)s

2019 ◽  
Author(s):  
Ain Uddin ◽  
Weifan Sang ◽  
Yong Gao ◽  
Kyle Plunkett
Keyword(s):  
Film Formation ◽  
Chemical Reduction ◽  
Water Soluble ◽  
Phenylene Vinylene ◽  
Polymer Modification ◽  
Polymer Backbone ◽  
Crosslinking Process ◽  
Conducting Membranes ◽  
In Situ Crosslinking

The synthesis of poly(p-xylylene)s (PPXs) with sidechains containing alkyl bromide functionality, and their post-polymer modification, is described. The PPXs were prepared by a diimide hydrogenation of poly(p-phenylene vinylene)s (PPVs) that were originally synthesized by a Gilch polymerization. The polymer backbone reduction was carried out with hydrazine hydrate in toluene at 80 °C to provide polymers with the sidechain-containing bromide functionality intact. To demonstrate post-polymer modification of the sidechains, the resulting PPX polymers were modified with trimethylamine to form tetraalkylammonium ion functionality and were evaluated as anion conducting membranes. While PPX homopolymers containing tetralkylammonium ions were completely water soluble and not able to form valuable films, PPX copolymers containing mixed tetraalkylammonium ions and hydrophobic chains were capable of film formation and alkaline stability. In addition, an in situ crosslinking process that used N,N,N',N'-tetramethyl-1,6-hexanediamine during the tetraalkylammonium formation of brominated PPX polymers was also evaluated and gave reasonable films with conductivities of ~10 mS-cm-1.

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.

scholarly journals A thin, deformable, high-performance supercapacitor implant that can be biodegraded and bioabsorbed within an animal body

2021 ◽  
Vol 7 (2) ◽  
pp. eabe3097
Author(s):  
Hongwei Sheng ◽  
Jingjing Zhou ◽  
Bo Li ◽  
Yuhang He ◽  
Xuetao Zhang ◽  
...  
Keyword(s):  
High Performance ◽  
Electronic Devices ◽  
Form Factors ◽  
Time Frame ◽  
Water Soluble ◽  
Two Dimensional ◽  
Medical Electronics ◽  
Thin Structure ◽  
Shed Light

It has been an outstanding challenge to achieve implantable energy modules that are mechanically soft (compatible with soft organs and tissues), have compact form factors, and are biodegradable (present for a desired time frame to power biodegradable, implantable medical electronics). Here, we present a fully biodegradable and bioabsorbable high-performance supercapacitor implant, which is lightweight and has a thin structure, mechanical flexibility, tunable degradation duration, and biocompatibility. The supercapacitor with a high areal capacitance (112.5 mF cm−2 at 1 mA cm−2) and energy density (15.64 μWh cm−2) uses two-dimensional, amorphous molybdenum oxide (MoOx) flakes as electrodes, which are grown in situ on water-soluble Mo foil using a green electrochemical strategy. Biodegradation behaviors and biocompatibility of the associated materials and the supercapacitor implant are systematically studied. Demonstrations of a supercapacitor implant that powers several electronic devices and that is completely degraded after implantation and absorbed in rat body shed light on its potential uses.

Synthesis and short DNA in situ loading and delivery of 4 nm-aperture flexible organic frameworks

2021 ◽  
Author(s):  
Ze-Kun Wang ◽  
Jia-Le Lin ◽  
Yun-Chang Zhang ◽  
Chen-Wu Yang ◽  
Ya-Kun Zhao ◽  
...  
Keyword(s):  
Cancer Cells ◽  
Water Soluble

Water-soluble hydrazone-connected 3D flexible organic frameworks have been revealed to in situ load and deliver short DNA into normal and cancer cells.

scholarly journals A novel zinc complex with antibacterial and antioxidant activity

BMC Chemistry ◽  
2021 ◽  
Vol 15 (1) ◽  
Author(s):  
Yun Zhang ◽  
Xiaojing Li ◽  
Jia Li ◽  
Md. Zaved Hossain Khan ◽  
Fanyi Ma ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Acute Toxicity ◽  
Intestinal Absorption ◽  
Antioxidant Activities ◽  
Zinc Ion ◽  
Water Soluble ◽  
Zinc Supplement ◽  
Citrate Complex ◽  
Morphology Characterization

Abstract Background In order to enhance the antibacterial activity and reduce the toxicity of Zn2+, novel complexes of Zn(II) were synthesized. Results A water-soluble zinc-glucose-citrate complex (ZnGC) with antibacterial activity was synthesized at pH 6.5. The structure, morphology, characterization, acute toxicity, antibacterial and antioxidant activities, and in situ intestinal absorption were investigated. The results showed that zinc ion was linked with citrate by coordinate bond while the glucose was linked with it through intermolecular hydrogen bonding. The higher the molecular weight of sugar is, the more favorable it is to inhibit the formation of zinc citrate precipitation. Compared with ZnCl2, ZnGC complex presented better antibacterial activity against Staphylococcus aureus (S. aureus, Gram-positive) and Escherichia coli (E. coli, Gram-negative). Conclusions The results of acute toxicity showed no obvious toxicity in this test and in situ intestinal absorption study, suggesting that ZnGC complex could be used as a potential zinc supplement for zinc deficiency.

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.

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