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.

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.

Dioxazine pigments

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Robert Christie ◽  
Adrian Abel
Keyword(s):  
High Performance ◽  
Industrial Applications ◽  
Textile Dye ◽  
Linear Arrangement ◽  
Natural Colorant ◽  
X Ray ◽  
Organic Pigments ◽  
Tyrian Purple ◽  
Violet Color ◽  
The Individual

Abstract This chapter provides an overview of the structural and synthetic chemistry, and the industrial applications, of dioxazine pigments, a small group of high performance organic pigments. The color violet (or purple) has frequently assumed a prominent position in history, on account of its rarity and cost. The natural colorant Tyrian purple and the first synthetic textile dye, Mauveine, are prime examples of this unique historical feature. CI Pigment Violet 23, also referred to as Dioxazine Violet or Carbazole Violet, is one of the most universally used organic pigments, by far the most important industrial pigment in the violet shade area. Dioxazine Violet is also unique as the dominant industrial violet pigment providing a brilliant, intense violet color and an excellent all-round set of fastness properties. The pigment has a polycyclic molecular structure, originally described wrongly as a linear arrangement, and later shown to adopt an S-shaped arrangement on the basis of X-ray structural analysis. Two other dioxazine pigments are of rather lesser importance. The synthesis and manufacturing route to CI Pigment Violet 23 is described in the review. Finally, a survey of the principal current applications of the individual dioxazine pigments is presented.

scholarly journals Discoloration of Historical Plastic Objects: New Insight into the Degradation of β-Naphthol Pigment Lakes

Polymers ◽  
2021 ◽  
Vol 13 (14) ◽  
pp. 2278
Author(s):  
Anna Micheluz ◽  
Eva Mariasole Angelin ◽  
João Almeida Lopes ◽  
Maria João Melo ◽  
Marisa Pamplona
Keyword(s):  
Light Exposure ◽  
Molecular Structures ◽  
Conservation Science ◽  
Organic Pigment ◽  
Organic Pigments ◽  
Before And After ◽  
The Individual ◽  
Determining Factor ◽  
Insight Into ◽  
Historical Samples

Light is a determining factor in the discoloration of plastics, and photodegradation processes can affect the molecular structures of both the polymer and colorants. Limited studies focused on the discoloration of heritage plastics in conservation science. This work investigated the discoloration of red historical polyethylene (PE) objects colored with PR 48:2 and PR 53:1. High-density and low-density PE reference polymers, neat pigment powders, and historical samples were assessed before and after accelerated photoaging. The applied methodology provided insight into the individual light-susceptibility of polyethylenes, organic pigment lakes, and their combined effect in the photoaging of historical plastic formulations. After light exposure, both PE references and historical samples yellowed, PR53:1 faded, and PR 48:2 darkened; however, both organic pigments faded severely in the historical samples. This highlights the role played by the plastic binder likely facilitating the pigment photofading. Fourier transform infrared spectroscopy and mass spectrometry techniques—EGA-MS, PY-GC/MS, and TD-GC/MS—were successfully employed for characterizing the plastic formulations and degradation. The identification of phthalic compounds in both aged β-naphthol powders opens new venues for studies on their degradation. This work’s approach and analytical methods in studying the discoloration of historical plastics are novel, proving their efficacy, reliability, and potentiality.

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.

scholarly journals Remote sensing of aerosols by synergy of caliop and modis

2018 ◽  
Vol 176 ◽  
pp. 08012
Author(s):  
Rei Kudo ◽  
Tomoaki Nishizawa ◽  
Akiko Higurashi ◽  
Eiji Oikawa
Keyword(s):  
Remote Sensing ◽  
Biomass Burning ◽  
Sea Salt ◽  
Water Soluble ◽  
Dust Particles ◽  
Vertical Profiles ◽  
Dust Event ◽  
Carbonaceous Particles ◽  
The Individual ◽  
Better Than

For the monitoring of the global 3-D distribution of aerosol components, we developed the method to retrieve the vertical profiles of water-soluble, light absorbing carbonaceous, dust, and sea salt particles by the synergy of CALIOP and MODIS data. The aerosol product from the synergistic method is expected to be better than the individual products of CALIOP and MODIS. We applied the method to the biomass-burning event in Africa and the dust event in West Asia. The reasonable results were obtained; the much amount of the water-soluble and light absorbing carbonaceous particles were estimated in the biomass-burning event, and the dust particles were estimated in the dust event.

scholarly journals Transfer Printing of Conductive Thin Films on PDMS with Soluble Substrates for Flexible Biosensors

2020 ◽  
Vol 2 (1) ◽  
pp. 47
Author(s):  
Steffen Hadeler ◽  
Sebastian Bengsch ◽  
Maren S. Prediger ◽  
Marc Christopher Wurz
Keyword(s):  
Physical Vapor Deposition ◽  
Electrochemical Impedance ◽  
Three Dimensional ◽  
Impedance Measurement ◽  
Water Soluble ◽  
Electrode Spacing ◽  
Conductive Layer ◽  
Electrode Structure ◽  
Neural Implants ◽  
The Individual

The resolution of commercially available electrocorticography (ECoG) electrodes is limited due to the large electrode spacing and, therefore, allows only a limited identification of the active nerve cell area. This paper describes a novel manufacturing process for neural implants with higher spatial resolution combining micro technological processes and Polydimethylsiloxane (PDMS) as the flexible, biocompatible material. The conductive electrode structure is deposited on a water-soluble transfer substrate by Physical Vapor Deposition (PVD) processes. Subsequently, the structure is contacted. Finally, the transfer to PDMS and dissolution of the transfer substrate takes place. In this way, high-resolution conductive structures can be produced on the PDMS. Transferred gold structures exhibit higher adhesion and conductivity than transferred platinum structures. The adhesion was improved by applying a silica surface modification to the conductive layer prior to transferring. Furthermore, the conductive layer is flexible, conductive up to an elongation of 10%, and resistant to sodium chloride solution, mimicking brain fluids. Using the introduced production process, an ECoG electrode was manufactured and characterized for its functionality in an electrochemical impedance measurement. Furthermore, the electrodes are flexible enough to adapt to different shapes. The transfer process can also be carried out in a three-dimensional mold to produce electrodes tailored to the individual patient.

scholarly journals Evaluation of anthocyanin encapsulation efficiency into yeast cell by plasmolysis, ethanol, and ultrasound treatments using alone or in combination

Food Research ◽  
2019 ◽  
Vol 4 (2) ◽  
pp. 557-562
Author(s):  
M.D. Lieu ◽  
T.T.H. Hoang ◽  
H.N.T. Nguyen ◽  
T.K.T. Dang
Keyword(s):  
Yeast Cell ◽  
Encapsulation Efficiency ◽  
Color Stability ◽  
Water Soluble ◽  
Impact Factors ◽  
Time Treatment ◽  
Treated Sample ◽  
Potential Applications ◽  
The Individual ◽  
First Time

Anthocyanin is a water-soluble color compound of the flavonoid which was successfully encapsulation in Saccharomyces cerevisiae by plasmolysis, ethanol, and ultrasound treatments using alone or in combination in the first time. Treatment agents significantly enhanced the encapsulation efficiency of anthocyanin fluid. The encapsulation yield (EY) of the combined factors was higher than the individual impact factors. Ethanol 10% (v/v) and ultrasound 180 seconds for the highest EY 40.22±0.67%, then ethanol 10% (v/v) and NaCl 10% (w/v) for EY 36.45±0.35%, NaCl 10% and ultrasound for EY 32.14±0.98% lowest. The color stability evaluation of the capsules was carried out at 80°C for 30 minutes. The color lost rate was determined by the spectrometer. The color loss of samples with the un-treatment yeast was 20.45±1.21%, higher than the treated sample. This suggests that anthocyanin encapsulation by yeast cell is efficient in overcoming the effects of high temperatures and having potential applications in food processing.

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.

scholarly journals Pharmacodynamic Analysis of the Activity of Quinupristin-Dalfopristin against Vancomycin-ResistantEnterococcus faecium with Differing MBCs via Time-Kill-Curve and Postantibiotic Effect Methods

1998 ◽  
Vol 42 (9) ◽  
pp. 2188-2192 ◽  
Author(s):  
Jeffrey R. Aeschlimann ◽  
Michael J. Rybak
Keyword(s):  
Antibacterial Activities ◽  
Water Soluble ◽  
Postantibiotic Effect ◽  
Curve Method ◽  
Highly Correlated ◽  
Kill Curve ◽  
The Individual ◽  
Time Kill

ABSTRACT Quinupristin-dalfopristin (Q-D) is a new water-soluble, semisynthetic antibiotic that is derived from natural streptogramins and that is combined in a 30:70 ratio. A number of studies have described the pharmacodynamic properties of this drug, but most have investigated only staphylococci or streptococci. We evaluated the relationship between Q-D, quinupristin (Q), and/or dalfopristin (D) susceptibility parameters and antibacterial activities against 22 clinical isolates of vancomycin-resistant Enterococcus faecium (VREF) by using the concentration-time-kill-curve method and by measuring postantibiotic effects. Q-D, Q, and D MICs and minimum bactericidal concentrations (MBCs) ranged from 0.125 to 1 and 0.25 to 64, 8 to 512 and >512, and 2 to 8 and 8 to 512 μg/ml, respectively. There were no significant relationships between susceptibilities to the individual components and the susceptibilities to the Q-D combination product. In the time-kill-curves studies, Q-D at a concentration of 6 μg/ml was at least bacteriostatic against all VREF tested. There was increased activity against more susceptible isolates when the isolates were grouped either by Q-D MBCs or by Q MICs. By multivariate regression analyses, the percent change in the inoculum from that at the baseline was significantly correlated with the Q MIC (R = 0.74; P = 0.008) and the Q-D concentration-to-MBC ratio (R = 0.58;P = 0.02) and was inversely correlated with the Q-D MBC-to-MIC ratio (R = 0.68; P = 0.003). A strong correlation existed between the killing rate and the Q-D concentration-to-MBC ratio (R = 0.99;P < 0.0001). Time to 99.9% killing was best correlated with the Q-D MBC (R = 0.96;P < 0.0001). The postantibiotic effect ranged from 0.2 to 3.2 h and was highly correlated with the Q-D concentration-to-MBC ratio (R = 0.96;P < 0.0001) and was less highly correlated with the Q MIC (R = 0.42; P = 0.04). Further study of these relationships with in vitro or in vivo infection models that simulate Q-D pharmacokinetics should further define the utility of these pharmacodynamic parameters in the prediction of Q-D activity for the treatment of VREF infections in humans.

scholarly journals Composition and mass size distribution of nitrated and oxygenated aromatic compounds in ambient particulate matter from southern and central Europe – implications for origin

2019 ◽  
Author(s):  
Zoran Kitanovski ◽  
Pourya Shahpoury ◽  
Constantini Samara ◽  
Aristeidis Voliotis ◽  
Gerhard Lammel
Keyword(s):  
Particulate Matter ◽  
Size Fraction ◽  
Ambient Air ◽  
Water Soluble ◽  
Atmospheric Particulate Matter ◽  
Polycyclic Aromatic ◽  
Mass Size ◽  
Water Soluble Organic Carbon ◽  
Soluble Organic Carbon ◽  
The Individual

Abstract. Nitro-monoaromatic hydrocarbons (NMAHs), such as nitrocatechols, nitrophenols and nitrosalicylic acids, are important constituents of atmospheric particulate matter (PM) water soluble organic carbon (WSOC) and humic-like substances (HULIS). Nitrated and oxygenated derivatives of polycyclic aromatic hydrocarbons (NPAHs, OPAHs) are toxic and ubiquitous in the ambient air; due to their light absorption properties, together with NMAHs they are part of aerosol brown carbon (BrC). We investigated the winter concentrations of these substance classes in size-resolved particulate matter (PM) from two urban sites in central and southern Europe, i.e. Mainz (MZ), Germany and Thessaloniki (TK), Greece. ∑11NMAH concentrations in PM10 and total PM were 0.51–8.38 and 12.1–72.1 ng m−3 at MZ and TK site, respectively, whereas ∑8OPAHs were 47–1636 and 858–4306 pg m−3, and ∑17NPAHs were ≤ 90 and 76–578 pg m−3, respectively. NMAHs and the water-soluble OPAHs contributed 0.4 and 1.8 %, and 0.0001 and 0.0002 % to the HULIS mass, at MZ and TK, respectively. The mass size distributions of the individual substances generally peaked in the smallest or second smallest size fraction i.e.,

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