Indanthrone blue

Last updated
Indanthrone blue
Indanthren.svg
Indanthrone-3D-balls.png
Names
Preferred IUPAC name
6,15-Dihydrodinaphtho[2,3-a:2′,3′-h]phenazine-5,9,14,18-tetrone
Other names
C.I. vat blue 4, carbon paper blue, blue O, carbanthrene blue 2R, fenan blue RSN, graphtol blue RL, medium blue, monolite fast blue 3R, indanthrene, indanthrone, pigment blue 60, C.I. 69800
Identifiers
3D model (JSmol)
367131
ChemSpider
ECHA InfoCard 100.001.251 OOjs UI icon edit-ltr-progressive.svg
E number E130 (colours)
PubChem CID
UNII
  • InChI=1S/C28H14N2O4/c31-25-13-5-1-3-7-15(13)27(33)21-17(25)9-11-19-23(21)29-20-12-10-18-22(24(20)30-19)28(34)16-8-4-2-6-14(16)26(18)32/h1-12,29-30H Yes check.svgY
    Key: UHOKSCJSTAHBSO-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C28H14N2O4/c31-25-13-5-1-3-7-15(13)27(33)21-17(25)9-11-19-23(21)29-20-12-10-18-22(24(20)30-19)28(34)16-8-4-2-6-14(16)26(18)32/h1-12,29-30H
    Key: UHOKSCJSTAHBSO-UHFFFAOYAY
  • O=C6c5c4Nc3c(c2C(=O)c1ccccc1C(=O)c2cc3)Nc4ccc5C(=O)c7ccccc67
Properties
C28H14N2O4
Molar mass 442.430 g·mol−1
Appearancedark blue solid
Density 1.6 g/ml
Melting point 470-500 °C (decomposes)
Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Indanthrone blue, also called indanthrene, is an organic compound with the formula (C14H6O2NH)2. It is a dark blue solid that is a common dye as well as a precursor to other dyes. [1]

Contents

Preparation

The compound is made from 2-aminoanthraquinone treated with potassium hydroxide.

Synthesis Indanthrone.svg
Procedure for producing indanthrone from 2-aminoanthraquinone.

By dimerization of 2-aminoanthraquinone (1) under strongly alkaline conditions at 220-235 °C, the intermediate 3 is obtained in two steps, which cyclizes intramolecularly and is oxidized to indanthrone 5. [2]

Applications

It is a pigment that can be used in the following media: acrylic, alkyd, casein, encaustic, fresco, gouache, linseed oil, tempera, pastel, and watercolor painting. It is used to dye unmordanted cotton and as a pigment in quality paints and enamels. As a food dye, it has E number E130, but it is not approved for use in either the United States or the European Union. [3] [4] It has excellent light fastness, but may bleed in some organic solvents.

Organic Semiconductor

As an organic semiconductor, indanthrone has capabilities for utilization as a photocatalyst for oxygen generation from water utilizing solar energy. [5] [6] Indanthrone's characteristic as a nonlinear optics light absorber, allows for its use as an optical limiter , which can be employed, for instance, in laser protective filters. [7]

Colorant

Indanthrone is utilized as a blue pigment (C.I. Pigment Blue 60), primarily in the process of vat dyeing, often referred to as C.I. Vat Blue 4. [8] Indanthrone is a vat dye, synthesized to provide highest color fastness for the dyeing and printing of predominantly cellulose-based textile fibers. Fabrics dyed with indanthrene fulfill the highest standards and exhibit exceptional wash fastness, boil fastness, light fastness, weather fastness and chlorine fastness.

Trademark

Indanthrone blue was the first example of the brand "Indanthren" (an acronym for Indigo from anthracene ) introduced by BASF in 1901. [9] [10] [11] One result is that even now, in Japan vat dyes are commonly described as thren(e) dyes (スレン染料), derived from the Japanese transliteration of the brand. [12] [13]

Related Research Articles

<span class="mw-page-title-main">Dye</span> Soluble chemical substance or natural material which can impart color to other materials

A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution and may require a mordant to improve the fastness of the dye on the fiber.

<span class="mw-page-title-main">Indigo dye</span> Chemical compound, food additive and dye

Indigo dye is an organic compound with a distinctive blue color. Indigo is a natural dye extracted from the leaves of some plants of the Indigofera genus, in particular Indigofera tinctoria. Dye-bearing Indigofera plants were commonly grown and used throughout the world, particularly in Asia, with the production of indigo dyestuff economically important due to the historical rarity of other blue dyestuffs.

A lake pigment is a pigment made by precipitating a dye with an inert binder, or mordant, usually a metallic salt. Unlike vermilion, ultramarine, and other pigments made from ground minerals, lake pigments are organic. Manufacturers and suppliers to artists and industry frequently omit the lake designation in the name. Many lake pigments are fugitive because the dyes involved are not lightfast. Red lakes were particularly important in Renaissance and Baroque paintings; they were often used as translucent glazes to portray the colors of rich fabrics and draperies.

<span class="mw-page-title-main">Copper phthalocyanine</span> Synthetic blue pigment from the group of phthalocyanine dyes

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<span class="mw-page-title-main">Azo compound</span> Organic compounds with a diazenyl group (–N=N–)

Azo compounds are organic compounds bearing the functional group diazenyl.

<span class="mw-page-title-main">Acenaphthene</span> Chemical compound

Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. It is a colourless solid. Coal tar consists of about 0.3% of this compound.

<span class="mw-page-title-main">Quinacridone</span> Organic compound used as a pigment

Quinacridone is an organic compound used as a pigment. Numerous derivatives constitute the quinacridone pigment family, which finds extensive use in industrial colorant applications such as robust outdoor paints, inkjet printer ink, tattoo inks, artists' watercolor paints, and color laser printer toner. As pigments, the quinacridones are insoluble. The development of this family of pigments supplanted the alizarin dyes.

<span class="mw-page-title-main">Acid dye</span> Dye applied to low pH textile

An acid dye is a dye that is typically applied to a textile at low pH. They are mainly used to dye wool, not cotton fabrics. Some acid dyes are used as food colorants, and some can also be used to stain organelles in the medical field.

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Vat dyes are a class of dyes that are classified as such because of the method by which they are applied. Vat dyeing is a process that refers to dyeing that takes place in a bucket or vat. The original vat dye is indigo, once obtained only from plants but now often produced synthetically.

<span class="mw-page-title-main">2-Naphthol</span> Chemical compound

2-Naphthol, or β-naphthol, is a fluorescent colorless (or occasionally yellow) crystalline solid with the formula C10H7OH. It is an isomer of 1-naphthol, differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, but more reactive. Both isomers are soluble in simple alcohols, ethers, and chloroform. 2-Naphthol is a widely used intermediate for the production of dyes and other compounds.

<span class="mw-page-title-main">Anthraquinone dyes</span>

Anthraquinone dyes are an abundant group of dyes comprising a anthraquinone unit as the shared structural element. Anthraquinone itself is colourless, but red to blue dyes are obtained by introducing electron donor groups such as hydroxy or amino groups in the 1-, 4-, 5- or 8-position. Anthraquinone dyestuffs are structurally related to indigo dyestuffs and are classified together with these in the group of carbonyl dyes.

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Structural of methine dyes

<span class="mw-page-title-main">Vat Yellow 1</span> Chemical compound

Vat Yellow 1 is a vat dye, yellow in appearance under some conditions used in cloth dyeing. Its synonyms are flavanthrone and Indofast Yellow, and it is in the class of anthraquinone-type compounds.

<span class="mw-page-title-main">Pigment Violet 29</span> Organic compound used as a pigment and dye

Pigment Violet 29 is an organic compound that is used as a pigment and vat dye. Its colour is dark red purple, or bordeaux.

<span class="mw-page-title-main">Violanthrone</span> Chemical compound

Violanthrone, also known as dibenzanthrone, is an organic compound that serves as a vat dye and a precursor to other vat dyes. X-ray crystallography confirms that the molecule is planar with C2v symmetry. Isomeric with violanthrone is isoviolanthrone, which has a centrosymmetric structure.

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<span class="mw-page-title-main">Dibromoanthanthrone</span> Chemical compound

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<span class="mw-page-title-main">Pigment violet 23</span> Chemical compound

Pigment violet 23 is an organic compound that is a commercial pigment. It is member of the dioxazine family of heterocyclic compounds, but derived from carbazoles. It is prepared by condensation of chloranil and 3-amino-N-ethylcarbazole. It has a centrosymmetric angular structure. For many years, the structure was assigned, incorrectly, as having a "linear structure" which differ in terms of the carbazole ring fusion.

<span class="mw-page-title-main">Carbonyl dyes</span>

Carbonyl dyes are dyes which comprise at least two conjugated carbonyl groups. Both anthraquinone dyes and indigo dyes belong to the group of carbonyl dyes. The most important natural dyes - indigo, Tyrian purple, alizarin and carmine - have this partial structure. The most important synthetic carbonyl dyes are based on anthraquinone.

References

  1. Bien, Hans-Samuel; Stawitz, Josef; Wunderlich, Klaus (2000). "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a02_355. ISBN   3527306730.
  2. Heinrich Zollinger (2003), [ , p. 289, at Google Books Color Chemistry: Syntheses, Properties, and Applications of Organic Dyes and Pigments] (3. ed.), Weinheim: WILEY-VCH Verlag, p. 289, ISBN   3-906390-23-3 {{citation}}: Check |url= value (help)
  3. Summary of Color Additives for Use in the United States in Foods, Drugs, Cosmetics, and Medical Devices, Food and Drug Administration
  4. Current EU approved additives and their E Numbers, Food Standards Agency
  5. C. A. Linkous, D. K. Slattery: Solar photocatalytic hydrogen production from water using a dual bed photosystem. In Proceedings of the 2000 Hydrogen Program Annual Review, Volume I. (PDF).
  6. D. K. Slattery et al: Semiempirical MO and Voltammetric estimation of ionization potentials of organic pigments. Comparison to gas phase ultraviolet photoelectron spectroscopy. In: Dyes and Pigments 49, 2001, pp. 21-27.
  7. Y.-P. Sun, J. E. Riggs: Organic and inorganic optical limiting materials. From fullerenes to nanoparticles. In International Reviews in Physical Chemistry. 18, no. 1, 1999, pp. 43-90.
  8. W. Herbst, K. Hunger: Industrial Organic Pigments. Preparation, properties, application. 2nd ed., Wiley-VCH, Weinheim 1995, ISBN 3-527-28744-2.
  9. Entry on Indanthron-Pigmente . at: Römpp Online . Georg Thieme Verlag, retrieved 16. Januar 2013.
  10. "Marken - Registerauskunft - Indanthren". DPMAregister (in German). Retrieved 29 August 2020. Anmeldetag: 05.08.1901 / Inhaber: BASF AG
  11. Zollinger, Heinrich (2003). Color Chemistry: Syntheses, Properties, and Applications of Organic Dyes and Pigments. John Wiley & Sons. p. 255. ISBN   978-3-906390-23-9 . Retrieved 29 August 2020. The German word Indanthren is an acronym for Indigo aus Anthrazen
  12. "Colourful World III". www.eonet.ne.jp. Retrieved 29 August 2020. バット染料の主たる製造元は、ドイツの化学会社でありその時の商標が、 "インダンスレン" であったことからスレン染料と呼ぶ場合も多くあります
  13. "アルテモンド 豆知識 / スレン染料". www.artemondo.co.jp. スレン染料(threne dye)とは、バット染料(vat dye)の俗称