Basic Red 18

Last updated
Basic Red 18
BasicRed18.png
Names
Other names
Aizen Cathilon Red GTLH, Astrazon Red GTL
Identifiers
3D model (JSmol)
ECHA InfoCard 100.034.482 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 237-946-0
PubChem CID
UNII
  • InChI=1S/C19H25ClN5O2/c1-5-23(12-13-25(2,3)4)16-8-6-15(7-9-16)21-22-19-11-10-17(24(26)27)14-18(19)20/h6-11,14H,5,12-13H2,1-4H3/q+1
    Key: TZXATTMVGZDPHM-UHFFFAOYSA-N
  • CCN(CC[N+](C)(C)C)C1=CC=C(C=C1)N=NC2=C(C=C(C=C2)[N+](=O)[O-])Cl
Properties
C19H25Cl2N5O2
Molar mass 426.34 g·mol−1
Appearancedark red solid
Melting point 45.5–46.5 °C (113.9–115.7 °F; 318.6–319.6 K)
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H302, H318, H412
P264, P270, P273, P280, P301+P312, P305+P351+P338, P310, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Basic Red 18 is a cationic azo dye used for coloring textiles. The chromophore is the cation, which contains many functional groups, but most prominently the quaternary ammonium center.

It is produced by azo coupling of 2-chloro-4-nitrophenyldiazonium cation with the quaternary ammonium salt derived from N-ethyl-N-(2-chloroethyl)aniline and trimethylamine. [1]

Like many dyes, methods for the removal of Basic Red 18 from waste streams has received much attention. [2]

Related Research Articles

<span class="mw-page-title-main">Amine</span> Chemical compounds and groups containing nitrogen with a lone pair (:N)

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

<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">Ammonium</span> Chemical compound

The ammonium cation is a positively charged polyatomic ion with the chemical formula NH+4 or [NH4]+. It is formed by the protonation of ammonia. Ammonium is also a general name for positively charged (protonated) substituted amines and quaternary ammonium cations, where one or more hydrogen atoms are replaced by organic or other groups.

<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">Quaternary ammonium cation</span> Polyatomic ions of the form N(–R)₄ (charge +1)

In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure [NR4]+, where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.

<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.

<span class="mw-page-title-main">Counterion</span> Ion which negates another oppositely-charged ion in an ionic molecule

In chemistry, a counterion is the ion that accompanies an ionic species in order to maintain electric neutrality. In table salt the sodium ion is the counterion for the chloride ion and vice versa.

<span class="mw-page-title-main">Azo dye</span> Class of organic compounds used as dye

Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C-N=N-C linkage. Azo dyes are synthetic dyes and do not occur naturally. Most azo dyes contain only one azo group but there are some that contain two or three azo groups, called "diazo dyes" and "triazo dyes" respectively. Azo dyes comprise 60-70% of all dyes used in food and textile industries. Azo dyes are widely used to treat textiles, leather articles, and some foods. Chemically related derivatives of azo dyes include azo pigments, which are insoluble in water and other solvents.

<span class="mw-page-title-main">Diazonium compound</span> Group of organonitrogen compounds

Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group [R−N+≡N]X where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide.

In organic chemistry, an azo coupling is an organic reaction between a diazonium compound and another aromatic compound that produces an azo compound. In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the electrophile and the activated carbon act as a nucleophile. In most cases, including the examples below, the diazonium compound is also aromatic.

A substantive dye or direct dye is a dye that adheres to its substrate, typically a textile, by non-ionic forces.

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

Tetramethylammonium hydroxide (TMAH or TMAOH) is a quaternary ammonium salt with molecular formula N(CH3)4+ OH. It is commonly encountered in form of concentrated solutions in water or methanol. TMAH in solid state and its aqueous solutions are all colorless, but may be yellowish if impure. Although TMAH has virtually no odor when pure, samples often have a strong fishy smell due to presence of trimethylamine which is a common impurity. TMAH has several diverse industrial and research applications.

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

Azo violet (Magneson I; p-nitrobenzeneazoresorcinol) is an azo compound with the chemical formula C12H9N3O4. It is used commercially as a violet dye and experimentally as a pH indicator, appearing yellow below pH 11, and violet above pH 13. It also turns deep blue in the presence of magnesium salt in a slightly alkaline, or basic, environment. Azo violet may also be used to test for the presence of ammonium ions. The color of ammonium chloride or ammonium hydroxide solution will vary depending upon the concentration of azo violet used. Magneson I is used to test Be also; it produces an orange-red lake with Be(II) in alkaline medium.

Polymers with the ability to kill or inhibit the growth of microorganisms such as bacteria, fungi, or viruses are classified as antimicrobial agents. This class of polymers consists of natural polymers with inherent antimicrobial activity and polymers modified to exhibit antimicrobial activity. Polymers are generally nonvolatile, chemically stable, and can be chemically and physically modified to display desired characteristics and antimicrobial activity. Antimicrobial polymers are a prime candidate for use in the food industry to prevent bacterial contamination and in water sanitation to inhibit the growth of microorganisms in drinking water.

<span class="mw-page-title-main">Paper chemicals</span> Chemicals used in paper manufacturing

Paper chemicals designate a group of chemicals that are used for paper manufacturing, or modify the properties of paper. These chemicals can be used to alter the paper in many ways, including changing its color and brightness, or by increasing its strength and resistance to water. The chemicals can be defined on basis of their usage in the process.

<span class="mw-page-title-main">Tetramethylammonium</span> Polyatomic ion (N(CH₃)₄, charge +1)

Tetramethylammonium (TMA) is the simplest quaternary ammonium cation. It has the chemical formula [Me4N]+ and consists of four methyl groups attached to a central nitrogen atom. The cation is isoelectronic with neopentane. It is positively-charged and can only be isolated in association with a counter-ion. Common salts include tetramethylammonium chloride and tetramethylammonium hydroxide. Tetramethylammonium salts are used in chemical synthesis and in pharmacological research. It confers no color to its salts.

1-Vinylimidazole is a water-soluble basic monomer that forms quaternizable homopolymers by free-radical polymerization with a variety of vinyl and acrylic monomers. The products are functional copolymers, which are used as oil field chemicals and as cosmetic auxiliaries. 1-Vinylimidazole acts as a reactive diluent in UV lacquers, inks, and adhesives.

<i>N</i>-Ethyl-<i>N</i>-(2-chloroethyl)aniline Chemical compound

N-Ethyl-N-(2-chloroethyl)aniline is the organic compound with the formula C6H5N(Et)(CH2CH2Cl) (Et = ethyl). It is a low-melting colorless solid that is an alkylating agent. The compound is a precursor to several cationic azo dyes via reaction of the chloroethyl group with tertiary amines or pyridine followed by azo coupling. Examples of derived dyes include C. I. Basic Red 18, Maxilon Red 2GL, and Yoracryl Red 2G.

Cationization of cotton is an electro kinetic phenomena for surface charge of cotton. The cotton surface is charged with negative ions. Cationization alters the characterization of the surface of the cotton which allows salt free dyeing and improves the dye ability of cotton. The process involves the chemical reaction of cationic reactive agents with cellulose.

In organic chemistry, alkylammonium refers to cations of the formula [R4−nNHn]+, where R = alkyl and 1≤ n ≤ 4. The cations with four alkyl substituents, i.e., [R4N]+, are further classified as quaternary ammonium cations and are discussed more thoroughly in the article with that title. In contrast to quaternary ammonium cations, other members of the alkylammonium cations do not exist appreciably in the presence of strong base because they undergo deprotonation, yielding the parent amine. The alkylammonium cations containing N-H centers are colorless and often hydrophilic.

References

  1. Klaus Hunger; Peter Mischke; Wolfgang Rieper; et al. (2005). "Azo Dyes". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245. ISBN   3527306730..
  2. B.Noroozi; G. A.Sorial; H.Bahrami; M.Arami (2008). "Adsorption of binary mixtures of cationic dyes". Dyes and Pigments. 76 (3): 784–791. doi:10.1016/j.dyepig.2007.02.003.