Reactive Red 1

Structural formula
Trisodium salt
General
Surname	Reactive Red 1
other names	Trisodium 5 - [(4,6-dichloro-1,3,5-triazin-2-yl) amino] -4-hydroxy-3 - [( E ) - (2-sulfonatophenyl) diazenyl] -2,7- naphthalene disulfonate IUPAC Procion brilliant red 2BS
Molecular formula	C 19 H 9 Cl 2 N 6 Na 3 O 10 S 3
Brief description	bluish red powder that dissolves in water with a yellowish red color.
External identifiers / databases
CAS number 17752-85-1 EC number 241-743-2 ECHA InfoCard 100.037.933 PubChem 87291 ChemSpider 20157100 Wikidata Q27290579
properties
Molar mass	717.4 g mol −1
Physical state	firmly
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

CI Reactive Red 1 is an azo dye of the performance group of reactive dyes , which for dyeing of cotton is used.

Manufacturing

Reaction of H-acid ( 1 ) with trichlorotriazine ( 2 ) at 0-5 ° C. gives the condensation product ( 3 ). This is referred to as coupling component with the diazonium salt ( 5 ) which is obtained by diazotization of 2-aminobenzenesulfonic acid ( 4 ) with sodium nitrite , obtained in acid solution to Reactive Red 1 ( 6 reacted,):

Synthesis of CI Reactive Red 1

In an alternative synthesis sequence , diazotized 2-aminobenzenesulfonic acid is first reacted with N- acetyl-H acid to form a monoazo dye. After the acetyl protective group has been split off, condensation with trichlorotriazine takes place to give the end product.

use

Reactive Red 1 is one of the first reactive dyes with a dichlorotriazine anchor, which was patented by ICI in 1955 and marketed under the trade name Procion Brillantrot 2BS . The starting point was the observation that although this dye has a low affinity for cellulose fibers , it produces intense dyeings with very good wet fastness properties even at room temperature from an aqueous, alkaline solution . The dichlorotriazine group forms a chemical bond with the hydroxyl groups of the cellulose.

A disadvantage of the dye is its sensitivity to hydrolysis . It therefore only plays a subordinate role in reactive dyeing, but is used as an intermediate in the production of monochlorotriazine dyes. An example of this is the making of Reactive Red 227 :

Synthesis of CI Reactive Red 227 ( 3 ) by condensation of parabase ester ( 1 ) with CI Reactive Red 1 ( 2 )

Individual evidence

1. ↑ ^{a b c d} Patent DE1062367 : Process for the production of monoazo dyes. Applied on November 19, 1955 , published July 13, 1959 , applicant: ICI Ltd., inventor: William Elliot Stephen. ‌
2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
3. ^ E. Siegel: Reactive Groups . In: K. Venkataraman (Ed.): The Chemistry of Synthetic Dyes . VI Reactive Dyes. Academic Press, New York, London 1972, pp. 124 ( limited preview in Google Book search).
4. ^ Heinrich Zollinger: Color Chemistry . 3rd, revised edition. Wiley-VCH, Weinheim 2003, ISBN 3-906390-23-3 , pp. 225 ff . ( limited preview in Google Book search).