Study on Denim treatments
Literature Survey Page 2
INDIGO AND POTASSIUM PERMANGANATE
Indigo has been used as a dye for as much as 4,000 years but it wasn‘t until 1883 that its
chemical structure was elucidated. However, its interaction with permanganate had not beenstudied in much depth until recently when E. Malik found isatin and anthranilic acid among theoxidation products that occur when indigo dye is bleached with potassium permanganate. It isalso well know and documented that isatin is formed in high yield when indigo is oxidized withnitric acid or chromic acid or a mixture of the two.The formation of isatin from indigo due to permanganate oxidation is understandable fromthe general reactive behaviour of KMnO4 toward carbon-carbon double bonds, which in greatmany cases results in the cleaving of the double bonds with the formation of carbonylcompounds.
Because the central double bond is also part of indigo‘s chromophoric group, the bleaching
action of KMnO
on this dye is also explainable. What is more difficult to understand is how freeanthranilic acid can occur as the end product of permanganate oxidation in light of the fact thatall aminobenzoic acids, when unprotected at the amino groups, are rapidly degraded in thepresence of permanganate.Metallic salts may combine with indigo oxidation by
products such as anthranilic acid toform a latent yellowish discolouration product in acid wash denim which is wet processed bypotassium permanganation. Assessments made by M. N. Larsen using atomic absorptionspectrometry indicate that a reduction in some denim metallic salt levels is associated withreduced yellowing.Potassium permanganate is one of the preferred bleaching agents for the so-called acid washprocess used industrially to create special looks in denim garments. These looks can range fromvery slight random bleaching effects to an almost complete white out of the blue indigo dye.