Reactions of Wool with Cyanuric Chloride

Abstract

The reaction of wool with cyanuric chloride from an acetone-water mixture results in crosslinking only if the wool has previously been reduced. Introduction of cyanuric chloride from acetone solution and subsequent aqueous aftertreat ment causes complete reaction of all three chlorine sites in cyanuric chloride, while under comparable conditions in solution only one site is reactive. Esterification of the carboxyl groups in the wool results in a stabilization of two thirds of the chlorine sites suggesting that carboxyl groups are involved in the hydrolysis of at least two of the three chlorine sites. The intermediate formation of activated esters and their subsequent rapid hydrolysis is discussed as a possible mechanism. A 1:1 1 correspondence between the number of carboxyl groups in wool and the number of chlorine atoms in the 3- and 5-positions of cyanuric chloride indicates a stoichiometric reaction rather than a catalytic participation of the carboxyl groups. The immobilization of cyanuric chloride molecules within the wool either through direct co valent bond formation or through electrostatic interactions with amino groups is postulated.