\\;ith the object of preparing a cell~~lose ether containing diazotizable anlino groups, sever1 differeiit forms of cellulose, or cell~~lose derivatives, \\.ere treated \vith 10 cliffere~it reagents under a variety of conditions. Reasons \vhy only one reagent under one set of conditions gave a product with a substantial degree of substitution (0.35) and with satisfactory physical properties are presented. This resulti~lg ether, the w-(p-an~inoacetopl~e~lone) ether of cellulose, was prepared by the reaction between w-chloro-p-aminoacetopllei~one ancl ethanol-nraslled sodacellulose (from wood pulp, cotton, paper, or rayon). I t can be (a) diazotized and coi~plecl with any of the usual reagents to yield cellulose-azo colors, (b) santl~ated, before or after coupli~ig, and spun as rayon filament; if uncouplecl a t this point it can be diazotized and coupled, (c) dyed directly with acid dyes, (d) renclered organo-soluble by nitration, and (e) carbosymethylated after coupling to yield colored, water-soluble derivatives. I t is insoluble in the usual cellulose reagents, and is as stable t o acid and allcaline hydrolysis as cellulose.T h e purpose of the work described in this paper was the preparation of cellulose ethers containing primary aromatic amino groups. On diazotization and coupling such ethers sho~~lcl produce azo compounds in which the chromophore groups form part of the molecule of the cell~~lose derivatives, which should bc as stable as cellulose t o most reagents. Analogous nitro c o m p o~~n d s , because the>. may be recluced t o the corresponding aromatic amines, are also of interest. Ethers rather than esters were investigated because the former are more resistant to hyclrolysis.A n~lrnber of attempts to prepare colorecl cell~~lose derivatives have been reportecl. In 1926 Peacocli (42) obtained ~v h a t he regarded as a superficial coloring of cotton by treating it with nz-nitrobenzyl-phenyldinlethy-Iammonium cliloricle, cliazotizing, ancl coupling. A similar result was obtained by Iiursanov and S O I O~I~O V (33). 20,21,22,23) T h e usual etherification reaction between allrali cellulose ancl an organic halide forms the basis for a nulnber of patents (7,8,9,10,11,28) For personal use only.