GB537921A - Coupling components for use in colour photography and the manufacture thereof and of intermediates therefor - Google Patents

Abstract

537,921. Substituted benzene sulphonic acid chlorides and esters ; synthetic resins ; cellulose derivatives. KODAK, Ltd. (Eastman Kodak Co.). Jan. 3, 1940, Nos. 183 and 6941. [Classes 2 (ii) and 2 (iii)] [Also in Group XX] p-Benzoylacetaminobenzenesulphonyl chloride is prepared by the reaction of benzoylacetanilide with chlorsulphonic acid. p-(#-p<SP>1</SP>- Anisoylacetamino)-benzenesulphonyl chloride and p-acetaminobenzenesulphonyl chloride are similarly prepared. Methyl, ethyl, n-propyl, n-amyl, ethylene- α : #<SP>1</SP>-di-, #-ethoxyethyl, #-benzyloxyethyl, #- (#-benzyloxyethoxy)-ethyl, #-(#-butoxyethoxy)- ethyl, and #-(p-ter-butylphenoxy)-ethyl pbenzoylacetaminobenzenesulphonates are prepared by the reaction of the appropriate alcohol with p-benzoylacetaminobenzenesulphonyl chloride in the presence of pyridine. The 2 :4-diamylphenyl ester is prepared by the reaction of the sodium salt of 2 : 4-diamylphenol with the sulphonyl chloride in xylene solution. #-(p-ter-Butylphenoxy)-ethyl- and - n - amyl p - - anisoylacetaminobenzenesulphonates are prepared by the first method, using p-anisoylacetaminobenzenesulphonyl chloride. The sulphonyl chlorides can also be condensed with alcohols in acetic acid solution using sodium acetate as the condensing agent. With higher water-insoluble alcohols, the condensation may be effected in the alcohol itself. The sulphonic chlorides may also be reacted with substances of high molecular weight containing hydroxyl groups, such as polybydroxystyrene, polyvinyl alcohol and cellulose or its derivatives. The specified benzoylacetamino derivatives may also be prepared by reacting p-acetaminobenzenesulphonylchloride with an alcohol, hydrolysing with aqueous hydrochloric acid to split off the acetyl group, and reacting the product with ethyl benzoylacetate. The sulphonic esters are useful as couplers in colour photography.