Phenoxy carbonyl derivatives of a paraphenylenediamine color developer and their use in an image-receiving sheet for color diffusion transfer

#The present invention relates to new paraphenylenediamine derivatives which are useful in forming indoaniline or azomethine dyes by reaction with color formers, and more particularly to a receiving sheet for a diffusion transfer photographic element containing the new paraphenylenediamine derivatives.

#In diffusion transfer photography, formation of a dye image in a receiving sheet may be effected by diffusion of a color former from the negative portion of a film pack to the receiving sheet of the film pack. The diffusion is normally a function of imagewise non-exoposed areas of the film pack, and a positive dye image is formed by coupling of the transferred color former with oxidized paraphenylenediamine to form a stable, non-diffusing dye. Many different systems have been proposed for supplying oxidized paraphenylenediamine color developer to the receiving sheet, such as incorporating a paraphenylene diamine color developer or precursor thereof in the film pack or the processing solution, but these proposals all suffer from the known disadvantage of paraphenylenediamine, namely its lack of stability to aerial oxidation and other forms of environmental degradation, its tendency to fog a silver halide emulsion, its allergenic properties, and the like.

#There is thus a need for a derivative of a paraphenylenediamine color developer that can be incorporated into a receiving sheet of a diffusion transfer film unit and that is available for coupling with a color former to form a stable dye, without liberation of paraphenylenediamine.

#Preparation of: ##STR7##

#To a solution of 10.6g of sodium carbonate in 100.0 ml water were added 100.0 ml dioxane and 21.4g 4-diethylamino-2-methylaniline hydrochloride. The solution was cooled to 10.degree. C and 15.6g phenylchloroformate was slowly added to the cooled solution, followed by addition of 200.0 of water. The reaction mass was stirred for 15 minutes and then diluted to 1 liter with water. The reaction product was worked up by dissolving the solid in ether followed by drying over sodium sulfate, and evaporation of the ether and recrystallization from a high boiling petroleum ether. The yield was 26g of a product melting at 117.degree.-118.degree. C and having the structure shown above. The carbon hydrogen nitrogen analysis was as follows:

#______________________________________ Calc. Found ______________________________________ C 72.45 72.23; 72.23 H 7.43 7.61; 7.37 N 9.39 9.41; 9.36 ______________________________________