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UNITED STATES PATENT OFFICE 2,339,309 PHOTOGRAPHIC REDUCING COMPOST on and PROCESS John Raul Weber, South River, N.J., and Lynn Barratt Morris, Washington, D

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UNITED STATES PATENT OFFICE 2,339,309 PHOTOGRAPHIC REDUCING COMPOST on and PROCESS John Raul Weber, South River, N.J., and Lynn Barratt Morris, Washington, D Patented Jan. 18, 1944 2,339,309 UNITED STATES PATENT OFFICE 2,339,309 PHOTOGRAPHIC REDUCING COMPOST ON AND PROCESS John Raul Weber, South River, N.J., and Lynn Barratt Morris, Washington, D. C., assignors, by mesne assignments, to E. I. du Pont de Nemours & Company, Wilmington, Del, a cor poration of Delaware No Drawing. Application September 25, 1941, Serial No. 412,340 21 Claims. (C. 95-88) This invention relates to photographic compo forms set forth above, which may undergo re sitions and more particularly to photographic arrangement depending upon whether the COm processing solutions and to photographic proc pound is in acid or alkaline medium, or upon esses for utilizing such compositions. In one of physical characteristics such as temperature and its more specific aspects it relates to photographic pressure. reducing solutions for treating silver salts and photographic processes utilizing such solutions. Furthermore, it is conceivable, considering the In some of its further aspects it relates to new Second formula, that it forms a salt when in alka chemical compositions for photographic develop line Solution e. g. the sodium sulfinate when in ment and toning. Sodium hydroxide solution. It is further con O ceivable that in acid solution it forms salts on the This invention has for an object to provide new imino group, for instance, a hydrochloride. and useful reducing compositions for silver salts. Since the utility of the compound in accord A further object is to provide a reducing agent ance with this invention does not depend upon which can be used for the reduction of photo the exact structure of the oxygenated reaction graphic images in alkaline, neutral or acid media. 5 product of thiourea or hydrocarbon substituted A still further object is to provide more effective thiourea with hydrogen peroxide, and for conven and more economical reducing agents which can ience, the names imino-amino-methane sulfinic be used in acid media. A still further object is to acid or formamidine sulfinic acid will be used. provide new and useful developer solutions. An The expression an imino-amino-methane sulfinic other object is to provide developer solutions for 20 acid will be used to cover formamidine sulfinic reversal processes. Yet another object is to pro acid and its derivatives which are capable of re vide a practical and economical means for toning ducing silver salts. a silver image to produce warm and pleasing To be more specific, it has been found that an brown to sepia toned images. Still other objects imino-amino-methane sulfinic acid in aqueous will be apparent from the following description 25 Solution and especially formamidine sulfinic acid of the invention. is capable of preferential reduction of exposed It has been found that the oxygenated reaction silver halide grains in the presence of unexposed products of hydrogen peroxide with thiourea and silver halides to give a photographic image so certain of its hydrocarbon substitution products long as the solution is definitely acid. However, have considerable utility in photographic proc 30 if the pH of the solution is increased toward neu essing baths especially for reducing silver salts to tral, the reduction potential of the compound in metallic silver in photographic elements. creases, tending to give an overall blackening ef The exact structure of oxygenated reaction fect which is relatively weak at a pH of 6 but products of thiourea, with hydrogen peroxide pre quite powerful at pH values in excess of 6.8. pared from these reactants in neutral solution is 35 The last mentioned effect is advantageously not known with certainty. It has been called used in accordance with one aspect of the inven thiourea dioxide by some investigators which is tion in reversal processes. The Ordinary proc indicative of a formula such as that set forth in esses of preparing positive images by removal of (A) below. Others, however, have advanced the a negative image, followed by reduction of the name imino-amino-methane-sulfinic acid and 40 remaining silver halides in a reducing solution formamidine sulfinic acid which implies a struc containing an imino-amino-methane sulfinic ture having formula (B): acid, can be carried out with or without a sec O Ond exposure to light. The most convenient methods employ no second exposure, but merely C 45 consist of immersing the film, after the original NH O image has been removed and the emulsion cleared NE OBI / and Washed in a solution containing sufficient (B) C-S formamidine sulfinic acid to reduce the silver N. NE O Salts to metallic silver. While acid solutions are It is possible that both formulae may be equally 50 useful, especially if re-exposure is resorted to, correct, because the compound may exist in sev it has been found that alkaline solutions of an eral desmotropic forms. It is possible that the imino-amino-methane sulfinic acid have a power compound exists in a desmotropic form wherein ful reducing action on exposed or unexposed it. an equilibrium normally obtains between the two USidinehalide sulfinic grains. acid. This is especially true of formam 2 2,339,309 In a further aspect of the invention an imino EXAMPLE WI amino-methane sulfinic acid is used in acid solu Formamidine sulflinic acid-------- grams-- 4.5 tion as the ordinary developer. Such solutions Potassium bromide---------------- do---- 3 are capable of reducing the silver halide grains Potassium metabisulfite------------do---- 4.5 of an exposed photographic emulsion to form a Water ----------------------- milliliters-- 1000 metallic silver image. A silver halide emulsion containing latent images as formed by exposure Alkaline developer solutions suitable for the to an original scene or by printing from a de second developer in producing images by re veloped photographic element, is treated in an versal methods can be made by admixing the aqueous acid solution containing Sufficient of an 0 ingredients set forth in the following examples imino-amino-methane sulflinic acid to develop in any desired order. the exposed silver salts. Formanidine sulfinic EXAMPLE v1.1 acid developers, however, are preferred. Formamidine sulfinic acid.-------- a.S.- 25 In still another aspect of the invention, Potassium sulfite------------------ do---- 50 aqueous acidic solutions containing Small 5 Potassium bromide---------------- do---- 30 amounts of an imino-amino-methane sulfinic Sodium hydroxide-----------------do---- 20 acid are used to redevelop a bleached silver 1000 image. A photographic element containing a Water ----------------------- milliliters.-- bleached silver image is immersed in an aqueous ExAMPLE VIII acidic solution of the type described in sufficient 20 Formanidine sulfinic acid-------- gaS. 5 amount to reduce the silver salts. The resulting Hydroquinone--------------------- do---- 10 image is characterized by various tones depend Potassium carbonate---------------do---- 30 ing upon the particular pH value of the devel Potassium sulfite------------------ do---- 50 oper formula. Water ----------------------- milliliters.-- 1000 The treating solutions used in the processes 25 outlined above may contain in addition to the EXAMPLE IX imino-amino-methane sulfinic acid various modi Formamidine sulfinic acid.-------- granS.-- 30 fying agents which are useful in developer Solu Sodium sulfite---------------------do---- 55 tions such as restrainers, preservatives, agents Potassium bromide---------------- do---- 38 for controlling image tone, wetting agents, hard 30 Sodium hydroxide----------------- do---- 25 eners, materials whose presence retards the rate Water ----------------------- milliliters-- 000 of diffusion of the solution in emulsion layers etc. The invention, however, is not limited to EXAMPLE X solutions, on the contrary, dry reducing composi Formamidine sulfinic acid -------- gaS.-- 36 tions containing the specified ingredients with 3 Sodium carbonate----------------- do---- 50 the exception of water are comprehended. Sodium sulfite-------------------- do---- 40 The invention will be further illustrated, but Water ----------------------- milliliterS.-- 1000 is not intended to be limited by the following examples. The first group consists of developer EXAMPLE X solutions useful for Ordinary development of 40 Formamidine sulfinic acid.--------3.a.S. 8 silver images or sepia toning by redevelopment. Potassium bromide---------------- do---- 15 They can be made by admixing the ingredients Sodium hydroxide----------------- do---- 15 in any desired order with water. Dry composi Water ----------------------milliliters-- 1000 tions can be made in a similar manner by ad The amount of formanidine sulflinic acid is mixing the components in dry forms. 45 not limited to that set forth in the above ex EXAMPLE I amples but may be varied over a wide range. Formamidine sulfinic acid-------- grams-- 18 The amount to be used varies somewhat in ac Sodium bisulfite------------------- do---- 36 cordance with the material treated. Potassium bromide---------------- do---- 6 50 Acid development Water -----------------------milliliters-- 1000 In the acid reduction or development pro cedures a range of concentrations from about ExAMPLE II 0.5% to 2.0% by Weight of formamidine sulfinic Formamidine sulfinic acid-------- grams-- 15 acid in respect to the final weight of the solution Sodium bisulfite------------------- do---- 20 55 represents a practical range. N-hydrocarbon Potassium bromide---------------- do---- 5 substituted formamidine sulfinic acids. can be Potassium metabisulfite------------
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