US2193015A - Developer containing sulphonamide groups - Google Patents

Description

.i airented Mar. 12, ihiifi Arnold Weissbergcr, Rochester, N. Y., assignor to Eastman Kodak Company,

Rochester, N. Y., a

corporation of New Jersey No Drawing. Application May 24, 1939, Serial No. 275,487

10 Claims.

This invention relates to photographic developers and more particularly to photographic developers containing sulphonamide groups.

It is known that photographic developers of the p-phenylene diamine type are valuable compounds for producing fine grain black and white photographic images and also that these compounds, especially when they contain alkyl substituents, are useful as developers in processes for producing colored photographic images. The p-phenylene diamine developers, however, have several defects. One disadvantage of these developers is that they are not greatly soluble in the developing solutions. Another disadvantage is that they are highly allergenic, that is, they are poisonous to the human skin and are, therefore, somewhat dangerous to use. When the pphenylenediamines are used in color processes, it has also been found that they do not always produce the desired color in the final image.

It is, therefore, the principal object of the present invention to provide an entirely new class of photographic developingtagents of the p-phenylenediamine type. A further object is to provide photographic developing agents which are more soluble in the developing solutions than c0mpounds previously used. A still further object is to provide developing agents which are less allergenic, that is, less poisonous to the human skin than compounds hitherto known. A still further object is to provide photographic developing agents of the substituted p-phenylene-diamine type which are useful in photographic color processes for the purpose of producing images of the desired color.

These objects are accomplished by the present invention by the use, as developing agents. of compounds of the general formula:

"onnwusowm N e-moth ncsulphonnmldocthyli-amlnoaulllne development CzHl-NHSCMCH; N-eihyl-Bmethanesulphonamidoethyl-i-aminoaniline l CzHs C2ll4S OzN He N-fl-sulphonamidoethyl-4-aminoaniline (CHflr-SOr-NHC H3 Nfi p-aminophenylaminn ethane sulphon-methylamide Ca s Q ma N (CHz)z--S0 NHCH3 N-fi-p-nmino phenyl ethyl aminoethanesulphonanethylmmidc These compounds may be formed by the reaction of primary amines with alkyl or substituted alkyl sulphonyl chlorides for example, methane sulphonyl chloride, or through other intermediates or by the reaction of primary amines with chlorides or other derivatives of half esters of sulphuric acid. The solubilizing and other beneficial properties are secured by the SO2NH2, or -NHSOz-- group, which may contain alkyl 35 substituents as indicated in the general formula above. The aryl nucleus of the developer may be attached to either side of this solubilizing group as indicated by the specific examples.

These compounds may be substituted in the aromatic ring with other groups including halide, amino, substituted amino, azo, alkyl and aryl groups. These groups have a tendency to alter the color of the final dye image and the color may be controlled in this way.

When used for the formation of colored photographic images, the developers of my invention may be used in conjunction with any well known coupler compounds such as those described in Fischer U. S. Patent 1,102,028. June 30, 1914; Mannes 8: Godowsky U. S. Patent 2,108,602, February 15, 1938; Mannes, Godowslry and Peterson U. S. Patent 2,115,394, April 26, 1938; and Marines, Godowsky and Peterson U. S. Patent 2.126.337, August 9, 1938.

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'ihe following examples, which are illustrative only, indicate developing solutions which he used according to my invention.

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Example 1 A. llethyl43-methanesuiphonamidoethyil minoauil ne "gram" 1 Water to cc 1000 Add Example 2 The coupler used to form a colored image may be incorporated in the emulsion layer prior to exposure and a colored image formed by developmerit in the following solution:

N- ethyl-p-methanesulphonamidoethyl-3- For the formation of a fine-grain black and White image, the following developing solution may he used:

N 5 methanesulphonamidoethyl-e-aminoaniline grams 5 Sodium sulphite do 30 Sodium carbonate -do- 30 Water to cc 1000 All of the developers described in the present application may he used for the purpose of producing fine grain, black and white photographic images. Although all of these developers may be used also to form colored images in conjunction with witable color forming coupler compounds, the developers in which the substituted nitrogen atom of the p-phenylenediamine contains an allayl group in addition to the sulphonamido alkyl group have been found to be superior as color developers. These developers are those in which X in the general formula above is an alkyl group.

The developing agents described in the present application may be used to form photographic images by development of exposed silver halide contained in the usual gelatin carrier or in car riers such as collodion, water permeable cellulose esters, or water permeable synthetic resins. The sensitive layers may be carried on any suitable support such as glass, paper, cellulose esters or synthetic resins. They may be used with multilayer films where two or more layers are coated on the same side of a support or where the layers are coated on the opposite sides of a support.

The examples and formulae of the present specification are illustrative only and it is to be understood that my invention is to be taken only as limited by the scope of the appended claims.

I claim:

1. A photographic developing agent having the following general formula:

R-Su

areaois 3. A photographic developing agent comprising a nitrogen substituted sulphonamidoallryllaminoaniline.

4:. A photographic developing agent comprising a N-/s-sulphonamidoalkyi-4-an1inoaniline.

5. A color forming photographic developer 4 comprising compound having the general formula:

x Nlla- -1\' RSu where X is allcyl R is alkylene Su is SO2NH2 -SOzNI-IR --NHSO2R R is hydrogen alkyl 6. A photographic developing solution for producing a colored image comprising a developing agent having the general formula:

X is alkyl R is alkylene R is hydrogen alkyl and a compound which is coupled with the developing agent at the primary amino group on photographic development to form a colored image.

'7. A color forming photographic developer comprising an N-alkyl-methanesulphonamidoalkyl-i-aminoaniline.

8. A developing solution for producing a colored photographic image comprising an N-alkylmethanesulphonamidoalkyl 4 aminoaniline and a compound which couples with the developing agent at the primary amino group to form a colored image on development.

9. A color forming photographic developer N ethyl-fi-methanesulphonamidoethyl-4-aminoaniline.

10. A developing solution for producing a colored image comprising N-ethyLc-methanesulphonamidoethyl-4-aminoaniline as a developing agent and a compound which couples with the developing agent at the primary amino group to produce a colored image on photographic development.

ARNOLD WEISSBERGER.