Patent GB-537466-A (GB)
Title: Improvements in intermediates for use in photographic processes and their application
IPC: C07F9/09
Filed: 1939-09-23
Abstract: 537,466. Amino compounds ; photographic processes. KODAK, Ltd. (Eastman Kodak Co.). Sept. 23, 1939, No. 26535. [Class 2 (iii)] [Also in Group XX] Phenylene diamine derivatives of the general formulae shown in Figs. 1 and 2, where R<SP>1</SP> ... R<SP>5</SP> are hydrogen atoms or alkyl, homocyclic or heterocyclic groups (which may be substituted), and R<SP>1</SP> may also be an organic or inorganic acid radicle, are used as photographic developers in solutions which may contain another organic developing agent and also a colour coupler. The compounds may be made by reducing the corresponding m-aminobenzyl nitro, nitroso or azo compounds, which are obtained by nitrating or nitrosating the m-aminobenzyl compounds or coupling the latter with a diazo compound. The reduction is preferably effected by hydrogen in the presence of a hydrogenation catalyst, e.g. nickel. Some of the parent m-aminobenzyl compounds may be made by nitrating a benzyl alcohol, and catalytically reducing the resulting m-aminobenzyl alcohol in presence of a solvent, or by nitrating a benzaldehyde and reducing the product. The preparation of a large number .of parent m-aminobenzyl compounds is described, including m-aminobenzyl alcohol, 3-amino-4-methylbenzyl alcohol, mmethylamino-benzyl alcohol, m-dimethylaminobenzyl alcohol, mono- and di-m-#-hydroxyethylaminobenzyl alcohols, mono- and dim-glycerylaminobenzyl alcohols, N-ethyl-N-#- hydroxyethyl-m-aminobenzyl acetate, m-ethylgycerylaminobenzyl alcohol, 2-nitro-5-aminobenzyl methyl carbinol, 3-nitro-4-aminophenyl ethyl carbinol methyl ether, 2-amino-4-methyl- 5-nitrobenzyl acetate, glycol mono-(2-amino-4- methoxy-5-nitro) benzyl ether, 2-amino-4- ethoxy-5-nitrobenzyl methyl ether, 4-phenoxy- 2:5-dinitrobenzyl alcohol, 2-nitro-5 (4'-nitrophenyl)-aminobenzyl methyl carbinol, sym-di- (p-nitro-m-α-hydroxyethyl) phenyl ethylenediamine, (2-nitro-5-α-hydroxyethyl) phenylglycine amide, 3-(N-ethyl-N-#-acetoxyethyl)-amino-4-methylbenzyl alcohol, 2-nitro- 4-methoxy-5-dimethylaminobenzyl methyl ether, (2-methyl-4-nitro-5-oxymethyl)- phenylglycine amide, 2-nitro-4-ethyl-5- (##- dimethoxyethyl) aminobenzyl alcohol, N- (2- methyl-4-nitro-5-oxymethyl)-phenyl-N-ethylglycine methyl ester, and 2-nitro-4-methyl-5- (di-#-methoxyethyl)-aminobenzyl alcohol. The nitro groups in these compounds may be reduced by catalytic hydrogenation to give the desired phenylenediamines. The production of azo compounds, which give the phenylenediamines on reduction, is described from ochloraniline and N-ethyl-N-#-hydroxyethyl-maminobenzyl acetate, p-bromaniline and maminobenzyl alcohol, 2-methoxy-4-nitraniline and m-dimethylaminobenzyl alcohol, pbromaniline and m-#-hydroxyethylaminobenzyl alcohol, 2:4-dinitraniline and m-aminobenzyl alcohol, 2-brom-4-nitraniline and m-glycerylaminobenzyl alcohol, 2:4-dinitro-6-chloraniline and m-ethylglycerylaminobenzyl alcohol &c. Examples are also given of the production of the diamines by reduction of a nitroso group and of products in which the group OR<SP>1</SP> is a sulphuric or phosphoric acid group. Specifications 15055/12, 2562/13, [both in Class 98 (ii)], 390,093, 427,520, 458,664, 458,665, 474,353, and 503,752, [all in Group XX], are referred to.