Patent GB-790131-A (GB)
Title: Light-sensitive layers for the production of tanned images
Filed: 1955-05-27
Abstract: 4 - Azido - benzal - acetylacetone - 2 - sulphonic acid sodium salt is made by condensation of 4-azido-2-benzaldehyde-sulphonic acid sodium salt with acetyl-acetone.  4 - Azido - diacetyl - 2 - sulphonic acid sodium salt is made similarly by condensation with diacetyl.]  4 - Azido - 1 - o  - nitro - styryl - 2 - sulphonic acid sodium salt is made similarly by condensation with nitromethane. 4,41 - Diazido - stilbene - 2,21 - bis(sulphonamido) - 411 - phenyl - hydroxy - ethyl ether is made by reaction of 4,41-diazido-stilbene-2,21-disulphonyl chloride with b -hydroxy-p-phenetidine.  4 - Azido - 41 - fluorostilbene - 2,21 - disulphonic acid sodium salt is made by thermal decomposition of the diazonium-boro-fluoride of 4-nitro-41-aminostilbene-2,21-disulphonic acid sodium salt, reduction, diazotization and reaction with sodium azide.  4,41 - Diazidostilbene - 2,21 - disulphonamide is made by reaction of 4,41-dinitrostilbene-2,21-disulphonyl chloride with ammonia, reduction, tetrazotization and reaction with sodium azide. 4,41,411,4111 - Tetra - azido - 2,21,211,2111 - bis (disulphimido)-stilbene is made by dry condensation of p-nitrotoluene-2-sulphonyl chloride and p-nitrotoluene-2-sulphonamide, oxidation with sodium hypochlorite in alcoholic solution, catalytic reduction of the nitro groups to amino groups, diazotization and reaction with sodium azide.  4 - Azido - stilbene - 2,21 - disulphonic acid sodium salt is made by diazotizing 4-nitro-41-amino-stilbene-2,21-disulphonic acid, boiling the diazo compound with absolute alcohol, reducing and then diazotizing the nitro group and reacting with sodium azide.  4 - Azido - 41 - hydroxystilbene - 2,21 - disulphonic acid sodium salt is made similarly by boiling with 20 per cent sulphuric acid instead of absolute alcohol.  4 - Azido - benzal - vinylketone - 2 - sulphonic acid sodium salt is made by condensation of 4-azido-2-benzaldehyde-sulphonic acid sodium salt with methyl-vinylketone.  4 - Azido - benzal - ketobutanol - 2 - sulphonic acid sodium salt is made similarly by condensation with ketobutanol. 4,41 - Diazido - 5,51 - dichloro - stilbene - 2,21 - disulphonic acid di-sodium salt is made from the corresponding dinitro compound by reduction, tetrazotization and reaction with sodium azide.  Other azido- and diazido-styryl compounds are quoted in the Specification.ALSO:Polyamides soluble in hot aqueous lower alcohols for sensitization with azido-styryl compounds (see Group IV (b)), to produce layers for photo-mechanical purposes (see Group XX), are made by simultaneous condensation of hexamethylene diamine or other diamines, which may be mono-alkylated at a nitrogen atom, adipic acid or other dicarboxylic acids (salts of the diamines and acids may count as two components), and an amino-carboxylic acid or ester or amide but preferably lactam thereof under anaerobic conditions using high temperatures and long reaction time.  The condensation mixtures may be (1) hexamethylene diamine adipate and e -caprolactam in ratio 3 : 2 by weight, (2) the same in ratio 1 : 1 by weight, (3) hexamethylene diamine adipate, 4,41-diamino dicyclo hexylmethane adipate and e -caprolactam in ratio 1 : 1 : 1 by weight, (4) hexamethylene diamine adipate, ethylene diamine adipate, 9-amino-nonanic acid, e -caprolactam, xylenol and hexamethylene diamine in ratio 3 : 3 : 3 : 3 : 1 : 0.4 by weight, (5) hexamethylene diamine adipate, the decane dicarboxylic acid salt of undecane-methylene diamine and 3-caprolactam in ratio 6 : 3 : 2 by weight, (6) hexamethylene diamine adipate, N-mono-methyl hexamethylene diamine adipate and e -caprolactam in ratio 6 : 2 : 5.5 by weight.