Patent GB-732544-A (GB)
Title: Improvements relating to processes for making reproductions especially printing plates, with the application of diazo compounds
IPC: G03F7/022
Filed: 1952-03-21
Abstract: N : N1 - di - (benzoquinone - (311 - 411)-diazide - (311) - 111 - sulphonyl) - 4 : 41 - diaminobenzene (example 1). made by reacting benzoxazolone - 5 - sulphochloride with 4 : 41-diaminoazobenzene in dioxane with sufficient pyridine to combine with the hydrogen chloride produced, splitting the oxazolone ring by heating with caustic soda to produce N : N1-di-(311-amino - 411 - hydroxybenzene - 111 - sulphonyl)-4 : 41-diaminoazobenzene and diazotizing this. Benzoquinone - (1 : 2) - diazide - (2) - 4 - N - [p - p - (21 - naphthol - 11 - azo) - phenyl] - sulphonamide (example 3) made by condensing benzoxazolone-5-sulphochloride and p-nitraniline in dioxane in presence of pyridine, reducing the benzoxazolone - 5 - (N - p - nitrophenyl)-sulphonamide produced to form the corresponding amino compound, diazotizing and coupling this with b -naphthol, splitting the oxazolone ring with caustic soda and diazotizing the resulting product.ALSO:N : N1 - di(benzoquinone - (311 - 411) - diazide-(311) - 111 - sulphophenyl - p - aminobenzenesulphonyl) - o - phenylene diamine (example 2) made by reacting benzoxazolone - 5 - sulphochloride with N : N1-di-(41-aminobenzene-11-sulphonyl) - 1 : 2 - phenylene diamine in dioxane with sufficient pyridine to combine with the hydrogen chloride produced, splitting the oxazolone ring with caustic soda and diazotizing the product.  N : N1 - di - (benzoquinone - (311-411) - diazide - (311) - 1 - sulphophenyl) - 4 : 41 - diaminodiphenyl (example 4) made similarly using 4 : 41-diaminodiphenyl in place of the specified phenylenediamine of example 2.  N : O - di - [benzoquinone -(111 : 211) - diazide-(211) - 411 - sulphonyl] - 4 - hydroxy - 41 - aminodiphenyl (example 6) made by condensing benzoquinone - (1 : 2) - diazide - (2) - 4 - sulphochloride with 4-amino-41-hydroxydiphenyl in dioxane in presence of pyridine and long digestion of the product with water. Benzoquinone - (1 : 2) - diazide(2) - 4 - (N-21-fluorenyl)-sulphonamide, (example 7), made as in example 2 using 2-aminofluorene in place of the specified phenylenediamine.  O - [naphthoquinone - (1 : 2) - diazide - (2) - 5-sulphonyl] - glycol (example 8) made by heating the corresponding sulphochloride with glycol.  O - O1 - di - [511 - methyl - benzoquinone-(111 : 211) - diazide - (211) - 411 - sulphonyl] - 4 : 41 dihydroxydiphenyl sulphone (example 9) made by reaction between 5-methyl-benzoquinone-(1 : 2)-diazide-(2)-4-sulphochloride and 4 : 41-dihydroxy diphenyl sulphone in presence of sodium carbonate.  N : N - di[6 - methyl - benzoquinone - (1 : 2)-diazide - (2) - 411 sulphonyl] - 4 : 41 - diaminodiphenylmethane (example 10) made from 7-methylbenzoxazolone - 5 - sulphochloride and 4 : 41-diaminodiphenyl methane by the procedure of example 2.  The N-ethyl-b -naphthylamide, the b -naphthol ester, the di-hydroquinone ester (example 11); the 91 : 41-dichlorphenol ester (example 12); the 2 : 4 : 4-trihydroxy-diphenyl ester (example 13); and the 1-hydroxy-5-benzoylaminonaphthalene ester (example 14) of naphthoquinone-(1 : 2)-diazide-(2)-5-sulphonic acid are made by a method analogous to that of example 9.