Patent GB-723382-A (GB)
Title: Light-sensitive diazotype layers and photomechanical printing plates
IPC: G03F7/022
Filed: 1952-08-08
Abstract: 1,8 - Naphthosultam - 4 - sulphon - N - ethylanilide and the corresponding -N-ethyl-b -naphthylamide and -N-p-aminodiphenylamide; and di - (1 : 8 - naphthosultam - 4 - sulphon) - 4 : 41-diaminodiphenyl are coupled in the other position to the sultam nitrogen with diazobenzene in ammoniacal dioxane at 0 DEG  C; and 1,8 - naphthosultam - 4 - sulphonic acid-phenyl-ester is coupled in the same position with diazotized p-nitraniline in dioxane and pyridene to form azo dyes used as intermediates in the preparation of the corresponding ortho-sultam diazides as described in Group IV (b). Specification 633,746, [Group XVI] is referred to.ALSO:As light-sensitive constituents in photographic reproduction material the compounds have the formula R1-N = R = N ­ N where R represents a quinonoid ring derived from an aromatic ring and R1 aryl, acyl or sulphonyl; and in which R1 may form a condensed ring system with R. When R has two alkoxy groups in para position to each other and R1 is arylsulphonyl the compounds are particularly suitable for the purpose.  As regards nomenclature R is designated as benzoquinone or naphthoquinone because of the quinonoid structure.  Particular compounds are:-  N - (41 - methyl - benzene - 11 - sulphonyl) - imino - (1) - 2,5 - diethoxy - benzoquinone - (1,4) - diazide-(4) (example 1) made by condensing 2-amino - hydroquinone - diethyl - ether with p - toluene-sulphochloride in dioxane or benzene in presence of pyridine to form p-toluene-sulphenyl - amido - 2,5 - diethoxy - benzene, which is nitrated to form p-toluene-sulphenyl-amido - 4 - nitro - 2,5 - diethoxy - benzene, reduced to the corresponding amino compound and diazotized.  The corresponding dimethoxy, diphenylmethoxy and 1-anthracene-sulphonamido compounds are made similarly.  N - (21,41 - dichlorobenzene - sulphonyl) - imino - (1) - 2,5 - diethoxy - benzoquinone -(1,4) - diazide - (4) (example 2) is made by a method analogous to that of example 1.  N - (benzene - sulphonyl) - imino - (1) - 2,5, - diethoxy - benzoquinone - (1,4) - diazide - (4) (example 3) is made by the process of example 1.  N - (41 - methyl - benzene - sulphonyl) - imino - (1) - 2 - methoxy - 5 - methyl - benzoquinone - (1,4)-diazide-(4) (example 4) made by condensing 1-amino - 2 - methyl - 5 - ethoxy - benzene with p - toluene - sulphochloride and following the procedure of example 1. The corresponding 2-5-dimethyl, 2-chloro and 2-methyl compounds are made similarly.  N - (2 - naphthalene - sulphonyl) - imino -(1) - 2,5 - diethoxy - benzoquinone - (1,4) - diazide -(4) and N - (1 - naphthalene - sulphonyl) - imino - (1) - 2,5 - dimethoxy - benzoquinone - (1,4) - diazide - (4) (example 5) are made by a method analogous to that of example 1.  Di - N - (4,41 - diphenyl - disulphonyl) - 2,5 - diethoxy benzoquinone - (1,4) - diazide - (4) (example 6) is made by condensation of 1-aminohydroquinone - 2,5 - diethyl - ether with 4,41-diphenyl-disulphochloride, nitration, reduction and diazotization of the product as in example 1.  N - (41 - amino - benzene - 11 - sulphonyl) - imino - (1) - 2,5 - diethoxy - benzoquinone - (1,4) - diazide - (4) (example 7) is made by reacting p-acetylaminobenzene - sulphochloride with 2 - amino - hydroquinone - diethyl ether and following the method of example 1 to form N-(41 - acetylaminobenzene - sulphonyl) - imino - 2,5 - diethoxy - benzoquinone - (1,4) - diazide - (4) and saponifying this.  N - (butyl - sulphonyl) - imino - (1) - 2,5 -diethoxybenzoquinone - (1,4) - diazide - (4) (example 8) is made by the method of example 1.  N - (benzoxazolone - 51 - sulphonyl) - imino - (1) - 2,5 - dimethoxy - benzoquinone - (1,4) - di - azide - (4) (example 9) is made by reacting benzoxazolone - 5 - sulphochloride with amino - hydroquinone - dimethyl - ether in dioxane in presence of pyridine and nitrating, reducing and diazotizing the product as in example 1.  N - (41 - methyl - benzene - sulphonyl) - imino - (1) - naphthoquinone - (1,4) - diazide - (4) (example 10) is made by condensing p-toluene-sulphochloride with 1-naphthylamine and nitrating, reducing and diazotizing the product as in example 1. 1 - benzoylimino - naphtho - quinone - diazide - (4) is made by diazotization of 1 - benzoylamino - 4 - naphthylamine with di - nitrogen - trioxide.  1 - Benzoylimino - 2,5 - dimethoxy - benzoquinone - diazide - (4) (example 11) is made, similarly, by diazotization with dinitrogen-trioxide <FORM:0723382/IV (b)/1> (example 12) is made by treating the diazonium salt of 2-amino-carbazole with ammonia water. N - phenyl - imino - (1) - 2 - anilido - sulphonyl - benzoquinone - (1,4) - diazide - (4) (example 13) is made by condensing 1-chloro-4-nitrobenzene-2-sulphochloride with aniline in dioxane, heating the resulting 1-chloro-4-nitrobenzene-2-sulphonanilide with excess aniline to produce 4 - nitrodiphenyl - amine - 2 - sulphonanilide, reducing this to the corresponding amino compound and diazotizing.  1,8 - naphthosultam - diazide - (2) - 4 - sulphon - N - ethyl - anilide (example 14); 1,8 - naphtho - sultam - diazide - (2) - 4 - sulphon - N - ethyl - b  - naphthylamide (example 15); 1,8 - naphtho - sultam - diazide - (2) - 4 - sulphon - N - p - aminodiphenylamin (example 16); di - (1,8 - naphthosultam - diazide - (2) - 4 - sulphon) - 4,41 - diaminodiphenyl (example 17) and 1,8 - naphthosultam - diazide - (2) - 4 - sulphonic acid phenyl ester (example 18) are made by reducing the corresponding azo dyes (for preparation of which (see Group IV (c)).  Specification 633,746, [Group XVI], is referred to.