GB538869A - Improvements in light-sensitive diazo compounds - Google Patents

Abstract

538,869. N-Aminoaryl-substituted heterocyclic compounds. MURRAY, H. D.. and TYRRELL, A. Jan. 11, 1940, Nos. 597/40, 598/40 and 1883/41. [Class 2 (iii)] [Also in Group XX] A photographic diazotype layer contains a diazo compound derived from an amine of the general formula wherein X and Y each represent either a carbonyl group or a methylene group and X and Y are members of the same ring. X and Y may be both carbonyl groups as in N-(4-aminophenyl)-succinimide, N-(4-amino- 2: 5-diethoxyphenyl)-succinimide, N-(4-aminophenyl)-phthalimide, and N-(4-amino-2 : 5- diethoxyphenyl)-phthalimide; both methylene groups as in N-(4-aminophenyl)-morpholine and N-(4-aminophenyl)-piperidine ; or X may be carbonyl and Y methylane, as in N-(4- aminophenyl)-phthalimidine. The zinc and tin chloride double salts of the diazo compounds may be used. A sensitizing solution specified contains the zinc chloride double salt of diazotized N-(4-amino-2 : 5-diethoxyphenyl)- phthalimide. Specification 532,958 is referred to. N-( 4-amino-2 : 5-diethoxyphenyl)-phthalimide is prepared by adding phthalic anhydride to a solution of 2 : 5-diethoxyaniline in tetrahydronaphthalene and refluxing, nitrating and reducing the anilide obtained to give the anilic acid corresponding to the above compound, and heating this acid to 155‹ C. in an open dish. N-(4-aminophenyl)-morpholine and piperidine are prepared by refluxing together p-nitrochlorobenzene and morpholine or piperidine and reducing the nitro group. 2 : 5-Diethoxy-bromo- and -dibromo-benzene are prepared by brominating p-diethoxybenzene in glacial acetic acid and separating the products bv fractional distillation. 1-Bromo-2 : 5-diethoxy-4-nitrobenzene is prepared by nitrating 1-bromo-2 : 5-diethoxybenzene in glacial acetic acid. N-(4- Amino-2 : 5-diethoxyphenyl)-morpholine and -piperidine are prepared by refluxing morpholine or piperidine with 1-bromo-2 : 5- diethoxy-4-nitrobenzene and then reducing the nitro group. N-(4-Aminophenyl)-phthalamidine is prepared by nitrating N-phenylphthalamidine with potassium nitrate and concentrated sulphuric acid and reducing the nitro group. Specifications 282,894, [Class 98 (ii)], 347,430 and 425,235, [both in Group XX], also are referred to.