Patent GB-660353-A (GB)
Title: Improvements in dyes and in photographic materials containing the same
IPC: G03C1/83
Filed: 1948-01-16
Abstract: 5 - (5 - Acetanilido - 2 : 4 - pentadienylidene) - 1 : 3-diethyl-2-thiobarbituric acid is prepared by refluxing together 1 : 3-diethyl-2-thiobarbituric acid, glutaconic aldehyde dianilidide hydrochloride, acetic anhydride, and fused sodium acetate.  4 - (5 - Acetanilido - 2 : 4 - pentadienylidene) - 3 - phenyl - 5 - (4) - isoxazolone and 2 - (5 - acetanilido - 2 : 4 - pentadienylidene)-1 : 3-indanedione are similarly prepared.  4 - (5 - Acetanilido - 2 : 4 - pentadienylidene)-3 - methyl - 1 - phenyl - 5 - pyrazolone is prepared by allowing a mixture of 1-phenyl-3-methyl-5-pyrazolone, glutaconic aldehyde dianilide hydrochloride, absolute ethyl alcohol, and triethylamine at 0 DEG  C. to stand, and heating with acetic anhydride and triethylamine.  5 -Acetanilidomethylene - 1 : 3-diethylbarbituric acid is prepared by refluxing together 5-anilinomethylene - 1 : 3 - diethylbarbituric acid, acetic anhydride, and triethylamine.  5 - Anilinomethylene - 1 : 3 - diethylbarbituric acid is prepared by heating together 1 : 3-diethylbarbituric acid and diphenylformamidine in kerosene.  5 - (3 - Acetanilidoallylidene) - 1 : 3 - diphenylbarbituric acid is similarly prepared.  1 - p - Carboxyphenyl - 3 - pentadecyl - 5-pyrazolone is prepared by refluxing together ethyl palmityl acetate, p-hydrazinobenzoic acid, and glacial acetic acid.  1 : 3 - Diethyl - 2 - thiobarbituric acid is prepared by heating N : N1-diethylthiocarbamide with ethyl malonate in presence of sodium ethoxide.  3 - Acetylthioglycollylamino - 1 - phenyl - 5-pyrazolone is prepared by reacting 3-amino-1-phenyl-5-pyrazolone with acetylthioglycollyl chloride in dioxane.  Specifications 503,752, [Group XX], 517,769, and 624,462, [Group IV (c)], are referred to. The Specification as open to inspection under Sect. 91 comprises also the subject-matter of Specification 663,042.  This subject-matter does not appear in the Specification as accepted.ALSO:Unsymmetrical methine or polymethine oxonol dyes of the general formula <FORM:0660353/IV (c)/1> wherein X represents the atoms necessary to complete a barbituric acid, thiobarbituric acid, isoxazolone, or indanedione nucleus, n is 0, 1, or 2, and Y represents the atoms necessary to complete a pyrazolone nucleus, are prepared by reacting a barbituric acid, thiobarbituric acid, isoxazolone, or indanedione with a pyrazolone, one of the reactants being in the form of an o -acetanilido-methylene, -allylidene, or -pentadienylidene derivative. The reaction may be effected in the presence of triethylamine.  [1 : 3 - Diethyl - 2 - thiobarbituric acid - (5)] - [3 - methyl-1-phenyl-5-pyrazolone-(4)]-methineoxonol is prepared by refluxing together 4-acetanilidomethylene - 3 - methyl - 1 - phenyl - 5 - pyrazolone, 1 : 3-diethyl-2-thiobarbituric acid, pyridine, and triethylamine.  [1 : 3 - Diethylbarbituric acid - (5)] - [3 - methyl - 1 - phenyl - 5 - pyrazolone - (4)] - trimethineoxonol, [1 : 3 - diethyl - 2 - thiobarbituric acid - (5)] - [3 - methyl - 1 - p - sulphophenyl - 5 - pyrazolone - (4)] - pentamethineoxonol, [3 - acetylthioglycollylamino - 1 - phenyl - 5 - pyrazolone - (4)] - [1 : 3 - diethyl - 2 - thiobarbituric acid - (5)] - pentamethineoxonol, [1 : 3 - diphenyl - 2 - thiobarbituric acid - (5)] - [3 - methyl - 1 - phenyl - 5 - pyrazolone - (4)] - pentamethineoxonol, [1 : 3 - di - p - phenetylbarbituric acid - (5)] - [3 - methyl - 1 - phenyl - 5 - pyrazolone - (4)] - trimethineoxonol, [1 - ethylbarbituric acid - (5)] - [3 - methyl - 1 - phenyl - 5 - pyrazolone - (4)] - methineoxonol, [3 - amino - 1 - phenyl - 5 - pyrazolone - (4)] - [1 : 3 - diethylbarbituric acid - (5)]-methineoxonol, [1 : 3-di - p - phenetylbarbituric acid - (5)] - [3 - methyl - 1 - phenyl - 5 - pyrazolone - (4)] - methineoxonol, [1 : 3 - diethyl - 2 - thiobarbituric acid - (5)] - [3 - methyl - 1 - phenyl - 5 - pyrazolone - (4)] - trimethineoxonol, [1 - p - carboxyphenyl - 3 - pentadecyl - 5 - pyrazolone - (4)] - [1 : 3 - diethyl - 2 - thiobarbituric acid - (5)] - pentamethineoxonol, [3-methyl - 1 - p - sulphophenyl - 5 - pyrazolone - (4)]-[3 - phenyl - 5(4) - isoxazolone - (4)] - pentamethineoxonol, and [1 : 3 - indanedione - (2)] - [3 - methyl - 1 - phenyl - 5 - pyrazolone - (4)] - pentamethineoxonol are similarly prepared. Specifications 503,752, [Group XX], 517,769 and 624,462 are referred to.  The Specification as open to inspection under Sect. 91 comprises also the subject-matter of Specification 663,042.  This subject-matter does not appear in the Specification as accepted.