Patent GB-779505-A (GB)
Title: Improvements relating to fluorescent stilbyl ditriazole compounds and their use
Filed: 1955-03-17
Abstract: The invention comprises fluorescent stilbylditriazoles of the formula <FORM:0779505/IV(b)/1> wherein A is a benzene radical, B is a benzene or naphthalene radical, or a radical of the formula <FORM:0779505/IV(b)/2> and X is hydrogen or a substituent, there being no chromophores or aromatically bound hydroxy or amino groups present.  The invention also comprises a method of making such compounds by coupling one mol. either of a diazotized 4-aminostilbene-2-sulphonic acid or of a diazo compound of the aromatic series with one mol. of a m-diamino compound of the benzene series which can be coupled twice, oxidizing the o-aminoazo dyestuff obtained with one of the diazo compounds to form the corresponding 5 - amino - 2 - aryl - 1.2.3 - benztriazole compound, coupling this in 4-position with the one mol. of the other diazo compound, and oxidizing the azo-triazole obtained to form the ditriazole compound. Substituents such as halogen, alkyl, alkoxy, carboxy and sulpho may be present.  In examples: (1) 4 - aminostilbene-2-sulphonic acid is diazotized and coupled with 5 - amino - 2 - (31 - carboxyphenyl) - 1.2.3. - benztriazole, or alternatively diazotized m-aminobenzoic is coupled with 5-amino-2-(stilbyl-41)-1.2.3 - benztriazole - 21 - sulphonic acid, followed in each case by oxidation of the o-aminoazo dye with ammoniacal copper sulphate solution; (2) diazotized sulphanilic acid is coupled with 5-amino-2-(stilbyl-41)-1.2.3-benztriazole -21-sulphonic acid, followed by oxidation as under (1); (3) diazotized 2-amino-naphthalene-5-sulphonic acid is coupled with 5 - amino - 2- (stilby - 41) - 1.2.3 - benztriazole - 21.6-disulphonic acid followed by oxidation with sodium hypochlorite; (4) diazotized 4-amino-stilbene-2-sulphonic acid is coupled with 5-amino - 2 - (stilbyl - 41) - 1.2.3-benztriazole -21-sulphonic acid, followed by oxidation as under (1); (5) diazotized 4-aminostilbene-2-sulphonic acid is coupled with 5-amino-2-(stilbyl-41)-1.2.3-benztriazole-21.6 -disulphonic acid, followed by oxidation with sodium hypochlorite. Examples also describe the application of the product of Example (1) to poplin and to a white wash.  Other stilbyl ditriazoles are listed containing such further substituents as chlorine, acidyl-amino phenoxy, sulphonamide and sulphone.  Specification 668,199 is referred to.ALSO:The invention comprises fluorescent stilbyl ditriazoles of the formula:- <FORM:0779505/IV(b)/1> wherein A is a benezene radical, B is a benzene or naphthalene radical or a radical of the formula:- <FORM:0779505/IV(b)/2> and X is hydrogen or a substituent, there being no chromophores or aromatically bound hydroxy or amino groups present.  The invention also comprises a method of making such compounds by coupling one mol. either of a diazotized 4 - aminostilbene - 2 - sulphonic acid or of a diazo compound of the aromatic series with one mol. of a m-diamino compound of the benzene series which can be coupled twice, oxidizing the o-amino dyestuff obtained with one of the diazo compounds to form the corresponding 5 - amino - 2- aryl - 1.2.3 - benztriazole compound, coupling this in 4-position with the one mol. of the other diazo compound, and oxidizing the azo-triazole obtained to form the ditriazole compound. Substituents such halogen, alkyl, alkoxy, carboxy, and sulpho may be present.  In examples, (1) 4 - aminostilbene-2-sulphonic acid is diazotized and coupled with 5 - amino - 2 - (31 - carboxyphenyl) - 1.2.3 - benztriazole, or alternatively diazotized m - aminobenzoic is coupled with 5 - amino - 2 - (stilbyl - 41) - 1.2.3 - benztriazole - 21-sulphonic acid, followed in each case by oxidation of the o - aminoazo dye with ammoniacal copper sulphate solution; (2) diazotized sulphanilic acid is coupled with 5 - amino - 2 - (stilbyl - 41 -) - 1.2.3 - benztriazole - 21 - sulphonic acid, followed by oxidation as under (1); (3) diazotized 2-aminonaphthalene - 5 - sulphonic acid is coupled with 5 - amino - 2 - (stilbyl - 41)-1.2.3 - benztriazole - 21.6 - disulphonic acid followed by oxidation with sodium hypochlorite; (4) diazotized 4 - aminostilbene - 2 - sulphonic acid is coupled with 5 - amino2 - (stilbyl - 41 -) - 1.2.3 - benztriazole - 21 - 21 - sulphonic acid, followed by oxidation as under (1); (5) diazotized 4 - aminostilbene - 2 - sulphonic acid is coupled with 5 - amino - 2 - (stilbyl - 41 -) - 1.2.3 - benztriazole - 21.6 - disulphonic acid, followed by oxidation with sodium hypochlorite. Examples also describe the application of the product of Example 1 to poplin and to a white wash.  Other stilbyl ditriazoles are listed containing such further substituents as chlorine, acidylamino phenoxy, sulphonamide, and sulphone.