Patent GB-885483-A (GB)
Title: Improvements relating to fluorescent stilbyl triazole compounds and to their use
Filed: 1958-08-13
Abstract: 2-(Stilbyl-411)-acenaphtheno-41:51:4:5)-1:2:3 - triazoles of the formula <FORM:0885483/III/1> wherein at least one X represents a non-acid dissociating sulphonyl substituent SO2R, R being an aryl, alkyl, aralkyl, aryloxy, amino or organically substituted amino group and the other X's represent hydrogen or these and other ring positions may contain any non-ionogenic substituent which is neither chromophoric nor auxochromic, are added to hydrocarbons, fats, waxes and oils, to which they impart a brightening effect.ALSO:2-(Stilbyl-411)-(acenaphtheno-41 : 51 : 4 : 5)-1 : 2 : 3-triazoles of the formula <FORM:0885483/IV (a)/1> wherein at least one X represents a non-acid dissociating sulphonyl substituent SO2R, R being an aryl, alkyl, aralkyl, aryloxy, amino or organically substituted amino group and the other X's represent hydrogen or these and other ring positions may contain any non-ionogenic substituent which is neither chromophoric nor auxochromic, are added to polymers and copolymers of vinyl chloride, vinylidene chloride, acrylonitrile, styrene, ethylene and other olefines, superpolyamides such as nylon, superpolyurethanes and polyesters such as polyethylene terephthalate, to which they impart a brightening effect.ALSO:The invention comprises 2-(stilbyl-411)- (acenaphtheno-41 : 51 : 4 : 5)-1 : 2 : 3-triazoles of the formula <FORM:0885483/IV (b)/1> wherein at least one X represents a non-acid dissociating sulphonyl substituent SO2R, R being an aryl, alkyl, aralkyl, aryloxy, amino or organically substituted amino group (including piperidino and morpholino groups and alkyl, aryl and pyridylamino groups further substituted by amino hydroxy and alkoxy groups or chlorine atoms), and the other X's represent hydrogen or these and other ring positions may contain any non-ionogenic substituent which is neither chromophoric nor auxochromic, e.g. chloro, bromo, cyano, alkyl, alkoxy, aryl, aryloxy, acylamino, carboxylic and sulphonic acid ester or amide groups and alkyl or aryl sulphone groups.  The compounds are obtained (1) by reacting 2-(stilbyl-411)-(acenaphtheno-41 : 51 : 4 : 5)-1 : 2 : 3-triazole-211-, -2111- or -4111-sulphonic acids or alkali metal salts thereof with phosphorus halides and treating the corresponding sulphonic acid halides obtained with ammonia or primary or secondary amines, or with aromatic hydroxyl compounds or salts thereof, or with aromatic hydrocarbons in the presence of Friedel-Crafts catalysts, or by reduction to sulphinic acids and subsequent aralkylation or alkylation thereof, to form sulphonamide, aryl sulphonate, aryl sulphone or aralkyl or alkyl sulphone, respectively; or (2) by coupling diazotized 4-aminostilbene compounds containing a group -SO2R ortho or para to the vinylene linkage with a 5-amino-acenaphthene coupling ortho to the 5-amino group to form an orthoaminoazo dyestuff which is subsequently oxidised to the required optical brightening agent.  2-(Stilbyl-411)-(acenaphtheno-41 : 51 : 4 : 5)-1 : 2 : 3-triazole-211-sulphonic acid is obtained by oxidizing the ortho-aminoazo dyestuff obtained by coupling 5-amino-acenaphthene with diazotized 4-aminostilbene-2-sulphonic acid.  4 - Nitrostilbyl - 2 - (21 : 41 - dimethylphenyl) - sulphone is obtained by condensing benzaldehyde with 3-nitro-6 : 21 : 41-trimethyl-1 : 11-diphenyl sulphone in the presence of piperidine.  4 - aminostilbyl - 2 - (21 : 41 - dimethylphenyl) - sulphone is obtained by reduction of the corresponding 4-nitro-compound.ALSO:Ortho-aminoazo dyestuffs are obtained by coupling 5-aminoacenaphthenes having an unsubstituted position ortho to the amino group with diazotised 4-aminostilbene compounds containing a group -SO2R ortho or para to the vinylene linkage, R being hydrogen, aryl, alkyl, aralkyl, aryloxy, amino or organically substituted amino.  2-(Stilbyl-411)-(acenaphtheno-41 : 51 : 4 : 5)-1 : 2 : 3-triazoles of the formula <FORM:0885483/IV (c)/1> wherein at least one X represents a non-acid dissociating sulphonyl substituent SO2R, R being an aryl, alkyl, aralkyl, aryloxy, amino or organically substituted amino group, and the other X's represent hydrogen, or these and other ring positions may contain any non-ionogenic substituent which is neither chromophoric nor auxochromic, are applied to synthetic fibres derived from vinyl polymers, superpolyamides such as nylon, superpolyurethanes and polyesters such as polyethylene terephthalate, to which they impart a brightening effect.