Patent GB-908229-A (GB)
Title: Bis-(triazinylamino)-stilbene disulphonic acid brightening agents
Inventor: GEHM ROBERT
IPC: C07D251/68
Filed: 1960-01-21
Abstract: A household detergent consisting of a mixture of tetrapropylene benzene sulphonate, oleyl sulphate, sodium perborate, magnesium silicate, sodium silicate, sodium tripolyphosphate, sodium tetrapyrophosphate, sodium sulphate, carboxymethyl cellulose and water is admixed with optical brightening agents which in their anionic form have the general formula:-  <FORM:0908229/III/1> in which X represents a 1-aza-4-thiocyclo-hex-1-yl-4,4-dioxide radical, a 2,6-dimethyl-1-aza-4-thiacyclohex-1-yl-4,4-dioxide radical or a radical of the formula:-  <FORM:0908229/III/2> and Y is a hydroxy group, an amino group, a monosubstituted amino group such as an alkylamino, cycloalkylamino, arylamino, hydroxyalkylamino or alkoxyalkylamino group, a disubstituted amino group such as a dialkylamino, di(hydroxyalkyl) amino or di(alkoxyalkyl) amino group, a pyrrolidino, piperidino or morpholino group, a 1-aza-4-thiacyclohex-1-yl-4,4-dioxide radical or a group of the formula <FORM:0908229/III/3> or salts thereof with alkali metals, ammonia or primary, secondary or tertiary amines.  Specification 874,519 is referred to.ALSO:The invention comprises optical brightening agents which in their anionic form have the general formula:- <FORM:0908229/IV (b)/1> in which X represents a 1-aza-4-thiocyclo-hex-1-yl-4,4-dioxide radical, a 2,6-dimethyl-1-aza-4-thiacyclohex-1-yl-4,4-dioxide radical or a radical of the formula:- <FORM:0908229/IV (b)/2> and Y is a hydroxy group, an amino group, a monosubstituted amino group such as an alkylamino, cycloalkylamino, arylamino, hydroxyalkylamino or alkoxyalkylamino group, a disubstituted amino group such as a dialkylamino, di(hydroxyalkyl) amino or di(alkoxyalkyl) amino group, a pyrrolidino, piperidino or morpholino group, a 1-aza-4-thiacyclohex-1-yl-4,4-dioxide radical or a group of the formula <FORM:0908229/IV (b)/3> or salts thereof with alkali metals, ammonia or primary, secondary or tertiary amines.  The above brightening agents are prepared by reacting in any order two mols. of a cyanuric halide with one mol. of an alkali metal salt of a 4,41-diamino-stilbene disulphonic acid of the formula:- <FORM:0908229/IV (b)/4> and with two mols. of 1-aza-4-thia-cyclohexane-4,4-dioxide or two mols. of 2,6-dimethyl - 1 - aza-4-thiacyclohexane-4,4-dioxide, and further reacting the products obtained with aqueous alkali, ammonia, an alkylamine, a dialkylamine, a cycloalkylamine, a hydroxyalkylamine, a di(hydroxyalkyl) amine, an alkoxyalkylamine, a di(alkoxyalkyl) amine, an arylamine, pyrrolidine, morpholine, piperidine or 1 - aza-4-thiacyclo-hexane-4,4-dioxide or, after having reacted the said products or the initial compound (obtained by the reaction of cyanuric acid halide with 4,41-diaminostilbene disulphonic acid) with ammonia, the resulting compounds are treated with a mixture of aqueous formaldehyde and 1-aza-4-thiacyclohexane-4,4-dioxide or, after having reacted the initial compound (obtained by the reaction of cyanuric halide with 4,41-diaminostilbene disulphonic acid) with 2 mols. of aqueous alkali, a primary or secondary amine, pyrrolidine, piperidine or morpholine, the remaining chlorine substituents are replaced by means of ammonia and the resulting amino compound is condensed with formaldehyde and 2 mols. of 1-aza-4-thiacyclohexane-4,4-dioxide.  Specification 874,519 is referred to.ALSO:Foils, films, felts, fibres, threads, yarns, flocks and woven and non-woven fabrics of natural, regenerated and synthetic material, such as leather, synthetic polymers (plastics), cotton, household washing, paper, native or regenerated cellulose and linear polyamides (e.g. polycaprolactam) are brightened by treatment with optical brightening agents which in their anionic form have the general formula:-  <FORM:0908229/IV (b)/1> in which X represents a 1-aza-4-thiocyclohex-1-yl-4,4-dioxide radical, a 2,6-dimethyl-1-aza-4-thiocyclohex-1-yl-4,4-dioxide radical or a radical of the formula:-  <FORM:0908229/IV (b)/2> and Y is a hydroxy group, an amino group, a monosubstituted amino group such as an alkylamino, cycloalkylamino, arylamino, hydroxyalkylamino or alkoxyalkylamino group, a disubstituted amino group such as a dialkylamino, di(hydroxyalkyl) amino or di(alkoxyalkyl) amino group, a pyrrolidino, piperidino or morpholino group, a 1-aza-4-thiocyclohex-1-yl-4,4-dioxide radical or a group of the formula <FORM:0908229/IV (b)/3> or salts thereof with alkali metals, ammonia or primary, secondary or tertiary amines.  Other ingredients which may be present in the aqueous treatment bath are formic acid, hydrogen peroxide, tetrapropylene benzene chromium trioxide to trichloracetic acid in solution in an aromatic hydrocarbon, e.g. toluene.  Material treated by either process may be dried at an elevated temperature. Treatment enhances the adhesion of the fabric for materials of other high molecular synthetic or high molecular natural substances, e.g. gelatin, polyvinyl alcohol, polyvinyl butyral, polyethylene and polyamides.  In an example, a polyethylene terephthalate fabric is bathed for 10 secs. in a solution of 100 parts by weight of water, 2.5 parts by weight of trichloracetic acid, 0.25 part by weight of chromium trioxide and 0.2 part by weight of a wetting agent, and is then dried in an oven.  The dried fabric is then united with a polyamide film by pressing them together under the influence of heat.