Patent GB-654028-A (GB)
Title: Manufacture of brightening agents for textile and other organic fibrous materials
Filed: 1948-10-23
Abstract: Compounds of the general formula <FORM:0654028/IV (b)/1> (in which Ar is an aromatic radical and Y is the radical of a 1,3,5-triazine ring which may be substituted in the 3,5-positions by primary, secondary or tertiary amino groups) are prepared by reacting 4,41-diaminostilbene compounds, mono-acylated by the Ar-O-alkylene-CO-group, with a halogen 1,3,5-triazine compound and, if desired, replacing further halogen atoms of the 1,3,5-traizine ring by primary, secondary or tertiary amino groups.  Alternatively, an N-mono-1,3,5-triazinyl derivative of a 4,41-diaminostilbene is acylated to introduce the Ar-O-alkylene-CO-grouping.  Compounds containing free amino groups may then be treated with formaldehyde as described in Specification 595,065.  In examples: (1) the nitro-compound prepared by condensing 4,41-nitroaminostilbene-2,21-disulphonic acid with cyanuric chloride is reacted with concentrated ammonia, dimethylamine or diethanolamine, reduced with iron and hydrochloric acid, and then reacted with phenoxyacetyl chloride; (2) the nitro compound obtained by condensing 4,41 - nitroaminostilbene - 2,21 - disulphonic acid with aniline is reduced and then reacted with phenoxyacetyl chloride; (3) cyanuric chloride, 4,41 - nitroaminostilbene - 2,21 - disulphonic acid and ammonia are condensed and reduced, and the product reacted with p-cresoxyacetyl chloride; (4) the nitro compound obtained by condensing 4,41 - nitroaminostilbene - 2,21 - disulphonic acid with 4-chlorophenoxyacetyl chloride is reduced and reacted with cyanuric chloride and ammonia; (5) the reduced condensation product from cyanuric chloride, 4,41-nitroaminostilbene-2,21-disulphonic acid and ammonia is reacted with 4-chloro-2-methyl-phenoxyacetyl chloride; and (6) the condensation product from cyanuric chloride, 4,41-nitroaminostilbene-2,21-disulphonic acid and ammonia is reduced and reacted with phenoxypropionyl chloride. Many other compounds within the scope of the general formula are specified.ALSO:Compounds of the general formula <FORM:0654028/IV (c)/1> (in which Ar is an aromatic radical and Y is the radical of a 1,3,5-triazine ring which may be substituted in the 3,5-positions by primary, secondary or tertiary amino groups) are used for optical bleaching and for imparting a brilliance to dyed textile materials.  Compounds containing free amino groups may be treated with formaldehyde as described in Specification 595,065.  In examples : (1) the nitro-compound prepared by condensing 4,41 nitroaminostilbene-2,21-disulphonic acid with cyanuric chloride is reacted with concentrated ammonia, dimethylamine or diethanolamine, reduced with iron and hydrochloric acid, and then reacted with phenoxy-acetyl chloride ; (2) the nitro compound obtained by condensing 4,41 - nitroaminostilbene - 2,21 - disulphonic acid with aniline is reduced and then reacted with phenoxyacetyl chloride ; (3) cyanuric chloride, 4,41 - nitroaminostilbene - 2,21 - disulphonic acid and ammonia are condensed, reduced, and the product reacted with p-cresoxyacetyl chloride ; (4) the nitro compound obtained by condensing 4,41-nitroaminostilbene-2,21-disulphonic acid with 4-chlorophenoxyacetyl chloride is reduced and reacted with cyanuric chloride and ammonia; (5) the reduced condensation product from cyanuric chloride, 4,41 - nitroaminostilbene - 2,21 - disulphonic acid and ammonia is reacted with 4 - chloro - 2 - methyl - phenoxyacetyl chloride ; (6) the condensation product from cyanuric chloride, 4,41 - nitroaminostilbene - 2,21-disulphonic acid and ammonia is reduced and reacted with phenoxypropionyl chloride ; (7) silk is brightened by treatment with the product of (1) in presence of formic acid; (8) nylon is brightened by treatment with the product of (2) in presence of formic acid, and (9) bleached wool is dyed with Alizarin Light Blue AR in the presence of the product of (2) and formic acid.  Many other brightening agents within the scope of the general formula are specified.