Patent GB-736452-A (GB)
Title: A process for the optical brightening of organic materials, compositions for use therein and materials treated
IPC: C07D263/62
Filed: 1953-05-08
Abstract: An optical brightening of organic materials is obtained by treating the materials with a compound having the general formula: <FORM:0736452/IV (c)/1> where A is a naphthylene radical, B is the same as A or an ortho-phenylene radical, R1 and R2 are alkyl or hydroxyalkyl groups and X is the anion of a strong inorganic or organic acid.  The radicals A and B may be substituted with halogen atoms or alkyl, alkoxy, aryloxy or acylamino groups. Examples of such compounds are given wherein A and B are both naphthylene radicals or A is naphthylene and B is methyl-substituted ortho-phenylene, the naphthylene radical being annulated to the oxacyanine radical in 11,21 : 4,5, 21,11 : 4,5 or 21,31 : 4,5 positions.  In these examples R1 and R2 are methyl, ethyl, n-propyl, n-butyl, n-hexyl or n-octyl radicals and X is the anion of p-toluene sulphonic, benzene sulphonic, methyl sulphuric, sulphuric, or hydrochloric acid.  X may also be derived from hydrobromic or hydroiodic acid.  The compound may be applied to textile materials consisting of cotton, ramie, flax, viscose rayon, cellulose acetate, cellulose propionate, methyl or benzyl cellulose, superpolyamides, superpolyurethanes, polyvinyl chloride or acetate or mixed polymers thereof, or e -caprolactam fibres, in aqueous or alcoholic solution or in starch compositions. The aqueous solution may also contain ammonia and the textile material may be immersed in a bath of the solution at temperatures up to 90 DEG  C.  Wood-pulp fibres and paper may also be treated. Specification 424,559 is referred to.ALSO:A compound for optically brightening organic textile and other materials has the general formula p  <FORM:0736452/IV (b)/1> where A is naphthylene, B is naphthylene or ortho-phenylene, R1 and R2 are alkyl or hydroxyalkyl and X is the anion of a strong organic or inorganic acid.  The radicals A and B may be further substituted with halogen atoms or alkyl, alkoxy, aryloxy or acylamino groups.  Various compounds are described in which A and B are both naphthylene or A is naphthylene and B is methyl-substituted ortho-phenylene, R1 and R2 being methyl, ethyl, n-propyl, n-butyl, n-hexyl or n-octyl groups and X the anion of paratoluenesulphonic, benzene sulphonic, methyl sulphuric, sulphuric, hydrochloric, hydrobromic or hydroiodic acid.  The compounds may be produced by condensation of 2-methyl naphtho-11.21 : 4.5,21.11 : 4.5 or 21.31 : 4.5) oxazoles or 2-methylbenzoxazole. N-alkyl ammonium salts with corresponding 2-methylmercapto compounds in the form of their N-alkyl ammonium salts with splitting off of methylmercaptan at a raised temperature, or the previously formed N-alkyl ammonium salt of one component can be condensed with the second component in the presence of an alkylating agent, whilst the previous formation of the N-alkyl ammonium salt can be performed in the reaction mixture before the condensation takes place.  The alkylating agent may be a dialkyl sulphate, an alkyl or hydroxyalkyl halide or an alkyl ester of an aromatic sulphonic acid.  The following compounds are made in this way: [3 - methyl - (naphtho - 11.21 : 4.5) - oxazolo]-[3.5 dimethyl - benzoxazolo] - monomethincyanine - p - toluene sulphonate; [3 - methyl-(naphtho - 21.11 : 4.5) - oxazolo] - [3.5 - dimethylbenzoxazolo] - monomethincyanine - p - toluene sulphonate; [3 - methyl - (naptho - 21.31 : 4.5)-oxazolo] - [3.5 - dimethylbenzoxazolo] - monomethincyanine - p - toluene sulphonate; bis-[3 - methyl - (naphtho - 11.21 : 4.5) - oxazolo]-monomethincyanine - p - toluene sulphonate; bis[3 - methyl - (naphtho - 21.11 : 4.5) - oxazolo]-monomethincyanine - p - toluene sulphonate; bis - [3 - methyl(naphtho - 21.31 : 4.5) - oxazolo]-monomethincyanine - p - toluene sulphonate; [3 - methyl (naphtho - 11.21 : 4.5) - oxazolo]-[3 - methyl - (naphtho - 21.11 : 4.5) - oxazolo]-monomethincyanine - p - toluene sulphonate; [3 - n - propyl - (naphtho - 11.21 : 4.5) - oxazolo]-[3-n-propyl - 5 - methyl - benzoxazolo] - monomethincyanine - p - toluene sulphonate; [3 - n-butyl - (naphtho - 21.11 : 4.5 - oxazolo] - [3 - n-butyl - 5 - methyl - benzoxazolo] - monomethincyanine - p - toluene sulphonate; [3 - n - octyl-(naphtho - 21.31 : 4.5) - oxazolo] - [3 - n - octyl-5 - methyl - benzoxazolo] - monomethincyanine-p - toluene sulphonate; bis - [3 - ethyl-(naphtho - 11.21 : 4.5) - oxazolo] - monomethincyanine - p - toluene sulphonate; bis - [3 - n-hexyl - (naphtho - 21.11 : 4.5) - oxazolo] - monomethincyanine - p - toluene sulphonate and the corresponding benzene sulphonates, methosulphates, sulphates or chlorides. Specification 424,559 is referred to.ALSO:An optical brightening compound having the general formula:-<FORM:0736452/V/1> where A is a naphthylene radical, B is the same as A or an o-phenylene radical, R1 and R2 are alkyl or hydroxyalkyl groups and X is the union of a strong organic or inorganic acid, may be added in aqueous solution to starch to obtain a pure white starch powder or a product for application in aqueous solution to textile materials, e.g. of cotton. The radicals A and B may be substituted with halogen atoms or alkyl, alkoxy, aryloxy or acylaminogroups.  Examples of such compounds are given where A and B are both naphthylene radicals, or where A is naphthylene and B is methyl-substituted o-phenylene, the naphthylene radical being annulated to the oxacyanine radical in the 11. 21: 4.5, 21:11:4.5, or 21.31 :4.5 positions.  In these examples R1 and R2 are methyl, ethyl, n-propyl, n-butyl, n-hexyl, and n-octyl radicals, and X is the anion of p-toluene sulphonic, benzene sulphonic, methyl sulphuric, sulphuric or hydrochloric acid.  X may also be derived from hydrobromic or hydroiodic acid. Specification 424,559, [Group IV], is referred to.