Patent GB-787429-A (GB)
Title: New stilbene compounds
IPC: C07D521/00
Filed: 1955-02-16
Abstract: The invention comprises stilbene compounds (and salts thereof) in which at least one of the groupings <FORM:0787429/IV (b)/1> wherein R is an hydrocarbon radicle, is attached to (a) the radical of a mono- or poly-carboxylic acid, (b) a cyanuric acid residue, (c) the radical of a carbonic acid semi-ester or semi-amide, or (d) the radical of a polyisocyanate.  These products may be incorporated in detergent compositions as brightening agents or materials such as linen, straw, or leather may be brightened therewith, or they may be incorporated in spinning or casting masses for the production of synthetic materials.  Acids specified under (a) above are phenoxyacetic, alkylated or halogenated aromatic carboxylic acids, acetic acid, propionic acid, benzoic acid, oxalic, fumaric, or terephthalic acids. The products may be prepared by diazotizing 4-amino - 41 - nitrostilbene - 2,21 - disulphonic acid, reducing the diazo group to hydrazino, condensing with a b -keto-butyraldehyde acetal to form the pyrazolyl derivative, reducing nitro to amino, and substituting the amino by one of the radicals (a), (b), (c) or (d) above, or alternatively by starting from 4,41-diaminostilbene - 2,21 - disulphonic acid and substituting by one of said radicals first, and then proceeding to the pyrazolyl derivative.  In examples, (1) white linen is washed with a detergent composition comprising a compound prepared by acylation of 4-(3-methylpyrazolyl-41 - aminostilbene - 2,21 - disulphonic acid with methoxy acetic acid anhydride or methoxyacetyl chloride or corresponding acetyl-, propionyl-, chloracetyl-, benzoyl-, or phenoxyacetyl compounds; (2) cotton fabric is dyed with a black dye in presence of a product prepared from 1 mol. 4-(3-methylpyrazolyl)-41 - aminostilbene - 2,21 - disulphonic acid and 1 mol. cyanuric chloride followed by reaction with ammonia; (3) nettlecloth is bleached with chlorine in presence of a compound prepared from 1 mol. cyanuric chloride, 2 mols. 4-(3-methylpyrazolyl) - 41 - aminostilbene - 2,21-disulphonic acid and 1 mol. morpholine; (4) bleached nettlecloth is brightened with the reaction product of 4-(3-methylpyrazolyl)-41-aminostilbene - 2,21 - disulphonic acid and phenyl isocyanate; (5) yellowish-white paper is treated with the product of chloroformic acid phenyl ester and 4-(3-methylpyrazolyl)-41 - aminostilbene - 2,21 - disulphonic acid; (6) aqueous dispersions of the sodium and barium salts of the compound referred to under (3) above are added to conventional viscose spinning solutions.ALSO:The invention comprises stilbene compounds (and salts thereof) in which at least one of the groupings <FORM:0787429/IV (b)/1> wherein R is a hydrocarbon radical, is attached to (a) the radical of a mono- or poly-carboxylic acid; (b) a cyanuric acid residue; (c) the radical of a carbonic acid semi-ester or semi-amide, or (d) the radical of a polyisocyanate.  These products may be incorporated in detergent baths as brightening agents, and materials such as linen, straw, or leather may be brightened therewith.  Acids specified under (a) above are phenoxyacetic acid, alkylated or halogenated aromatic carboxylic acids, acetic acid, propionic acid, benzoic acid, oxalic, fumaric, or terephthalic acid.  In examples: (1) white linen is washed in a detergent bath containing a compound prepared by acylation of 4-(3-methylpyrazolyl) - 41 - aminostilbene - 2,21 - disulphonic acid with methoxy-acetic acid anhydride or methoxyacetyl chloride or corresponding acetyl-, propionyl-, chloracetyl-, benzoyl-, or phenoxy-acetyl compounds; (3) nettlecloth is bleached with chlorine in presence of a compound prepared from 1 mol. of cyanuric chloride, 2 mols. of 4-(3-methylpyrazolyl)-41-aminostilbene-2, 21-disulphonic acid and 1 mol. of morpholine; (4) bleached nettlecloth is brightened with the reaction product of 4-(3-methylpyrazolyl) - 41 - aminostilbene - 2,21-disulphonic acid and phenyl isocyanate; (5) yellowish-white paper is treated with the product of chloroformic acid phenyl ester and 4-(3 - methylpyrazolyl) - 41 - aminostilbene - 2,21-disulphonic acid.ALSO:The invention comprises stilbene compounds (and salts thereof) in which at least one of the groupings: <FORM:0787429/IV (a)/1> wherein R is a hydrocarbon radical, is attached to (a) the radical of a mono- or poly-carboxylic acid; (b) a cyanuric acid residue; (c) the radical of a carbonic acid semi-ester or semi-amide; or (d) the radical of a polyisocyanate.  These products may be incorporated as brightening agents in spinning or casting masses, e.g. viscose, for the production of synthetic fibres or films. Acids specified under (a) above are phenoxyacetic acid, alkylated or halogenated aromatic carboxylic acids, acetic acid, propionic acid, benzoic acid, oxalic, fumaric or terephthalic acid.